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{{Short description|Cyclic compound (C2H4O)}}
{{Redirect|Oxirane|oxiranes as a class of molecules|epoxide}}
{{Redirect|Oxirane|oxiranes as a class of molecules|epoxide}}{{Distinguish|Ethylene dione|Ethyl oxide}}
{{chembox
{{Use dmy dates|date=January 2022}}
| verifiedrevid = 408562214
{{Chembox
| ImageFileL1 = Ethylene-oxide-2D-skeletal.png
| Watchedfields = changed
| ImageSizeL1 = 100 px
| verifiedrevid = 446701253
| ImageFileR1 = Ethylene-oxide-from-xtal-3D-balls.png
| ImageFileL1 = Ethylene oxide.svg
| ImageSizeR1 = 150 px
| ImageSizeL1 = 100 px
| IUPACName = oxirane
| ImageClassL1 = skin-invert
| SystematicName =
| ImageFileR1 = Ethylene-oxide-from-xtal-3D-balls.png
| OtherNames = epoxyethane, ethylene oxide, dimethylene oxide,oxacyclopropane
| ImageSizeR1 = 150 px
| Section1 = {{Chembox Identifiers
| PIN = Oxirane<ref>{{cite book |author=] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=] |pages=714 |isbn=978-0-85404-182-4 |doi=10.1039/9781849733069}}</ref>
| Abbreviations = EO, EtO
| SystematicName = Epoxyethane<br>Oxacyclopropane
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| OtherNames = Ethylene oxide<br>Dimethylene oxide<br>1,2-Epoxyethane<br>-crown-1<br>Epoxide
| ChemSpiderID = 6114
| Section1 = {{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}}
|Abbreviations = EO, EtO
| UNII = JJH7GNN18P
|Beilstein = 102378
| InChIKey = IAYPIBMASNFSPL-UHFFFAOYAX
|ChEMBL = 1743219
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| StdInChI = 1S/C2H4O/c1-2-3-1/h1-2H2
|ChemSpiderID = 6114
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|Gmelin = 676
| StdInChIKey = IAYPIBMASNFSPL-UHFFFAOYSA-N
|UNII_Ref = {{fdacite|correct|FDA}}
| CASNo = 75-21-8
|UNII = JJH7GNN18P
| CASNo_Ref = {{cascite|correct|CAS}}
|UNNumber = 1040
| EINECS = 200-849-9
|InChIKey = IAYPIBMASNFSPL-UHFFFAOYAX
| EINECSCASNO =
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| PubChem = 6354
|StdInChI = 1S/C2H4O/c1-2-3-1/h1-2H2
| SMILES = C1CO1
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| InChI = 1/C2H4O/c1-2-3-1/h1-2H2
|StdInChIKey = IAYPIBMASNFSPL-UHFFFAOYSA-N
| RTECS = KX2450000
|CASNo = 75-21-8
| MeSHName = Ethylene+Oxide
| ChEBI_Ref = {{ebicite|correct|EBI}} |CASNo_Ref = {{cascite|correct|CAS}}
| ChEBI = 27561 |EINECS = 200-849-9
|PubChem = 6354
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D03474 |SMILES = O1CC1
|InChI = 1/C2H4O/c1-2-3-1/h1-2H2
| ATCCode_prefix =
|RTECS = KX2450000
| ATCCode_suffix =
|MeSHName = Ethylene+Oxide
| ATC_Supplemental =}}
|ChEBI_Ref = {{ebicite|correct|EBI}}
| Section2 = {{Chembox Properties
|ChEBI = 27561
| Formula = C<sub>2</sub>H<sub>4</sub>O
|KEGG_Ref = {{keggcite|correct|kegg}}
| MolarMass = 44.05 g mol<sup>−1</sup>
|KEGG = D03474
| Appearance = colorless gas
}}
| Density = 0.882 g/mL, 7.360 lbs/gallon
| Section2 = {{Chembox Properties
| MeltingPt = −111.3 °C
|Formula = {{chem2|C2H4O}}
| Melting_notes =
|MolarMass = 44.052{{nbsp}}g·mol<sup>−1</sup><ref name=r3430>], p. 3.430</ref>
| BoilingPt = 10.7 °C
|Appearance = Colorless gas
| Boiling_notes =
|Odor = Like diethyl ether<ref>Ethylene oxide, odor</ref>
| Solubility = miscible
|Density = 0.8821{{nbsp}}g·cm<sup>−3</sup><ref name=r3430/>
| SolubleOther =
|Dipole = 1.94{{nbsp}}D<ref name=r1520/>
| Solvent =
|MeltingPtC = −112.46
| LogP =
|MeltingPt_ref =<ref name=r3430/>
| VaporPressure =
|BoilingPtC = 10.4
| HenryConstant =
|BoilingPt_ref =<ref name=r3430/>
| AtmosphericOHRateConstant =
|Solubility = Miscible
| pKa =
|VaporPressure = 1.46{{nbsp}}atm (20{{nbsp}}°C)<ref name=PGCH/>
| pKb =}}
|RefractIndex = 1.3597 (589{{nbsp}}nm)<ref name=r3430/>
| Section3 = {{Chembox Structure
|MagSus = −30.5·10<sup>−6</sup>{{nbsp}}cm<sup>3</sup>/mol<ref>], p. 3.576</ref>
| CrystalStruct =
}}
| Coordination =
| Section3 = {{Chembox Thermochemistry
| MolShape =}}
|DeltaHf = −52.6{{nbsp}}kJ·mol<sup>−1</sup><ref name=r522>], p. 5.22</ref>
| Section4 = {{Chembox Thermochemistry
| DeltaHf = −52.6 kJ mol<sup>−1</sup> |DeltaGf = −13.0{{nbsp}}kJ·mol{{sup|−1}}<ref name=r522/>
|Entropy = 242.5{{nbsp}}J·mol<sup>−1</sup>·K<sup>−1</sup><ref name=r522/>
| DeltaHc =
| Entropy = 243 J mol<sup>−1</sup> K<sup>−1</sup> |HeatCapacity = 47.9{{nbsp}}J·mol<sup>−1</sup>·K<sup>−1</sup><ref name=r522/>
}}
| HeatCapacity =}}
| Section5 = {{Chembox Pharmacology | Section4 = {{Chembox Hazards
|ExternalSDS =
| AdminRoutes =
|GHSPictograms = {{GHS flame}}{{GHS skull and crossbones}}{{GHS health hazard}}
| Bioavail =
|MainHazards = ]<br>Extremely flammable
| Metabolism =
| HalfLife = |NFPA-H = 3
|NFPA-F = 4
| ProteinBound =
|NFPA-R = 3
| Excretion =
|HPhrases = {{H-phrases|220|230|301|314|331|335|336|340|350|360FD|372}}
| Legal_status =
|PPhrases = {{P-phrases|202|210|260|280|301+310+330|303+361+353|305+351+338+310|410+403}}<ref name="sigmaaldrich 2020">{{cite web |title=Ethylene oxide 387614 |url=https://www.sigmaaldrich.com/catalog/product/aldrich/387614?lang=en&region=GB |website=Sigma-Aldrich |access-date=1 September 2020 |archive-url=https://web.archive.org/web/20201205212012/https://www.sigmaaldrich.com/catalog/product/aldrich/387614?lang=en&region=US |archive-date=5 December 2020 |url-status=live}} </ref>
| Legal_US =
|FlashPtC = −20
| Legal_UK =
|FlashPt_ref =<ref name=r1520>], p. 15.20</ref>
| Legal_AU =
|AutoignitionPtC = 429
| Legal_CA =
|AutoignitionPt_ref=<ref name=r1520/>
| PregCat =
|ExploLimits = 3 to 100%
| PregCat_AU =
|PEL = TWA 1{{nbsp}}ppm 5{{nbsp}}ppm <ref name=PGCH>{{PGCH|0275}}</ref>
| PregCat_US =}}
|REL = Ca TWA <0.1{{nbsp}}ppm (0.18{{nbsp}}mg/m<sup>3</sup>) C 5{{nbsp}}ppm (9{{nbsp}}mg/m<sup>3</sup>) <ref name=PGCH/>
| Section6 = {{Chembox Explosive
|IDLH = Ca <ref name=PGCH/>
| ShockSens =
|LC50 = 836{{nbsp}}ppm (mouse, 4{{nbsp}}hr)<br>4000{{nbsp}}ppm (rat, 4{{nbsp}}hr)<br>800{{nbsp}}ppm (rat, 4{{nbsp}}hr)<br>819{{nbsp}}ppm (guinea pig, 4{{nbsp}}hr)<br>1460{{nbsp}}ppm (rat, 4{{nbsp}}hr)<br>835{{nbsp}}ppm (mouse, 4{{nbsp}}hr)<br>960{{nbsp}}ppm (dog, 4{{nbsp}}hr)<ref>{{IDLH|75218|Ethylene oxide}}</ref>
| FrictionSens =
}}
| ExplosiveV =
| Section5 = {{Chembox Related
| REFactor =}}
|OtherFunction = ],<br>],<br>]
| Section7 = {{Chembox Hazards
|OtherFunction_label = heterocycles
| EUClass =
}}
| EUIndex =
| MainHazards = ]
| NFPA-H = 3
| NFPA-F = 4
| NFPA-R = 3
| NFPA-O =
| RPhrases =
| SPhrases =
| RSPhrases =
| FlashPt = −20 °C
| Autoignition =
| ExploLimits = 3 to 100%
| PEL =}}
| Section8 = {{Chembox Related
| OtherAnions =
| OtherCations =
| OtherFunctn = ],<br> ],<br> ]
| Function = heterocycles
| OtherCpds =}}
}} }}


'''Ethylene oxide''', also called '''oxirane''', is the ] with the ] {{chem|C|2|H|4|O}}. It is a cyclic ether. This means that it is composed of 2 alkyl groups attached to an oxygen atom in a cyclic shape (circular). This colorless flammable gas with a faintly sweet odor is the simplest ], a three-membered ring consisting of two carbon and one oxygen atom. Because of its special molecular structure, ethylene oxide easily participates in the ], opening its cycle, and thus easily ]. Ethylene oxide is ]ic with ]. '''Ethylene oxide''' is an ] with the ] {{chem2|C2H4O}}. It is a cyclic ] and the simplest ]: a three-membered ] consisting of one ] atom and two ] atoms. Ethylene oxide is a colorless and ] gas with a faintly sweet odor. Because it is a ], ethylene oxide easily participates in a number of ]s that result in ring-opening. Ethylene oxide is ]ic with ] and with ]. Ethylene oxide is industrially produced by ] of ] in the presence of a ] ].

Although it is a vital raw material with diverse applications, including the manufacture of products like ] and ] that are often more effective and less toxic than alternative materials, ethylene oxide itself is a very hazardous substance: at room temperature it is a flammable, carcinogenic, ], irritating, and anaesthetic gas with a misleadingly pleasant aroma.


The chemical reactivity that is responsible for many of ethylene oxide's hazards has also made it a key industrial chemical that supports the living standards of advanced societies. Although too dangerous for direct household use and generally unfamiliar to consumers, ethylene oxide is used industrially for making many consumer products as well as non-consumer chemicals and intermediates. Ethylene oxide is important or critical to the production of detergents, thickeners, solvents, plastics, and various organic chemicals such as ], ethanolamines, simple and complex glycols, polyglycol ethers and other compounds. As a poison gas that leaves no residue on items it contacts, pure ethylene oxide is a ] that is widely used in hospitals and the medical equipment industry to replace steam in the sterilization of heat-sensitive tools and equipment, such as disposable plastic syringes.<ref>{{cite book|url=http://books.google.com/?id=oJy5wdzi0yUC&pg=PA309|page=309|title=Encyclopedia of Chemical Processing and Design|volume=20|author=John J. McKetta, William A. Cunningham|publisher=CRC Press|year=1984|isbn=0824724704}}</ref> The reactivity that is responsible for many of ethylene oxide's hazards also makes it useful. Although too dangerous for direct household use and generally unfamiliar to consumers, ethylene oxide is used for making many consumer products as well as non-consumer chemicals and intermediates. These products include detergents, thickeners, solvents, plastics, and various organic chemicals such as ], ethanolamines, simple and complex ], ]s, and other compounds. Although it is a vital raw material with diverse applications, including the manufacture of products like ] and ] (PEG) that are often more effective and less toxic than alternative materials, ethylene oxide itself is a very hazardous substance. At room temperature it is a very flammable, ], ], irritating; and ] gas.<ref name=Ullmann/>


Ethylene oxide is industrially produced by direct ] of ] in the presence of ] ]. It is extremely flammable and explosive and is used as a main component of ]s;<ref name=e1/><ref name=e2/> therefore, it is commonly handled and shipped as a refrigerated liquid.<ref name=Ullmann>Siegfried Rebsdat, Dieter Mayer "Ethylene Oxide" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2005.{{DOI|10.1002/14356007.a10_117}}.</ref> Ethylene oxide is a surface ] that is widely used in hospitals and the medical equipment industry to ] of heat-sensitive tools and equipment, such as disposable plastic syringes.<ref>{{cite book |page=309 |title=Encyclopedia of Chemical Processing and Design |volume=20 |author1=McKetta, John J. |author2=Cunningham, William A. |publisher=CRC Press |year=1984 |isbn=0-8247-2470-4 |url=https://books.google.com/books?id=oJy5wdzi0yUC&pg=PA309}}</ref> It is so flammable and extremely explosive that it is used as a main component of ]s;<ref name=e1/><ref name=e2/> therefore, it is commonly handled and shipped as a refrigerated liquid to control its hazardous nature.<ref name=Ullmann>Rebsdat, Siegfried and Mayer, Dieter (2005) "Ethylene Oxide" in ''Ullmann's Encyclopedia of Industrial Chemistry''. Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a10_117}}.</ref><ref>, SuperFoodly, 10 April 2017</ref>


==History== ==History==
Ethylene oxide was first reported in 1859 by the ] chemist ],<ref>{{cite journal|author=Wurtz, A.|journal= Compt. Rend.|volume= 48|pages= 101–104 |year=1859| title=}}</ref> who prepared it by treating ] with ]: Ethylene oxide was first reported in 1859 by the ] chemist ],<ref>{{cite journal |author=Wurtz, A. |journal=Comptes rendus |volume=48 |pages=101–105 |year=1859 |title=Sur l'oxyde d'éthylène |url=http://gallica.bnf.fr/ark:/12148/bpt6k30054/f101.image}}</ref> who prepared it by treating ] with ]:


:Cl–CH<sub>2</sub>CH<sub>2</sub>–OH + KOH → (CH<sub>2</sub>CH<sub>2</sub>)O + KCl + H<sub>2</sub>O : {{chem2 | Cl\sCH2CH2\sOH + KOH -> (CH2CH2)O + KCl + H2O }}


Wurtz measured the ] of ethylene oxide as 13.5 °C, slightly higher than the present value, and discovered the ability of ethylene oxide to react with acids and salts of metals.<ref name="oe1">{{cite book Wurtz measured the ] of ethylene oxide as {{convert|13.5|C|}}, slightly higher than the present value, and discovered the ability of ethylene oxide to react with acids and salts of metals.<ref name="oe1">{{cite book
|chapter = Part I. Structure and properties of ethylene oxide. Features of the reactivity of ethylene oxide and the structure of its molecules |chapter=Part I. Structure and properties of ethylene oxide. Features of the reactivity of ethylene oxide and the structure of its molecules
|title = Ethylene oxide |title=Ethylene oxide
|editor1=Zimakov, P.V. |editor2=Dyment, O. H. |publisher=Khimiya
| editor= PV Zimakova and Ph. O. Dymenta
|year=1967
|publisher = Khimiya
|pages=15–17}}</ref> Wurtz mistakenly assumed that ethylene oxide has the properties of an organic base. This misconception persisted until 1896, when ] found that ethylene oxide is not an ].<ref name="oe1"/><ref>{{cite journal |author=Bredig, G. |author2=Usoff, A. |year=1896 |title=Ist Acetylen ein Elektrolyt? |trans-title=Is acetylene an electrolyte? |journal=Zeitschrift für Elektrochemie |volume=3 |issue=6 |pages=116–117 |doi=10.1002/bbpc.189600028 |url=https://books.google.com/books?id=0cPmAAAAMAAJ&pg=PA116}}</ref> That it differed from other ]s — particularly by its propensity to engage in the addition reactions typical of ] — had long been a matter of debate. The heterocyclic triangular structure of ethylene oxide was proposed by 1868 or earlier.<ref>], ed., ''Lehrbuch der organischen Chemie für den Unterricht auf Universitäten'' ... , 3rd ed. (Braunschweig, Germany: Friedrich Vieweg und Sohn, 1868), vol. 2, .<br>See also of the 1876 edition: Eugen F. von Gorup-Besanez, ed., ''Lehrbuch der organischen Chemie für den Unterricht auf Universitäten'' ..., 5th ed. (Braunschweig, Germany: Friedrich Vieweg und Sohn, 1876), vol. 2.</ref>
|year = 1967
|pages = 15–17}}</ref> Wurtz mistakenly assumed that ethylene oxide has the properties of an organic base. This misconception persisted until 1896 when ] found that ethylene oxide is not an ].<ref name="oe1" /> Its distinct difference with ]s, in particular, its propensity to join the addition reactions typical of unsaturated compounds, had long been a matter of debate. Only in 1893, the heterocyclic triangular structure of ethylene oxide had been proposed.<ref name="oe1" />


Wurtz's 1859 synthesis long remained the only method of preparing ethylene oxide, despite numerous attempts, including by Wurtz himself, to produce ethylene oxide directly from ].<ref name="ect">{{cite book |chapter=Ethylene Oxide |title=Kirk-Othmer Encyclopedia of Chemical Technology. Elastomers, synthetic to Expert Systems |edition=4 |location=New York |publisher=John Wiley & Sons |year=1994 |isbn=978-0-471-48514-8 |volume=9 |pages=450–466}}</ref> Only in 1931 did French chemist Theodore Lefort develop a method of direct oxidation of ethylene in the presence of ] ].<ref>Lefort, T.E. (23 April 1935) "Process for the production of ethylene oxide". {{US patent|1998878}}</ref> Since 1940, almost all industrial production of ethylene oxide has relied on this process.<ref>{{cite journal |title=Manufacture and Uses of Ethylene Oxide and Ethylene Glycol |author=McClellan, P. P. |journal=Ind. Eng. Chem. |year=1950 |volume=42 |pages=2402–2407 |issue=12 |doi=10.1021/ie50492a013}}</ref> Sterilization by ethylene oxide for the preservation of ]s was patented in 1938 by the ] chemist ]. Ethylene oxide achieved industrial importance during ] as a precursor to both the coolant ] and the ] ].{{Citation needed|date=October 2023}}
The first synthesis method had long remained the only, despite numerous attempts of scientists, including Wurtz himself, to produce ethylene oxide directly from ].<ref name="ect">{{cite book
| chapter = Ethylene Oxide
|title = Kirk-Othmer Encyclopedia of Chemical Technology. Elastomers, synthetic to Expert Systems
| edition = 4| location = New York
|publisher = John Wiley & Sons
|year = 1994
|volume = 9
|pages = 450–466}}</ref> Only in 1931, French chemist Theodore Lefort developed a method of direct oxidation of ethylene in the presence of ] ].<ref>{{cite web
|author = Lefort, T.E.
|year = 1935
|url = http://www.freepatentsonline.com/1998878.pdf
|title = Process for the production of ethylene oxide. United States Patent 1998878
|accessdate = 2009-09-23}}</ref> Since 1940, almost all industrial production of ethylene oxide has used this process.<ref>{{cite journal|title= Manufacture and Uses of Ethylene Oxide and Ethylene Glycol| author= P. P. McClellan| journal= Ind. Eng. Chem.|year= 1950| volume= 42|pages= 2402–2407| doi= 10.1021/ie50492a013}}</ref> Sterilization by ethylene oxide for the preservation of ]s was patented in 1938 by the ] chemist ]. Ethylene oxide achieved industrial importance during ] as a precursor to both the coolant ] and the ] ].


==Molecular structure and properties== ==Molecular structure and properties==
] ]
]


The epoxy cycle of ethylene oxide is an almost regular triangle with bond angles of about 60° and a significant angular ] corresponding to the energy of 105 kJ/mol.<ref>{{cite encyclopedia |chapter=Voltage molecules |title=Chemical Encyclopedia |editor=Knunyants, I. L. |encyclopedia=Soviet encyclopedia |year=1988 |volume=3 |pages=330–334}}</ref><ref name="traven">{{cite book |author=Traven VF |title=Organic chemistry: textbook for schools |editor=V. F. Traven |publisher=ECC "Academkniga" |year=2004 |volume=2 |pages=102–106 |isbn=5-94628-172-0}}</ref> For comparison, in ] the C–O–H angle is about 110°; in ]s, the C–O–C angle is 120°. The ] about each of the principal axes are ''I<sub>A</sub>''={{val|32.921|e=-40|u=g·cm{{sup|2}}}}, ''I<sub>B</sub>''={{val|37.926|e=-40|u=g·cm{{sup|2}}}} and ''I<sub>C</sub>''={{val|59.510|e=-40|u=g·cm{{sup|2}}}}.<ref>{{cite journal |author=Cunningham G. L. |author2=Levan W. I. |author3=Gwinn W. D. |title=The Rotational Spectrum of Ethylene Oxide |journal=Phys. Rev. |year=1948 |volume=74 |issue=10 |page=1537 |bibcode=1948PhRv...74.1537C |doi=10.1103/PhysRev.74.1537}}</ref>
The epoxy cycle of ethylene oxide is an almost regular triangle with bond angles of about 60° and a significant angular stress corresponding to the energy of 105 kJ/mol.<ref>{{cite book
|chapter= Voltage molecules
|title = Chemical Encyclopedia
| editor = Knunyants, IL
|publisher = "Soviet encyclopedia"
|year = 1988
|volume = 3
|pages = 330–334}}</ref><ref name="traven">
{{cite book|author = Traven VF
|title = Organic chemistry: textbook for schools| editor = VFTraven
|publisher = ECC "Academkniga"
|year = 2004
|volume = 2
|pages = 102–106
|isbn = 5946281720}}</ref> For comparison, in ]s the C–O–H angle is about 110°; in ]s, the C–O–C angle is 120°. The ] about the principal axes are ''I<sub>A</sub>'' = 32.921×10<sup>−40</sup> g·cm², ''I<sub>B</sub>'' = 37.926×10<sup>−40</sup> g·cm² and ''I<sub>C</sub>'' = 59.510×10<sup>−40</sup> g·cm².<ref>{{cite journal
|author = Cunningham G. L., Levan W. I., Gwinn W. D.
|title = The Rotational Spectrum of Ethylene Oxide
|doi=10.1103/PhysRev.74.1537
|journal = Phys. Rev.
|year = 1948
|volume = 74| page = 1537
}}</ref> The ] at a temperature in the range 17–176 °C is 6.26×10<sup>−30</sup> C·m.<ref>{{cite web
|date = 1 April 2009
|url = http://chemanalytica.com/book/novyy_spravochnik_khimika_i_tekhnologa/12_obshchie_svedeniya/6106
|title = The dipole moments of certain substances
|publisher = ChemAnalitica.com
|accessdate = 2009-09-21}}</ref>


The relative instability of the carbon-oxygen bonds in the molecule is revealed by the comparison in the table of the energy required to break two C–O bonds in the ethylene oxide or one C–O bond in ] and ]:<ref>{{cite book The relative instability of the carbon-oxygen bonds in the molecule is revealed by the comparison in the table of the energy required to break two C–O bonds in the ethylene oxide or one C–O bond in ] and ]:<ref>{{cite book |title=Energy of chemical bonds. Ionization potentials and electron affinity |editor=Kondrat'ev, VN |publisher=Nauka |year=1974 |pages=77–78}}</ref>
{| Class="wikitable" style="text-align:center"
|title = Energy of chemical bonds. Ionization potentials and electron affinity
! Reaction
|editor =Kondrat'ev, VN
! ΔH°<sub>298</sub>, kJ/mol
|publisher = Nauka
! Method
|year = 1974
|pages = 77–78}}</ref>
{| Class = "wikitable" style="text-align:center"
! Reaction
! ΔH°<sub>298</sub>, kJ/mol
! Method
|- |-
| '''(C<sub>2</sub>H<sub>4</sub>)O → C<sub>2</sub>H<sub>4</sub> + O''' (cleavage of two bonds) | '''{{chem2|(C2H4)O -> C2H4 + O}}''' (cleavage of two bonds)
|354.38 | 354.38
|Calculated, from atomic enthalpies | Calculated, from atomic enthalpies
|- |-
|'''] → C<sub>2</sub>H<sub>5</sub> + OH''' (breaking one bond) |'''{{chem2|] -> C2H5 + OH}}''' (breaking one bond)
|405.85 | 405.85
|Electron impact | Electron impact
|- |-
|'''] → CH<sub>3</sub>O + CH<sub>3</sub>''' (breaking one bond) |'''{{chem2|] -> CH3O + CH3}}''' (breaking one bond)
|334.72 | 334.72
|Calculated using enthalpies of radicals formation | Calculated using enthalpies of radicals formation
|} |}


This instability determines the chemical activity of ethylene oxide and explains the ease of opening its cycle in ]s (see ]). This instability correlates with its high reactivity, explaining the ease of its ]s (see ]).


