| Revision as of 13:49, 15 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 470770203 of page Ethyl_acetate for the Chem/Drugbox validation project (updated: ''). |
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{{Short description|Organic compound (CH₃CO₂CH₂CH₃)}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 443743534 |
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| verifiedrevid = 477003783 |
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| Name = Ethyl acetate |
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| ImageFile1 = Ethyl acetate2.svg |
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| Name = Ethyl ethanoate |
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| ImageFile1 = Ethyl-acetate-2D-skeletal.svg |
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| ImageSize1 = 160px |
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| ImageSize1 = 200px |
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| ImageName1 = Skeletal formula |
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| ImageName1 = Skeletal formula |
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| ImageFile2 = Ethyl-acetate-3D-balls.png |
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| ImageFile2 = File:Ethyl-acetate-from-xtal-3D-bs-17.png |
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| ImageSize2 = 200px |
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| ImageName2 = Ball-and-stick model |
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| ImageName2 = Ball-and-stick model |
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| PIN = Ethyl acetate <!-- Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) --> |
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| IUPACName = Ethyl acetate |
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| SystematicName = Ethyl ethanoate |
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| ImageAlt3 = Ethyl acetate |
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| ImageFile3 = Ethyl acetate in a 50mL-beaker.jpg |
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| OtherNames = Ethyl ester</br>Acetic ester</br>Ester of ethanol |
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|ImageSize3 = 150px |
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| Section1 = {{Chembox Identifiers |
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| SystematicName = Ethyl ethanoate |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| OtherNames = {{ubl|Acetic ester|Acetic ether|Ethyl ester of acetic acid}} |
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| Section1 = {{Chembox Identifiers |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 27750 |
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| ChEBI = 27750 |
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| SMILES = O=C(OCC)C |
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| SMILES = O=C(OCC)C |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 8525 |
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| ChemSpiderID = 8525 |
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| PubChem = 8857 |
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| PubChem = 8857 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D02319 |
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| KEGG = D02319 |
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| InChI = 1/C4H8O2/c1-3-6-4(2)5/h3H2,1-2H3 |
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| InChI = 1/C3H8O2/c1-3-6-4(2)5/h3H2,1-2H3 |
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| InChIKey = XEKOWRVHYACXOJ-UHFFFAOYAD |
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| InChIKey = XEKOWRVHYACXOJ-UHFFFAOYAD |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 141-78-6 |
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| CASNo = 141-78-6 |
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| RTECS = AH5425000 |
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| RTECS = AH5425000 |
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| Beilstein = 506104 |
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}} |
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| Gmelin = 26306 |
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| Section2 = {{Chembox Properties |
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}} |
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| Formula = C<sub>4</sub>H<sub>8</sub>O<sub>2</sub> |
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| Section2 = {{Chembox Properties |
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| MolarMass = 88.105 g/mol |
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| C=4 | H=8 | O=2 |
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| Appearance = colorless liquid |
