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Revision as of 23:11, 6 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (changes to verified and watched fields - updated 'DrugBank_Ref', 'ChEMBL_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:WikiProject_Chemicals|errors← Previous edit Latest revision as of 14:56, 5 December 2024 edit undoKisaragiAyami (talk | contribs)144 editsm Reactions and applicationsTag: Visual edit 
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{{Redirect|Propiolactone|α-propiolactone|Methyloxiranone}}
{{lowercase}} {{lowercase title}}
{{chembox {{chembox
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 396299809 | verifiedrevid = 444422830
| Name = β-Propiolactone | Name = β-Propiolactone
| ImageFile = propiolactone.png | ImageFile = Beta-Propiolactone-2D-skeletal.svg
| ImageSize = 120px | ImageSize = 120px
| ImageName = Skeletal formula | ImageName = Skeletal formula
| ImageFile1 = Beta-Propiolactone-3D-balls.png | ImageFile1 = Beta-Propiolactone-3D-balls.png
| ImageSize1 = 180px | ImageSize1 = 180px
| ImageName1 = Balla-and-stick model | ImageName1 = Balla-and-stick model
| PIN = Oxetan-2-one
| IUPACName = oxetan-2-one<br />3-hydroxypropanoic acid lactone
| OtherNames = Propiolactone<br />β-propiolactone<br>2-oxetanone | OtherNames = Propiolactone<br />2-Oxetanone<br />3-Hydroxypropanoic acid lactone
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo = 57-57-8
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| CASNo_Ref = {{cascite|correct|CAS}}
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 49073
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1200627
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2275 | ChemSpiderID = 2275
| DrugBank = DB09348
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D05630
| PubChem = 2365
| RTECS = RQ7350000
| UNNumber = 2810
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 6RC3ZT4HB0 | UNII = 6RC3ZT4HB0
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = D05630
| InChI = 1/C3H4O2/c4-3-1-2-5-3/h1-2H2 | InChI = 1/C3H4O2/c4-3-1-2-5-3/h1-2H2
| InChIKey = VEZXCJBBBCKRPI-UHFFFAOYAQ | InChIKey = VEZXCJBBBCKRPI-UHFFFAOYAQ
Line 26: Line 37:
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VEZXCJBBBCKRPI-UHFFFAOYSA-N | StdInChIKey = VEZXCJBBBCKRPI-UHFFFAOYSA-N
| CASNo = 57-57-8
| CASNo_Ref = {{cascite|correct|CAS}}
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 49073
| SMILES = O=C1OCC1 | SMILES = O=C1OCC1
| EINECS = 200-340-1
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=3 | H=4 | O=2
| Formula = C<sub>3</sub>H<sub>4</sub>O<sub>2</sub>
| Appearance = Colorless liquid
| MolarMass = 72.06 g/mol
| Odor = slightly sweet<ref name=PGCH/>
| Appearance = colorless liquid
| Density = 1.1460 g/cm<sup>3</sup>
| Odor = pungent, acrylic
| MeltingPtC = -33.4
| Density = 1.146 g/cm<sup>3</sup>
| BoilingPtC = 162
| MeltingPt = -33.4 °C
| BoilingPt_notes = (decomposes)
| BoilingPt = 162 °C (dec.)
| RefractIndex = 1.4131 | RefractIndex = 1.4131
| Solubility = soluble | Solubility = 37 g/100 mL
| SolubleOther = miscible in organic solvents | SolubleOther = Miscible
| Solvent = organic solvents
| VaporPressure = 3 mmHg (25°C)<ref name=PGCH/>
}} }}
|Section3={{Chembox Hazards
| IDLH = Ca <ref name=PGCH>{{PGCH|0528}}</ref>
| REL = Ca<ref name=PGCH/>
| PEL = OSHA-Regulated ]<ref name=PGCH/>
| FlashPtF = 165
| FlashPt_ref = <ref name=PGCH/>
| ExploLimits = 2.9%-?<ref name=PGCH/>
| GHSPictograms = {{GHS06}}{{GHS07}}{{GHS08}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|315|319|330|350}}
| PPhrases = {{P-phrases|201|202|260|264|271|280|281|284|302+352|304+340|305+351+338|308+313|310|320|321|332+313|337+313|362|403+233|405|501}}
}}
}} }}


'''β-Propiolactone''' is an ] of the ] family, with a four-membered ring. It is a clear, colorless liquid with a slightly sweet odor, highly soluble in water and miscible with ], ], ] and ].<ref name="nih"/><ref name="merck"> '''β-Propiolactone''', often simply called '''propiolactone''', is an ] with the formula {{chem2|CH2CH2CO2}}. It is a ] family, with a four-membered ring. It is a colorless liquid with a slightly sweet odor, highly soluble in water and organic solvents.<ref name="nih"/><ref name="merck">''Merck Index'', 12th Edition, entry 8005.</ref> The carcinogenicity of this compound has limited its commercial applications.<ref>{{cite book |doi=10.1002/14356007.a15_063 |chapter=Ketenes |title=Ullmann's Encyclopedia of Industrial Chemistry |date=2001 |last1=Miller |first1=Raimund |last2=Abaecherli |first2=Claudio |last3=Said |first3=Adel |last4=Jackson |first4=Barry |isbn=978-3-527-30385-4 }}</ref>
''Merck Index'', 12th Edition, entry 8005.
</ref> The word '''propiolactone''' usually refers to this compound, although it may also refer to ].


