2-Ethoxyethyl acetate

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2-Ethoxyethyl acetate
2-Ethoxyethyl acetate.svg
Names
Preferred IUPAC name
2-Ethoxyethyl acetate
Other names
Ethyglycol acetate; Ethylene glycol mono ethyl ether acetate; 2-EEA; Ethoxyethanol acetate; EGA; Cellosolve acetate; Ethoxol acetate; Oxidol acetate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.491 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-839-2
PubChem CID
RTECS number
  • KK8225000
UNII
UN number 1172
  • InChI=1S/C6H12O3/c1-3-8-4-5-9-6(2)7/h3-5H2,1-2H3
    Key: SVONRAPFKPVNKG-UHFFFAOYSA-N
  • CCOCCOC(=O)C
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:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
Danger
H226, H302, H312, H332, H360
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 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. [1]

Contents

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. [2] [3]

Uses

2-Ethoxyethyl acetate has been used to dissolve polyester and short oil alkyd resins. [4] It has also been used in coatings, dyes, insecticides, soaps and cosmetics. [5] It is also a solvent for nitro-cellulose and is being used for the same applications as ethyl glycol [4] [6]

In automobile lacquers it has been used to reduce evaporation and to impart a high gloss. [7]

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. [8] [9] [10] 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. [9]

Safety

2-Ethoxyethyl acetate can cause a slight skin and eye irritation after exposure. [6] High exposure can lead to kidney damage and paralysis. [11] In animals, reproductive and teratogenic effects have been observed. [11]

Related Research Articles

<span class="mw-page-title-main">Ethanol</span> Organic compound (CH₃CH₂OH)

Ethanol is an organic compound with the chemical formula CH3CH2OH. It is an alcohol, with its formula also written as C2H5OH, C2H6O or EtOH, where Et stands for ethyl. Ethanol is a volatile, flammable, colorless liquid with a characteristic wine-like odor and pungent taste. As a psychoactive depressant, it is the active ingredient in alcoholic beverages, and the second most consumed drug globally behind caffeine.

<span class="mw-page-title-main">Ethylene glycol</span> Organic compound ethane-1,2-diol

Ethylene glycol is an organic compound with the formula (CH2OH)2. It is mainly used for two purposes: as a raw material in the manufacture of polyester fibers and for antifreeze formulations. It is an odorless, colorless, flammable, viscous liquid. It has a sweet taste, but is toxic in high concentrations. This molecule has been observed in outer space.

<span class="mw-page-title-main">Butanone</span> Chemical compound

Butanone, also known as methyl ethyl ketone (MEK) or ethyl methyl ketone, is an organic compound with the formula CH3C(O)CH2CH3. This colorless liquid ketone has a sharp, sweet odor reminiscent of acetone. It is produced industrially on a large scale, but occurs in nature only in trace amounts. It is partially soluble in water, and is commonly used as an industrial solvent. It is an isomer of another solvent, tetrahydrofuran.

<span class="mw-page-title-main">Propylene glycol</span> Chemical compound

Propylene glycol (IUPAC name: propane-1,2-diol) is a viscous, colorless liquid. It is almost odorless and has a faintly sweet taste. Its chemical formula is CH3CH(OH)CH2OH. As it contains two alcohol groups, it is classified as a diol. An aliphatic diol may also be called a glycol. It is miscible with a broad range of solvents, including water, acetone, and chloroform. In general, glycols are non-irritating and have very low volatility.

<span class="mw-page-title-main">Diethyl ether</span> Organic chemical compound

Diethyl ether, or simply ether, is an organic compound with the chemical formula (CH3CH2)2O, sometimes abbreviated as Et2O. It is a colourless, highly volatile, sweet-smelling, extremely flammable liquid. It belongs to the ether class of organic compounds. It is a common solvent. It was formerly used as a general anesthetic.