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| Density = 0.897 g/cm³, liquid |
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| Appearance = Colorless liquid |
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| Odor = nail polish-like, fruity |
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| Solubility = 8.3 g/100 mL (20 °C) |
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| Density = 0.902 g/cm<sup>3</sup> |
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| Solvent = ],</br> ], ],</br> ] |
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| Solubility = 8.3 g/100 mL (at 20 °C) |
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| SolubleOther = Miscible |
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| Solvent = ], ], {{nowrap|]}}, ] |
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| MeltingPtC = −83.6 |
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| SolubleOther = Miscible |
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| BoilingPtC = 77.1 |
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| MeltingPtC = −83.6 |
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| Viscosity = 0.426 ] at 25 °C |
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| RefractIndex = 1.3720 |
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| BoilingPtC = 77.1 |
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| Viscosity = 426 ] (0.426 ]) at 25 °C |
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}} |
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| RefractIndex = 1.3720 |
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| Section3 = {{Chembox Structure |
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| pKa = 25 |
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| Dipole = 1.78 ] |
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| LogP = 0.71<ref name="chemsrc">{{Cite web|url=https://www.chemsrc.com/en/cas/141-78-6_1094578.html|title=ethyl acetate MSDS }}</ref> |
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}} |
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| VaporPressure = {{convert|73|mmHg|kPa|abbr=on}} at 20 °C<ref name=NIOSH>{{PGCH|0260}}</ref> |
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| Section7 = {{Chembox Hazards |
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| MagSus = {{val|−54.10|e=-6|u=cm<sup>3</sup>/mol}} |
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| ExternalMSDS = |
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}} |
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| MainHazards = Flammable (F),<br />Irritant (Xi) |
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| Section3 = {{Chembox Structure |
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| NFPA-H = 1 |
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| Dipole = 1.78 ] |
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| NFPA-F = 3 |
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}} |
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| NFPA-R = |
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| Section4 = |
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| RPhrases = {{R11}}, {{R36}}, {{R66}}, {{R67}} |
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| Section5 = |
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| SPhrases = {{S16}}, {{S26}}, {{S33}} |
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| Section6 = |
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| FlashPt = −4 °C |
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| Section7 = {{Chembox Hazards |
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| LD50 = 11.3 g/kg, rat |
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| ExternalSDS = |
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}} |
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| MainHazards = {{ubl|Flammable (F),|Irritant (Xi)}} |
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| Section8 = {{Chembox Related |
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| NFPA-H = 2 |
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| Function = ]s |
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| NFPA-F = 3 |
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| OtherFunctn = ],<br />],<br />] |
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| NFPA-R = 0 |
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| OtherCpds = ],<br />] |
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| GHSPictograms = {{GHS flame}} {{GHS exclamation mark}}<ref name="GESTIS">{{GESTIS|ZVG=12040 |CAS=141-78-6 |Name=Ethyl acetate |Date=7 December 2020 }}</ref> |
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}} |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|225|319|336}}<ref name=GESTIS/> |
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| PPhrases = {{P-phrases|210|233|240|305+351+338|403+235}}<ref name=GESTIS/> |