==Physical properties== ==Physical properties==
Ethylene oxide is a colorless gas at 25 °C and is a mobile liquid at 0 °C – viscosity of liquid ethylene oxide at 0 °C is about 5.5 times lower than that of water. The gas has a characteristic sweet odor of ether, noticeable when its concentration in air exceeds 500 ppm.<ref name="atsdr">{{cite web Ethylene oxide is a colorless gas at {{convert|25|C|}} and is a mobile liquid at {{convert|0|C|}} – viscosity of liquid ethylene oxide at 0&nbsp;°C is about 5.5 times lower than that of water. The gas has a characteristic sweet odor of ether, noticeable when its concentration in air exceeds 500{{nbsp}}ppm.<ref name="atsdr">{{cite web
|url = http://www.atsdr.cdc.gov/MHMI/mmg137.html | url=http://www.atsdr.cdc.gov/MHMI/mmg137.html
|title = Medical Management Guidelines for Ethylene Oxide | title=Medical Management Guidelines for Ethylene Oxide
|work = Medical Management Guidelines (MMGs) | work=Medical Management Guidelines (MMGs)
|publisher = Agency for Toxic Substances and Disease Registry | publisher=Agency for Toxic Substances and Disease Registry
| access-date=29 September 2009
|accessdate = 2009-09-29}}</ref> Ethylene oxide is readily soluble in water, ], ] and many organic solvents.<ref>{{cite web
| url-status=dead
|url = http://slovari.yandex.ru/~%D0%BA%D0%BD%D0%B8%D0%B3%D0%B8/%D0%91%D0%A1%D0%AD/%D0%AD%D1%82%D0%B8%D0%BB%D0%B5%D0%BD%D0%B0%20%D0%BE%D0%BA%D0%B8%D1%81%D1%8C/
| archive-url=https://web.archive.org/web/20110606033044/http://www.atsdr.cdc.gov/MHMI/mmg137.html
|title = Ethylene oxide
| archive-date=6 June 2011
|publisher = ]
}}</ref> Ethylene oxide is readily soluble in water, ], ], and many organic solvents.<ref>{{cite web
|accessdate = 2009-09-25
| url=http://dic.academic.ru/dic.nsf/bse/154711/Этилена
|language =Russian}}</ref>
| title=Этилена окись (Ethylene oxide)

| publisher=]
Main thermodynamical constants are:<ref name="sch1">{{cite web| date = 1 April 2009 года| url= http://chemanalytica.com/book/novyy_spravochnik_khimika_i_tekhnologa/12_obshchie_svedeniya/6084
| access-date=25 September 2009
|title = Термодинамические показатели органических соединений
| language=ru
|publisher = ChemAnalitica.com
|accessdate = 2009-09-21}}</ref>
* Standard molar ], C<sub>p</sub>° = 48.19 J/(mol·K);
* Standard ] of formation, ΔH°<sub>298</sub> = –51.037 kJ/mol;
* Standard ], S°<sub>298</sub> = 243.4 J/(mol·K);
* ], ΔG°<sub>298</sub> = –11.68 kJ/mol;
* ], ΔH<sub>c</sub>° = –1306 kJ/mol.<ref name="en">{{cite book
|chapter= Ethylene oxide|title=Chemical encyclopedia|editor=Knunyants, I. L.|year=1988|pages=990–991|volume=5}}</ref>

The ] of liquid ethylene oxide, at the interface with its own steam, is 35.8 mJ/m<sup>2</sup> at –50.1 °C and 27.6 mJ/m<sup>2</sup> at –0.1 °C.<ref>{{cite web
|date = 1 April 2009
|url = http://chemanalytica.com/book/novyy_spravochnik_khimika_i_tekhnologa/12_obshchie_svedeniya/6118
|title = Surface tension of liquefied gas at the border with its own steam
|publisher = ChemAnalitica.com
|accessdate = 2009-09-21}}</ref>

The boiling point increases with the vapor pressure as follows:<ref>{{cite web
|date = 1 April 2009
|url = http://chemanalytica.com/book/novyy_spravochnik_khimika_i_tekhnologa/12_obshchie_svedeniya/6061
|title = boiling point or sublimation (°C) organic matter in the vapor pressure above 101.3 kPa
|publisher = ChemAnalitica.com
|accessdate = 2009-09-21
}}</ref> }}</ref>
57.7 (2 atm), 83.6 (5 atm) and 114.0 (10 atm).


Main thermodynamical constants are:<ref name="sch1">{{cite web |title=Термодинамические показатели органических соединений |lang=ru |date=1 April 2009 |publisher=ChemAnalitica.com |url=http://chemanalytica.com/book/novyy_spravochnik_khimika_i_tekhnologa/12_obshchie_svedeniya/6084 |access-date=21 September 2009}}</ref>
] decreases with temperature with the values of 0.577 kPa·s at –49.8 °C, 0.488 kPa·s at –38.2 °C, 0.394 kPa·s at –21.0 °C and 0.320 kPa·s at 0 °C.<ref>{{cite web
* The ] of liquid ethylene oxide, at the interface with its own vapor, is {{convert|35.8|mJ/m2||abbr=on}} at {{convert|-50.1|C|}} and {{convert|27.6|mJ/m2||abbr=on}} at {{convert|-0.1|C|}}.<ref>{{cite web |title=Surface tension of liquefied gas at the border with its own steam |date=1 April 2009 |publisher=ChemAnalitica.com |url=http://chemanalytica.com/book/novyy_spravochnik_khimika_i_tekhnologa/12_obshchie_svedeniya/6118 |access-date=21 September 2009}}</ref>
|date = 1 April 2009
* The boiling point increases with the vapor pressure as follows:<ref>{{cite web |title=Boiling point or sublimation (°C) organic matter in the vapor pressure above 101.3 kPa |date=1 April 2009 |publisher=ChemAnalitica.com |url=http://chemanalytica.com/book/novyy_spravochnik_khimika_i_tekhnologa/12_obshchie_svedeniya/6061 |access-date=21 September 2009}}</ref> {{convert|57.7|C|}} ({{convert|2|atm|kPa psi|abbr=on}}), {{convert|83.6|C|}} ({{convert|5|atm|kPa psi|abbr=on}}), and {{convert|114.0|C|}} ({{convert|10|atm|kPa psi|abbr=on}}).
|url = http://chemanalytica.com/book/novyy_spravochnik_khimika_i_tekhnologa/12_obshchie_svedeniya/6112
* ] decreases with temperature with the values of 0.577{{nbsp}}kPa·s at {{convert|-49.8|C|}}, 0.488 kPa·s at {{convert|-38.2|C|}}, 0.394{{nbsp}}kPa·s at {{convert|-21.0|C|}}, and 0.320{{nbsp}}kPa·s at {{convert|0|C|}}.<ref>{{cite web |title=Viscosity of organic compounds |date=1 April 2009 |publisher=ChemAnalitica.com |url=http://chemanalytica.com/book/novyy_spravochnik_khimika_i_tekhnologa/12_obshchie_svedeniya/6112 |access-date=21 September 2009}}</ref>
|title = viscosity of organic compounds
|publisher = ChemAnalitica.com
|accessdate = 2009-09-21
}}</ref>


Between –91 °C and 10.5 °C, vapor pressure ''p'' (in mmHg) varies with temperature (T in °C) as lg ''p'' = 6.251 – 1115.1/(244.14 + T).<ref>{{cite web Between {{convert|−91|and|10.5|C}}, vapor pressure ''p'' (in mmHg) varies with temperature (''T'' in °C) as
: <math>\lg p=6.251 - \frac{1115.1}{244.14 + T}</math>.<ref>{{cite web |title=Vapor pressure of organic compounds |date=1 April 2009 |publisher=ChemAnalitica.com |url=http://chemanalytica.com/book/novyy_spravochnik_khimika_i_tekhnologa/12_obshchie_svedeniya/6063 |access-date=21 September 2009}}</ref>
|date = 1 April 2009
|url = http://chemanalytica.com/book/novyy_spravochnik_khimika_i_tekhnologa/12_obshchie_svedeniya/6063
|title = vapor pressure of organic compounds
|publisher = ChemAnalitica.com
|accessdate = 2009-09-21
}}</ref>


{| Class = "wikitable" style="text-align:center" {| Class="wikitable" style="text-align:center"
|+Properties of liquid ethylene oxide<ref name="ect" /> |+ Properties of liquid ethylene oxide<ref name="ect"/>
! Temperature, °C
! Steam pressure, kPa
! Enthalpy of the liquid,<br/> J/g
! Enthalpy of vaporization,<br/> J/g
! Density, kg/L
! ], J/(kg·K)
! ], W/(m·K)
|- |-
| –40 °C ! Temperature, °C
! Vapor pressure, kPa
! Enthalpy of the liquid, J/g
! Enthalpy of vaporization, J/g
! Density, kg/L
! ], J/(kg·K)
! ], W/(m·K)
|-
| −40
| 8.35 | 8.35
| 0 | 0
Line 272: Line 180:
| 0.20 | 0.20
|- |-
| −20
| –20 °C
| 25.73 | 25.73
| 38.8 | 38.8
Line 280: Line 188:
| 0.18 | 0.18
|- |-
| 0 °C | 0
| 65.82 | 65.82
| 77.3 | 77.3
Line 288: Line 196:
| 0.16 | 0.16
|- |-
| 20 °C | 20
| 145.8 | 145.8
| 115.3 | 115.3
Line 296: Line 204:
| 0.15 | 0.15
|- |-
| 40 °C | 40
| 288.4 | 288.4
| 153.2 | 153.2
Line 304: Line 212:
| 0.14 | 0.14
|- |-
| 60 °C | 60
| 521.2 | 521.2
| 191.8 | 191.8
Line 312: Line 220:
| 0.14 | 0.14
|- |-
| 80 °C | 80
| 875.4 | 875.4
| 232.6 | 232.6
Line 320: Line 228:
| 0.14 | 0.14
|- |-
| 100 °C | 100
| 1385.4 | 1385.4
| 277.8 | 277.8
Line 328: Line 236:
| 0.13 | 0.13
|- |-
| 120 °C | 120
| 2088 | 2088
| 330.4 | 330.4
Line 336: Line 244:
| N/A* | N/A*
|- |-
| 140 °C | 140
| 3020 | 3020
| 393.5 | 393.5
Line 344: Line 252:
| N/A | N/A
|- |-
| 160 °C | 160
| 4224 | 4224
| 469.2 | 469.2
Line 352: Line 260:
| N/A | N/A
|- |-
| 180 °C | 180
| 5741 | 5741
| 551.2 | 551.2
Line 360: Line 268:
| N/A | N/A
|- |-
| 195.8 °C | 195.8
| 7191 | 7191
| N/A | N/A
Line 367: Line 275:
| N/A | N/A
| N/A | N/A
|} |}
<nowiki>*</nowiki>N/A – data not available. <nowiki>*</nowiki>N/A – data not available.


{| Class = "wikitable" style="text-align:center" {| Class="wikitable" style="text-align:center"
|+Properties of ethylene oxide vapor <ref name="ect" /> |+ Properties of ethylene oxide vapor <ref name="ect"/>
|-
! Temperature, K
! Temperature, K
! Entropy, J/(mol·K)
! Heat of formation, kJ/mol ! Entropy, J/(mol·K)
! Free energy of formation, kJ/mol ! Heat of formation, kJ/mol
! Free energy of formation, kJ/mol
! Viscosity Pa·s
! Thermal conductivity, W/(m·K) ! Viscosity, μPa·s
! Thermal conductivity, W/(m·K)
! Heat capacity, J/(mol·K) ! Heat capacity, J/(mol·K)
|- |-
| 298 | 298
| 242.4 | 242.4
| –52.63 | −52.63
| –13.10 | −13.10
| N/A | N/A
| N/A | N/A
Line 390: Line 299:
| 300 | 300
| 242.8 | 242.8
| –52.72 | −52.72
| –12.84 | −12.84
| 9.0 | 9.0
| 0.012 | 0.012
Line 398: Line 307:
| 400 | 400
| 258.7 | 258.7
| –56.53 | −56.53
| 1.05 | 1.05
| 13.5 | 13.5
Line 406: Line 315:
| 500 | 500
| 274.0 | 274.0
| –59.62 | −59.62
| 15.82 | 15.82
| 15.4 | 15.4
Line 414: Line 323:
| 600 | 600
| 288.8 | 288.8
| –62.13 | −62.13
| 31.13 | 31.13
| 18.2 | 18.2
Line 422: Line 331:
| 700 | 700
| 302.8 | 302.8
| –64.10 | −64.10
| 46.86 | 46.86
| 20.9 | 20.9
Line 430: Line 339:
| 800 | 800
| 316.0 | 316.0
| –65.61 | −65.61
| 62.80 | 62.80
| N/A | N/A
Line 439: Line 348:


==Chemical properties== ==Chemical properties==
Ethylene oxide readily reacts with various compounds, breaking a C–O bond and opening the cycle. Its typical reactions are with nucleophiles which proceed via the ] mechanism both in acidic (weak nucleophiles: water, alcohols) and alkaline media (strong nucleophiles: OH<sup>–</sup>, RO<sup>–</sup>, NH<sub>3</sub>, RNH<sub>2</sub>, RR'NH, etc.).<ref name="traven" /> The general reaction scheme is Ethylene oxide readily reacts with diverse compounds with opening of the ring. Its typical reactions are with nucleophiles which proceed via the ''']''' mechanism both in acidic (weak nucleophiles: water, alcohols) and alkaline media (strong nucleophiles: OH<sup>−</sup>, RO<sup>−</sup>, NH<sub>3</sub>, RNH<sub>2</sub>, RR'NH, etc.).<ref name="traven"/> The general reaction scheme is
: ]

: ]


and more specific reactions are described below. and more specific reactions are described below.


===Addition of water and alcohols=== ===Addition of water and alcohols===
Aqueous solutions of ethylene oxide are rather stable and can exist for a long time without any noticeable chemical reaction, but adding a small amount of acid, such as strongly diluted ], immediately leads to the formation of ], even at room temperature: Aqueous solutions of ethylene oxide are rather stable and can exist for a long time without any noticeable chemical reaction. However adding a small amount of acid, such as strongly diluted ], immediately leads to the formation of ], even at room temperature:

: (CH<sub>2</sub>CH<sub>2</sub>)O + H<sub>2</sub>O → HO–CH<sub>2</sub>CH<sub>2</sub>–OH : (CH<sub>2</sub>CH<sub>2</sub>)O + H<sub>2</sub>O → HO–CH<sub>2</sub>CH<sub>2</sub>–OH


The reaction also occurs in the gas phase, in the presence of a ] salt as a catalyst.<ref name="oe3">{{cite book The reaction also occurs in the gas phase, in the presence of a ] salt as a catalyst.<ref name="oe3">{{cite book |chapter=Chapter III. Review of the individual reactions of ethylene oxide |title=Ethylene oxide |editor1=Zimakov, P.V. |editor2=Dyment, O. H. |publisher=Khimiya |year=1967 |pages=90–120}}</ref>
|chapter= Chapter III. Review of the individual reactions of ethylene oxide
|title = Ethylene oxide
|editor=PV Zimakova and Mr. O. Dymenta
| location = M.
|publisher = Khimiya
|year = 1967
|pages = 90–120}}</ref>


The reaction is usually carried out at about 60 °C with a large excess of water, in order to prevent the reaction of the formed ethylene glycol with ethylene oxide that would form di- and ]:<ref>{{cite web The reaction is usually carried out at about {{convert|60|C|}} with a large excess of water, in order to prevent the reaction of the formed ethylene glycol with ethylene oxide that would form ] and ]:<ref>{{cite web |title=Epoxyethane (Ethylene Oxide) |work=Alkenes menu |publisher=Chemguide |url=https://www.chemguide.co.uk/organicprops/alkenes/epoxyethane.html |access-date=5 October 2009}}</ref>
|url = http://www.chemguide.co.uk/organicprops/alkenes/epoxyethane.html
|title = Epoxyethane (Ethylene Oxide)
|work = Alkenes menu
|publisher = Chemguide
|accessdate = 2009-10-05
}}</ref>

:2 (CH<sub>2</sub>CH<sub>2</sub>)O + H<sub>2</sub>O → HO–CH<sub>2</sub>CH<sub>2</sub>–O–CH<sub>2</sub>CH<sub>2</sub>–OH


:3 (CH<sub>2</sub>CH<sub>2</sub>)O + H<sub>2</sub>O → HO–CH<sub>2</sub>CH<sub>2</sub>–O–CH<sub>2</sub>CH<sub>2</sub>–O–CH<sub>2</sub>CH<sub>2</sub>–OH : 2 (CH<sub>2</sub>CH<sub>2</sub>)O + H<sub>2</sub>O → HO–CH<sub>2</sub>CH<sub>2</sub>–O–CH<sub>2</sub>CH<sub>2</sub>–OH
: 3 (CH<sub>2</sub>CH<sub>2</sub>)O + H<sub>2</sub>O → HO–CH<sub>2</sub>CH<sub>2</sub>–O–CH<sub>2</sub>CH<sub>2</sub>–O–CH<sub>2</sub>CH<sub>2</sub>–OH


The use of alkaline catalysts may lead to the formation of ]: The use of alkaline catalysts may lead to the formation of ]:


:n (CH<sub>2</sub>CH<sub>2</sub>)O + H<sub>2</sub>O → HO–(–CH<sub>2</sub>CH<sub>2</sub>–O–)<sub>n</sub>–H : n (CH<sub>2</sub>CH<sub>2</sub>)O + H<sub>2</sub>O → HO–(–CH<sub>2</sub>CH<sub>2</sub>–O–)<sub>n</sub>–H


Reactions with ]s proceed similarly yielding ethylene glycol ethers: Reactions with ] proceed similarly yielding ethylene glycol ethers:


: (CH<sub>2</sub>CH<sub>2</sub>)O + C<sub>2</sub>H<sub>5</sub>OH → HO–CH<sub>2</sub>CH<sub>2</sub>–OC<sub>2</sub>H<sub>5</sub> : (CH<sub>2</sub>CH<sub>2</sub>)O + C<sub>2</sub>H<sub>5</sub>OH → HO–CH<sub>2</sub>CH<sub>2</sub>–OC<sub>2</sub>H<sub>5</sub>


:2 (CH<sub>2</sub>CH<sub>2</sub>)O + C<sub>2</sub>H<sub>5</sub>OH → HO–CH<sub>2</sub>CH<sub>2</sub>–O–CH<sub>2</sub>CH<sub>2</sub>–OC<sub>2</sub>H<sub>5</sub> : 2 (CH<sub>2</sub>CH<sub>2</sub>)O + C<sub>2</sub>H<sub>5</sub>OH → HO–CH<sub>2</sub>CH<sub>2</sub>–O–CH<sub>2</sub>CH<sub>2</sub>–OC<sub>2</sub>H<sub>5</sub>


Reactions with lower alcohols occur less actively than with water and require more severe conditions, such as heating to 160 °C and pressurizing to 3 MPa and adding an acid or alkali catalyst. Reactions with lower alcohols occur less actively than with water and require more severe conditions, such as heating to {{convert|160|C|}} and pressurizing to {{convert|3|MPa||abbr=on}} and adding an acid or alkali catalyst.


Reactions of ethylene oxide with fatty alcohols proceed in the presence of ] metal, ] or ] and are used for the synthesis of ].<ref name="oe3" /> Reactions of ethylene oxide with fatty alcohols proceed in the presence of ] metal, ], or ] and are used for the synthesis of ].<ref name="oe3"/>


===Addition of carboxylic acids and their derivatives=== ===Addition of carboxylic acids and their derivatives===
Reactions of ethylene oxide with ]s in the presence of a catalyst results in incomplete and with ] in complete glycol esters: Reactions of ethylene oxide with ]s in the presence of a catalyst results in glycol mono- and diesters:
: (CH<sub>2</sub>CH<sub>2</sub>)O + CH<sub>3</sub>CO<sub>2</sub>H → HOCH<sub>2</sub>CH<sub>2</sub>–O<sub>2</sub>CCH<sub>3</sub>

: (CH<sub>2</sub>CH<sub>2</sub>)O + CH<sub>3</sub>COOH → HO–CH<sub>2</sub>CH<sub>2</sub>–OCOCH<sub>3</sub> : (CH<sub>2</sub>CH<sub>2</sub>)O + (CH<sub>3</sub>CO)<sub>2</sub>O → CH<sub>3</sub>CO<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>O<sub>2</sub>CCH<sub>3</sub>

: (CH<sub>2</sub>CH<sub>2</sub>)O + (CH<sub>3</sub>CO)<sub>2</sub>O → CH<sub>3</sub>COO–CH<sub>2</sub>CH<sub>2</sub>–OCOCH<sub>3</sub>


The addition of acid ]s proceeds similarly: The addition of acid ]s proceeds similarly:
: (CH<sub>2</sub>CH<sub>2</sub>)O + CH<sub>3</sub>CONH<sub>2</sub> → HOCH<sub>2</sub>CH<sub>2</sub>NHC(O)CH<sub>3</sub>


Addition of ethylene oxide to higher carboxylic acids is carried out at elevated temperatures (typically {{convert|140-180|C|}}) and pressure ({{convert|0.3-0.5|MPa||abbr=on}}) in an inert atmosphere, in presence of an alkaline catalyst (concentration 0.01–2%), such as hydroxide or carbonate of sodium or potassium.<ref>{{cite book |title=Nonionic surfactants: organic chemistry |editor1=van Os |editor2=N. M. |publisher=CRC Press |year=1998 |pages=129–131 |isbn=978-0-8247-9997-7 |url=https://books.google.com/books?id=YoZ6CjYNLoQC&pg=PA129}}</ref> The carboxylate ion acts as ] in the reaction:
: (CH<sub>2</sub>CH<sub>2</sub>)O + CH<sub>3</sub>CONH<sub>2</sub> → HO–CH<sub>2</sub>CH<sub>2</sub>–NHCOCH<sub>3</sub>
: (CH<sub>2</sub>CH<sub>2</sub>)O + RCO<sub>2</sub><sup>−</sup> → RCO<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>O<sup>−</sup>

: RCO<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>O<sup>−</sup> + RCO<sub>2</sub>H → RCO<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>OH + RCO<sub>2</sub><sup>−</sup>
Addition of ethylene oxide to higher carboxylic acids is carried out at elevated temperatures (typically 140–180 °C) and pressure (0.3–0.5 MPa) in an inert atmosphere, in presence of an alkaline catalyst (concentration 0.01–2%), such as hydroxide or carbonate of sodium or potassium.<ref>{{cite book
|title = Nonionic surfactants: organic chemistry
|editor=N. M. van Os
|publisher = CRC Press
|year = 1998
|pages = 129–131|url=http://books.google.com/?id=YoZ6CjYNLoQC&pg=PA129
|isbn = 9780824799977}}</ref> The carboxylate ion acts as ] in the reaction:

:RCOOH + OH<sup>–</sup> → RCOO<sup>–</sup> + H<sub>2</sub>O

: (CH<sub>2</sub>CH<sub>2</sub>)O + RCOO<sup>–</sup> → RCOOCH<sub>2</sub>CH<sub>2</sub>O<sup>–</sup>

:RCOOCH<sub>2</sub>CH<sub>2</sub>O<sup>–</sup> + RCOOH → RCOOCH<sub>2</sub>CH<sub>2</sub>OH + RCOO<sup>–</sup>


===Adding ammonia and amines=== ===Adding ammonia and amines===
Ethylene oxide reacts with ] forming a mixture of mono-, di- and triethanolamine. The reaction is stimulated by adding a small amount of water. Ethylene oxide reacts with ] forming a mixture of mono-, di-, and tri- ]s. The reaction is stimulated by adding a small amount of water.