<span class="mw-page-title-main">Acrylic acid</span> Chemical compound

Acrylic acid (IUPAC: prop-2-enoic acid) is an organic compound with the formula CH2=CHCOOH. It is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus. This colorless liquid has a characteristic acrid or tart smell. It is miscible with water, alcohols, ethers, and chloroform. More than a million tons are produced annually.

<span class="mw-page-title-main">Methyl acetate</span> Chemical compound

Methyl acetate, also known as MeOAc, acetic acid methyl ester or methyl ethanoate, is a carboxylate ester with the formula CH3COOCH3. It is a flammable liquid with a characteristically pleasant smell reminiscent of some glues and nail polish removers. Methyl acetate is occasionally used as a solvent, being weakly polar and lipophilic, but its close relative ethyl acetate is a more common solvent being less toxic and less soluble in water. Methyl acetate has a solubility of 25% in water at room temperature. At elevated temperature its solubility in water is much higher. Methyl acetate is not stable in the presence of strong aqueous bases or aqueous acids. Methyl acetate is not regulated as a volatile organic compound in the USA.

<span class="mw-page-title-main">2-Butoxyethanol</span> Chemical compound

2-Butoxyethanol is an organic compound with the chemical formula BuOC2H4OH. This colorless liquid has a sweet, ether-like odor, as it derives from the family of glycol ethers, and is a butyl ether of ethylene glycol. As a relatively nonvolatile, inexpensive solvent, it is used in many domestic and industrial products because of its properties as a surfactant. It is a known respiratory irritant and can be acutely toxic, but animal studies did not find it to be mutagenic, and no studies suggest it is a human carcinogen. A study of 13 classroom air contaminants conducted in Portugal reported a statistically significant association with increased rates of nasal obstruction and a positive association below the level of statistical significance with a higher risk of obese asthma and increased body mass index.

2-Chloroethanol (also called ethylene chlorohydrin or glycol chlorohydrin) is an organic chemical compound with the chemical formula HOCH2CH2Cl and the simplest beta-halohydrin (chlorohydrin). This colorless liquid has a pleasant ether-like odor. It is miscible with water. The molecule is bifunctional, consisting of both an alkyl chloride and an alcohol functional group.

Glycol ethers are a class of chemical compounds consisting of alkyl ethers that are based on glycols such as ethylene glycol or propylene glycol. They are commonly used as solvents in paints and cleaners. They have good solvent properties while having higher boiling points than the lower-molecular-weight ethers and alcohols.

<span class="mw-page-title-main">Isopropyl acetate</span> Chemical compound

Isopropyl acetate is an ester, an organic compound which is the product of esterification of acetic acid and isopropanol. It is a clear, colorless liquid with a characteristic fruity odor.

<span class="mw-page-title-main">2-Ethoxyethanol</span> Chemical compound

2-Ethoxyethanol, also known by the trademark Ethyl cellosolve, is a solvent used widely in commercial and industrial applications. It is a clear, colorless, nearly odorless liquid that is miscible with water, ethanol, diethyl ether, acetone, and ethyl acetate.

<span class="mw-page-title-main">2-Methoxyethanol</span> Chemical compound

2-Methoxyethanol, or methyl cellosolve, is an organic compound with formula C
3
H
8
O
2
that is used mainly as a solvent. It is a clear, colorless liquid with an ether-like odor. It is in a class of solvents known as glycol ethers which are notable for their ability to dissolve a variety of different types of chemical compounds and for their miscibility with water and other solvents. It can be formed by the nucleophilic attack of methanol on protonated ethylene oxide followed by proton transfer:

<span class="mw-page-title-main">Dimethyl carbonate</span> Chemical compound

Dimethyl carbonate (DMC) is an organic compound with the formula OC(OCH3)2. It is a colourless, flammable liquid. It is classified as a carbonate ester. This compound has found use as a methylating agent and as a co-solvent in lithium-ion batteries. Notably, dimethyl carbonate is a weak methylating agent, and is not considered as a carcinogen. Instead, dimethyl carbonate is often considered to be a green reagent, and it is exempt from the restrictions placed on most volatile organic compounds (VOCs) in the United States.