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| FlashPtC = −4 |
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| LD50 = 11.3 g/kg, rat |
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| PEL = TWA 400 ppm (1400 mg/m<sup>3</sup>)<ref name=NIOSH/> |
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| ExploLimits = 2.0–11.5%<ref name=NIOSH/> |
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| IDLH = 2000 ppm<ref name=NIOSH/> |
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| REL = TWA 400 ppm (1400 mg/m<sup>3</sup>)<ref name=NIOSH/> |
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| LC50 = 16,000 ppm (rat, 6 h)<br/>12,295 ppm (mouse, 2 h)<br/>1600 ppm (rat, 8 h)<ref name=IDLH>{{IDLH|141786|Ethyl acetate}}</ref> |
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| LCLo = 21 ppm (guinea pig, 1 h)<br/>12,330 ppm (mouse, 3 h)<ref name=IDLH/> |
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}} |
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| Section8 = {{Chembox Related |
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| OtherFunction_label = ]s |
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| OtherFunction = {{ubl|],|],|]}} |
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| OtherCompounds = {{ubl|],|],|] }} |
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}} |
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}} |
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'''Ethyl acetate''' (] '''ethyl ethanoate''', commonly abbreviated EtOAc, ETAC or EA) is the ] with the formula {{chem2|CH3CO2CH2CH3}}, simplified to {{chem2|C4H8O2}}. This flammable, colorless liquid has a characteristic sweet smell (similar to ]s) and is used in ]s, ]s, and the ] process of tea and coffee. Ethyl acetate is the ] of ] and ]; it is manufactured on a large scale for use as a ].<ref name=Ullmann>{{Ullmann|first1=Wilhelm|last1=Riemenschneider|first2=Hermann M.|last2=Bolt|title=Esters, Organic|doi=10.1002/14356007.a09_565.pub2}}</ref> |
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==Production and synthesis== |
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Ethyl acetate was first synthesized by the ] in 1759 by distilling a mixture of ethanol and acetic acid.<ref>{{cite journal|last=Parker|first=Joseph|title=The Edinburgh Encyclopaedia|journal=The Edinburgh Encyclopaedia |volume=5|year=1832|url=https://books.google.com/books?id=8-JEAQAAMAAJ}}</ref> |
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In 2004, an estimated 1.3 million tonnes were produced worldwide.<ref name=Ullmann/><ref>{{cite journal|last=Dutia|first=Pankaj|date=August 10, 2004|title=Ethyl Acetate: A Techno-Commercial Profile|journal=Chemical Weekly|pages=184|url=http://www.chemicalweekly.com/Profiles/Ethyl_Acetate.pdf#page=6|access-date=2009-03-21|format=PDF}}</ref> The combined annual production in 1985 of Japan, North America, and Europe was about 400,000 tonnes. The global ethyl acetate market was valued at $3.3 billion in 2018.<ref>{{Cite web|url=https://www.visiongain.com/global-ethyl-acetate-market-to-be-valued-at-3-3-billion-in-2018-reports-visiongain/|title="Global Ethyl Acetate Market to be valued at $3.3 billion in 2018" reports Visiongain|date=2019-09-05|website=Visiongain|language=en-US|access-date=2019-09-05}}</ref> |
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Ethyl acetate is synthesized in industry mainly via the classic ] reaction of ] and ]. This mixture converts to the ester in about 65% ] at room temperature: |
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:{{chem2|CH3CO2H + CH3CH2OH → CH3CO2CH2CH3 + H2O}} |
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The reaction can be accelerated by acid catalysis and the equilibrium can be shifted to the right by removal of water. |
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It is also prepared in industry using the ], by combining two equivalents of ] in the presence of an ] catalyst: |
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:{{chem2|2 CH3CHO → CH3CO2CH2CH3}} |
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] is used to manufacture ethyl acetate by the ] of ] by ]:<ref name=Misono>{{cite journal | last1 = Misono | first1 = Makoto | year = 2009 | title = Recent progress in the practical applications of heteropolyacid and perovskite catalysts: Catalytic technology for the sustainable society | journal = Catalysis Today | volume = 144 | issue = 3–4| pages = 285–291 | doi = 10.1016/j.cattod.2008.10.054 }}</ref> |
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:{{chem2|C2H4 + CH3CO2H → CH3CO2C2H5}} |
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<!--Not mentioned for EtOAc in otherwise thorough Ullmann's===By dehydrogenation of ethanol=== |