: (CH<sub>2</sub>CH<sub>2</sub>)O + NH<sub>3</sub> → HO–CH<sub>2</sub>CH<sub>2</sub>–NH<sub>2</sub> : (CH<sub>2</sub>CH<sub>2</sub>)O + NH<sub>3</sub> → HO–CH<sub>2</sub>CH<sub>2</sub>–NH<sub>2</sub>


:2 (CH<sub>2</sub>CH<sub>2</sub>)O + NH<sub>3</sub> → (HO–CH<sub>2</sub>CH<sub>2</sub>)<sub>2</sub>NH : 2 (CH<sub>2</sub>CH<sub>2</sub>)O + NH<sub>3</sub> → (HO–CH<sub>2</sub>CH<sub>2</sub>)<sub>2</sub>NH


:3 (CH<sub>2</sub>CH<sub>2</sub>)O + NH<sub>3</sub> → (HO–CH<sub>2</sub>CH<sub>2</sub>)<sub>3</sub>N : 3 (CH<sub>2</sub>CH<sub>2</sub>)O + NH<sub>3</sub> → (HO–CH<sub>2</sub>CH<sub>2</sub>)<sub>3</sub>N


Similarly proceed the reactions with primary and secondary amines: Similarly proceed the reactions with primary and secondary amines:

: (CH<sub>2</sub>CH<sub>2</sub>)O + RNH<sub>2</sub> → HO–CH<sub>2</sub>CH<sub>2</sub>–NHR : (CH<sub>2</sub>CH<sub>2</sub>)O + RNH<sub>2</sub> → HO–CH<sub>2</sub>CH<sub>2</sub>–NHR


Dialkylamino ethanols can further react with ethylene oxide, forming amino polyethylene glycols:<ref name="ect" /> Dialkylamino ethanols can further react with ethylene oxide, forming amino polyethylene glycols:<ref name="ect"/>


:n (CH<sub>2</sub>CH<sub>2</sub>)O + R<sub>2</sub>NCH<sub>2</sub>CH<sub>2</sub>OH → R<sub>2</sub>NCH<sub>2</sub>CH<sub>2</sub>O–(–CH<sub>2</sub>CH<sub>2</sub>O–)<sub>n</sub>–H : n (CH<sub>2</sub>CH<sub>2</sub>)O + R<sub>2</sub>NCH<sub>2</sub>CH<sub>2</sub>OH → R<sub>2</sub>NCH<sub>2</sub>CH<sub>2</sub>O–(–CH<sub>2</sub>CH<sub>2</sub>O–)<sub>n</sub>–H


Trimethylamine reacts with ethylene oxide in the presence of water, forming ]:<ref>{{cite book ] reacts with ethylene oxide in the presence of water, forming ]:<ref>{{cite book
|author1=Petrov, AA |author2=Balian HV |author3=Troshchenko AT |chapter=Chapter 12. Amino alcohol |title=Organic chemistry |editor=Stadnichuk |edition=5 |location=St. Petersburg |year=2002 |page=286 |isbn=5-8194-0067-4}}</ref>
|author = Petrov, AA, Balian HV, Troshchenko AT
: (CH<sub>2</sub>CH<sub>2</sub>)O + (CH<sub>3</sub>)<sub>3</sub>N + H<sub>2</sub>O → <sup>+</sup>OH<sup>−</sup>
|chapter= Chapter 12. Amino alcohol
|title = Organic chemistry| editor= Stadnichuk
|edition = 5|location = St. Petersburg.
|year = 2002
|page = 286
|isbn = 5819400674}}</ref>

: (CH<sub>2</sub>CH<sub>2</sub>)O + (CH<sub>3</sub>)<sub>3</sub>N + H<sub>2</sub>O → <sup>+</sup>OH<sup>–</sup>


Aromatic primary and secondary amines also react with ethylene oxide, forming the corresponding arylamino alcohols. Aromatic primary and secondary amines also react with ethylene oxide, forming the corresponding arylamino alcohols.


===Halide addition=== ===Halide addition===
Ethylene oxide readily reacts with aqueous solutions of ], ] and ]s to form ]s. The reaction occurs easier with the last two acids: Ethylene oxide readily reacts with aqueous solutions of ], ], and ]s to form ]s. The reaction occurs easier with the last two acids:

: (CH<sub>2</sub>CH<sub>2</sub>)O + HCl → HO–CH<sub>2</sub>CH<sub>2</sub>–Cl : (CH<sub>2</sub>CH<sub>2</sub>)O + HCl → HO–CH<sub>2</sub>CH<sub>2</sub>–Cl


The reaction with these acids competes with the acid-catalyzed hydration of ethylene oxide; therefore, there is always a by-product of ethylene glycol with an admixture of diethylene glycol. For a cleaner product, the reaction is conducted in the gas phase or in an organic solvent. The reaction with these acids competes with the acid-catalyzed hydration of ethylene oxide; therefore, there is always a by-product of ethylene glycol with an admixture of ]. For a cleaner product, the reaction is conducted in the gas phase or in an organic solvent.


Ethylene fluorohydrin is obtained differently, by boiling ] with a 5–6% solution of ethylene oxide in ]. The ether normally has a water content of 1.5–2%; in absence of water, ethylene oxide polymerizes.<ref>{{cite book Ethylene fluorohydrin is obtained differently, by boiling ] with a 5–6% solution of ethylene oxide in ]. The ether normally has a water content of 1.5–2%; in absence of water, ethylene oxide polymerizes.<ref>{{cite book |author1=Sheppard, William A. |author2=Sharts, Clay M. |title=Organic Fluorine Chemistry |publisher=W. A. Benjamin |year=1969 |page=98 |isbn=0-8053-8790-0 |url=https://archive.org/details/organicfluorinec0000shep |url-access=registration}}</ref>
|author = William A. Sheppard, Clay M. Sharts
|title = Organic Fluorine Chemistry
|publisher = W.A. Benjamin
|year = 1969
|page= 98
|isbn = 0805387900}}</ref>


Halohydrins can also be obtained by passing ethylene oxide through aqueous solutions of metal halides:<ref name="oe3" /> Halohydrins can also be obtained by passing ethylene oxide through aqueous solutions of metal halides:<ref name="oe3"/>
: 2 (CH<sub>2</sub>CH<sub>2</sub>)O + CuCl<sub>2</sub> + 2 H<sub>2</sub>O → 2 HO–CH<sub>2</sub>CH<sub>2</sub>–Cl + Cu(OH)<sub>2</sub>↓

:2 (CH<sub>2</sub>CH<sub>2</sub>)O + CuCl<sub>2</sub> + 2 H<sub>2</sub>O → 2 HO–CH<sub>2</sub>CH<sub>2</sub>–Cl + Cu(OH)<sub>2</sub>↓


===Metalorganic addition=== ===Metalorganic addition===
Interaction of ethylene oxide with organomagnesium compounds, which are ], can be regarded as ] influenced by ] organometallic compounds. The final product of the reaction is a primary alcohol: Interaction of ethylene oxide with ] compounds, which are ], can be regarded as ] influenced by ] organometallic compounds. The final product of the reaction is a primary alcohol:
: <chem>(CH2CH2)O{} + RMgBr -> R-CH2CH2-OMgBr ->

\overset{primary~alcohol}{R-CH2CH2-OH}</chem>
: <math>\mathsf{(CH_2CH_2)O+RMgBr}\rightarrow\mathsf{R\!\!-\!\!CH_2CH_2\!\!-\!\!OMgBr\ \xrightarrow{H_2O}\ R\!\!-\!\!CH_2CH_2\!\!-\!\!OH}</math>


Similar mechanism is valid for other organometallic compounds, such as alkyl lithium: Similar mechanism is valid for other organometallic compounds, such as alkyl lithium:
: <chem>(CH2CH2)O{} + \overset{alkyl~lithium}{RLi} -> R-CH2CH2-OLi -> R-CH2CH2-OH</chem>


===Other addition reactions===
: <math>\mathsf{(CH_2CH_2)O+RLi}\rightarrow\mathsf{R\!\!-\!\!CH_2CH_2\!\!-\!\!OLi\ \xrightarrow{H_2O}\ R\!\!-\!\!CH_2CH_2\!\!-\!\!OH}</math>


===Other addition reactions===
====Addition of hydrogen cyanide==== ====Addition of hydrogen cyanide====
Ethylene oxide easily reacts with the ] forming ethylene cyanohydrin: Ethylene oxide easily reacts with ] forming ]:

: (CH<sub>2</sub>CH<sub>2</sub>)O + HCN → HO–CH<sub>2</sub>CH<sub>2</sub>–CN : (CH<sub>2</sub>CH<sub>2</sub>)O + HCN → HO–CH<sub>2</sub>CH<sub>2</sub>–CN


A slightly chilled (10–20 °C) aqueous solution of ] can be used instead of HCN:<ref>{{cite journal A slightly chilled (10–20&nbsp;°C) aqueous solution of ] can be used instead of HCN:<ref>{{OrgSynth |author=Kendall, E. C. and McKenzie, B. |year=1923 |title=o-Chloromercuriphenol |volume=3 |pages=57 |prep=cv1p0256}}</ref>
: 2 (CH<sub>2</sub>CH<sub>2</sub>)O + Ca(CN)<sub>2</sub> + 2 H<sub>2</sub>O → 2 HO–CH<sub>2</sub>CH<sub>2</sub>–CN + Ca(OH)<sub>2</sub>
|url = http://www.orgsyn.org/orgsyn/pdfs/cv1p0256.pdf
|title = Ethylene cyanohydrin
|journal = Organic Syntheses|volume= 1|page=256|year=1941}}</ref>

:2 (CH<sub>2</sub>CH<sub>2</sub>)O + Ca(CN)<sub>2</sub> + 2 H<sub>2</sub>O → 2 HO–CH<sub>2</sub>CH<sub>2</sub>–CN + Ca(OH)<sub>2</sub>


Ethylene cyanohydrin easily loses water, producing ]: Ethylene cyanohydrin easily loses water, producing ]:
: HO–CH<sub>2</sub>CH<sub>2</sub>–CN → CH<sub>2</sub>=CH–CN + H<sub>2</sub>O

:HO–CH<sub>2</sub>CH<sub>2</sub>–CN → CH<sub>2</sub>=CH–CN + H<sub>2</sub>O


====Addition of hydrogen sulfide and mercaptans==== ====Addition of hydrogen sulfide and mercaptans====
When reacting with the ], ethylene oxide forms 2-mercaptoethanol and thiodiglycol, and with alkylmercaptans it produces 2-alkyl mercaptoetanol: When reacting with the ], ethylene oxide forms ] and ], and with alkylmercaptans it produces 2-alkyl mercaptoetanol:

: (CH<sub>2</sub>CH<sub>2</sub>)O + H<sub>2</sub>S → HO–CH<sub>2</sub>CH<sub>2</sub>–HS : (CH<sub>2</sub>CH<sub>2</sub>)O + H<sub>2</sub>S → HO–CH<sub>2</sub>CH<sub>2</sub>–HS
: 2 (CH<sub>2</sub>CH<sub>2</sub>)O + H<sub>2</sub>S → (HO–CH<sub>2</sub>CH<sub>2</sub>)<sub>2</sub>S

:2 (CH<sub>2</sub>CH<sub>2</sub>)O + H<sub>2</sub>S → (HO–CH<sub>2</sub>CH<sub>2</sub>)<sub>2</sub>S

: (CH<sub>2</sub>CH<sub>2</sub>)O + RHS → HO–CH<sub>2</sub>CH<sub>2</sub>–SR : (CH<sub>2</sub>CH<sub>2</sub>)O + RHS → HO–CH<sub>2</sub>CH<sub>2</sub>–SR


The excess of ethylene oxide with an aqueous solution of hydrogen sulfide leads to the tris-(hydroxyethyl) sulfonyl hydroxide: The excess of ethylene oxide with an aqueous solution of hydrogen sulfide leads to the tris-(hydroxyethyl) sulfonyl hydroxide:
: 3 (CH<sub>2</sub>CH<sub>2</sub>)O + H<sub>2</sub>S → OH<sup>−</sup>

:3 (CH<sub>2</sub>CH<sub>2</sub>)O + H<sub>2</sub>S → OH<sup>–</sup>


====Addition of nitrous and nitric acids==== ====Addition of nitrous and nitric acids====
Reaction of ethylene oxide with aqueous solutions of ], ], ], ] or ] leads to the formation of 2-nitroethanole:<ref>{{cite journal Reaction of ethylene oxide with aqueous solutions of ], ], ], ], or ] leads to the formation of ]:<ref>{{OrgSynth |author=Noland, Wayland E. |prep=CV5P0833 |title=2-Nitroethanol|volume=5|pages=833|year=1973}}</ref>
|url = http://www.orgsyn.org/orgsyn/pdfs/CV5P0833.pdf
|title = 2-Nitroethanol
|journal = Organic Syntheses|volume=5|page=833|year=1973}}</ref>


:2 (CH<sub>2</sub>CH<sub>2</sub>)O + Ca(NO<sub>2</sub>)<sub>2</sub> + 2 H<sub>2</sub>O → 2 HO–CH<sub>2</sub>CH<sub>2</sub>–NO<sub>2</sub> + Ca(OH)<sub>2</sub> :2 (CH<sub>2</sub>CH<sub>2</sub>)O + Ca(NO<sub>2</sub>)<sub>2</sub> + 2 H<sub>2</sub>O → 2 HO–CH<sub>2</sub>CH<sub>2</sub>–NO<sub>2</sub> + Ca(OH)<sub>2</sub>


With ], ethylene oxide forms mono- and ]s:<ref>{{cite book With ], ethylene oxide forms mono- and ]:<ref>{{cite book |author=Orlova, EY |title=Chemistry and technology of high explosives: Textbook for high schools |edition=3 |publisher=Khimiya |year=1981 |page=278}}</ref>
: <chem>(CH2CH2)O{} + \overset{nitric\atop acid}{HNO3} -> HO-CH2CH2-ONO2 -> O2NO-CH2CH2-ONO_2</chem>
|author = Orlova, EY
|title = Chemistry and technology of high explosives: Textbook for high schools
|edition = 3
|publisher = Khimiya
|year = 1981
|page= 278}}</ref>

: <math>\mathsf{(CH_2CH_2)O+HNO_3}\rightarrow\mathsf{HO\!\!-\!\!CH_2CH_2\!\!-\!\!ONO_2\ \xrightarrow{+\ HNO_3}\ O_2NO\!\!-\!\!CH_2CH_2\!\!-\!\!ONO_2}</math>


====Reaction with compounds containing active methylene groups==== ====Reaction with compounds containing active methylene groups====
In the presence of alcoholates, reactions of ethylene oxide with compounds containing active methylene group leads to the formation of ]s:<ref>{{cite book In the presence of ]s, reactions of ethylene oxide with compounds containing active methylene group leads to the formation of ]:<ref>{{cite book |author=Vogel, A. I. |title=Vogel's Textbook of practical organic chemistry |edition=5 |location=UK |publisher=Longman Scientific & Technical |year=1989 |page=1088 |isbn=0-582-46236-3 |url=https://archive.org/details/Vogels_Textbook_of_Practical_Organic_Chemistry_5ed_1989_Longman_WW}}</ref>
: ]
|author = Vogel A.I.
|title = Vogel's Textbook of practical organic chemistry
|edition = 5|location = UK
|publisher = Longman Scientific & Technical
|year = 1989
|page = 1088
|isbn = 0582462363}}</ref>

: ]

====Additions with aromatic compounds====
Ethylene oxide enters into the ] with benzene to form ]:


====Alkylation of aromatic compounds====
: ]
Ethylene oxide enters into the ] with benzene to form ]:
: ]


] can be obtained in one stage if this reaction is conducted at elevated temperatures (315–440 °C) and pressures (0.35–0.7 MPa), in presence of an aluminosilicate catalyst.<ref>{{cite web ] can be obtained in one stage if this reaction is conducted at elevated temperatures ({{convert|315–440|C|}}) and pressures ({{convert|0.35–0.7|MPa||abbr=on}}), in presence of an aluminosilicate catalyst.<ref>Watson, James M. and Forward, Cleve (17 April 1984) "Reaction of benzene with ethylene oxide to produce styrene" {{US patent|4443643}}</ref>
|url = http://www.freepatentsonline.com/4443643.pdf
|title = United States Patent 4443643. Reaction of benzene with ethylene oxide to produce styrene
|accessdate = 2009-10-13}}</ref>


====Synthesis of crown ethers==== ====Synthesis of crown ethers====
A series of polynomial ]s, known as ]s, can be synthesized with ethylene oxide. One method is the cationic cyclopolymerization of ethylene oxide, limiting the size of the formed cycle:<ref name="crown">{{cite book A series of polynomial ]s, known as ]s, can be synthesized with ethylene oxide. One method is the cationic cyclopolymerization of ethylene oxide, limiting the size of the formed cycle:<ref name="crown">{{cite book |author=Hiraoka M. |title=Crown Compounds. Their Characteristics and Applications |publisher=Kodansha |year=1982 |pages=33–34 |isbn=4-06-139444-4}}</ref>
|author = Hiraoka M.
|title = Crown Compounds. Their Characteristics and Applications
|publisher = Kodansha
|year = 1982
|pages= 33–34
|isbn =4061394444}}</ref>


:n (CH<sub>2</sub>CH<sub>2</sub>)O → (–CH<sub>2</sub>CH<sub>2</sub>–O–)<sub>n</sub> : ''n'' (CH<sub>2</sub>CH<sub>2</sub>)O → (–CH<sub>2</sub>CH<sub>2</sub>–O–)<sub>''n''</sub>


To suppress the formation of other linear polymers the reaction is carried out in a highly dilute solution.<ref name="crown" /> To suppress the formation of other linear polymers the reaction is carried out in a highly dilute solution.<ref name="crown" />


Reaction of ethylene oxide with ] in the presence of caesium salts leads to the formation of an 11-membered heterocyclic compound which has the complexing properties of crown ethers:<ref name>{{cite journal Reaction of ethylene oxide with ] in the presence of caesium salts leads to the formation of an 11-membered heterocyclic compound which has the complexing properties of crown ethers:<ref name="autogenerated1">{{cite journal |author=H. W. Roesky |author2=H. G. Schmidt |title=Reaction of Ethylene Oxide with Sulfur Dioxide in the Presence of Cesium Ions: Synthesis of 1,3,6,9,2 λ <sup>4</sup>-Tetraoxathia-2-cycloundecanone |journal=Angewandte Chemie International Edition |year=1985 |volume=24|issue=8 |page=695 |doi=10.1002/anie.198506951}}</ref>
: ]
|author = Roesky H. W., Schmidt H. G.
|title = Reaction of Ethylene Oxide with Sulfur Dioxide in the Presence of Cesium Ions: Synthesis of 1,3,6,9,2 λ <sup>4</sup>-Tetraoxathia-2-cycloundecanone
| journal = Angewandte Chemie International Edition
|year = 1985|doi=10.1002/anie.198506951
|volume = 24
|page = 695
}}</ref>

: ]


===Isomerization=== ===Isomerization===
When ethylene oxide is heated to about 400 °C, or to 150–300 °C in the presence of a catalyst (], ], etc.), it ] into ]:<ref name="petrov">{{cite book When heated to about {{convert|400|C||sigfig=2}}, or to {{convert|150–300|C||sigfig=2}} in the presence of a catalyst (], ], etc.), ethylene oxide ] into ]:<ref name="petrov">{{cite book
|author = Petrov, AA, Balian HV, Troshchenko AT |author1=Petrov, AA |author2=Balian HV |author3=Troshchenko AT |chapter=Chapter 4. Ethers
|title=Organic chemistry |edition=5
|chapter= Chapter 4. Ethers
|location=St. Petersburg
|title = Organic chemistry| edition=5
|year=2002
|location = St. Petersburg.
|pages=159–160
|year = 2002
|isbn=5-8194-0067-4}}</ref>
|pages = 159–160
: <chem>(CH2CH2)O -> \overset{acetaldehyde}{CH3CHO}</chem>
|isbn = 5819400674}}</ref>


The radical mechanism was proposed to explain this reaction in the gas phase; it comprises the following stages:<ref name="benson">{{cite journal
: <math>\mathsf{(CH_2CH_2)O\ \xrightarrow{200\ ^oC,\ Al_2O_3}\ CH_3CHO}</math>
|author=Benson S. W.
|title=Pyrolysis of Ethylene Oxide. A Hot Molecule Reaction
|journal=The Journal of Chemical Physics
|year=1964
|volume=40 |issue=1
|page=105
|bibcode=1964JChPh..40..105B
|doi=10.1063/1.1729851}}</ref>


{{Numbered block|: |(CH<sub>2</sub>CH<sub>2</sub>)O ↔ •CH<sub>2</sub>CH<sub>2</sub>O• → CH<sub>3</sub>CHO*|{{EquationRef|1}}}}
The radical mechanism was proposed by Sidney W. Benson to explain this reaction in the gas phase; it comprises the following stages:<ref name="benson">{{cite journal
|author = Benson S. W.
|title = Pyrolysis of Ethylene Oxide. A Hot Molecule Reaction
|doi=10.1063/1.1729851| journal = The Journal of Chemical Physics
|year = 1964
|volume = 40
| page = 105
}}</ref>


1) (CH<sub>2</sub>CH<sub>2</sub>)O ↔ •CH<sub>2</sub>CH<sub>2</sub>O• → CH<sub>3</sub>CHO* {{Numbered block|: |CH<sub>3</sub>CHO* → CH<sub>3</sub>• + CHO•|{{EquationRef|2}}}}


2) CH<sub>3</sub>CHO* → CH<sub>3</sub>• + CHO• {{Numbered block|: |CH<sub>3</sub>CHO* + M → CH<sub>3</sub>CHO + M*|{{EquationRef|3}}}}


In reaction ({{EquationNote|3}}), '''M''' refers to the wall of the reaction vessel or to a heterogeneous catalyst.
3) CH<sub>3</sub>CHO* + M → CH<sub>3</sub>CHO + M*
The moiety CH<sub>3</sub>CHO* represents a short-lived (lifetime of 10<sup>−8.5</sup> seconds), activated molecule of acetaldehyde. Its excess energy is about 355.6 kJ/mol, which exceeds by 29.3 kJ/mol the ] of the C-C bond in acetaldehyde.<ref name="benson"/>


In absence of a catalyst, the thermal isomerization of ethylene oxide is never selective and apart from acetaldehyde yields significant amount of by-products (see section ]).<ref name="oe2"/>
In reaction 3), '''M''' refers to the wall of the reaction vessel or to a heterogeneous catalyst.
The moiety CH<sub>3</sub>CHO* represents a short-lived (lifetime of 10<sup>–8.5</sup> seconds), activated molecule of acetaldehyde. Its excess energy is about 355.6 kJ/mol, which exceeds by 29.3 kJ/mol the ] of the C-C bond in acetaldehyde.<ref name="benson" />

In absence of a catalyst, the thermal isomerization of ethylene oxide is never selective and apart from acetaldehyde yields significant amount of by-products (see section ]).<ref name="oe2"/>


===Reduction reaction=== ===Reduction reaction===
Ethylene oxide can be hydrogenated into ethanol in the presence of a catalyst, such as ], ], ],<ref name="oe2" /> ]s, ] and some other ]s.<ref name="reduction">{{cite book Ethylene oxide can be hydrogenated into ethanol in the presence of a catalyst, such as ], ], ],<ref name="oe2"/> ]s, ], and some other ]s.<ref name="reduction">{{cite book
|author = Hudlický M. |author=Hudlický, M.
|title = Reductions in Organic Chemistry |title=Reductions in Organic Chemistry
|location = Chichester |location=Chichester
|publisher = Ellis Horwood Limited |publisher=Ellis Horwood Limited
|year = 1984 |year=1984
|page = 83 |page=83
|isbn = 0853123454}}</ref> |isbn=0-85312-345-4}}</ref>
: <chem>(CH2CH2)O{} + H2 -> \underset{ethanol}{C2H5OH}</chem>

: <math>\mathsf{(CH_2CH_2)O+H_2\ \xrightarrow{80\ ^oC,\ Ni}\ C_2H_5OH}</math>

Conversely, with some other catalysts, ethylene oxide may be ''reduced'' by hydrogen to ethylene with the yield up to 70%. The reduction catalysts include mixtures of zinc dust and ], of lithium aluminium hydride with ] (the reducing agent is actually ], formed by the reaction between LiAlH<sub>4</sub> and TiCl<sub>2</sub>) and of ] with ]{{Disambiguation needed|date=June 2011}} in ].<ref name="reduction" />


Conversely, with some other catalysts, ethylene oxide may be ''reduced'' by hydrogen to ethylene with the yield up to 70%. The reduction catalysts include mixtures of zinc dust and ], of lithium aluminium hydride with ] (the reducing agent is actually ], formed by the reaction between LiAlH<sub>4</sub> and TiCl<sub>3</sub>) and of ] with ] in ].<ref name="reduction"/>
: <math>\mathsf{(CH_2CH_2)O+H_2\ \xrightarrow{Zn\ +\ CH_3COOH}\ CH_2\!\!=\!\!CH_2+H_2O}</math>
: <chem>(CH2CH2)O{} + H2 -> \underset{ethylene}{CH2=CH2} + H2O</chem>


===Oxidation=== ===Oxidation===
Ethylene oxide can further be oxidized, depending on the conditions, to ] or ]: Ethylene oxide can further be oxidized, depending on the conditions, to ] or ]:
: <chem>(CH2CH2)O{} + O2 -> \overset{glycolic\ acid}{HOCH2CO2H}</chem>


Deep gas-phase reactor oxidation of ethylene oxide at {{convert|800-1000|K|}} and a pressure of {{convert|0.1–1|MPa||abbr=on}} yields a complex mixture of products containing O<sub>2</sub>, H<sub>2</sub>, ], ], ], ], ], ], ], ], and ].<ref>{{cite journal
: <math>\mathsf{(CH_2CH_2)O+O_2\ \xrightarrow{AgNO_3}\ HOCH_2COOH}</math>
|author=Dagaut P. |author2=Voisin D. |author3=Cathonnet M. |author4=Mcguinness M. |author5=Simmie J. M.