<span class="mw-page-title-main">Ethyl acrylate</span> Chemical compound

Ethyl acrylate is an organic compound with the formula CH2CHCO2CH2CH3. It is the ethyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor. It is mainly produced for paints, textiles, and non-woven fibers. It is also a reagent in the synthesis of various pharmaceutical intermediates.

<span class="mw-page-title-main">1,1,2,2-Tetrachloroethane</span> Chemical compound

1,1,2,2-tetrachloroethane (TeCA), also known by the brand names Bonoform, Cellon and Westron, is an organic compound. It is colorless liquid and has a sweet odor. It is used as an industrial solvent and as a separation agent. TeCA is toxic and it can be inhaled, consumed or absorbed through the skin. After exposure, nausea, dizziness or even liver damage may occur.

Ethylene glycol poisoning is poisoning caused by drinking ethylene glycol. Early symptoms include intoxication, vomiting and abdominal pain. Later symptoms may include a decreased level of consciousness, headache, and seizures. Long term outcomes may include kidney failure and brain damage. Toxicity and death may occur after drinking even in a small amount as ethylene glycol is more toxic than other diols.

<span class="mw-page-title-main">Acetic acid</span> Colorless and faint organic acid found in vinegar

Acetic acid, systematically named ethanoic acid, is an acidic, colourless liquid and organic compound with the chemical formula CH3COOH. Vinegar is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water. It has been used, as a component of vinegar, throughout history from at least the third century BC.

Isopropyl alcohol is a colorless, flammable, organic compound with a pungent alcoholic odor.

Butyl acrylate is an organic compound with the formula C4H9O2CCH=CH2. A colorless liquid, it is the butyl ester of acrylic acid. It is used commercially on a large scale as a precursor to poly(butyl acrylate). Especially as copolymers, such materials are used in paints, sealants, coatings, adhesives, fuel, textiles, plastics, and caulk.

References

  1. Ketting J. "Ethyl Glycol Acetate - KH Chemicals". KH Chemicals. Retrieved 2018-03-29.
  2. Pohanish RP (2017-06-05). Sittig's Handbook of Toxic and Hazardous Chemicals and Carcinogens. William Andrew. ISBN   978-0-323-38969-3.
  3. 2-Ethoxyethyl acetate: Summary Risk Assessment (Report). European Chemicals Agency. 2008.
  4. 1 2 JETLAG. "Ethyl glycol acetate - Coating Terms - Kansai Altan". www.kansaialtan.com (in Turkish). Retrieved 2018-03-29.
  5. 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. doi:10.2307/3429914. JSTOR   3429914. PMC   1568274 . PMID   6499802.
  6. 1 2 Proctor NH, Hughes JP, Hathaway GJ (2004). Proctor and Hughes' Chemical Hazards of the Workplace. John Wiley & Sons. ISBN   978-0-471-26883-3.
  7. Montgomery JH (2010-12-12). Groundwater Chemicals Desk Reference, 3rd Edition. CRC Press. ISBN   9781420032765.
  8. "Chemical Sampling Information | 2-Ethoxyethyl acetate". www.osha.gov. Retrieved 2018-03-29.
  9. 1 2 "Selected Alkoxyethanols: 2-Ethoxyethanol and 2-Eropoxyethanol" (PDF). Concise International Chemical Assessment Document 67. World Health Organization. 2009.
  10. 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". Toxicology and Applied Pharmacology. 165 (1): 63–73. doi:10.1006/taap.2000.8927. PMID   10814554. S2CID   12036787.
  11. 1 2 "2-Ethoxyethyl acetate". NIOSH Pocket Guide to Chemical Hazards. Centers for Disease Control and Prevention.