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2-Ethoxyethyl acetate
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2-Ethoxyethyl acetate.svg 200px 2-Ethoxyethyl acetate Ethyglycol acetate; Ethylene glycol mono ethyl ether acetate; 2-EEA; Ethoxyethanol acetate; EGA; Cellosolve acetate; Ethoxol acetate; Oxidol acetate 111-15-9 8095 203-839-2 KK8225000 1172 DG1O0Z7390 13839109 1S/C6H12O3/c1-3-8-4-5-9-6(2)7/h3-5H2,1-2H3 SVONRAPFKPVNKG-UHFFFAOYSA-N CCOCCOC(=O)C
6 12 3 0.973 (20 °C) < −62 °C 156 229 g/L (20 °C) 270 Pa (20 °C)
51 380 02 07 08 Danger 226 302 312 332 360 201 280 308 313
2-Ethoxyethyl acetate is an organic compound with the formula CH3CH2OCH2CH2O2CCH3. It is the ester of ethoxyethanol and acetic acid. A colorless liquid, it is partially soluble in water.http://www.khchemicals.com/product-categories/acetates/ethylglycolacetate/ Ethyl Glycol Acetate - KH Chemicals Ketting Joris vanc KH Chemicals 2018-03-29
Properties
2-Ethoxyethyl acetate is a liquid at room temperature that is used as a solvent. It can be absorbed through inhalation, ingestion, and dermally and should be avoided. It may form an explosive mixture with air. It is also incompatible with strong acids, strong alkalis and nitrates. It may form unstable peroxides and it can soften many plastics, attack plastics, rubber and coatings.https://books.google.com/books?id=PlDpCAAAQBAJ&dq=2-ethoxyethyl+acetate&pg=PA1261 Sittig's Handbook of Toxic and Hazardous Chemicals and Carcinogens Pohanish Richard P. vanc 2017-06-05 William Andrew 978-0-323-38969-3 2008 2-Ethoxyethyl acetate: Summary Risk Assessment https://echa.europa.eu/documents/10162/d02e2d1c-0f53-4cf6-aec8-f1697fcf2db3 European Chemicals Agency
Uses
2-Ethoxyethyl acetate has been used to dissolve polyester and short oil alkyd resins.http://www.kansaialtan.com/en/terms/ara/Ethyl%20glycol%20acetate Ethyl glycol acetate - Coating Terms - Kansai Altan JETLAG www.kansaialtan.com tr 2018-03-29 2018-03-31 https://web.archive.org/web/20180331035846/http://www.kansaialtan.com/en/terms/ara/Ethyl%20glycol%20acetate dead It has also been used in coatings, dyes, insecticides, soaps and cosmetics. Guest D, Hamilton ML, Deisinger PJ, DiVincenzo GD Pulmonary and percutaneous absorption of 2-propoxyethyl acetate and 2-ethoxyethyl acetate in beagle dogs Environmental Health Perspectives 57 177–83 August 1984 6499802 1568274 10.2307/3429914 3429914 It is also a solvent for nitro-cellulose and is being used for the same applications as ethyl glycol
In automobile lacquers it has been used to reduce evaporation and to impart a high gloss.https://books.google.com/books?id=bc8sXbYv7qMC&dq=2-ethoxyethyl+acetate&pg=PA1229 Groundwater Chemicals Desk Reference, 3rd Edition Montgomery John H. vanc 2010-12-12 CRC Press 9781420032765
Metabolism
2-Ethoxyethyl acetate is rapidly metabolized to 2-ethoxyethanol in the blood via hydrolysis. Then, 2-ethoxyethanol is metabolized, mainly by alcohol dehydrogenase, to 2-ethoxyacetaldehyde, which is further metabolized by aldehyde dehydrogenase to 2-ethoxyacetic acid (2-EAA) in the liver. These two compounds are the likely active metabolites, which are thought to be involved in some of the toxic effects. Also in the liver, ethylene glycol is produced.https://www.osha.gov/dts/chemicalsampling/data/CH_239300.html Chemical Sampling Information 2-Ethoxyethyl acetate www.osha.gov 2018-03-29https://www.who.int/ipcs/publications/cicad/ethoxy_propoxyethanol.pdf Concise International Chemical Assessment Document 67 Selected Alkoxyethanols: 2-Ethoxyethanol and 2-Eropoxyethanol World Health Organization 2009 Gargas ML, Tyler TR, Sweeney LM, Corley RA, Weitz KK, Mast TJ, Paustenbach DJ, Hays SM 12036787 A toxicokinetic study of inhaled ethylene glycol ethyl ether acetate and validation of a physiologically based pharmacokinetic model for rat and human Toxicology and Applied Pharmacology 165 1 63–73 May 2000 10814554 10.1006/taap.2000.8927 All this reactions belong to the phase I of the biotransformation process. In rats, EAA can be conjugated with glycine or may suffer O-deethylated. After this, it can be metabolized to carbon dioxide. An extra pathway in these animals involves microsomal P450 mixed function oxidases, with deethylation producing acetaldehyde and ethylene glycol.
Safety
2-Ethoxyethyl acetate can cause a slight skin and eye irritation after exposure.https://books.google.com/books?id=y3-Ef3y53PkC&dq=2-ethoxyethyl+acetate&pg=PR1 Proctor and Hughes' Chemical Hazards of the Workplace Proctor Nick H. Hughes James P. Hathaway Gloria J. vanc 2004 John Wiley & Sons 978-0-471-26883-3 High exposure can lead to kidney damage and paralysis. https://www.cdc.gov/niosh/npg/npgd0259.html NIOSH Pocket Guide to Chemical Hazards 2-Ethoxyethyl acetate Centers for Disease Control and Prevention In animals, reproductive and teratogenic effects have been observed.
References
Category:Glycol ethers
Category:Acetate esters
Category:Solvents
Category:Glycol esters