|title=The oxidation of ethylene oxide in a jet-stirred reactor and its ignition in shock waves
Deep gas-phase reactor oxidation of ethylene oxide at 800–1000 K and a pressure of 0.1–1 MPa yields a complex mixture of products containing O<sub>2</sub>, H<sub>2</sub>, ], ], ], ], ], ], ], ] and ].<ref>{{cite journal
|journal=Combustion and Flame
|author = Dagaut P., Voisin D., Cathonnet M., Mcguinness M., Simmie J. M.
|year=1996
|title = The oxidation of ethylene oxide in a jet-stirred reactor and its ignition in shock waves
|volume=156 |issue=1–2
|journal = Combustion and Flame
|pages=62–68
|year = 1996
|doi=10.1016/0010-2180(95)00229-4
|volume = 156
|bibcode=1996CoFl..106...62D }}</ref>
| pages = 62–68
}}</ref>


===Dimerization=== ===Dimerization===
In the presence of acid catalysts, ethylene oxide can be dimerized into ]: In the presence of acid catalysts, ethylene oxide dimerizes to afford ]:
: ]


The reaction mechanism is as follows:<ref name="oe2"/>
: ]
: ]


The dimerization reaction is unselective. By-products include ] (due to ]). The selectivity and speed of dimerization can be increased by adding a catalyst, such as platinum, platinum-palladium, or ] with ]. 2-methyl-1,3-] is formed as a side product in the last case.<ref>Stapp, Paul R. (21 December 1976) "Cyclodimerization of ethylene oxide" {{US patent|3998848}}</ref>
The reaction mechanism is as follows:<ref name="oe2" />

: ]

The dimerization reaction is not selective, and there are always by-products, such as ] (due to ]). The selectivity and speed of dimerization can be increased by adding a catalyst, such as platinum, platinum-palladium or ] with ]; however, 2-methyl-1,3-] is formed as a side product in the last case.<ref>{{cite web
|url = http://www.freepatentsonline.com/3998848.pdf
|title = United States Patent 3998848. Cyclodimerization of ethylene oxide}}</ref>


===Polymerization=== ===Polymerization===
Liquid ethylene oxide can form ]s. The polymerization can proceeds via radical and ionic mechanisms, but only the latter has a wide practical application.<ref name="glycol">{{cite book Liquid ethylene oxide can form ]s. The polymerization can proceed via radical and ionic mechanisms, but only the latter has a wide practical application.<ref name="glycol">{{cite book
|author1=Dyment, ON |author2=Kazanskii, KS |author3=Miroshnikov AM |title=Гликоли и другие производные окисей этилена и пропилена |trans-title=Glycols and other derivatives of ethylene oxide and propylene
|author = Dyment, ON, Kazanskii, KS, Miroshnikov AM
|editor=Dyment, ON
|title = glycol and other derivatives of ethylene oxide and propylene
|publisher=Khimiya
|editor = ON Dymenta
|year=1976
|publisher = Khimiya
|pages=214–217}}</ref> ] of ethylene oxide is assisted by ] acids (], ]), Lewis acids (], ], etc.), ]s, or more complex reagents:<ref name="glycol"/>
|year = 1976
: <math chem>n\ce{(CH2CH2)O ->}\ \overbrace{\ce{(CH2CH2-O-)}_n}^\ce{polyethyleneglycol}</math>
|pages = 214–217}}</ref> ] of ethylene oxide is assisted by protonic acids (], ]), Lewis acids (], ], etc.), ]s or more complex reagents:<ref name="glycol" />

: <math>\mathsf{n(CH_2CH_2)O\ \xrightarrow{SnCl_4}\ (-\!CH_2CH_2\!\!-\!\!O\!-)_n}</math>


The reaction mechanism is as follows.<ref name="poly">{{cite book The reaction mechanism is as follows.<ref name="poly">{{cite book
|title = Polymeric materials encyclopedia |title=Polymeric materials encyclopedia
|editor= Joseph C. Salamone |editor=Salamone, Joseph C.
|publisher = CRC Press |publisher=CRC Press
|year = 1996 |year=1996
|volume = 8 |volume=8
|pages = 6036–6037 |pages=6036–6037
|isbn = 9780849324703}}</ref> At the first stage, the catalyst (MX<sub>m</sub>) is initiated by alkyl-or acylhalogen or by compounds with active hydrogen atoms, usually water, alcohol or glycol: |isbn=978-0-8493-2470-3}}</ref> At the first stage, the catalyst (MX<sub>m</sub>) is initiated by alkyl-or acylhalogen or by compounds with active hydrogen atoms, usually water, alcohol, or glycol:


:MX<sub>m</sub> + ROH → MX<sub>m</sub>RO<sup>–</sup>H<sup>+</sup> : MX<sub>m</sub> + ROH → MX<sub>m</sub>RO<sup>−</sup>H<sup>+</sup>


The resulting active complex reacts with ethylene oxide via the '''S<sub>N</sub>2''' mechanism: The resulting active complex reacts with ethylene oxide via the '''S<sub>N</sub>2''' mechanism:
: (CH<sub>2</sub>CH<sub>2</sub>)O + MX<sub>m</sub>RO<sup>−</sup>H<sup>+</sup> → (CH<sub>2</sub>CH<sub>2</sub>)O•••H<sup>+</sup>O<sup>−</sup>RMX<sub>m</sub>
: (CH<sub>2</sub>CH<sub>2</sub>)O•••H<sup>+</sup> O<sup>−</sup>RMX<sub>m</sub> → HO–CH<sub>2</sub>CH<sub>2</sub><sup>+</sup> + MX<sub>m</sub>RO<sup>−</sup><sub>2</sub>


: (CH<sub>2</sub>CH<sub>2</sub>)O + MX<sub>m</sub>RO<sup>–</sup>H<sup>+</sup> → (CH<sub>2</sub>CH<sub>2</sub>)O•••H<sup>+</sup>O<sup>–</sup>RMX<sub>m</sub> : HO–CH<sub>2</sub>CH<sub>2</sub><sup>+</sup> + n (CH<sub>2</sub>CH<sub>2</sub>)O → HO–CH<sub>2</sub>CH<sub>2</sub>–(O–CH<sub>2</sub>CH<sub>2</sub>)<sub>n</sub><sup>+</sup>

: (CH<sub>2</sub>CH<sub>2</sub>)O•••H<sup>+</sup> O<sup>–</sup>RMX<sub>m</sub> → HO–CH<sub>2</sub>CH<sub>2</sub><sup>+</sup> + MX<sub>m</sub>RO<sup>–</sup><sub>2</sub>

:HO–CH<sub>2</sub>CH<sub>2</sub><sup>+</sup> + n (CH<sub>2</sub>CH<sub>2</sub>)O → HO–CH<sub>2</sub>CH<sub>2</sub>–(O–CH<sub>2</sub>CH<sub>2</sub>)<sub>n</sub><sup>+</sup>


The chain breaks as The chain breaks as


:HO–CH<sub>2</sub>CH<sub>2</sub>–(O–CH<sub>2</sub>CH<sub>2</sub>)<sub>n</sub><sup>+</sup> + MX<sub>m</sub>RO<sup>–</sup> → HO–CH<sub>2</sub>CH<sub>2</sub>–(O–CH<sub>2</sub>CH<sub>2</sub>)<sub>n</sub>–OR + MX<sub>m</sub> : HO–CH<sub>2</sub>CH<sub>2</sub>–(O–CH<sub>2</sub>CH<sub>2</sub>)<sub>n</sub><sup>+</sup> + MX<sub>m</sub>RO<sup>−</sup> → HO–CH<sub>2</sub>CH<sub>2</sub>–(O–CH<sub>2</sub>CH<sub>2</sub>)<sub>n</sub>–OR + MX<sub>m</sub>


:H(O–CH<sub>2</sub>CH<sub>2</sub>)<sub>n</sub>–O–CH<sub>2</sub>–CH<sub>2</sub><sup>+</sup> + MX<sub>m</sub>RO<sup>–</sup> → H(O–CH<sub>2</sub>CH<sub>2</sub>)<sub>n</sub>–O–CH=CH<sub>2</sub> + MX<sub>m</sub> + ROH : H(O–CH<sub>2</sub>CH<sub>2</sub>)<sub>n</sub>–O–CH<sub>2</sub>–CH<sub>2</sub><sup>+</sup> + MX<sub>m</sub>RO<sup>−</sup> → H(O–CH<sub>2</sub>CH<sub>2</sub>)<sub>n</sub>–O–CH=CH<sub>2</sub> + MX<sub>m</sub> + ROH


] of ethylene oxide is assisted by bases, such as ]s{{Disambiguation needed|date=June 2011}} ]s, ]s or other compounds of alkali or ]s.<ref name="glycol" /> The reaction mechanism is as follows:<ref name="poly" /> ] of ethylene oxide is assisted by bases, such as ]s, ]s, ]s, or other compounds of alkali or ]s.<ref name="glycol"/> The reaction mechanism is as follows:<ref name="poly"/>


: (CH<sub>2</sub>CH<sub>2</sub>)O + RONa → RO–CH<sub>2</sub>CH<sub>2</sub>–O<sup>–</sup>Na<sup>+</sup> : (CH<sub>2</sub>CH<sub>2</sub>)O + RONa → RO–CH<sub>2</sub>CH<sub>2</sub>–O<sup>−</sup>Na<sup>+</sup>


:RO–CH<sub>2</sub>CH<sub>2</sub>–O<sup>–</sup>Na<sup>+</sup> + n (CH<sub>2</sub>CH<sub>2</sub>)O → RO–(CH<sub>2</sub>CH<sub>2</sub>–O)<sub>n</sub>–CH<sub>2</sub>CH<sub>2</sub>–O<sup>–</sup>Na<sup>+</sup> : RO–CH<sub>2</sub>CH<sub>2</sub>–O<sup>−</sup>Na<sup>+</sup> + n (CH<sub>2</sub>CH<sub>2</sub>)O → RO–(CH<sub>2</sub>CH<sub>2</sub>–O)<sub>n</sub>–CH<sub>2</sub>CH<sub>2</sub>–O<sup>−</sup>Na<sup>+</sup>


:RO–(CH<sub>2</sub>CH<sub>2</sub>–O)<sub>n</sub>–CH<sub>2</sub>CH<sub>2</sub>–O<sup>–</sup>Na<sup>+</sup> → RO–(CH<sub>2</sub>CH<sub>2</sub>–O)<sub>n</sub>–CH=CH<sub>2</sub> + NaOH : RO–(CH<sub>2</sub>CH<sub>2</sub>–O)<sub>n</sub>–CH<sub>2</sub>CH<sub>2</sub>–O<sup>−</sup>Na<sup>+</sup> → RO–(CH<sub>2</sub>CH<sub>2</sub>–O)<sub>n</sub>–CH=CH<sub>2</sub> + NaOH


:RO–(CH<sub>2</sub>CH<sub>2</sub>–O)<sub>n</sub>–CH<sub>2</sub>CH<sub>2</sub>–O<sup>–</sup>Na<sup>+</sup> + H<sub>2</sub>O → RO–(CH<sub>2</sub>CH<sub>2</sub>–O)<sub>(n+1)</sub>OH + NaOH : RO–(CH<sub>2</sub>CH<sub>2</sub>–O)<sub>n</sub>–CH<sub>2</sub>CH<sub>2</sub>–O<sup>−</sup>Na<sup>+</sup> + H<sub>2</sub>O → RO–(CH<sub>2</sub>CH<sub>2</sub>–O)<sub>(n+1)</sub>OH + NaOH


===Thermal decomposition=== ===Thermal decomposition===
Ethylene oxide is relatively stable to heating – in the absence of a catalyst, it does not dissociate up to 300 °C, and only above 570 °C there is a major ] decomposition, which proceeds through the radical mechanism.<ref name="oe2">{{cite book Ethylene oxide is relatively stable to heating – in the absence of a catalyst, it does not dissociate up to {{convert|300|C|}}, and only above {{convert|570|C|}} there is a major ] decomposition, which proceeds through the radical mechanism.<ref name="oe2">{{cite book
|chapter= Chapter II. Chemical properties of ethylene oxide |chapter=Chapter II. Chemical properties of ethylene oxide
|title = Ethylene oxide |title=Ethylene oxide
|editor1=Zimakov, P.V. |editor2=Dyment, O. H. |publisher=Khimiya
|editor=PV Zimakova and Mr. O. Dymenta
|year=1967
|publisher = Khimiya
|pages=57–85}}</ref> The first stage involves ], however high temperature accelerates the radical processes. They result in a gas mixture containing acetaldehyde, ethane, ethyl, methane, hydrogen, carbon dioxide, ], and ].<ref>{{cite journal
|year = 1967
|author1=Neufeld L.M. |author2=Blades A.T.
|pages = 57–85}}</ref> The first stage involves ], however high temperature accelerated the radical processes. They result in a gas mixture containing acetaldehyde, ethane, ethyl, methane, hydrogen, carbon dioxide, ] and ].<ref>{{cite journal
|title=The Kinetics of the Thermal Reactions of Ethylene Oxide
|author = Neufeld L.M., Blades A.T.
|journal=Canadian Journal of Chemistry
|title = The Kinetics of the Thermal Reactions of Ethylene Oxide
|year=1963
|journal = Canadian Journal of Chemistry
|volume=41 |issue=12
|year = 1963|url=http://article.pubs.nrc-cnrc.gc.ca/ppv/RPViewDoc?issn=1480-3291&volume=41&issue=12&startPage=2956|doi=10.1139/v63-434
|pages=2956–2961
|volume = 41
|doi=10.1139/v63-434
|page = 2956}}</ref> High-temperature ] (830–1200 K) at elevated pressure in an inert atmosphere leads to a more complex composition of the gas mixture, which also contains ] and ].<ref name="Lifshitz">{{cite journal|author = Lifshitz A., Ben-Hamou H.
}}</ref> High-temperature ] ({{convert|830–1200|K|}}) at elevated pressure in an inert atmosphere leads to a more complex composition of the gas mixture, which also contains ] and ].<ref name="Lifshitz">{{cite journal |author=Lifshitz A. |author2=Ben-Hamou H.
|title = Thermal reactions of cyclic ethers at high temperatures. 1. Pyrolysis of ethylene oxide behind reflected shocks
|title=Thermal reactions of cyclic ethers at high temperatures. 1. Pyrolysis of ethylene oxide behind reflected shocks
|journal = The Journal of Physical Chemistry
|journal=The Journal of Physical Chemistry
|year = 1983|doi=10.1021/j100233a026
|year=1983
|volume = 87
|volume=87 |issue=10
|page = 1782
|pages=1782–1787
}}</ref> Contrary to the isomerization, initiation of the chain occurs mainly as follows:<ref name="Lifshitz" />
|doi=10.1021/j100233a026

}}</ref> Contrary to the isomerization, initiation of the chain occurs mainly as follows:<ref name="Lifshitz"/>
: (CH<sub>2</sub>CH<sub>2</sub>)O → •CH<sub>2</sub>CH<sub>2</sub>O• → CH<sub>2</sub>O + CH<sub>2</sub>: : (CH<sub>2</sub>CH<sub>2</sub>)O → •CH<sub>2</sub>CH<sub>2</sub>O• → CH<sub>2</sub>O + CH<sub>2</sub>:


When carrying the thermal decomposition of ethylene oxide in the presence of transition metal compounds as catalysts, it is possible not only to reduce its temperature, but also to have ]{{Disambiguation needed|date=June 2011}} as the main product, that is to reverse the ethylene oxide synthesis reaction. When carrying the thermal decomposition of ethylene oxide in the presence of transition metal compounds as catalysts, it is possible not only to reduce its temperature, but also to have ] as the main product, that is to reverse the ethylene oxide synthesis reaction.


===Other reactions=== ===Other reactions===
] ions or ] transform ethylene oxide into ]s (ethylene sulfides):<ref>{{cite book ] ions or ] transform ethylene oxide into ] (ethylene sulfide):<ref>{{cite book
|author = Gilchrist T. |author=Gilchrist T.
|title = Heterocyclic Chemistry |title=Heterocyclic Chemistry
|publisher = Pearson Education |publisher=Pearson Education
|year = 1985 |year=1985
|pages = 411–412 |pages=411–412
|isbn = 8131707938}}</ref> |isbn=81-317-0793-8}}</ref>

: (CH<sub>2</sub>CH<sub>2</sub>)O + (NH<sub>2</sub>)<sub>2</sub>C=S → (CH<sub>2</sub>CH<sub>2</sub>)S + (NH<sub>2</sub>)<sub>2</sub>C=O : (CH<sub>2</sub>CH<sub>2</sub>)O + (NH<sub>2</sub>)<sub>2</sub>C=S → (CH<sub>2</sub>CH<sub>2</sub>)S + (NH<sub>2</sub>)<sub>2</sub>C=O
: ]


Reaction of ] with ethylene oxide produces ]:<ref name="oe3"/>
: ]

Reaction of ] with ethylene oxide produces ]:<ref name="oe3" />

: (CH<sub>2</sub>CH<sub>2</sub>)O + PCl<sub>5</sub> → Cl–CH<sub>2</sub>CH<sub>2</sub>–Cl + POCl<sub>3</sub> : (CH<sub>2</sub>CH<sub>2</sub>)O + PCl<sub>5</sub> → Cl–CH<sub>2</sub>CH<sub>2</sub>–Cl + POCl<sub>3</sub>


Other dichloro derivatives of ethylene oxide can be obtained by combined action of ] (SOCl<sub>2</sub>) and ] and of ] and ].<ref name="march2"> Other dichloro derivatives of ethylene oxide can be obtained by combined action of ] (SOCl<sub>2</sub>) and ] and of ] and ].<ref name="march2">
{{cite book {{cite book
|author = Michael Smith, Michael B. Smith, Jerry March |author1=Smith, Michael B. |author2=March, Jerry
|title = Advanced organic chemistry. Reactions, Mechanisms and Structure |title=Advanced organic chemistry. Reactions, Mechanisms, and Structure
|publisher = Wiley-Interscience |publisher=Wiley-Interscience
|year=2007
|year = 2007|url=http://books.google.com/?id=JDR-nZpojeEC
|isbn =0471720917}}</ref> |isbn=978-0-471-72091-1
|url=https://books.google.com/books?id=JDR-nZpojeEC
}}</ref>


] reacts with ethylene oxide forming chloroethyl esters of phosphorous acid:<ref name="oe3" /> ] reacts with ethylene oxide forming chloroethyl esters of phosphorous acid:<ref name="oe3"/>


: (CH<sub>2</sub>CH<sub>2</sub>)O + PCl<sub>3</sub> → Cl–CH<sub>2</sub>CH<sub>2</sub>–OPCl<sub>2</sub> : (CH<sub>2</sub>CH<sub>2</sub>)O + PCl<sub>3</sub> → Cl–CH<sub>2</sub>CH<sub>2</sub>–OPCl<sub>2</sub>


:2 (CH<sub>2</sub>CH<sub>2</sub>)O + PCl<sub>3</sub> → (Cl–CH<sub>2</sub>CH<sub>2</sub>–O)<sub>2</sub>PCl : 2 (CH<sub>2</sub>CH<sub>2</sub>)O + PCl<sub>3</sub> → (Cl–CH<sub>2</sub>CH<sub>2</sub>–O)<sub>2</sub>PCl


:3 (CH<sub>2</sub>CH<sub>2</sub>)O + PCl<sub>3</sub> → Cl–CH<sub>2</sub>CH<sub>2</sub>–O)<sub>3</sub>P : 3 (CH<sub>2</sub>CH<sub>2</sub>)O + PCl<sub>3</sub> → Cl–CH<sub>2</sub>CH<sub>2</sub>–O)<sub>3</sub>P

The reaction product of ethylene oxide with ]s in the presence of ] is a complex iodoethyl ether:<ref name="march2" />


The reaction product of ethylene oxide with ]s in the presence of ] is a complex iodoethyl ester:<ref name="march2"/>
: (CH<sub>2</sub>CH<sub>2</sub>)O + RCOCl + NaI → RC(O)–OCH<sub>2</sub>CH<sub>2</sub>–I + NaCl : (CH<sub>2</sub>CH<sub>2</sub>)O + RCOCl + NaI → RC(O)–OCH<sub>2</sub>CH<sub>2</sub>–I + NaCl


Heating ethylene oxide to 100 °C with ], in a non-polar solvent in the presence of ''bis''-(triphenylphosphine)-nickel(0) results in ]:<ref>{{cite book|author = L. Fieser, M. Fieser Heating ethylene oxide to 100&nbsp;°C with ], in a non-polar solvent in the presence of ''bis''-(triphenylphosphine)-nickel(0) results in ]:<ref>{{cite book |author1=Fieser, L.
|author2=Fieser, M.
|title = Reagents for Organic Synthesis
|title=Reagents for Organic Synthesis
|publisher =Wiley
|publisher=Wiley
|volume = 7|year=1979
|volume=7
|page= 545
|year=1979
|isbn =9780471029182}}</ref>
|page=

|isbn=978-0-471-02918-2
: ]
|url=https://archive.org/details/reagentsfororgan07fies_0/page/545
|url-access=registration
}}</ref>
: ]


In industry, a similar reaction is carried out at high pressure and temperature in the presence of quaternary ammonium or phosphonium salts as a catalyst.<ref>{{cite book In industry, a similar reaction is carried out at high pressure and temperature in the presence of quaternary ammonium or phosphonium salts as a catalyst.<ref>{{cite book
|author = Sheldon RA |author=Sheldon RA
|title= Chemicals from synthesis gas: catalytic reactions of CO and, Volume 2 |title=Chemicals from synthesis gas: catalytic reactions of CO and, Volume 2
|page=193
|url=http://books.google.com/?id=s1_rjRUlu1EC&pg=PA193|page=193
|publisher = Springer |publisher=Springer
|year = 1983 |year=1983
|isbn=9027714894}}</ref> |isbn=90-277-1489-4
|url=https://books.google.com/books?id=s1_rjRUlu1EC&pg=PA193}}</ref>


Reaction of ethylene oxide with ] at 80–150 °C in the presence of a catalyst leads to the formation of ]:<ref name="fiser">{{cite book Reaction of ethylene oxide with ] at 80–150&nbsp;°C in the presence of a catalyst leads to the formation of ]:<ref name="fiser">{{cite book
|author = L. Fieser, M. Fieser |author1=Fieser, L. |author2=Fieser, M.
|title = Reagents for Organic Synthesis |title=Reagents for Organic Synthesis
|publisher = Wiley |publisher=Wiley
|year = 1977|isbn=9780471258735 |year=1977 |isbn=978-0-471-25873-5
|volume = 6 |volume=6
|page= 197}}</ref> |page=197}}</ref>
: ]


Substituting formaldehyde by other aldehydes or ketones results in a 2-substituted 1,3-dioxolane (yield: 70–85%, catalyst: tetraethylammonium bromide).<ref name="fiser"/>
: ]


Catalytic ] of ethylene oxide gives hydroxypropanal which can be hydrogenated to ]:<ref>Han, Yuan-Zhang and Viswanathan, Krishnan (13 February 2003) "Hydroformylation of ethylene oxide" {{US patent|20030032845}}</ref>
Substituting formaldehyde by other aldehydes or ketones results in a 2-substituted 1,3-dioxolane (yield: 70–85%, catalyst: tetraetilammoniybromid).<ref name="fiser" />
: <chem>(CH2CH2)O + CO + H2 -> CHO-CH2CH2-OH -> HO-CH2CH2CH2-OH</chem>


==Laboratory synthesis==
Catalytic ] of ethylene oxide results in hydroxypropanal and further in propane-1,3-diol:<ref>{{cite web
|url = http://www.freepatentsonline.com/20030032845.pdf
|title = United States Patent 20030032845. Hydroformylation of ethylene oxide}}</ref>


: <math>\mathsf{(CH_2CH_2)O+CO+H_2}\rightarrow\mathsf{CHO\!\!-\!\!CH_2CH_2\!\!-\!\!OH\ \xrightarrow{+H_2}\ HO\!\!-\!\!CH_2CH_2CH_2\!\!-\!\!OH}</math>

==Laboratory synthesis==
===Dehydrochlorination of ethylene and its derivatives=== ===Dehydrochlorination of ethylene and its derivatives===
Dehydrochlorination of ], developed by Wurtz back in 1859, still remains one of the most common laboratory methods of producing ethylene oxide: Dehydrochlorination of ], developed by Wurtz in 1859, remains a common laboratory route to ethylene oxide:


:Cl–CH<sub>2</sub>CH<sub>2</sub>–OH + NaOH → (CH<sub>2</sub>CH<sub>2</sub>)O + NaCl + H<sub>2</sub>O : <chem>Cl-CH2CH2-OH + NaOH -> (CH2CH2)O + NaCl + H2O</chem>


The reaction is carried out at elevated temperature, and beside ] or ], ], ], ] or ]s of alkali or alkaline earth metals can be used.<ref name="oe5">{{cite book The reaction is carried out at elevated temperature, and beside ] or ], ], ], ], or ]s of alkali or alkaline earth metals can be used.<ref name="oe5">{{cite book
|chapter= Chapter V. Producing ethylene oxide through ethylene |chapter=Chapter V. Producing ethylene oxide through ethylene
|title = Ethylene oxide |title=Ethylene oxide
|editor1=Zimakov, P.V. |editor2=Dyment, O. H. |publisher=Khimiya
|editor=PV Zimakova and O. Dymenta
|year=1967
|publisher = Khimiya
|pages=155–182}}</ref>
|year = 1967
|pages = 155–182}}</ref>