==Production==
β-Propiolactone is "reasonably expected to be a human carcinogen" (], 1999).<ref name="nih">
β-Propiolactone is prepared industrially by the reaction of ] and ] in the presence of ] or ] as catalyst:<ref name=Ullmann>{{Ullmann|doi=10.1002/14356007.a13_507|title=Hydroxycarboxylic Acids, Aliphatic|year=2000|last1=Miltenberger|first1=Karlheinz}}</ref>
- ] substance profile. Accessed on 2009-07-10.
</ref> It was once widely used in the manufacture of ] and its ], but its use has been mostly phased out in favor of safer and less expensive alternatives. β-Propiolactone is a disinfectant and has been used to sterilize blood plasma, vaccines, tissue grafts, surgical instruments, and enzymes.<ref name="nih"/> The principal current use of propiolactone is an intermediate in the synthesis of other chemical compounds.


]
β-Propiolactone will slowly react with water and ] to produce ] (hydracryclic acid).

In the research laboratory, propiolactones have been produced by the ] of ]s.<ref>{{cite journal|title=Low Pressure Carbonylation of Epoxides to β-Lactones |author=John W. Kramer |author2=Daniel S. Treitler |author3=Geoffrey W. Coates|journal=Org. Synth.|year=2009|volume=86|page=287|doi=10.15227/orgsyn.086.0287|doi-access=free}}</ref>

==Reactions and applications==
It reacts with many nucleophiles in a ring-opening reactions. With water ] occurs to produce ] (hydracryclic acid). Ammonia gives the ], which is a commercial process.<ref name=Ullmann/>

Propiolactone was once widely produced as an intermediate in the production of ] and its ]. That application has been largely displaced in favor of safer and less expensive alternatives. β-Propiolactone is an excellent sterilizing and sporicidal agent, but its carcinogenicity precludes that use.<ref name="nih"/> It is used to ] a wide variety of viruses,<ref>{{cite journal|doi=10.1111/j.1749-6632.1960.tb40931.x|title=Investigations of the Use of Beta-Propiolactone in Virus Inactivation|year=1960|last1=Logrippo|first1=Gerald A.|journal=Annals of the New York Academy of Sciences|volume=83|issue=4|pages=578–594|pmid=14417982|bibcode=1960NYASA..83..578L|s2cid=6025589}}</ref> for instance the ], as a step in vaccine production.<ref>{{cite journal|journal=Science|title=Development of an inactivated vaccine candidate for SARS-CoV-2|author1=Qiang Gao |author2=Linlin Bao |author3=Haiyan Mao |author4=Lin Wang |author5=Kangwei Xu |author6=Minnan Yang |author7=Yajing Li |author8=Ling Zhu |author9=Nan Wang |author10=Zhe Lv |author11=Hong Gao |author12=Xiaoqin Ge |author13=Biao Kan |author14=Yaling Hu |author15=Jiangning Liu |author16=Fang Cai |author17=Deyu Jiang |author18=Yanhui Yin |author19=Chengfeng Qin |author20=Jing Li |author21=Xuejie Gong |author22=Xiuyu Lou |author23=Wen Shi |author24=Dongdong Wu |author25=Hengming Zhang |author26=Lang Zhu |author27=Wei Deng |author28=Yurong Li |author29=Jinxing Lu |author30=Changgui Li |author31=Xiangxi Wang |author32=Weidong Yin |author33=Yanjun Zhang |author34=Chuan Qin |date=2020-07-03|doi=10.1126/science.abc1932|volume=369|issue=6499|pages=77–81|pmid=32376603|pmc=7202686|bibcode=2020Sci...369...77G|doi-access=free}}</ref> The principal use of propiolactone is an intermediate in the synthesis of other chemical compounds.<ref name=Ullmann/>
] (AKD), a propiolactone derivative that is used in papermaking.]]

==Safety==
β-Propiolactone is "reasonably anticipated to be a human carcinogen" (], 1999).<ref name="nih"> - US Department of Health and Human Services, Report on Carcinogens, National Toxicology Program, Thirteenth Edition, 2 October 2014. Accessed on 2015-01-03.</ref> It is one of 13 "OSHA-regulated carcinogens," chemicals regarded occupational carcinogens by the U.S. ], despite not having an established ].<ref name="cdc"> - ]. Accessed on 2013-11-06.</ref>


==See also== ==See also==
* ], an isomer of β-propiolactone * ], an isomer of β-propiolactone
* ] (2,4-Oxetanone) * ] (2,4-oxetanone)
* ] * ]
<!--* ]--><!--* ]--> <!--* ]--><!--* ]-->
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{{DEFAULTSORT:Propiolactone, beta-}} {{DEFAULTSORT:Propiolactone, beta-}}
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