2-Ethoxyethyl acetate
| |
| Names | |
|---|---|
| IUPAC name
2-Ethoxyethylacetate
| |
| Other names
Ethyglycol acetate; Ethylene glycol mono ethyl ether acetate; 2-EEA; Ethoxyethanol acetate; EGA; Cellosolve acetate; Ethoxol acetate; Oxidol acetate
| |
| Identifiers | |
| ECHA InfoCard | 100.003.491 |
CompTox Dashboard (EPA)
|
|
| Properties | |
| C6H12O3 | |
| Molar mass | 132.159 g·mol−1 |
| Density | 0.973 (20 °C) |
| Melting point | < -62 °C |
| Boiling point | 156 °C (313 °F; 429 K) |
| 229 g/L (20 °C) | |
| Vapor pressure | 270 Pa (20 °C) |
| Hazards | |
| GHS labelling: | |
| H226, H302 + H312 + H332, H360FD | |
| P201, P280, P308 + P313 | |
| Flash point | 51 °C (124 °F; 324 K) |
| 380 °C (716 °F; 653 K) | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
2-Ethoxyethyl acetate is a colorless, clear liquid, which is partially soluble in water.[1] It is a flammable liquid when it is exposed to heat or flame and it can react with oxidizing materials. When it is heated there is a explosion hazard (vapor). At the end of distillations mild explosions have occurred.[2]
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.[3][4]
Uses
2-Ethoxyethyl acetate has been used to dissolve polyester and short oil alkyd resins.[5] It has also been used in coatings, dyes, insecticides, soaps and cosmetics.[6] It is also a solvent for nitro-cellulose and is being used for the same applications as ethyl glycol[5][7]
In automobile lacquers it has been used to reduce evaporation and to impart a high gloss.[8]
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.[9][10][11] 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.[10]
Symptoms
It can cause a slight skin and eye irritation after exposure.[7]
References
- ^ Ketting, Joris. "Ethyl Glycol Acetate - KH Chemicals". KH Chemicals. Retrieved 2018-03-29.
{{cite news}}: Unknown parameter|name-list-format=ignored (|name-list-style=suggested) (help) - ^ Simmons, H. Leslie; Lewis, Richard J. (1997). Building Materials: Dangerous Properties of Products in MasterFormat Divisions 7 and 9. John Wiley & Sons. ISBN 978-0-442-02289-1.
{{cite book}}: Unknown parameter|name-list-format=ignored (|name-list-style=suggested) (help) - ^ Pohanish, Richard P. (2017-06-05). Sittig's Handbook of Toxic and Hazardous Chemicals and Carcinogens. William Andrew. ISBN 978-0-323-38969-3.
{{cite book}}: Unknown parameter|name-list-format=ignored (|name-list-style=suggested) (help) - ^ "2-Ethoxyethyl acetate, SUMMARY RISK ASSESSMENT". 2005.
{{cite journal}}: Cite journal requires|journal=(help) - ^ a b JETLAG. "Ethyl glycol acetate - Coating Terms - Kansai Altan". www.kansaialtan.com (in Turkish). Retrieved 2018-03-29.
- ^ Guest D, Hamilton ML, Deisinger PJ, DiVincenzo GD (August 1984). "Pulmonary and percutaneous absorption of 2-propoxyethyl acetate and 2-ethoxyethyl acetate in beagle dogs". Environmental Health Perspectives. 57: 177–83. PMC 1568274. PMID 6499802.
- ^ a b Proctor, Nick H.; Hughes, James P.; Hathaway, Gloria J. (2004). Proctor and Hughes' Chemical Hazards of the Workplace. John Wiley & Sons. ISBN 978-0-471-26883-3.
{{cite book}}: Unknown parameter|name-list-format=ignored (|name-list-style=suggested) (help) - ^ Montgomery, John H. (2010-12-12). Groundwater Chemicals Desk Reference, 3rd Edition. CRC Press. ISBN 9781420032765.
{{cite book}}: Unknown parameter|name-list-format=ignored (|name-list-style=suggested) (help) - ^ "Chemical Sampling Information | 2-Ethoxyethyl acetate". www.osha.gov. Retrieved 2018-03-29.
- ^ a b "Selected Alkoxyethanols: 2-Ethoxyethanol and 2-Eropoxyethanol" (PDF). Concise International Chemical Assessment Document 67. World Health Organization. 2009.
- ^ Gargas ML, Tyler TR, Sweeney LM, Corley RA, Weitz KK, Mast TJ, Paustenbach DJ, Hays SM (May 2000). "A toxicokinetic study of inhaled ethylene glycol ethyl ether acetate and validation of a physiologically based pharmacokinetic model for rat and human" (PDF). Toxicology and Applied Pharmacology. 165 (1): 63–73. doi:10.1006/taap.2000.8927. PMID 10814554.