With a high yield (90%) ethylene oxide can be produced by treating ] with ethyl hypochlorite; substituting calcium by other alkaline earth metals reduces the reaction yield:<ref name="oeII">{{cite book
Chloroethanol, in turn, is synthesized using one of the following methods:<ref name="oe5" />
|chapter=Part II. Synthesis of ethylene oxide. Overview of reactions of formation of ethylene oxide and other α-oxides

|title=Ethylene oxide
* By reacting ethylene glycol with hydrochloric acid:
|editor1=Zimakov, P.V. |editor2=Dyment, O. H. |publisher=Khimiya

|year=1967
::HO–CH<sub>2</sub>CH<sub>2</sub>–OH + HCl → HO–CH<sub>2</sub>CH<sub>2</sub>–Cl + H<sub>2</sub>O
|pages=145–153}}</ref>

: <chem>2 CH3CH2-OCl + CaO -> 2 (CH2CH2)O + CaCl2 + H2O</chem>
* By reacting ethylene with ]:

::CH<sub>2</sub>=CH<sub>2</sub> + HOCl → HO–CH<sub>2</sub>CH<sub>2</sub>–Cl

* By chlorination of ethylene:

::CH<sub>2</sub>=CH<sub>2</sub> + Cl<sub>2</sub> + H<sub>2</sub>O → HO–CH<sub>2</sub>CH<sub>2</sub>–Cl + HCl

Another convenient and old method of ethylene oxide synthesis is reaction of an ] with chloroethyl acetate:<ref name="oeII">{{cite book
|chapter = Part II. Synthesis of ethylene oxide. Overview of reactions of formation of ethylene oxide and other α-oxides
|title = Ethylene oxide
|editor=PV Zimakova and Mr. O. Dymenta
|publisher = Khimiya
|year = 1967
|pages = 145–153}}</ref>

:Cl–CH<sub>2</sub>CH<sub>2</sub>–OCOCH<sub>3</sub> + 2 KOH → (CH<sub>2</sub>CH<sub>2</sub>)O + KCl + CH<sub>3</sub>COOK + H<sub>2</sub>O

With a high yield (90%) ethylene oxide can be produced by reacting ] with ethyl hypochlorite; substituting calcium by other alkaline earth metals reduces the reaction yield:<ref name="oeII" />

:2 CH<sub>3</sub>CH<sub>2</sub>–OCl + CaO → 2 (CH<sub>2</sub>CH<sub>2</sub>)O + CaCl<sub>2</sub> + H<sub>2</sub>O

In turn, ethylhypochlorite is synthesized as follows:

:Cl<sub>2</sub> + NaOH + CH<sub>3</sub>CH<sub>2</sub>OH → CH<sub>3</sub>CH<sub>2</sub>OCl + NaCl + H<sub>2</sub>O


===Direct oxidation of ethylene by peroxy acids=== ===Direct oxidation of ethylene by peroxy acids===
Ethylene can be directly oxidized into ethylene oxide using ]s, for example, ] or ''meta''-chloro-peroxybenzoic acid:<ref>{{cite book Ethylene can be directly oxidized into ethylene oxide using ]s, for example, ] or ''meta''-chloro-peroxybenzoic acid:<ref>{{cite book
|author = McMurry J. |author=McMurry J.
|title = Organic chemistry |title=Organic chemistry
|edition = 7 |edition=7
|publisher = Thomson |publisher=Thomson
|year = 2008 |year=2008
|page= 661 |page=661
|isbn = 0495112585}}</ref> |isbn=978-0-495-11258-7}}</ref>
: ]


Oxidation by peroxy acids is efficient for higher alkenes, but not for ethylene. The above reaction is slow and has low yield, therefore it is not used in the industry.<ref name="oeII"/>
: ]

Oxidation by peroxy acids is efficient for higher alkenes, but not for ethylene. The above reaction is slow and has low yield, therefore it is not used in the industry.<ref name="oeII" />


===Other preparative methods=== ===Other preparative methods===
Other synthesis methods include<ref name="oeII" /> reaction of diiodo ethane with ]: Other synthesis methods include<ref name="oeII"/> reaction of diiodo ethane with ]:
: <chem>I-CH2CH2-I + Ag2O -> (CH2CH2)O + 2AgI</chem>


and decomposition of ] at {{convert|200–210|C|}} in the presence of ]:
:I–CH<sub>2</sub>CH<sub>2</sub>–I + Ag<sub>2</sub>O → (CH<sub>2</sub>CH<sub>2</sub>)O + 2 AgI
: ]


==Industrial synthesis==
and decomposition of ethylene carbonate at 200–210 °C in the presence of ]:


: ]

==Industrial synthesis==
===History=== ===History===
Commercial production of ethylene oxide dates back to 1914 when ] built the first factory which used the chlorohydrin process (reaction of ethylene chlorohydrin with calcium hydroxide). The chlorohydrin process was unattractive for several reasons, including low efficiency and loss of valuable chlorine into ].<ref>{{cite journal Commercial production of ethylene oxide dates back to 1914 when ] built the first factory which used the chlorohydrin process (reaction of ethylene chlorohydrin with calcium hydroxide). The chlorohydrin process was unattractive for several reasons, including low efficiency and loss of valuable chlorine into ].<ref>{{cite journal
|author = Norris J.F. |author=Norris, J.F.
|title = The Manufacture of War Gases in Germany |title=The Manufacture of War Gases in Germany
|journal = Journal of Industrial and Engineering Chemistry |journal=Journal of Industrial and Engineering Chemistry
|year = 1919 |year=1919
|volume = 11 |volume=11 |issue=9
|pages=817–829
|page = 817}}</ref> More efficient direct oxidation of ethylene by air was invented by Lefort in 1931 and in 1937 ] opened the first plant using this process. It was further improved in 1958 by Shell Oil Co. by replacing air with oxygen and using elevated temperature of 200–300 °C and pressure (1–3 MPa).<ref name = "industrial"/> This more efficient routine accounted for about half of ethylene oxide production in the 1950s in the U.S., and after 1975 it completely replaced the previous methods.<ref name = "industrial" >{{cite book
|doi=10.1021/ie50117a002
|author = Weissermel K., Arpe H-J.
|url=https://zenodo.org/records/1428740
|title = Industrial organic chemistry
}}</ref> More efficient direct oxidation of ethylene by air was invented by Lefort in 1931 and in 1937 ] opened the first plant using this process. It was further improved in 1958 by Shell Oil Co. by replacing air with oxygen and using elevated temperature of {{convert|200–300|C||sigfig=2}} and pressure ({{convert|1–3|MPa||abbr=on}}).<ref name="industrial"/> This more efficient route accounted for about half of ethylene oxide production in the 1950s in the US, and after 1975 it completely replaced the previous methods.<ref name="industrial" >{{cite book
| edition = 4
|author1=Weissermel K. |author2=Arpe H-J. |title=Industrial organic chemistry
|location = Weinheim
|edition=4
|publisher = Wiley-VCH
|location=Weinheim
|year = 2003
|publisher=Wiley-VCH
|pages = 145–148
|year=2003
|isbn = 9783527305780}}</ref>
|pages=145–148
|isbn=978-3-527-30578-0}}</ref>
The production of ethylene oxide accounts for approximately 11% of worldwide ethylene demand.<ref> {{Webarchive|url=https://web.archive.org/web/20150307115926/http://www.ceresana.com/en/market-studies/chemicals/ethylene/ |date=7 March 2015}}. Ceresana.com (December 2010). Retrieved on 8 May 2017.</ref>


===Chlorohydrin process of production of ethylene oxide=== ===Chlorohydrin process of production of ethylene oxide===
Although the chlorohydrin process is almost entirely superseded in the industry by the direct oxidation of ethylene, the knowledge of this method is still important for educational reasons and because it is still used in the production of ].<ref>{{cite web Although the chlorohydrin process is almost entirely superseded in the industry by the direct oxidation of ethylene, the knowledge of this method is still important for educational reasons and because it is still used in the production of ].<ref>{{cite web
|title=Process Economics Program Report 2D
|date = February 1985
|date=February 1985
|url = http://www.sriconsulting.com/PEP/Public/Reports/Phase_84/RP002D/
|title = Process Economics Program Report 2D |work=PEP Report
|publisher=SRI Consulting
|work = PEP Report
|url=http://www.sriconsulting.com/PEP/Public/Reports/Phase_84/RP002D/
|publisher = SRI Consulting
|accessdate = 2009-11-19}}</ref> The process consists of three major steps: synthesis of ethylene chlorohydrin, dehydrochlorination of ethylene chlorohydrin to ethylene oxide and purification of ethylene oxide. Those steps are carried continuously. In the first column, hypochlorination of ethylene is carried out as follows:<ref name="uk">{{cite book |access-date=19 November 2009}}</ref> The process consists of three major steps: synthesis of ethylene chlorohydrin, dehydrochlorination of ethylene chlorohydrin to ethylene oxide and purification of ethylene oxide. Those steps are carried continuously. In the first column, hypochlorination of ethylene is carried out as follows:<ref name="uk">{{cite book
|author = Yukelson II |author=Yukelson I.I.
|title = The technology of basic organic synthesis |title=The technology of basic organic synthesis
|publisher = Khimiya |publisher=Khimiya
|year = 1968 |year=1968
|pages = 554–559}}</ref> |pages=554–559}}</ref>


:Cl<sub>2</sub> + H<sub>2</sub>O → HOCl + HCl : Cl<sub>2</sub> + H<sub>2</sub>O → HOCl + HCl


:CH<sub>2</sub>=CH<sub>2</sub> + HOCl → OH–CH<sub>2</sub>CH<sub>2</sub>–Cl : CH<sub>2</sub>=CH<sub>2</sub> + HOCl → HO–CH<sub>2</sub>CH<sub>2</sub>–Cl


:CH<sub>2</sub>=CH<sub>2</sub> + Cl<sub>2</sub> → Cl–CH<sub>2</sub>CH<sub>2</sub>–Cl : CH<sub>2</sub>=CH<sub>2</sub> + Cl<sub>2</sub> → Cl–CH<sub>2</sub>CH<sub>2</sub>–Cl


To suppress the conversion of ethylene into the ] (the last reaction), the concentration of ethylene is maintained at about 4–6%, and the solution is heated by steam to the boiling point.<ref name="uk" /> To suppress the conversion of ethylene into the ] (the last reaction), the concentration of ethylene is maintained at about 4–6%, and the solution is heated by steam to the boiling point.<ref name="uk"/>


Next, aqueous solution of ethylene chlorohydrin enters the second column, where it reacts with a 30% solution of calcium hydroxide at 100 °C:<ref name="uk" /> Next, aqueous solution of ethylene chlorohydrin enters the second column, where it reacts with a 30% solution of calcium hydroxide at {{convert|100|C|}}:<ref name="uk"/>


:2 OH–CH<sub>2</sub>CH<sub>2</sub>–Cl + Ca(OH)<sub>2</sub> → 2 (CH<sub>2</sub>CH<sub>2</sub>)O + CaCl<sub>2</sub> + H<sub>2</sub>O : 2 HO–CH<sub>2</sub>CH<sub>2</sub>–Cl + Ca(OH)<sub>2</sub> → 2 (CH<sub>2</sub>CH<sub>2</sub>)O + CaCl<sub>2</sub> + 2H<sub>2</sub>O


The produced ethylene oxide is purified by ]. The chlorohydrin process allows to reach 95% conversion of ethylene chlorohydrin. The yield of ethylene oxide is about 80% of the theoretical value; for 1 ton of ethylene oxide, about 200&nbsp;kg of ethylene dichloride is produced.<ref name="uk" /> The produced ethylene oxide is purified by ]. The chlorohydrin process allows to reach 95% conversion of ethylene chlorohydrin. The yield of ethylene oxide is about 80% of the theoretical value; for {{convert|1|t|}} of ethylene oxide, about {{convert|200|kg||abbr=on}} of ethylene dichloride is produced.<ref name="uk"/> But, the major drawbacks of this process are high chlorine consumption and effluent load. This process is now obsolete.


===Direct oxidation of ethylene=== ===Direct oxidation of ethylene===

====Usage in global industry==== ====Usage in global industry====
Direct oxidation of ethylene was patented by Lefort in 1931. This method was repeatedly modified for industrial use, and at least four major variations are known. They all use oxidation by oxygen or air and a silver-based catalyst, but differ in the technological details and hardware implementations.<ref name="eos">{{cite book Direct oxidation of ethylene was patented by Lefort in 1931. This method was repeatedly modified for industrial use, and at least four major variations are known. They all use oxidation by oxygen or air and a silver-based catalyst, but differ in the technological details and hardware implementations.<ref name="eos">{{cite book
|chapter = Catalitic Oxidation of Olefins |chapter=Catalitic Oxidation of Olefins
|title = Advances in catalysis and related subjects |title=Advances in catalysis and related subjects
| editor= D.D. Eley, H. Pines, P.B. Weisz |editor1=Eley, D.D. |editor2=Pines, H. |editor3=Weisz, P.B. |location=New York
|publisher=Academic Press Inc
| location = New York
|year=1967
|publisher = Academic Press Inc
|volume=17
|year = 1967
|pages=156–157}}</ref>
|volume = 17
|pages = 156–157}}</ref>


] (currently a division of ]) was the first company to develop the direct oxidation process. Since 1994, it uses the so-called METEOR process ('''M'''ost ''' E'''ffective '''T'''echnology for '''E'''thylene '''O'''xide '''R'''eactions) which is characterized by high productivity, low initial capital investment and low operating costs. The method is the exclusive property of the company; it is used only at its own plants and accounts for about 20% of the global ethylene oxide production.<ref name="cmpa">{{cite book ] (currently a division of ]) was the first company to develop the direct oxidation process.<ref name="cmpa">{{cite book
|author1=Bloch H. P. |author2=Godse A. |title=Compressors and modern process applications |publisher=John Wiley and Sons
|author = Bloch H. P., Godse A.
|year=2006
|title = Compressors and modern process applications|publisher = John Wiley and Sons
|pages=295–296
|year = 2006
|isbn=978-0-471-72792-7
|pages = 295–296
|isbn = 9780471727927
}}</ref> }}</ref>


A similar production method was developed by Scientific Design Co., but it received wider use because of the licensing system – it accounts for 25% of the world's production and for 75% of world's licensed production of ethylene oxide.<ref name = "cmpa"/><ref>{{cite web A similar production method was developed by Scientific Design Co., but it received wider use because of the licensing system – it accounts for 25% of the world's production and for 75% of world's licensed production of ethylene oxide.<ref name="cmpa"/><ref>{{cite web |title=Ethylene Oxide/Ethylene Glycol Process |work=Process Licensing and Engineering |publisher=Scientific Design Company |url=http://www.scidesign.com/Business/EO%20-%20EG%20Process/EO_EG_Process.htm |access-date=3 October 2009 |url-status=dead |archive-url=https://web.archive.org/web/20110716014802/http://www.scidesign.com/Business/EO%20-%20EG%20Process/EO_EG_Process.htm |archive-date=16 July 2011}}</ref> A proprietary variation of this method is used by Japan Catalytic Chemical Co., which adapted synthesis of both ethylene oxide and ethylene glycol in a single industrial complex.
|url = http://www.scidesign.com/Business/EO%20-%20EG%20Process/EO_EG_Process.htm
|title = Ethylene Oxide/Ethylene Glycol Process
|work = Process Licensing and Engineering
|publisher = Scientific Design Company
|accessdate = 2009-10-03}}</ref> A proprietary variation of this method is used by Japan Catalytic Chemical Co., which adapted synthesis of both ethylene oxide and ethylene glycol in a single industrial complex.


A different modification was developed Shell International Chemicals BV. Their method is rather flexible with regard to the specific requirements of specific industries; it is characterized by high selectivity with respect to the ethylene oxide product and long lifetime of the catalyst (3 years). It accounts for about 40% of global production.<ref name="cmpa" /> A different modification was developed Shell International Chemicals BV. Their method is rather flexible with regard to the specific requirements of specific industries; it is characterized by high selectivity with respect to the ethylene oxide product and long lifetime of the catalyst (3 years). It accounts for about 40% of global production.<ref name="cmpa"/>


Older factories typically use air for oxidation whereas newer plants and processes, such as METEOR and Japan Catalytic, favor oxygen.<ref>{{cite book Older factories typically use air for oxidation whereas newer plants and processes, such as METEOR and Japan Catalytic, favor oxygen.<ref>{{cite book
|author1=Chauvel A. |author2=Lefebvre G. |title=Petrochemical processes 2. Major Oxygenated, Chlorinated and Nitrated Derivatives
|author = Chauvel A., Lefebvre G.
|edition=2
|title = Petrochemical processes 2. Major Oxygenated, Chlorinated and Nitrated Derivatives
|location=Paris
|edition = 2
|publisher=Editions Technip
|location = Paris
|year=1989
|publisher = Editions Technip
|volume=2
|year = 1989
|page=4
|volume = 2
|isbn=2-7108-0563-4}}</ref>
|page= 4
|isbn = 2710805634}}</ref>


====Chemistry and kinetics of the direct oxidation process==== ====Chemistry and kinetics of the direct oxidation process====
Formally, the direct oxidation process is expressed by the following equation: Formally, the direct oxidation process is expressed by the following equation:


: <math>\mathsf{2CH_2\!\!=\!\!CH_2+O_2\ \xrightarrow{Ag}\ 2(CH_2CH_2)O}</math> : <chem>2CH_2=CH2 + O2 -> 2(CH2CH2)O</chem>, ΔH=−105 kJ/mol


However, significant yield of carbon dioxide and water is observed in practice, which can be explained by the complete oxidation of ethylene or ethylene oxide: However, significant yield of carbon dioxide and water is observed in practice, which can be explained by the complete oxidation of ethylene or ethylene oxide:


:CH<sub>2</sub>=CH<sub>2</sub> + 3 O<sub>2</sub> → 2 CO<sub>2</sub> + 2 H<sub>2</sub>O : CH<sub>2</sub>=CH<sub>2</sub> + 3 O<sub>2</sub> → 2 CO<sub>2</sub> + 2 H<sub>2</sub>O, ΔH=−1327{{nbsp}}kJ/mol
: (CH<sub>2</sub>CH<sub>2</sub>)O + 2.5 O<sub>2</sub> → 2 CO<sub>2</sub> + 2 H<sub>2</sub>O, ΔH=−1223{{nbsp}}kJ/mol


According to a kinetic analysis by Kilty and Sachtler, the following reactions describe the pathway leading to EO. In the first step, a ] (O<sub>2</sub><sup>−</sup>) species is formed:<ref name="kilty">{{cite journal
:2 (CH<sub>2</sub>CH<sub>2</sub>)O + 5 O<sub>2</sub> → 4 CO<sub>2</sub> + 4 H<sub>2</sub>O
|author=Kilty P. A. |author2=Sachtler W. M. H.

|title=The Mechanism of the Selective Oxidation of Ethylene to Ethylene Oxide
The process of heterogeneous catalytic oxidation of ethylene was studied by P. A. Kilty and W. M. H. Sachtler, who suggested the following mechanism:<ref name="kilty">{{cite journal
|journal=Catalysis Reviews: Science and Engineering
|author = Kilty P. A., Sachtler W. M. H.
|year=1974
|title = The mechanism of the selective oxidation of ethylene to ethylene oxide
|volume=10
|pages=1–16
|doi=10.1080/01614947408079624 |doi=10.1080/01614947408079624
|journal = Catalysis Reviews: Science and Engineering
|year = 1974
|volume = 10
|pages = 1–16
}}</ref> }}</ref>
: O<sub>2</sub> + Ag → Ag<sup>+</sup>O<sub>2</sub><sup>−</sup>
This species reacts with ethylene
: Ag<sup>+</sup>O<sub>2</sub><sup>−</sup> + H<sub>2</sub>C=CH<sub>2</sub> → (CH<sub>2</sub>CH<sub>2</sub>)O + AgO
The resulting silver oxide then oxidizes ethylene or ethylene oxide to CO<sub>2</sub> and water. This reaction replenishes the silver catalyst. Thus the overall reaction is expressed as


:O<sub>2</sub> + 4 Ag(adj) → 4 Ag + 2 O<sup>2–</sup>(ads) : 7 CH<sub>2</sub>=CH<sub>2</sub> + 6 O<sub>2</sub> → 6 (CH<sub>2</sub>CH<sub>2</sub>)O + 2 CO<sub>2</sub> + 2 H<sub>2</sub>O
:O<sub>2</sub> + Ag → Ag<sup>+</sup> + O<sub>2</sub><sup>–</sup>
:O<sub>2</sub><sup>–</sup>(ads) + CH<sub>2</sub>=CH<sub>2</sub> → (CH<sub>2</sub>CH<sub>2</sub>)O + O(ads)
:6 O (ads) + CH<sub>2</sub>=CH<sub>2</sub> → 2 CO<sub>2</sub> + 2 H<sub>2</sub>O


and the maximum degree of conversion of ethylene to ethylene oxide is theoretically predicted to be 6/7 or 85.7%,<ref name="kilty"/> although higher yields are achieved in practice.<ref>{{cite journal |last1=Özbek |first1=M. O. |last2=van Santen |first2=R. A. |date=2013 |title=The Mechanism of Ethylene Epoxidation Catalysis |journal=Catalysis Letters |volume=143 |issue=2 |pages=131–141 |doi=10.1007/s10562-012-0957-3 |s2cid=95354803}}</ref>
Here (ads) refers to particles adsorbed on the catalyst surface and (adj) to particles of silver, directly adjacent to the oxygen atoms.


The catalyst for the reaction is metallic silver deposited on various matrixes, including ], ], various ]s and ]s, ], and ], and activated by certain additives (], ], ], etc.).<ref name="lebedev">{{cite book
Thus the overall reaction is expressed as
|author=Lebedev, N.N.
|title=Chemistry and Technology of Basic Organic and Petrochemical Synthesis
|year=1988
|edition=4
|publisher=Khimiya
|pages=420–424
|isbn=5-7245-0008-6
}}</ref> The process temperature was optimized as {{convert|220–280|C||sigfig=2}}. Lower temperatures reduce the activity of the catalyst, and higher temperatures promote the complete oxidation of ethylene thereby reducing the yield of ethylene oxide. Elevated pressure of {{convert|1-3|MPa||abbr=on}} increases the productivity of the catalyst and facilitates absorption of ethylene oxide from the reacting gases.<ref name="lebedev"/>


Whereas oxidation by air is still being used, oxygen (> 95% purity) is preferred for several reasons, such as higher molar yield of ethylene oxide (75–82% for oxygen vs. 63–75% for air), higher reaction rate (no gas dilution) and no need of separating nitrogen in the reaction products.<ref name="ect"/><ref>{{cite book
:7 CH<sub>2</sub>=CH<sub>2</sub> + 6 O<sub>2</sub> → 6 (CH<sub>2</sub>CH<sub>2</sub>)O + 2 CO<sub>2</sub> + 2 H<sub>2</sub>O
|author=Gunardson H.
|title=Industrial gases in petrochemical processing
|location=New York
|publisher=Marcel Dekker, Inc.
|year=1998
|pages=131–132
|isbn=0-8247-9908-9
}}</ref>


===Process overview===
and the maximum degree of conversion of ethylene to ethylene oxide is 6/7 or 85.7%.<ref name="kilty" />
The production of ethylene oxide on a commercial scale is attained with the unification of the following ]:
* Main reactor
* Ethylene oxide ]
* Ethylene oxide de-sorber
* ] and ]
* CO<sub>2</sub> scrubber and CO<sub>2</sub> de-scrubber


'''Main Reactor:''' The main reactor consists of thousands of catalyst tubes in bundles. These tubes are generally {{convert|6|to|15|m|abbr=on|round=5}} long with an inner diameter of {{convert|20|to|50|mm|abbr=on|1}}. The catalyst packed in these tubes is in the form of spheres or rings of diameter {{convert|3|to|10|mm|abbr=on}}. The operating conditions of {{convert|200-300|C||sigfig=2}} with a pressure of {{convert|1-3|MPa||abbr=on}} prevail in the reactor. To maintain this temperature, the cooling system of the reactor plays a vital role. With the aging of the catalyst, its selectivity decreases and it produces more exothermic side products of CO<sub>2</sub>.
The catalyst for the reaction is metallic silver deposited on various matrixes, including ], ], various ]s and ]s, ] and ], and activated by certain additives (], ], ], etc.).<ref name = "lebedev">{{cite book
|author = Lebedev, N.N.
|title = Chemistry and technology of basic organic and petrochemical synthesis
|edition = 4
|publisher = Khimiya
|pages = 420–424
|isbn = 5724500086}}</ref> The process temperature was optimized as 220–280 °C. Lower temperatures reduce the activity of the catalyst, and higher temperatures promote the complete oxidation of ethylene thereby reducing the yield of ethylene oxide. Elevated pressure of 1–3 MPa increases the productivity of the catalyst and facilitates absorption of ethylene oxide from the reacting gases.<ref name="lebedev" />


'''Ethylene oxide scrubber:''' After the gaseous stream from the main reactor, containing ethylene oxide (1–2%) and CO<sub>2</sub> (5%), is cooled, it is then passed to the ethylene oxide scrubber. Here, water is used as the scrubbing media which scrubs away majority of ethylene oxide along with some amounts of CO<sub>2</sub>, N<sub>2</sub>, CH<sub>2</sub>=CH<sub>2</sub>, CH<sub>4</sub> and ] (introduced by the recycle stream). Also, a small proportion of the gas leaving the ethylene oxide scrubber (0.1–0.2%) is removed continuously (combusted) to prevent the buildup of inert compounds (N<sub>2</sub>, Ar, and C<sub>2</sub>H<sub>6</sub>), which are introduced as impurities with the reactants.
Whereas oxidation by air is still being used, oxygen (> 95% purity) is preferred for several reasons, such as higher molar yield of ethylene oxide (75–82% for oxygen vs. 63–75% for air), higher reaction rate (no gas dilution) and no need of separating nitrogen in the reaction products.<ref name="ect" /><ref>{{cite book

|author = Gunardson H.
'''Ethylene oxide de-sorber:''' The aqueous stream resulting from the above scrubbing process is then sent to the ethylene oxide de-sorber. Here, ethylene oxide is obtained as the overhead product, whereas the bottom product obtained is known as the ''glycol bleed''. When ethylene oxide is scrubbed from the recycle gas with an aqueous solution, ethylene glycols (viz. mono-ethylene glycol, di-ethylene glycol and other poly-ethylene glycols) get unavoidably produced. Thus, in-order to prevent them from building up in the system, they are continuously bled off.
|title = Industrial gases in petrochemical processing

|location = New York
'''Stripping and distillation column:''' Here, the ethylene oxide stream is stripped off its low boiling components and then distilled in-order to separate it into water and ethylene oxide.
|publisher = Marcel Dekker, Inc.

|year = 1998
'''CO<sub>2</sub> scrubber:''' The recycle stream obtained from the ethylene oxide scrubber is compressed and a side-stream is fed to the CO<sub>2</sub> scrubber. Here, CO<sub>2</sub> gets dissolved into the hot aqueous solution of potassium carbonate (i.e., the scrubbing media). The dissolution of CO<sub>2</sub> is not only a physical phenomenon, but a chemical phenomenon as well, for, the CO<sub>2</sub> reacts with potassium carbonate to produce potassium hydrogen carbonate.
|pages = 131–132
: K<sub>2</sub>CO<sub>3</sub> + CO<sub>2</sub> + H<sub>2</sub>O → 2 KHCO<sub>3</sub>
|isbn = 0824799089}}</ref>

'''CO<sub>2</sub> de-scrubber:''' The above potassium carbonate solution (enriched with CO<sub>2</sub>) is then sent to the CO<sub>2</sub> de-scrubber where CO<sub>2</sub> is de-scrubbed by stepwise (usually two steps) ]. The first step is done to remove the hydrocarbon gases, and the second step is employed to strip off CO<sub>2</sub>.