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A specialized industrial route entails the catalytic ] of ]. This method is more cost effective than the esterification but is applied with surplus ethanol in a chemical plant. Typically, dehydrogenation is conducted with copper at an elevated temperature but below 250 °C. The copper may have its surface area increased by depositing it on ], promoting the growth of ]-like ] structures (]). Surface area can be again increased by deposition onto a ], typically ]. Traces of ] and ]s are beneficial to the process. Byproducts of the dehydrogenation include ], which is thought to arise primarily due to aluminum sites in the catalyst, ] and its ] products, higher esters, and ]s. Separations of the byproducts are complicated by the fact that ethanol forms an ] with water, as does ethyl acetate with ethanol and water, and ] (MEK, which forms from 2-butanol) with both ethanol and ethyl acetate. These azeotropes are broken by ] or ]. |
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--> |
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==Uses== |
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Ethyl acetate is used primarily as a ] and ], being favored because of its low cost, low toxicity, and agreeable odor.<ref name=Ullmann/> For example, it is commonly used to clean circuit boards and in some nail varnish removers (] is also used). ] beans and ] leaves are ]d with this solvent.<ref name="ico.org"> {{webarchive|url=https://web.archive.org/web/20070429084212/http://www.ico.org/decaffeination.asp |date=2007-04-29 }}</ref> It is also used in ]s as an activator or hardener. Ethyl acetate is present in ], ]s, and ]s. In perfumes it ], leaving the scent of the perfume on the skin. |
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Ethyl acetate is an ] for use in ] and study.<ref>{{Cite journal |last1=Littledyke |first1=M. |last2=Cherrett |first2=J. M. |date=June 1976 |title=Direct ingestion of plant sap from cut leaves by the leaf-cutting ants Atta cephalotes (L.) and acromyrmex octospinosus (reich) (Formicidae, Attini) |url=https://www.cambridge.org/core/journals/bulletin-of-entomological-research/article/abs/direct-ingestion-of-plant-sap-from-cut-leaves-by-the-leafcutting-ants-atta-cephalotes-l-and-acromyrmex-octospinosus-reich-formicidae-attini/AF32CE2FBBD06C93D5FC3DE8287B1777 |journal=Bulletin of Entomological Research |language=en |volume=66 |issue=2 |pages=205–217 |doi=10.1017/S0007485300006647 |issn=1475-2670}}</ref> In a ] charged with ethyl acetate, the vapors will kill the collected insect quickly without destroying it. Because it is not ], ethyl acetate also keeps the insect soft enough to allow proper mounting suitable for a collection. However, ethyl acetate is regarded as potentially doing damage to insect DNA, making specimens processed this way less than ideal for subsequent DNA sequencing.<ref>{{cite journal|pmid=35804181 |date=2022 |last1=Cilia |first1=G. |last2=Flaminio |first2=S. |last3=Quaranta |first3=M. |title=A novel and non-invasive method for DNA extraction from dry bee specimens |journal=Scientific Reports |volume=12 |issue=1 |page=11679 |doi=10.1038/s41598-022-15595-8 |pmc=9270346 |bibcode=2022NatSR..1211679C }}</ref> |
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===Laboratory uses=== |
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In the laboratory, mixtures containing ethyl acetate are commonly used in ] and ].<ref>{{OrgSynth|prep=v95p0001 |
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|title=Copper and Secondary Amine-Catalyzed Pyridine Synthesis from ''O''-Acetyl Oximes and α,β-Unsaturated Aldehydes |
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|first=Wei Wen|last=Tan |
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|first2=Bin|last2=Wu |
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|first3=Ye|last3=Wei |
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|first4=Naohiko|last4=Yoshikai |
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|year=2018 |
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|volume=95|pages=1–14 |
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|doi=10.15227/orgsyn.095.0001|doi-broken-date=2020-03-22}}</ref> Ethyl acetate is rarely selected as a reaction solvent because it is prone to ], ], and condensations. |
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===Occurrence in wines=== |
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Ethyl acetate is the most common ] in ], being the product of the most common volatile ] – ], and the ethyl alcohol generated during the ]. The aroma of ethyl acetate is most vivid in younger wines and contributes towards the general perception of "fruitiness" in the wine. Sensitivity varies, with most people having a perception threshold around 120 mg/L. Excessive amounts of ethyl acetate are considered a ]. |