===World production of ethylene oxide=== ===World production of ethylene oxide===
The world production of ethylene oxide was 19 million tonnes in 2008 and 18 million tonnes in 2007.<ref name="sri">{{cite web The world production of ethylene oxide was {{convert|20|Mt|e6ST|abbr=unit}} in 2009,<ref name=dutia/> {{convert|19|Mt|e6ST|abbr=unit}} in 2008 and {{convert|18|Mt|e6ST|abbr=unit}} in 2007.<ref name="sri">{{cite web
|title=Ethylene Oxide
|date = January 2009
|date=January 2009
|url = http://www.sriconsulting.com/WP/Public/Reports/eo/
|work=WP Report
|title = Ethylene Oxide
|publisher=SRI Consulting
|work = WP Report
|url=http://www.sriconsulting.com/WP/Public/Reports/eo/
|publisher = SRI Consulting
|accessdate = 2009-09-29}}</ref> This places ethylene oxide 14th most produced organic chemical, whereas the most produced one was ethylene with 113 million tonnes.<ref>{{cite web |access-date=29 September 2009}}</ref> This places ethylene oxide 14th most produced organic chemical, whereas the most produced one was ethylene with {{convert|113|Mt|e6ST|abbr=unit}}.<ref>{{cite web
|title=Ethylene
|date = January 2009
|date=January 2009
|url = http://www.sriconsulting.com/WP/Public/Reports/ethylene/
|work=WP Report
|title = Ethylene
|publisher=SRI Consulting
|work = WP Report
|url=http://www.sriconsulting.com/WP/Public/Reports/ethylene/
|publisher = SRI Consulting
|access-date=29 September 2009
|accessdate = 2009-09-29}}</ref> SRI Consulting forecasted the growth of consumption of ethylene oxide of 4.4% per year during 2008–2013 and 3% from 2013 to 2018.<ref name="sri" />
}}</ref> SRI Consulting forecasted the growth of consumption of ethylene oxide of 4.4% per year during 2008–2013 and 3% from 2013 to 2018.<ref name="sri"/>

In 2004, the global production of ethylene oxide by region was as follows:<ref name="iars"/>


{|class="wikitable" style="width:95%;"
In 2004, the global production of ethylene oxide by region was as follows:<ref name="iars" />
{| Class = "wikitable" width = 95% ! align="center" width=40%|Region
! Align = "center" width = 40%|Region ! align="center" width=30%|Number of major producers
! Align = "center" width = 30%|Number of major producers ! align="center" width=30%|Production, thousand tonnes
! Align = "center" width = 30%|Production, thousand tonnes
|- |-
|'''North America'''<br/> ]<br/> ]<br/> ] |'''North America'''<br>]<br>]<br>]
|align = "center"|<br/> 10<br/> 3<br/> 3 |style="text-align:center;"|<br>10<br>3<br>3
|align = "center"|<br/>4009<br/> 1084<br/> 350 |style="text-align:center;"|<br>4009<br>1084<br>350
|- |-
|'''South America'''<br/> ]<br/> ] |'''South America'''<br>]<br>]
|align = "center"|<br/> 2<br/> 1 |style="text-align:center;"|<br>2<br>1
|align = "center"|<br/>312<br/> 82 |style="text-align:center;"|<br>312<br>82
|- |-
|'''Europe'''<br/> ]<br/> ]<br/> ] <br/> ]<br/> ]<br/> ]<br/> ] <br/> ] |'''Europe'''<br>]<br>]<br>]<br>]<br>]<br>]<br>]<br>]
|align = "center"|<br/> 2<br/> 1<br/> 4<br/> 2<br/> 1<br/> 1<br/> 1<br/> no data |style="text-align:center;"|<br>2<br>1<br>4<br>2<br>1<br>1<br>1<br>No data
|align = "center"|<br/>770<br/> 215 <br/>995<br/> 460 <br/>100<br/> 115<br/>300<br/> 950 |style="text-align:center;"|<br>770<br>215<br>995<br>460<br>100<br>115<br>300<br>950
|- |-
|'''Middle East'''<br/> ]<br/> ]<br/> ] |'''Middle East'''<br>]<br>]<br>]
|align = "center"|<br/> 2<br/> 1<br/> 2 |style="text-align:center;"|<br>2<br>1<br>2
|align = "center"|<br/> 201 <br/>350<br/> 1781 |style="text-align:center;"|<br>201<br>350<br>1781
|- |-
|'''Asia'''<br/> ]<br/> ]<br/> ]<br/> ]<br/> ]<br/> ]<br/> ]<br/> ] |'''Asia'''<br>]<br>]<br>]<br>]<br>]<br>]<br>]<br>]
|align = "center"|<br/> No data<br/> 4<br/> 2<br/> 1<br/> 4<br/> 1<br/> 3<br/> 1 |style="text-align:center;"|<br>No data<br>4<br>2<br>1<br>4<br>1<br>3<br>1
|align = "center"|<br/> 1354<br/>820<br/> 488 <br/>175<br/>949<br/> 385 <br/>740<br/> 80 |style="text-align:center;"|<br>1354<br>820<br>488<br>175<br>949<br>385<br>740<br>80
|} |}


The world's largest producers of ethylene oxide are ] (3–3.5 million tonnes in 2006<ref name="aq">{{cite web The world's largest producers of ethylene oxide are ] ({{convert|3-3.5|Mt|e6ST|abbr=unit}} in 2006<ref name="aq">{{cite web
|author = Devanney M. T. |author=Devanney M. T.
|date = April 2007 |date=April 2007
|title=Ethylene Oxide
|url = http://www.sriconsulting.com/PEP/Public/Reports/Phase_2009/RP2I/
|work=SEH Peport
|title = Ethylene Oxide
|publisher=SRI Consulting
|work = SEH Peport
|url=http://www.sriconsulting.com/PEP/Public/Reports/Phase_2009/RP2I/
|publisher = SRI Consulting
|access-date=19 November 2009
|accessdate = 2009-11-19}}</ref>), ] (2000–2500 tonnes in 2006<ref name="aq" />), ] (1.328 million tonnes in 2008–2009<ref>{{cite web
}}</ref>), ] ({{convert|2000-2500|t|ST}} in 2006<ref name="aq"/>), ] ({{convert|1.328|Mt|e6ST|abbr=unit}} in 2008–2009<ref>{{cite web
|url = http://www.m-kagaku.co.jp/english/corporate/index.html
|title = Overview |title=Overview
|publisher = Mitsubishi Chemical Corporation |publisher=Mitsubishi Chemical Corporation
|df=dmy-all
|accessdate = 2009-10-12}}</ref><ref>{{cite web
|url=http://www.m-kagaku.co.jp/english/corporate/index.html
|url = http://www.shell.com/home/content/chemicals/products_services/our_products/ethylene_oxide_glycols/ethylene_glycols/manufacturing_locations/geismar/
|access-date=12 October 2009
|title = Shell Chemical LP – Geismar, United States of America
|url-status=dead
|work = Manufacturing locations
|archive-url=https://web.archive.org/web/20170225162257/http://www.m-kagaku.co.jp/english/corporate/index.html
|publisher = Shell Chemicals
|archive-date=25 February 2017
|accessdate = 2009-10-12}}</ref><ref>{{cite web
}}</ref><ref>{{cite web |title=Shell Chemical LP – Geismar, United States of America |work=Manufacturing locations |publisher=Shell Chemicals |url=http://www.shell.com/home/content/chemicals/products_services/our_products/ethylene_oxide_glycols/ethylene_glycols/manufacturing_locations/geismar/ |access-date=12 October 2009 |url-status=dead |archive-url=https://web.archive.org/web/20101018033052/http://www.shell.com/home/content/chemicals/products_services/our_products/ethylene_oxide_glycols/ethylene_glycols/manufacturing_locations/geismar/ |archive-date=18 October 2010}}</ref><ref>{{cite web |title=Shell Nederland Chemie BV – Moerdijk, Netherlands |work=Manufacturing locations |publisher=Shell Chemicals |url=http://www.shell.com/home/content/chemicals/products_services/our_products/ethylene_oxide_glycols/ethylene_glycols/manufacturing_locations/moerdijk/ |access-date=12 October 2009 |url-status=dead |archive-url=https://web.archive.org/web/20101018033102/http://www.shell.com/home/content/chemicals/products_services/our_products/ethylene_oxide_glycols/ethylene_glycols/manufacturing_locations/moerdijk/ |archive-date=18 October 2010}}</ref>), ] ({{convert|1.175|Mt|e6ST|abbr=unit}} in 2008–2009<ref>{{cite web
|url = http://www.shell.com/home/content/chemicals/products_services/our_products/ethylene_oxide_glycols/ethylene_glycols/manufacturing_locations/moerdijk/
|title=Segment Chemicals – Products
|title = Shell Nederland Chemie BV – Moerdijk, Netherlands
|date=28 February 2009
|work = Manufacturing locations
|publisher = Shell Chemicals |publisher=BASF
|url=http://www.report.basf.com/2008/en/subjects/products/chemicals.html
|accessdate = 2009-10-12}}</ref><ref>{{cite web
|access-date=12 October 2009
|url = http://www.cnoocshell.com/home/topic.aspx?topic=38
|url-status=dead
|title = Plants/Facilities and Capacity
|archive-url=https://web.archive.org/web/20160304223359/http://www.report.basf.com/2008/en/subjects/products/chemicals.html
|publisher = CNOOC and Shell Petrochemicals Company Limited
|archive-date=4 March 2016
|accessdate = 2009-10-12}}</ref>), ] (1.175 million tonnes in 2008–2009<ref>{{cite web
}}</ref>), ] (~{{convert|1|Mt|e6ST|abbr=unit}} in 2006<ref name="aq"/>), ] (~{{convert|1|Mt|e6ST|abbr=unit}} in 2006<ref name="aq"/>), and ] ({{convert|0.92|Mt|e6ST|abbr=unit}} in 2008–2009).<ref>{{cite web |title=Ethylene Oxide (EO) |publisher=Ineos Oxide |url=http://www.ineosoxide.com/21-Ethylene_Oxide__EO_.htm |access-date=12 October 2009 |url-status=dead |archive-url=https://web.archive.org/web/20130608060742/http://www.ineosoxide.com/21-Ethylene_Oxide__EO_.htm |archive-date=8 June 2013}}</ref>
|url = http://www.report.basf.com/2008/en/subjects/products/chemicals.html
|title = Segment Chemicals – Products
|publisher = BASF
|accessdate = 2009-10-12}}</ref>), ] (~1000 tonnes in 2006<ref name="aq" />), ] (~1 million tonnes in 2006<ref name="aq" />) and ] (0.92 million tonnes in 2008–2009).<ref>{{cite web
|url = http://www.ineosoxide.com/21-Ethylene_Oxide__EO_.htm
|title = Ethylene Oxide (EO)
|publisher = Ineos Oxide
|accessdate = 2009-10-12}}</ref>


==Applications== ==Applications==
] ]


Ethylene oxide is one of the most important raw materials used in the large-scale chemical production. Most ethylene oxide is used for synthesis of ]s, including diethylene glycol and triethylene glycol, that accounts for up to 75% of global consumption. Other important products include ethylene glycol ethers, ethanolamines and ethoxylates. Among glycols, ethylene glycol is used as ], in the production of ] and ] (PET – raw material for plastic bottles), liquid coolants and solvents. Polyethyleneglycols are used in perfumes, cosmetics, pharmaceuticals, ]s, ]s and ]s. Ethylene glycol ethers are part of brake fluids, detergents, solvents, lacquers and paints. Other products of ethylene oxide. Ethanolamines are used in the manufacture of soap and detergents and for purification of natural gas. Ethoxylates are reaction products of ethylene oxide with higher alcohols, acids or amines. They are used in the manufacture of detergents, surfactants, ]s and ]s.<ref>{{cite web Ethylene oxide is one of the most important raw materials used in large-scale chemical production. Most ethylene oxide is used for synthesis of ]s, including diethylene glycol and triethylene glycol, that accounts for up to 75% of global consumption. Other important products include ethylene glycol ethers, ethanolamines, and ethoxylates. Among glycols, ethylene glycol is used as ], in the production of ] and ] (PET – raw material for plastic bottles), liquid coolants, and solvents.
|url=http://www.shell.com/home/content/chemicals/products_services/our_products/ethylene_oxide_glycols/ethylene_glycols/product_overview/
|title = Ethylene oxide product overview
|work = Ethylene oxide
|publisher = Shell Chemicals
|accessdate = 2009-10-08}}</ref>


{| class="wikitable"
Whereas synthesis of ethylene glycols is the major application of ethylene oxide, its percentage varies greatly depending on the region: from 44% in the ], 63% in ] and 73% in ] to 90% in the rest of ] and 99% in ].<ref>{{cite web
|-
|url = http://www.icis.com/v2/chemicals/9075772/ethylene-oxide/uses.html
! Sector !! Demand share (%)
|title = Ethylene Oxide (EO) Uses and Market Data
|-
|work = Chemical Intelligence
| ] || 7
|publisher = Chemical Industry News & Intelligence (ICIS.com)
|-
|accessdate = 2009-10-08}}</ref>
| ] chemicals || 10
|-
| ] || 25
|-
| ] || 35
|-
| Personal care || 10
|-
| ] || 8
|-
| Others || 5
|-
| Total || 5.2{{nbsp}}Mt
|}


Polyethyleneglycols are used in perfumes, cosmetics, pharmaceuticals, ]s, ]s, and ]s. Ethylene glycol ethers are part of brake fluids, detergents, solvents, lacquers, and paints. Ethanolamines are used in the manufacture of soap and detergents and for purification of natural gas. Ethoxylates are reaction products of ethylene oxide with higher alcohols, acids, or amines. They are used in the manufacture of detergents, surfactants, ]s, and ]s.<ref>{{cite web |title=Ethylene oxide product overview |work=Ethylene oxide |publisher=Shell Chemicals |url=http://www.shell.com/home/content/chemicals/products_services/our_products/ethylene_oxide_glycols/ethylene_glycols/product_overview/ |access-date=8 October 2009 |url-status=dead |archive-url=https://web.archive.org/web/20101016145728/http://www.shell.com/home/content/chemicals/products_services/our_products/ethylene_oxide_glycols/ethylene_glycols/product_overview/ |archive-date=16 October 2010}}</ref>
=== Production of ethylene glycol ===
Ethylene glycol is industrially produced by non-catalytic hydration of ethylene oxide at a temperature of 200 °C and a pressure of 1.5–2 MPa:<ref name="MEG">{{cite book
|chapter= Ethylene
|title = Chemical Encyclopedia
| editor = IL Knunyants
|publisher = "Soviet encyclopedia"
|year = 1988
|volume = 5
|pages = 984–985}}</ref>


Whereas synthesis of ethylene glycols is the major application of ethylene oxide, its percentage varies greatly depending on the region: from 44% in the ], 63% in ], and 73% in ] to 90% in the rest of ], and 99% in ].<ref>{{cite web
: (CH<sub>2</sub>CH<sub>2</sub>)O + H<sub>2</sub>O → HOCH<sub>2</sub>CH<sub>2</sub>OH
|title=Ethylene Oxide (EO) Uses and Market Data
|work=Chemical Intelligence
|publisher=Chemical Industry News & Intelligence (ICIS.com)
|df=dmy-all
|url=http://www.icis.com/v2/chemicals/9075772/ethylene-oxide/uses.html
|access-date=8 October 2009
|url-status=dead
|archive-url=https://archive.today/20130128104012/http://www.icis.com/v2/chemicals/9075772/ethylene-oxide/uses.html
|archive-date=28 January 2013
}}</ref>


===Production of ethylene glycol===
By-products of the reaction are diethylene glycol, triethylene glycol and polyglycols with the total of about 10%, which are separated from the ethylene glycol by distillation at reduced pressure.<ref>{{cite book
Ethylene glycol is industrially produced by non-catalytic hydration of ethylene oxide at a temperature of {{convert|200|C|}} and a pressure of {{convert|1.5-2|MPa||abbr=on}}:<ref name="MEG">{{cite encyclopedia
|title = Handbook of Detergents, Part F: Production
|chapter=Ethylene
| editor=Uri Zoller, Paul Sosis
|title=Chemical Encyclopedia
|publisher = CRC Press
|editor=Knunyants, I. L.
|year = 2008
|encyclopedia=Soviet encyclopedia
|pages = 518–521
|year=1988
|isbn = 9780824703493}}</ref>
|volume=5
|pages=984–985
}}</ref>
: <chem>(CH2CH2)O + H2O -> HOCH2CH2OH</chem>


By-products of the reaction are diethylene glycol, triethylene glycol, and polyglycols with the total of about 10%, which are separated from the ethylene glycol by distillation at reduced pressure.<ref>{{cite book
Another synthesis method is the reaction of ethylene oxide and CO<sub>2</sub> (temperature 80–120 °C and pressure of 5.2 MPa) yielding ] and its subsequent hydrolysis with decarboxylation:<ref name = "MEG" />
|title=Handbook of Detergents, Part F: Production
|editor1=Zoller, Uri |editor2=Sosis, Paul |publisher=CRC Press
|year=2008
|pages=518–521
|isbn=978-0-8247-0349-3
}}</ref>


Another synthesis method is the reaction of ethylene oxide and CO2 (temperature {{convert|80–120|C|}} and pressure of {{convert|5.2|MPa||abbr=on}}) yielding ] and its subsequent hydrolysis with decarboxylation:<ref name="MEG"/>
: <math>\mathsf{(CH_2CH_2)O+CO_2}\rightarrow\mathsf{(O\!\!-\!\!CH_2CH_2\!\!-\!\!O)C\!\!=\!\!O\ \xrightarrow{+H_2O}\ HOCH_2CH_2OH}</math>
: <chem>(CH2CH2)O{} + CO2 -> \overset{ethylene\ carbonate}{(O-CH2CH_2-O)C=O} -> HOCH2CH2OH</chem>


Modern technologies of production of ethylene glycol include the following.<ref>{{cite web Modern technologies of production of ethylene glycol include the following.<ref>{{cite web
|author = Syed Naqvi|date = September 2009 |author=Naqvi, Syed |date=September 2009
|title=Process Economics Program Report 2I
|url = http://www.sriconsulting.com/PEP/Reports/Phase_2009/RP2I/
|work=PEP Peport
|title = Process Economics Program Report 2I
|publisher=SRI Consulting
|work = PEP Peport
|url=http://www.sriconsulting.com/PEP/Reports/Phase_2009/RP2I/
|publisher = SRI Consulting
|access-date=20 October 2009
|accessdate = 2009-10-20}}</ref> Shell OMEGA technology (Only Mono-Ethylene Glycol Advantage) is a two-step synthesis of ethylene carbonate using a ] halide as a catalyst. The glycol yield is 99–99.5%, with other glycols practically absent. The main advantage of the process is production of pure ethylene glycol without the need for further purification. The first commercial plant which uses this method was opened in 2008 in South Korea.<ref>, Shell</ref> Dow METEOR (Most Effective Technology for Ethylene Oxide Reactions) is an integrated technology for producing ethylene oxide and its subsequent hydrolysis into ethylene glycol. The glycol yield is 90–93%. The main advantage of the process is relative simplicity, using fewer stages and less equipment.
}}</ref> Shell OMEGA technology (Only Mono-Ethylene Glycol Advantage) is a two-step synthesis of ethylene carbonate using a ] halide as a catalyst. The glycol yield is 99–99.5%, with other glycols practically absent. The main advantage of the process is production of pure ethylene glycol without the need for further purification. The first commercial plant which uses this method was opened in 2008 in South Korea.<ref>, Shell (October 2008).</ref> Dow METEOR (Most Effective Technology for Ethylene Oxide Reactions) is an integrated technology for producing ethylene oxide and its subsequent hydrolysis into ethylene glycol. The glycol yield is 90–93%. The main advantage of the process is relative simplicity, using fewer stages and less equipment.