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==Reactions== |
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Ethyl acetate is only weakly Lewis basic, like a typical carboxylic acid ester. |
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Ethyl acetate ] to give ] and ]. Bases accelerate the hydrolysis, which is subject to the Fischer equilibrium mentioned above. In the laboratory, and usually for illustrative purposes only, ethyl esters are typically hydrolyzed in a two-step process starting with a stoichiometric amount of a strong base, such as ]. This reaction gives ethanol and ], which is unreactive toward ethanol: |
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:{{chem2|CH3CO2C2H5 + NaOH → C2H5OH + CH3CO2Na}} |
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In the ], anhydrous ethyl acetate and strong bases react to give ]:<ref>{{cite journal|journal=Org. Synth. | first1= J. K. H.|last1=Inglis|first2=K. C.|last2=Roberts | title = Ethyl Acetoacetate | volume = 6 | page= 36| doi= 10.15227/orgsyn.006.0036| year = 1926}}</ref> |
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:]{{clear|left}} |
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== Properties == |
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=== Physical properties === |
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] |
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] |
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Under normal conditions, ethyl acetate exists as a colorless, low-viscosity, and flammable liquid. Its melting point is −83 °C, with a melting enthalpy of 10.48 kJ/mol. At atmospheric pressure, the compound boils at 77 °C. The vaporization enthalpy at the boiling point is 31.94 kJ/mol. The vapor pressure function follows the ] |
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: <math>\log_{10}(p) = A - \frac{B}{T + C},</math> |
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where |
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: <math>p</math> is the vapor pressure in ], |
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: <math>T</math> is the ] in ]s, and |
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: <math>A = 4.22809</math>, <math>B = 1245.702</math>, <math>C = -55.189</math> are constants. |
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This function is valid within the temperature range of {{cvt|289|to(-)|349|K|C}}. |
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The ] in kJ/mol is calculated according to the empirical equation by Majer and Svoboda<ref name="Majer Svoboda">V. Majer, V. Svoboda: ''Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation''. Blackwell Scientific Publications, Oxford 1985, ISBN 0-632-01529-2.</ref> |
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: <math>\Delta H_\text{vap} = A\exp(-\beta\,T_\text{r})\,(1 - T_\text{r})^\beta,</math> |
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where |
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: <math>T_\text{r} = T/T_\text{c}</math> is the ], and <math>T_\text{c}</math> = 523.2 K is the ]. |
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: <math>A</math> = 54.26 kJ/mol and <math>\beta</math> = 0.2982 are constants. |
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The following table summarizes the most important thermodynamic properties of ethyl acetate under various conditions. |
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{| class="wikitable" |
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|+ Compilation of key thermodynamic properties |
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! Property !! Type !! Value !! Remarks !! References |
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| Standard enthalpy of formation || <math>\Delta_f H^0_\text{liquid}</math> <br> <math>\Delta_f H^0_\text{gas}</math> || −480.57 kJ/mol <br> −445.43 kJ/mol || as liquid <br> as gas || <ref name="Wiberg">K. B. Wiberg, L. S. Crocker, K. M. Morgan: ''Thermochemical studies of carbonyl compounds. 5. Enthalpies of reduction of carbonyl groups''. In: '']'' 113, 1991, pp. 3447–3450. ].</ref> |
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| Standard entropy || <math>S^0_\text{liquid}</math> <br> <math>S^0_\text{gas}</math> || 259.4 J/(mol·K) <br> 362.75 J/(mol·K) || as liquid <br> as gas || <ref name="Parks">G. S. Parks, H. M. Huffman, M. Barmore: ''Thermal data on organic compounds. XI. The heat capacities, entropies and free energies of ten compounds containing oxygen or nitrogen''. In: ''J. Am. Chem. Soc.'' 55, 1933, S. 2733–2740, ].</ref><ref name="Stull">D. R. Stull, Jr.: ''The Chemical Thermodynamics of Organic Compounds''. Wiley, New York, 1969.</ref> |
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| Combustion enthalpy || <math>\Delta_c H^0_\text{liquid}</math> || −2235.4 kJ/mol || || <ref name="Butwill">M. E. Butwill, J. D. Rockenfeller: ''Heats of combustion and formation of ethyl acetate and isopropyl acetate''. In: ''].'' 1, 1970, pp. 289–295. ].</ref> |
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| Heat capacity (25 °C) || <math>c_p</math> || 168.94 J/(mol·K) <br> 1.92 J/(g·K) <br> 113.64 J/(mol·K) <br> 1.29 J/(g·K) || as liquid <br><br> as gas || <ref name="Pintos">{{cite journal |first1=M. |last1=Pintos |first2=R. |last2=Bravo |first3=M. C. |last3=Baluja |first4=M. I. |last4=Paz Andrade |first5=G. |last5=Roux-Desgranges |first6=J.-P. E. |last6=Grolier |title=Thermodynamics of alkanoate + alkane binary mixtures. Concentration dependence of excess heat capacities and volumes |journal=Can. J. Chem. |year=1988 |volume=66 |issue=5 |pages=1179–1186 |doi=10.1139/v88-193 }}</ref><ref name="Stull" /> |
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| Critical temperature || <math>T_\text{c}</math> || 523.2 K || || <ref name="Majer Svoboda"/> |
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| Critical pressure || <math>p_\text{c}</math> || 38.82 bar || || <ref name="Ambrose">D. Ambrose, J. H. Ellender, H. A. Gundry, D. A. Lee, R. Townsend: ''Thermodynamic properties of organic oxygen compounds. LI. The vapour pressures of some esters and fatty acids''. In: '']'' 13, 1981, S. 795–802. ].</ref> |
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| Critical density ||<math>\rho_\text{c}</math> || 3.497 mol/L || || <ref name="Young">S. Young, G. L. Thomas: ''The vapour pressures, molecular volumes, and critical constants of ten of the lower esters''. In: '']'' 63, 1893, S. 1191.</ref> |
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| ] || <math>\omega_c</math> || 0.36641 || || <ref>J. Schmidt: ''Auslegung von Sicherheitsventilen für Mehrzweckanlagen nach ISO 4126-10'' {{in lang|de}}. In: '']'' 83, 2011, pp. 796–812. ].</ref> |
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==Safety== |
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The {{LD50}} for rats is 5620 mg/kg,<ref>Hazard Ethyl Acetate MSDS {{cite web|url=http://hazard.com/msds/mf/baker/baker/files/e2850.htm|title=Ethyl Acetate MSDS Number: E2850}}</ref> indicating low acute toxicity. Given that the chemical is naturally present in many organisms, there is little risk of toxicity. |
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Overexposure to ethyl acetate may cause ] of the eyes, nose, and throat. Severe overexposure may cause weakness, drowsiness, and unconsciousness.<ref>{{cite book|editor-last=Mackison|editor-first=F. W.|editor2-first=R. S.|editor2-last=Stricoff|editor3-first=L. J. Jr. |editor3-last=Partridge|title=NIOSH/OSHA – Occupational Health Guidelines for Chemical Hazards|series=DHHS (NIOSH) Publication No. 81–123|location=Washington, DC|publisher=U.S. Government Printing Office|date=January 1981}}</ref> Humans exposed to a concentration of 400 ppm in 1.4 mg/L ethyl acetate for a short time were affected by nose and throat irritation.<ref>{{cite book|editor-last=Clayton|editor-first=G.D.|editor2-first=F.E.|editor2-last=Clayton|title=Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology|edition=4th|location=New York, NY|publisher=John Wiley & Sons|date=1993–1994|page=2981}}</ref> Ethyl acetate is an irritant of the ] and ] of the ]. Animal experiments have shown that, at very high concentrations, the ester has ] depressant and lethal effects; at concentrations of 20,000 to 43,000 ppm (2.0–4.3%), there may be ] with ], symptoms of central nervous system depression, secondary ] and ]. In humans, concentrations of 400 ppm cause irritation of the nose and ]; cases have also been known of irritation of the conjunctiva with temporary opacity of the ]. In rare cases exposure may cause ] of the mucous membrane and ]. The irritant effect of ethyl acetate is weaker than that of ] or ].<ref>{{citation|title=Encyclopedia of Occupational Health and Safety|location=Geneva, Switzerland|publisher=International Labour Office|date=1983|page=782}}</ref> |
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==References== |
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{{reflist|30em}} |
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== External links == |
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* https://pubchem.ncbi.nlm.nih.gov/compound/ethyl_acetate#section=Toxicity |
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* for ethyl acetate |
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* Basic facts and contact SEKAB SEKAB ethyl acetate |
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* Calculation of , , , of ethyl acetate |
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{{Esters}} |
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