Conversion to ethylene glycol is also the means by which waste ethylene oxide is scrubbed before venting to the environment. Typically the EtO is passed over a matrix containing either sulfuric acid or potassium permanganate.{{citation needed|date=August 2018}}
=== Production of glycol ethers ===
The major industrial esters of mono-, di- and triethylene glycols are methyl, ethyl and normal butyl ethers, as well as their acetates and phthalates. The synthesis involves reaction of the appropriate ] with ethylene oxide:<ref>{{cite book
|title = Encyclopedia of chemical processing and design
|editor=John J. McKetta, William A. Cunningham
|location = New York
|publisher = Marcel Dekker, Inc
|year = 1984
|volume = 20
|pages = 259–260
|isbn = 0824724704}}</ref>


===Production of glycol ethers===
: (CH<sub>2</sub>CH<sub>2</sub>)O + ROH → HOCH<sub>2</sub>CH<sub>2</sub>OR
The major industrial esters of mono-, di-, and triethylene glycols are methyl, ethyl, and normal butyl ethers, as well as their acetates and phthalates. The synthesis involves reaction of the appropriate ] with ethylene oxide:<ref>{{cite book
|title=Encyclopedia of chemical processing and design
|editor1=McKetta, John J. |editor2=Cunningham, William A. |location=New York
|publisher=Marcel Dekker, Inc
|year=1984
|volume=20
|pages=259–260
|isbn=0-8247-2470-4
}}</ref>
: <chem>(CH2CH2)O + ROH -> HOCH2CH2OR</chem>
: <chem>(CH2CH2)O + HOCH2CH2OR -> HOCH2CH2OCH2CH2OR</chem>
: <chem>(CH2CH2)O + HOCH2CH2OCH2CH2OR -> HOCH2CH2OCH2CH2OCH2CH2OR</chem>


The reaction of monoesters with an acid or its anhydride leads to the formation of the esters:
: (CH<sub>2</sub>CH<sub>2</sub>)O + HOCH<sub>2</sub>CH<sub>2</sub>OR → HOCH<sub>2</sub>CH<sub>2</sub>OCH<sub>2</sub>CH<sub>2</sub>OR


: <chem>CH3CO2H + HOCH2CH2OR -> ROCH2CH2OCOCH3 + H2O</chem>
: (CH<sub>2</sub>CH<sub>2</sub>)O + HOCH<sub>2</sub>CH<sub>2</sub>OCH<sub>2</sub>CH<sub>2</sub>OR → HOCH<sub>2</sub>CH<sub>2</sub>OCH<sub>2</sub>CH<sub>2</sub>OCH<sub>2</sub>CH<sub>2</sub>OR


===Production of ethanolamines===
The reaction of monoesters with an acid or its anhydride leads to the formation of the esters:
In the industry, ]s (mono-, di-, and triethanolamines) are produced by reacting ] and ethylene oxide in anhydrous medium at a temperature of {{convert|40-70|C||-1}} and pressure of {{convert|1.5-3.5|MPa||abbr=on}}{{nbsp}}MPa:<ref>{{cite web
|title=Technology of ethanolamine
|work=Technology
|publisher=Himtek Engineering
|url=http://www.himtek.ru/cgi-bin/index.cgi?IdS=18&IdP=9&Lang=0
|access-date=22 October 2009
|archive-url=https://web.archive.org/web/20050302144745/http://www.himtek.ru/cgi-bin/index.cgi?IdS=18&IdP=9&Lang=0 |archive-date=2 March 2005
}}</ref>
: <chem>(CH2CH2)O + NH3 -> HOCH2CH2NH2</chem>
: <chem>2 (CH2CH2)O + NH3 -> (HOCH2CH2)2NH</chem>
: <chem>3 (CH2CH2)O + NH3 -> (HOCH2CH2)3N</chem>


All three ethanolamines are produced in the process, while ammonia and part of methylamine are recycled. The final products are separated by vacuum ]. Hydroxyalkylamines are produced in a similar process:
:CH<sub>3</sub>COOH + HOCH<sub>2</sub>CH<sub>2</sub>OR → ROCH<sub>2</sub>CH<sub>2</sub>OCOCH<sub>3</sub> + H<sub>2</sub>O


: <chem>(CH2CH2)O + RNH2 -> HOCH2CH2NHR</chem>
=== Production of ethanolamines ===
: <chem>2 (CH2CH2)O + RNH2 -> (HOCH2CH2)2NR</chem>
In the industry, ]s (mono-, di- and triethanolamines) are produced by reacting ] and ethylene oxide in anhydrous medium at a temperature of 40–70 °C and pressure of 1.5–3.5 MPa:<ref>{{cite web
|url = http://www.himtek.ru/cgi-bin/index.cgi?IdS=18&IdP=9&Lang=0
|title = Technology of ethanolamine
|work = Technology
|publisher = Himtek Engineering
|accessdate = 2009-10-22 |archiveurl = http://web.archive.org/web/20050302144745/http://www.himtek.ru/cgi-bin/index.cgi?IdS=18&IdP=9&Lang=0 |archivedate = 2005-03-02}}</ref>


Monosubstituted products are formed by reacting a large excess of amine with ethylene oxide in presence of water and at a temperature below {{convert|100|C|}}. Disubstituted products are obtained with a small excess of ethylene oxide, at a temperature of {{convert|120–140|C||-1}} and a pressure of {{convert|0.3-0.5|MPa||abbr=on|round=5}}.<ref>{{cite book
:CH<sub>2</sub>CH<sub>2</sub>)O + NH<sub>3</sub> → HOCH<sub>2</sub>CH<sub>2</sub>NH<sub>2</sub>
|vauthors=Chekalin MA, Passet BV, Ioffe BA
|title=The technology of organic dyes and intermediate products: A manual for technical
|edition=2 |publisher=Khimiya
|year=1980
|page=185
}}</ref><ref><span class="plainlinks"></span> NIOSH Workplace Safety and Health Topic. Retrieved 15 October 2012.</ref>


===Production of ethoxylates===
:2 (CH<sub>2</sub>CH<sub>2</sub>)O + NH<sub>3</sub> → (HOCH<sub>2</sub>CH<sub>2</sub>)<sub>2</sub>NH
{{Main|Ethoxylation}}
<!-- ] -->
Industrial production of ethoxylates is realized by a direct reaction of higher alcohols, acids, or amines with ethylene oxide in the presence of an alkaline catalyst at a temperature of {{convert|120–180|C||-1}}. Modern plants producing ethoxylates are usually based on the BUSS LOOP reactors technology,<ref name="buss">{{cite book
|title=Chemistry and technology of surfactants
|editor=Farn, R. J.
|publisher=Blackwell Publishing
|year=2006
|page=133
|isbn=1-4051-2696-5
}}</ref> which is based on a three-stage continuous process. In the first stage, the initiator or catalyst of the reaction and the feedstock are fed into the container, where they are mixed, heated, and vacuum dried. Then reaction is carried out in a special insulated reactor in an inert atmosphere (nitrogen) to prevent a possible explosion of ethylene oxide. Finally, the reaction mixture is neutralized, degassed, and purified.<ref>{{cite web |title=Alkoxylation |work=BUSS LOOP Reactor |publisher=Buss ChemTech AG |url=http://www.buss-ct.com/e/reaction_technology/alkoxylation.php?navid=36 |access-date=21 October 2009 |url-status=dead |archive-url=https://web.archive.org/web/20120308161412/http://www.buss-ct.com/e/reaction_technology/alkoxylation.php?navid=36 |archive-date=8 March 2012}}</ref>


===Production of acrylonitrile===
:3 (CH<sub>2</sub>CH<sub>2</sub>)O + NH<sub>3</sub> → (HOCH<sub>2</sub>CH<sub>2</sub>)<sub>3</sub>N
Currently, most ] (90% in 2008) is produced by the SOHIO method, which is based on the catalytic oxidation of ] in the presence of ammonia and bismuth phosphomolybdate. However, until 1960 a key production process was addition of ] to ethylene oxide, followed by dehydration of the resulting ]:<ref name="ACS Landmarks">{{cite web |title=The Sohio Acrylonitrile Process |work=National Historic Chemical Landmarks |publisher=American Chemical Society |url=http://portal.acs.org/portal/PublicWebSite/education/whatischemistry/landmarks/acrylonitrile/index.htm |access-date=25 June 2012 |url-status=dead |archive-url=https://archive.today/20130223214113/http://portal.acs.org/portal/PublicWebSite/education/whatischemistry/landmarks/acrylonitrile/index.htm |archive-date=23 February 2013}}</ref>
<ref>{{cite web
|title=13.1.3.5. Oxidative ammonolysis of hydrocarbons
|date=1 April 2009
|publisher=ChemAnalitica.com
|url=http://chemanalytica.com/book/novyy_spravochnik_khimika_i_tekhnologa/06_syre_i_produkty_promyshlennosti_organicheskikh_i_neorganicheskikh_veshchestv_chast_II/5015
|access-date=22 October 2009
}}</ref>
: {{chem2|(CH2CH2)O + HCN → HOCH2CH2CN}} {{underset|−{{chem2|H2O}}|→}} {{chem2|CH2\dCH\sCN}}


Addition of hydrocyanic acid to ethylene oxide is carried out in the presence of a catalyst (] and ]), and dehydration of cyanohydrin occurs in the gas phase upon the catalytic action of ].<ref>
All three ethanolamines are produced in the process, while ammonia and part of methylamine are recycled. The final products are separated by vacuum ]. Hydroxyalkylamines are produced in a similar process:
{{cite book
|author1=Andreas, F.
|author2=Grabe, K.
|title=Propylenchemie
|publisher=Akademie-Verlag
|year=1969
|pages=117–118
}}</ref>


==Non-industrial uses==
:CH<sub>2</sub>CH<sub>2</sub>)O + RNH<sub>2</sub> → HOCH<sub>2</sub>CH<sub>2</sub>NHR


The direct use of ethylene oxide accounts for only 0.05% (2004 data) of its global production.<ref name="iars"/> Ethylene oxide is used as a sterilizing agent, disinfecting agent and ] as a mixture with carbon dioxide (8.5–80% of ethylene oxide), nitrogen, or ] (12% ethylene oxide). It is applied for gas-phase sterilization of medical equipment and instruments, packaging materials, clothing, and surgical and scientific equipment;<ref name="iars">{{cite book
:2 (CH<sub>2</sub>CH<sub>2</sub>)O + RNH<sub>2</sub> → (HOCH<sub>2</sub>CH<sub>2</sub>)<sub>2</sub>NR
|chapter=Vol. 97. 1,3-Butadiene, Ethylene Oxide and Vinyl Halides (Vinyl Fluoride, Vinyl Chloride, and Vinyl Bromide)
|title=IARC Monographs on the Evaluation of Carcinogenic Risks to Humans
|location=Lyon
|publisher=International Agency for Research on Cancer
|year=2008
|chapter-url=http://monographs.iarc.fr/ENG/Monographs/vol97/
|pages=185–287
|isbn=978-92-832-1297-3
|df=dmy-all
|access-date=11 January 2019
|url-status=dead
|archive-url=https://web.archive.org/web/20161225052600/http://monographs.iarc.fr/ENG/Monographs/vol97/
|archive-date=25 December 2016
}}</ref> for processing of storage facilities (tobacco, packages of grain, sacks of rice, etc.), clothing, furs, and valuable documents.<ref name="ew">{{cite web |title=Ethylene oxide |work=Chemical Backgrounders Index |publisher=The Environment Writer |url=http://www.environmentwriter.org/resources/backissues/chemicals/ethylene_oxide.htm |access-date=29 September 2009 |url-status=dead |archive-url=https://web.archive.org/web/20060828211843/http://www.environmentwriter.org/resources/backissues/chemicals/ethylene_oxide.htm |archive-date=28 August 2006}}</ref>


===Healthcare sterilant===
Monosubstituted products are formed by reacting a large excess of amine with ethylene oxide in presence of water and at a temperature below 100 °C. Disubstituted products are obtained with a small excess of ethylene oxide, at a temperature of 120–140 °C and a pressure of 0.3–0.5 MPa.<ref>{{cite book
Ethylene oxide is one of the most commonly used sterilization methods in the healthcare industry because of its non-damaging effects for delicate instruments and devices that require sterilization, and for its wide range of material compatibility.<ref>{{cite web
|author = Chekalin MA, Passet BV, Ioffe BA
|title=Ethylene Oxide Sterilization
|title = The technology of organic dyes and intermediate products: A manual for technical
|edition = 2|publisher = Khimiya |publisher=Isometrix
|df=dmy-all
|year = 1980
|url=http://www.isomedix.com/services/eo-sterilization/
|page= 185}}</ref>
|url-status=bot: unknown
|archive-url=https://web.archive.org/web/20160402020015/http://www.isomedix.com/services/eo-sterilization/
|archive-date=2 April 2016
}}</ref> It is used for instruments that cannot tolerate heat, moisture, or abrasive chemicals, such as electronics, optical equipment, paper, rubber, and plastics.<ref>{{cite web
|title=3M on EtO sterilizers and EtO sterilization process.
|url=http://multimedia.3m.com/mws/mediawebserver?mwsId=SSSSSu7zK1fslxtUO8_x4x_Gev7qe17zHvTSevTSeSSSSSS--
|access-date=21 March 2013
}}</ref> It was developed in the 1940s as a sterilant by the US military, and its use as a medical sterilant dates to the late 1950s, when the McDonald process was patented for medical devices.<ref>{{cite web
|title=History of Ethylene Oxide
|publisher=Isometrix
|df=dmy-all
|url=http://www.isomedix.com/services/eo-sterilization/history-of-ethylene-oxide/
|url-status=bot: unknown
|archive-url=https://web.archive.org/web/20160402022440/http://www.isomedix.com/services/eo-sterilization/history-of-ethylene-oxide/
|archive-date=2 April 2016
}}</ref> The ] system was patented in the 1960s<ref>{{cite web
|title=Dr. H.W. Andersen's patent of Ethylene Oxide flexible chamber system.
|df=dmy-all
|url=http://www.ovguide.com/harold-willids-andersen-9202a8c04000641f800000000f160f69#
|access-date=21 March 2013
|url-status=dead
|archive-url=https://web.archive.org/web/20160306193908/http://www.ovguide.com/harold-willids-andersen-9202a8c04000641f800000000f160f69
|archive-date=6 March 2016
}}</ref> by Andersen Products,<ref>{{cite web
|title=Andersen Products
|url=http://anpro.com/index.htm
|access-date=21 March 2013
|url-status=dead
|archive-url=https://web.archive.org/web/20130226140948/http://anpro.com/index.htm
|archive-date=26 February 2013
}}</ref> and it remains the most commonly used system in several niche markets, notably the veterinary market and some international markets.<ref>{{cite web |title=University of Pennsylvania, EtO uses in veterinarian practices. |url=http://cal.vet.upenn.edu/projects/surgery/2220.htm |access-date=21 March 2013 |url-status=dead |archive-url=https://web.archive.org/web/20131109225657/http://cal.vet.upenn.edu/projects/surgery/2220.htm |archive-date=9 November 2013}}</ref> It relies on the use of a flexible sterilization chamber and an EtO cartridge for small volume sterilization, and where environmental and/or portability considerations dictate the use of a low dose. It is therefore referred to as the "flexible chamber sterilization" method, or the "gas diffusion sterilization" method.


In the United States, the operation of EtO sterilization is overseen by the ] through the ] (NESHAP).<ref>
=== Production of ethoxylates ===
{{cite web
<!-- ] -->
|last=US EPA
Industrial production of ethoxylates is realized by a direct reaction of higher alcohols, acids or amines with ethylene oxide in the presence of an alkaline catalyst at a temperature of 120–180 °C. Modern plants producing ethoxylates are usually based on the BUSS LOOP reactors technology,<ref name="buss">{{cite book
|first=OAR
|title = Chemistry and technology of surfactants
|title=Ethylene Oxide Emissions Standards for Sterilization Facilities: National Emission Standards for Hazardous Air Pollutants (NESHAP)
|editor= R. J. Farn
|format=Other Policies and Guidance
|publisher = Blackwell Publishing
|date=25 June 2015
|year = 2006
|url=https://www.epa.gov/stationary-sources-air-pollution/ethylene-oxide-emissions-standards-sterilization-facilities
|page = 133
|accessdate=30 December 2021
|isbn = 1405126965}}</ref> which is based on a three-stage continuous process. In the first stage, the initiator or catalyst of the reaction and the feedstock are fed into the container, where they are mixed, heated and vacuum dried. Then reaction is carried out in a special insulated reactor in an inert atmosphere (nitrogen) to prevent a possible explosion of ethylene oxide. Finally, the reaction mixture is neutralized, degassed and purified.<ref>{{cite web
}}
|url = http://www.buss-ct.com/e/reaction_technology/alkoxylation.php?navid=36
</ref>
|title = Alkoxylation
|work = BUSS LOOP Reactor
|publisher = Buss ChemTech AG
|accessdate = 2009-10-21}}</ref>


===Niche uses===
=== Production of acrylonitrile ===
Ethylene oxide is used as a ] and as an accelerator of maturation of tobacco leaves.<ref name="ew"/> Ethylene oxide is also used as a main component of ]s (fuel-air explosives).<ref name=e1>{{cite book |page=136 |title=Weapons of mass destruction: an encyclopedia of worldwide policy, technology, and history, Volume 2 |author1=Croddy, Eric |author2=Wirtz, James J. |isbn=1-85109-490-3 |publisher=ABC-CLIO |year=2005 |url=https://books.google.com/books?id=ZzlNgS70OHAC&pg=PA136}}</ref><ref name=e2>{{cite book |page= |title=Explosives |author1=Meyer, Rudolf |author2=Köhler, Josef |author3=Homburg, Axel |publisher=Wiley-VCH |year=2007 |isbn=978-3-527-31656-4 |url=https://archive.org/details/Explosives._6th_Edition}}</ref><ref>Hardy, Periam B.; Gay, Lewis L.; and Husler, Edward L. (2 January 1979) "Fuel-air type bomb" {{US patent|4132170}}</ref>
Currently, most ] (90% in 2008) is produced by the SOHIO method, which is based on the catalytic oxidation of ] in the presence of ammonia and bismuth phosphomolybdate. However, until 1960 a key production process was addition of ] to ethylene oxide, followed by dehydration of the resulting ]:<ref>{{cite web
|url = http://acswebcontent.acs.org/landmarks/landmarks/soh/soh_process.html
|title = The Sohio Acrylonitrile Process
|publisher = National Historic Chemical Landmarks
|accessdate = 2009-10-22}}</ref><ref>{{cite web
|date = 1 April 2009
|url = http://chemanalytica.com/book/novyy_spravochnik_khimika_i_tekhnologa/06_syre_i_produkty_promyshlennosti_organicheskikh_i_neorganicheskikh_veshchestv_chast_II/5015
|title = 13.1.3.5. Oxidative ammonolysis of hydrocarbons
|publisher = ChemAnalitica.com
|accessdate = 2009-10-22}}</ref>:


==Identification of ethylene oxide==
: <math>\mathsf{(CH_2CH_2)O+HCN}\rightarrow\mathsf{HOCH_2CH_2CN\ \xrightarrow\ CH_2\!\!=\!\!CH\!\!-\!\!CN }</math>
] is the principal method for analysis and detection of ethylene oxide.<ref name="iars"/>


An inexpensive test for ethylene oxide exploits its precipitation of solid hydroxides of metals when it is passed through aqueous solutions of their salts:
Addition of hydrocyanic acid to ethylene oxide is carried out in the presence of a catalyst (] and ]), and dehydration of cyanohydrin occurs in the gas phase upon the catalytic action of ].<ref>
{{cite book
|author = Andreas F., Grabe K.
|title = Propylenchemie|publisher =Akademie-Verlag
|year = 1969
|pages = 117–118}}</ref>


: <chem>2 (CH2CH2)O + MnCl2 + 2 H2O -> 2 HO-CH2CH2-Cl + Mn(OH)2 v</chem>
===Other uses===
The direct use of ethylene oxide accounts for only 0.05% (2004 data) of its global production.<ref name="iars" /> Ethylene oxide is used as a ] and disinfecting agent, as a mixture with carbon dioxide (8.5–80% of ethylene oxide), nitrogen or ] (12% ethylene oxide). It is applied for gas-phase sterilization of medical equipment and instruments, packaging materials and clothing, surgical and scientific equipment;<ref name="iars">{{cite book
|title = 1,3-Butadiene, Ethylene Oxide and Vinyl Halides (Vinyl Fluoride, Vinyl Chloride and Vinyl Bromide)
| edition = IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, Vol. 97
|location = Lyon
|publisher = International Agency for Research on Cancer
|year = 2008
|pages = 185–287
|isbn = 9789283212973}}</ref> for processing of storage facilities (tobacco, packages of grain, sacks of rice, etc.), clothing, furs and valuable documents.<ref name="ew">{{cite web
|url = http://www.environmentwriter.org/resources/backissues/chemicals/ethylene_oxide.htm
|title = Ethylene oxide
|work = Chemical Backgrounders Index
|publisher = The Environment Writer
|accessdate = 2009-09-29}}</ref>


Similarly, ethylene oxide is detected by the bright pink color of the indicator when passing air through aqueous solutions of some salts of sodium or potassium (chlorides, iodides, thiosulfates, etc.) with the addition of ]:<ref name="oe4">{{cite book
Ethylene oxide is also used as a flame retardant, accelerator of maturation of tobacco leaves and ].<ref name="ew" /> Ethylene oxide is also used as a main component of ]s (fuel-air explosives).<ref name=e1>{{cite book|url=http://books.google.com/?id=ZzlNgS70OHAC&pg=PA136|page=136|title=Weapons of mass destruction: an encyclopedia of worldwide policy, technology, and history, Volume 2|author=Eric Croddy, James J. Wirtz|isbn=1851094903|publisher=ABC-CLIO|year=2005}}</ref><ref name=e2>{{cite book|url=http://books.google.com/?id=ATiYCfo1VcEC&pg=PA142|page=142|title=Explosives|author=Rudolf Meyer, Josef Köhler, Axel Homburg|publisher=Wiley-VCH|year=2007|isbn=3527316566}}</ref><ref>{{cite web
|chapter=Chapter IV Methods of analysis of ethylene oxide
|url = http://www.freepatentsonline.com/4132170.pdf
|title=Ethylene oxide
|title = United States Patent 4132170. Fuel-air type bomb
|editor1=Zimakov, P.V.
|accessdate = 2009-10-22}}</ref>
|editor2=Dyment, O.H.
|publisher=Khimiya
|year=1967
|pages=128–140
}}</ref>


: <chem>(CH2CH2)O + NaCl + H2O -> HO-CH2CH2-Cl + NaOH</chem>
==Identification of ethylene oxide==


Other methods of ethylene oxide detection are<ref name="oe4"/> color reactions with ] derivatives and hydrolysis of ethylene glycol with ]. The produced ] is detected with ].
The simplest qualitative reaction for ethylene oxide uses its property to precipitate insoluble hydroxides of metals when it is passed through aqueous solutions of their salts, for example


{{anchor|Fire and explosion hazards}}
:2 (CH<sub>2</sub>CH<sub>2</sub>)O + MnCl<sub>2</sub> + 2 H<sub>2</sub>O → 2 HO–CH<sub>2</sub>CH<sub>2</sub>–Cl + Mn(OH)<sub>2</sub>↓


==Accidents==
Similarly, ethylene oxide is detected by the bright pink color of the indicator when passing air through aqueous solutions of some salts of sodium or potassium (chlorides, iodides, thiosulfates, etc.) with the addition of ]:<ref name="oe4">{{cite book
Ethylene oxide is extremely flammable, and its mixtures with air are explosive. When heated it may rapidly expand, causing fire and explosion.<ref>{{cite web |title=Ethylene oxide |work=ICSC/International Chemical Safety Cards |publisher=Institute of Industrial Safety, Labour Protection and Social Partnership |url=http://www.safework.ru/ilo/ICSC/cards/view/?0155 |access-date=21 September 2009 |url-status=dead |archive-url=https://web.archive.org/web/20051228201427/http://www.safework.ru/ilo/ICSC/cards/view/?0155 |archive-date=28 December 2005}}</ref> Several industrial accidents have been attributed to ethylene oxide explosion.<ref>{{cite web |title=CSB Issues Final Report in 2004 Explosion at Sterigenics International Facility in Ontario, California: Notes Lack of Engineering Controls, Understanding of Process Hazards – Investigations – News – CSB |website=csb.gov |url=http://www.csb.gov/csb-issues-final-report-in-2004-explosion-at-sterigenics-international-facility-in-ontario-california-notes-lack-of-engineering-controls-understanding-of-process-hazards/ |access-date=29 March 2018}}</ref><ref>{{cite web |title=Ethylene Oxide Explosion at Sterigenics – Safety Videos – Multimedia – CSB |website=csb.gov |url=http://www.csb.gov/videos/ethylene-oxide-explosion-at-sterigenics/ |access-date=29 March 2018}}</ref><ref>{{cite web |title=OSHA Inspection Detail |website=osha.gov |url=https://www.osha.gov/pls/imis/establishment.inspection_detail?id=105522072 |access-date=24 May 2018}}</ref>
|chapter = Chapter IV Methods of analysis of ethylene oxide
|title = Ethylene oxide
|editor=PV Zimakova and Mr. O. Dymenta
|publisher = Khimiya
|year = 1967
|pages = 128–140}}</ref>


The ] is {{convert|429|C|}}, ] of {{convert|571|C|}} at {{convert|101.3|kPa||abbr=on}}, minimum inflammable content in the air is 2.7%,<ref>{{cite web
: (CH<sub>2</sub>CH<sub>2</sub>)O + NaCl + H<sub>2</sub>O → HO–CH<sub>2</sub>CH<sub>2</sub>–Cl + NaOH
|year=1988
|title=Ethylene Oxide
|work=Health and Safety Guide
|publisher=International Programme on Chemical Safety (IPCS) INCHEM
|url=http://www.inchem.org/documents/hsg/hsg/hsg016.htm
|access-date=23 September 2009
}}</ref> and maximum limit is 100%. The NFPA 704 rating is Health, 3; Flammability, 4; Instability 2.<ref>{{cite web |title=ETHYLENE OXIDE WITH NITROGEN {{!}} CAMEO Chemicals {{!}} NOAA |website=cameochemicals.noaa.gov |url=https://cameochemicals.noaa.gov/chemical/19324 |access-date=2023-03-21}}</ref> Ethylene oxide in presence of water can hydrolyze to ethylene glycol and form polyethylene oxide, which then eventually is oxidized by air and leads to ] that can trigger explosive decomposition.


Fires caused by ethylene oxide are extinguished with conventional media including ], carbon dioxide, or water. Suppression of this activity can be done by blanketing with an ] until total pressure reaches the nonexplosive range. Extinguishing of burning ethylene oxide is complicated by its ability to continue burning in an inert atmosphere and in water solutions. Fire suppression is reached only upon dilution with water above 22:1.<ref>{{cite web
Other methods of ethylene oxide detection are<ref name="oe4" /> color reactions with ] derivatives and hydrolysis of ethylene glycol with ]. The produced ] is detected with ].
|title=Ethylene Oxide Safety Literature
|publisher=Shell Chemicals
|url=http://s01.static-shell.com/content/dam/shell/static/chemicals/downloads/products-services/ethylene-oxide-safetyliteraturevi.pdf
|access-date=23 October 2009
|url-status=dead
|archive-url=https://web.archive.org/web/20160303235017/http://s01.static-shell.com/content/dam/shell/static/chemicals/downloads/products-services/ethylene-oxide-safetyliteraturevi.pdf
|archive-date=3 March 2016
}}</ref>


===La Canonja, Spain accident===
The main physical method of ethylene oxide detection is ].<ref name="iars" />
On 14 January 2020 in an industrial estate near ], an explosion of an ethoxylation reactor owned by the chemical company Industrias Quimicas de Oxido de Etileno (IQOXE, part of the CL Industrial Group) occurred.<ref>{{cite web |title=Tarragona chemicals park running normally after IQOXE blast leaves two dead |last=Lopez |first=Jonathan |website=Icis |url=https://www.icis.com/explore/resources/news/2020/01/15/10459345/tarragona-chemicals-park-running-normally-after-iqoxe-blast-leaves-two-dead |access-date=16 January 2020}}</ref><ref>Galocha, A.; Zafra, M.; and Clemente, Y. (16 January 2020) . ''El País''</ref> The accident launched substantial debris over a radius of about two and a half kilometers, one piece penetrating a distant home and killing an occupant.<ref>. ''BBC''. 15 January 2020</ref> It is reported that at least three people were killed and seven injured as a direct result of the explosion.<ref>. ''El Mundo''. 15 January 2020</ref>


The company was, until the time of the explosion the only producer of ethylene oxide in Spain with an installed capacity of 140,000 tons/year. Half of that production was used to manufacture ethylene glycol for PET production.<ref>. IQOXE Company</ref> The accident will be investigated under EU regulations within the context of the ].
==Fire and explosion hazards==
Ethylene oxide is extremely flammable and its mixtures with air are explosive. When heated, it may rapidly expand causing fire and explosion.<ref>{{cite web
|url = http://www.safework.ru/ilo/ICSC/cards/view/?0155
|title = Ethylene oxide
|work = ICSC/International Chemical Safety Cards
|publisher = Institute of Industrial Safety, Labour Protection and Social Partnership
|accessdate = 2009-09-21}}</ref> The ] is 429 °C, minimum inflammable content in the air is 2.7%,<ref>{{cite web
|year = 1988
|url = http://www.inchem.org/documents/hsg/hsg/hsg016.htm
|title = Ethylene Oxide
|work = Health and Safety Guide
|publisher = International Programme on Chemical Safety (IPCS) INCHEM
|accessdate = 2009-09-23}}</ref> and the NPFA rating is ].<ref>{{cite web
|date = January 10, 2009
|url = http://www.sonoma-county.org/des/pdf/fire/bulletins/info_bulletin_nfpa_marking2009_04n.pdf
|title = Informational Bulletin NFPA-04N 2009
|publisher = Department of Emergency Services, County of Sonoma
|accessdate = 2009-10-23}}</ref>


===2020 sesame seeds contamination===
Fires caused by ethylene oxide are extinguished by traditional media, including foam, carbon dioxide or water. Extinguishing of burning ethylene oxide is complicated by that it can continue burning in an inert atmosphere and in water solutions. Fire suppression is reached only upon dilution with water above 22:1.<ref>{{cite web
In September 2020, high levels of ] were found in 268 tonnes of ] seeds from ]. The contamination had a level of 1000 to 3500 times the limit of 0.05 milligrams per kilogram for ethylene oxide allowed in ]. This pesticide is forbidden in Europe, where it is recognized to be ] and ]. A ] was made, half of the products had an ].<ref>{{cite web |title=EU toughens rules for sesame seeds from India |date=30 September 2020 |author=Clark, Marler |work=Food Safety News |url=https://www.foodsafetynews.com/2020/09/multi-country-recalls-due-to-ethylene-oxide-in-sesame-seeds/}}</ref><ref>{{cite web |title=franceinfo conso. A carcinogenic pesticide in sesame seeds |work=Pledge Times |author=Mandalia, Bhavi |date=21 November 2020 |url=https://pledgetimes.com/franceinfo-conso-a-carcinogenic-pesticide-in-sesame-seeds-2/ |archive-url=https://web.archive.org/web/20201201133316/https://pledgetimes.com/franceinfo-conso-a-carcinogenic-pesticide-in-sesame-seeds-2/ |archive-date=1 December 2020}}</ref>
|url = http://www-static.shell.com/static/chemicals/downloads/products_services/ethylene_oxide_safety_literature.pdf

|title = Ethylene Oxide Safety Literature
In September, alert was raised by Belgium by RASFF, but the product has also been sold in other EU single market countries such as France<ref>. economie.gouv.fr</ref> and Ireland.
|publisher = Shell Chemicals
|accessdate = 2009-10-23}}</ref>


==Physiological effects== ==Physiological effects==

===Effect on microorganisms=== ===Effect on microorganisms===
Exposure to ethylene oxide gas causes ] to microorganisms at a nuclear level.<ref>{{cite web |title=Ethylene Oxide Sterilization |website=NASPCO |url=http://naspco.com/sterilization/ |access-date=10 February 2017 |url-status=dead |archive-url=https://web.archive.org/web/20180708031254/http://naspco.com/sterilization/ |archive-date=8 July 2018}}</ref> The disinfectant effect of ethylene oxide is similar to that of sterilization by heat, but because of limited penetration, it affects only the surface. ETO sterilization can take up to 12 hours due to its slow action upon microorganisms, and lengthy processing and aeration time.<ref>{{cite web |title=Ethylene Oxide (ETO): Properties, Mode of Action and Uses |date=26 December 2013 |website=Microbe Online |url=https://microbeonline.com/ethylene-oxide-eto-properties-mode-action-uses/author=Tankeshwar, |access-date=10 February 2017}}{{Dead link|date=March 2022 |bot=InternetArchiveBot |fix-attempted=yes}}</ref>
Ethylene oxide inhibits growth of microorganisms (]) and when present in high concentrations, can completely destroy them. Strong alkylating properties make ethylene oxide a universal poison for ]: it causes clotting of proteins, deactivation of ]s and other biologically important components of a living organism.<ref name="kons">{{cite web

|url = http://www.konservanti.com/veshestva32.html
===Effects on humans and animals===
|title = Ethylene oxide
Ethylene oxide is an ]; it has irritating, sensitizing, and narcotic effects.<ref name="ChemAnalitica11">{{cite web
|work = Preserving agents
|title=Harmful substances. Section 4. Heterocyclic compounds. Triplex heterocyclic compounds
|publisher = preservatives in food industry
|date=1 April 2009
|accessdate = 2009-09-25}}</ref>
|publisher=ChemAnalitica.com
|url=http://chemanalytica.com/book/novyy_spravochnik_khimika_i_tekhnologa/11_radioaktivnye_veshchestva_vrednye_veshchestva_gigienicheskie_normativy/5177
|access-date=21 September 2009
}}</ref> Chronic exposure to ethylene oxide is also ]ic. The ] classifies ethylene oxide into group 1, meaning it is a proven ].<ref name="basesafework" >{{cite encyclopedia
|author=Collins J. L.
|title=Epoxy compounds
|encyclopedia=Encyclopedia of the ILO
|publisher=Institute of Industrial Safety, Labour Protection and Social Partnership
|url=http://base.safework.ru/iloenc?hdoc&nd=857300040&nh=0
|access-date=25 September 2009}}</ref><ref>{{cite book
|chapter=Vol. 60. Some Industrial Chemicals
|title=IARC Monographs on the Evaluation of Carcinogenic Risks to Humans
|location=Lyon
|publisher=International Agency for Research on Cancer
|year=1999
|chapter-url=http://monographs.iarc.fr/ENG/Monographs/vol60/
|isbn=978-92-832-1297-3
|df=dmy-all
|access-date=28 June 2007
|url-status=dead
|archive-url=https://web.archive.org/web/20160303232338/http://monographs.iarc.fr/ENG/Monographs/vol60/
|archive-date=3 March 2016
}}</ref> Ethylene oxide is classified as a class 2 carcinogen by the German MAK commission and as a class A2 carcinogen by the ACGIH. A 2003 study of 7,576 women exposed while at work in commercial sterilization facilities in the US suggests ethylene oxide is associated with ] incidence.<ref>{{cite journal |title=Ethylene oxide and breast cancer incidence in a cohort study of 7576 women (United States) |year=2003 |last1=Steenland |first1=K. |journal=Cancer Causes and Control |volume=14 |issue=6 |pages=531–9 |last2=Whelan |first2=E. |last3=Deddens |first3=J. |last4=Stayner |first4=L. |last5=Ward |first5=E. |pmid=12948284 |doi=10.1023/A:1024891529592 |s2cid=20888472}}</ref> A 2004 follow up study analyzing 18,235 men and women workers exposed to ethylene oxide from 1987 to 1998 concluded "There was little evidence of any excess cancer mortality for the cohort as a whole, with the exception of ] based on small numbers. Positive exposure-response trends for lymphoid tumors were found for males only. Reasons for the sex specificity of this effect are not known. There was also some evidence of a positive exposure-response for breast cancer mortality."<ref>{{cite journal
|title=Mortality analyses in a cohort of 18 235 ethylene oxide exposed workers: Follow up extended from 1987 to 1998
|last1=Steenland
|first1=K
|year=2004
|journal=Occupational and Environmental Medicine
|volume=61 |issue=1
|pages=2–7
|last2=Stayner
|first2=L
|last3=Deddens
|first3=J
|pmid=14691266
|pmc=1757803
}}</ref> An increased incidence of brain tumors and mononuclear cell leukemia was found in rats that had inhaled ethylene oxide at concentrations of {{convert|10|,|33|or|abbr=on|100|mL/m3}} over a period of two years.<ref name=msds2>. Agency for Toxic Substances and Disease Registry, US Public Health Services</ref> An increased incidence of peritoneal mesotheliomas was also observed in the animals exposed to concentrations of {{convert|33|and|100|mL/m3|abbr=on|4}}. Results of human epidemiological studies on workers exposed to ethylene oxide differ. There is evidence from both human and animal studies that inhalation exposure to ethylene oxide can result in a wide range of carcinogenic effects.

Ethylene oxide is toxic by inhalation, with a US ] permissible exposure limit calculated as a TWA (time weighted average) over 8 hours of 1{{nbsp}}ppm, and a short term exposure limit (excursion limit) calculated as a TWA over 15 minutes of 5{{nbsp}}ppm.<ref name="msds"/> At concentrations in the air about 200 parts per million, ethylene oxide irritates ]s of the nose and throat; higher contents cause damage to the trachea and bronchi, progressing into the partial collapse of the lungs. High concentrations can cause ] and damage the cardiovascular system; the damaging effect of ethylene oxide may occur only after 72 hours after exposure.<ref name="atsdr"/> The maximum content of ethylene oxide in the air according to the US standards (]) is {{convert|1.8|mg/m3||abbr=on}}.<ref>{{cite book
|author1=Carson P.A. |author2=Mumford C.J. |title=Hazardous Chemicals Handbooks
|location=Oxford
|publisher=Butterworth-Heinemann Ltd
|year=1994
|page=85
|isbn=0-7506-0278-3
}}</ref> ] has determined that the Immediately Dangerous to Life and Health level (IDLH) is 800 ppm.<ref>. Cdc.gov. Retrieved on 8 May 2017.</ref>


Because the odor threshold for ethylene oxide varies between 250 and 700 ppm, the gas is already at toxic concentrations when it can be smelled. Even then, the odor of ethylene oxide is sweet and aromatic and can easily be mistaken for the aroma of ], a common laboratory solvent of very low toxicity. In view of these insidious properties, continuous electrochemical monitoring is standard practice, and it is forbidden to use ethylene oxide to fumigate building interiors in the ] and some other jurisdictions.<ref name=bnpuk>{{cite web
Ethylene oxide acts more strongly against bacteria, especially ], than against ] and fungi.<ref name = "kons" /> The disinfectant effect of ethylene oxide is similar to that of sterilization by heat, but because of limited penetration, it affects only the surface. The Sterility Assurance Level, after a certain specified exposure to ethylene oxide is 10<sup>−6</sup>, meaning that the chance of finding a single bacterium is below 1 per million.<ref>{{cite web
|last=Chemicals Regulation Directorate
|author = Conviser S.
|title=Banned and Non-Authorised Pesticides in the United Kingdom
|url = http://www.infectioncontroltoday.com/articles/061feat4.html
|url=http://www.pesticides.gov.uk/guidance/industries/pesticides/topics/pesticide-approvals/pesticides-registration/Withdrawal-and-Restrictions/banned-and-non-authorised-pesticides |access-date=1 December 2009
|title = The Future of Ethylene Oxide Sterilization
|publisher = ICT Magazine
|accessdate = 2009-10-23
}}</ref> }}</ref>


Ethylene oxide causes acute poisoning, accompanied by a variety of symptoms.<ref name="ChemAnalitica11"/> Central nervous system effects are frequently associated with human exposure to ethylene oxide in occupational settings. Headache, nausea, and vomiting have been reported.{{clarify|date=February 2017|reason="50 years of reports and/or 50 years of symptoms post-exposure?"}} Peripheral neuropathy, impaired hand-eye coordination and memory loss have been reported in more recent case studies of chronically-exposed workers at estimated average exposure levels as low as 3 ppm (with possible short-term peaks as high as 700{{nbsp}}ppm).<ref name=msds2/> The metabolism of ethylene oxide is not completely known. Data from animal studies indicate two possible pathways for the metabolism of ethylene oxide: hydrolysis to ethylene glycol and glutathione conjugation to form ] and meththio-metabolites.
===Effects on humans and animals===
Ethylene oxide is an ]; it has irritating, sensitizing and narcotic effects.<ref name="ChemAnalitica11">{{cite web
|date = 1 April 2009
|url = http://chemanalytica.com/book/novyy_spravochnik_khimika_i_tekhnologa/11_radioaktivnye_veshchestva_vrednye_veshchestva_gigienicheskie_normativy/5177
|title = Harmful substances. Section 4. Heterocyclic compounds. Triplex heterocyclic compounds
|publisher = ChemAnalitica.com
|accessdate = 2009-09-21}}</ref> Chronic exposure to ethylene oxide also induces ]. The ] classifies ethylene oxide into group 1, meaning it is a proven ].<ref name = "basesafework" >{{cite web
|author = Collins J. L.
|url = http://base.safework.ru/iloenc?hdoc&nd=857300040&nh=0
|title = Epoxy compounds
|work = Encyclopedia of the ILO
|publisher = Institute of Industrial Safety, Labour Protection and Social Partnership
|accessdate = 2009-09-25}}</ref><ref></ref> A 2003 study of 7,576 women exposed while at work in commercial sterilization facilities in the U.S. suggests ethylene oxide is associated with ] incidence.<ref>{{cite journal |journal=Cancer Causes Control |year=2003 |volume=14 |issue=6 |pages=531–9 |title=Ethylene oxide and breast cancer incidence in a cohort study of 7576 women (United States) |author=Steenland K, Whelan E, Deddens J, Stayner L, Ward E |pmid=12948284 |doi=10.1023/A:1024891529592}}</ref> A 2004 follow up study analyzing 18,235 men and women workers exposed to ethylene oxide from 1987 to 1998 concluded "There was little evidence of any excess cancer mortality for the cohort as a whole, with the exception of ] based on small numbers. Positive exposure-response trends for lymphoid tumors were found for males only. Reasons for the sex specificity of this effect are not known. There was also some evidence of a positive exposure-response for breast cancer mortality."<ref>{{cite journal |journal=Occup Environ Med |year=2004 |volume=61 |issue=1 |pages=2–7 |title=Mortality analyses in a cohort of 18 235 ethylene oxide exposed workers: follow up extended from 1987 to 1998 |author=Steenland K, Stayner L, Deddens J |pmid=14691266 |pmc=1757803}}</ref>


Ethylene oxide easily penetrates through ordinary clothing and footwear, causing skin irritation and dermatitis with the formation of blisters, fever, and ].<ref name="ChemAnalitica11"/>
Ethylene oxide is toxic by inhalation with an U.S. ] permissible exposure limit of 1 ppm calculated as a time weighted average (TWA) over 8 hours of 1 ppm, and a short term exposure limit (excursion limit) calculated as a TWA over 15 minutes of 5 ppm. . At concentrations in the air about 200 parts per million, ethylene oxide irritates ]s of the nose and throat; higher contents cause damage to the trachea and bronchi, progressing into the partial collapse of the lungs. High concentrations can cause ] and damage the cardiovascular system; the damaging effect of ethylene oxide may occur only after 72 hours after exposure.<ref name="atsdr" /> The maximum content of ethylene oxide in the air according to the U.S. standards (]) is 1.8&nbsp;mg/m<sup>3</sup>.<ref>{{cite book
|author = Carson P.A., Mumford C.J.
|title = Hazardous Chemicals Handbooks
|location = Oxford
|publisher = Butterworth-Heinemann Ltd
|year = 1994
|page = 85
|isbn = 0750602783
}}</ref> ] has determined that the Immediately Dangerous to Life and Health level (IDLH) is 800 ppm.<ref></ref>


Toxicity data for ethylene oxide are as follows:<ref name="msds">{{cite book |author=Simmons, H. Leslie |title=Building Materials: Dangerous Properties of Products in MasterFormat Divisions 7 and 9 |year=1997 |publisher=John Wiley & Sons |isbn=978-0-442-02289-1 |page=146 |url=https://books.google.com/books?id=MH9DrW0UGvwC&pg=PA146}} {{Webarchive|url=https://web.archive.org/web/20150402124719/http://chemistry.umeche.maine.edu/Safety/ReadMSDS.html |date=2 April 2015}}.</ref>
Because the odor threshold for ethylene oxide varies between 250 and 700 ppm, the gas will already be at toxic concentrations when it can be smelled. Even then, the odor of ethylene oxide is sweet, aromatic, and can easily be mistaken for the pleasant aroma of ], a common laboratory solvent of very low toxicity. In view of these insidious warning properties, continuous electrochemical monitors are standard practice, and it is forbidden to use ethylene oxide to fumigate building interiors in the ] and some other jurisdictions.<ref name=bnpuk>{{cite web
* Eye exposure: {{convert|18|mg||abbr=on}}/6 hours (rabbit)
| last = Chemicals Regulation Directorate
* Oral: {{convert|72|mg/kg||abbr=on}} (rat, ]), {{convert|1186|mg/kg||abbr=on}} (rat, ]), {{convert|5112|mg/kg||abbr=on}} (rat, ])
| title = Banned and Non-Authorised Pesticides in the United Kingdom
* Inhalation: 12,500 ppm (human, ]), 960 ppm/4 hours (dog, ]) 33–50 ppm (rat or mouse, TC), 800 ppm/4 hours (rat or mouse, LC<sub>50</sub>)
| url = http://www.pesticides.gov.uk/approvals.asp?id=55| accessdate = 1 December 2009}}</ref>
* ]: {{convert|100|mg/kg||abbr=on}} (cat, LD<sub>Lo</sub>), {{convert|292|mg/kg||abbr=on}} (mouse, TD<sub>Lo</sub>) {{convert|900-2600|mg/kg||abbr=on}} (mouse, TD), {{convert|187|mg/kg||abbr=on}} (rat, LD<sub>50</sub>).
* ]: {{convert|750|mg/kg||abbr=on}} (mouse, TD<sub>Lo</sub>), {{convert|175|mg/kg||abbr=on}} (mouse, LD<sub>50</sub>)
* Intravenous injection: {{convert|175|mg/kg||abbr=on}} (rabbit, LD<sub>50</sub>), {{convert|290|mg/kg||abbr=on}} (mouse, LD<sub>50</sub>)
* The US Environmental Protection Agency (USEPA) estimated in 2016<ref>{{cite book |title=Evaluation of the Inhalation Carcinogenicity of Ethylene Oxide |publisher=US Environmental Protection Agency |year=2016 |url=https://cfpub.epa.gov/ncea/iris/iris_documents/documents/toxreviews/1025tr.pdf}}</ref> that for low doses, the inhalation of ethylene oxide for a lifetime could increase an individual's lifetime cancer risk by as much as 3.0{{nbsp}}×{{nbsp}}10<sup>−3</sup> per μg/m<sup>3</sup> (without considering that early-life exposures are likely more potent). The USEPA estimated the slope of the dose-response declines at higher doses, and extra cancer risk estimates for several occupational exposure scenarios are calculated.


==Global demand==
Ethylene oxide causes acute poisoning, accompanied by the following symptoms: slight heartbeat, muscle twitching, flushing, headache, diminished hearing, ], vomiting, dizziness, transient loss of consciousness and a sweet taste in the mouth. Acute intoxication is accompanied by a strong throbbing headache, dizziness, difficulty in speech and walking, sleep disturbance, pain in the legs, weakness, stiffness, sweating, increased muscular irritability, transient spasm of retinal vessels, enlargement of the liver and suppression of its antitoxic functions.<ref name = "ChemAnalitica11" />
Global EO demand has expanded from {{convert|16.6|Mt|e6ST|lk=in|abbr=unit}} in 2004 to {{convert|20|Mt|e6ST|abbr=unit}} in 2009, while demand for refined EO expanded from {{convert|4.64|Mt|e6ST|abbr=unit}} in 2004 to {{convert|5.6|Mt|e6ST|abbr=unit}} in 2008. In 2009, demand is estimated to have declined to about {{convert|5.2|Mt|e6ST|abbr=unit}}. Total EO demand registered a growth rate of 5.6% per annum during the period 2005 to 2009 and is projected to grow at 5.7% per annum during 2009 to 2013.<ref name=dutia>{{cite journal |last=Dutia |first=Pankaj |title=Ethylene Oxide: A Techno-Commercial Profile |journal=Chemical Weekly |date=26 January 2010 |url=http://www.chemicalweekly.com/Profiles/Ethylene_Oxide.pdf |url-status=dead |archive-url=https://web.archive.org/web/20150402145434/http://www.chemicalweekly.com/Profiles/Ethylene_Oxide.pdf |archive-date=2 April 2015}}</ref>


==Health and safety regulations==
Ethylene easily penetrates through the clothing and footwear, causing skin irritation and dermatitis with the formation of blisters, fever and ].<ref name="ChemAnalitica11" />
According to Merck Life Science UK 2020 Safety Data Sheet provided to the ]'s ] (REACH)—a 2006 ],<ref>. European Parliament. 18 December 2006</ref> ethylene oxide is "presumed to have carcinogenic potential for humans."<ref name="sigmaaldrich 2020"/>


The United States EPA published an ] (NPRM) in the 12 December 2019 Federal Register seeking to limit EtO emissions.<ref>{{cite web |title=ETO Advance NPRM |url=https://www.govinfo.gov/content/pkg/FR-2019-12-12/pdf/2019-26804.pdf}}</ref> Over the next couple of years, information was collected and a proposed air toxics rule published in the 13 April 2023 Federal Register.<ref>{{cite web |title=Federal Register :: Request Access |website=unblock.federalregister.gov |url=https://unblock.federalregister.gov/ |access-date=2023-05-26}}</ref> Following a 60 day comment period that could be extended, due to many comments requesting an extension, the EPA rules that could reduce EtO emissions, both direct and fugitive, by over 80% could be implemented within 18 months of publishing the final rule in the Federal Register.<ref>{{citation |title=U.S. EPA Public Meeting: ETO National Public Webinar |date=2 May 2023 |language=en |url=https://www.youtube.com/watch?v=eQV59R3jsxQ |access-date=2023-05-26}}</ref> Laboratory EtO emitters would still be exempt from the stricter compliance. Additionally, while effectively curbing EtO emissions in the USA, many industrial emitters may simply shift their EtO production to nearby less strict countries: Canada, Mexico, etc.
The ]s (LD<sub>50</sub>, or a dose required to kill half the members of a tested population after a certain time) for ethylene oxide are 72&nbsp;mg/kg (rat, oral) and 187&nbsp;mg/kg (rat, ] injection).<ref name="msds">{{cite web

|url = http://msds.chem.ox.ac.uk/ET/ethylene_oxide.html
In 2024, U.S. probed claims that popular Indian curry brands ] and ] carried ethylene oxide after Hong Kong and Singapore found the contamination in the products and took enforcement actions against them.<ref>{{cite news |date=2024-04-27 |title=MDH and Everest: US health officials probe Indian spice mix pesticide claims |language=en-GB |url=https://www.bbc.com/news/world-asia-india-68911475 |access-date=2024-05-29}}</ref>
|title = Safety data for ethylene oxide
|publisher = The Physical and Theoretical Chemistry Laboratory Oxford University
|accessdate = 2009-10-22}}</ref>


==References== ==References==
{{reflist|2}} {{Reflist}}

==Cited sources==
* {{cite book
|editor-last=Haynes |editor-first=William M.
|date=2011
|title=CRC Handbook of Chemistry and Physics
|title-link=CRC Handbook of Chemistry and Physics
|edition=92nd
|publisher=]
|location=Boca Raton, FL
|isbn=978-1439855119 |ref=Haynes
}}


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