2-Ethoxyethyl acetate

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2-Ethoxyethyl acetate
2-ethoxyethylacetaat t.png
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 pictograms GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
GHS Signal word 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).
Infobox references

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

Ethanol Organic chemical compound

Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic chemical compound. It is a simple alcohol with the chemical formula C2H6O. Its formula can be also written as CH
3−CH
2−OH or C
2H
5OH (an ethyl group linked to a hydroxyl group), and is often abbreviated as EtOH. Ethanol is a volatile, flammable, colorless liquid with a characteristic wine-like odor and pungent taste. It is a psychoactive drug, recreational drug, and the active ingredient in alcoholic drinks.

Acetonitrile, often abbreviated MeCN, is the chemical compound with the formula CH
3CN. This colourless liquid is the simplest organic nitrile. It is produced mainly as a byproduct of acrylonitrile manufacture. It is used as a polar aprotic solvent in organic synthesis and in the purification of butadiene. The N≡C−C skeleton is linear with a short C≡N distance of 1.16 Å.

Butanone Chemical compound

Butanone, also known as methyl ethyl ketone (MEK), is an organic compound with the formula CH3C(O)CH2CH3. This colourless 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.

Propylene glycol Chemical compound

Propylene glycol (IUPAC name: propane-1,2-diol) is a viscous, colorless liquid, which is nearly odorless but possesses a faintly sweet taste. Its chemical formula is CH3CH(OH)CH2OH. Containing two alcohol groups, it is classed as a diol. 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.

Vinyl chloride is an organochloride with the formula H2C=CHCl that is also called vinyl chloride monomer (VCM) or chloroethene. This colorless compound is an important industrial chemical chiefly used to produce the polymer polyvinyl chloride (PVC). About 13 billion kilograms are produced annually. VCM is among the top twenty largest petrochemicals (petroleum-derived chemicals) in world production. The United States currently remains the largest VCM manufacturing region because of its low-production-cost position in chlorine and ethylene raw materials. China is also a large manufacturer and one of the largest consumers of VCM. Vinyl chloride is a gas with a sweet odor. It is highly toxic, flammable, and carcinogenic. It can be formed in the environment when soil organisms break down chlorinated solvents. Vinyl chloride that is released by industries or formed by the breakdown of other chlorinated chemicals can enter the air and drinking water supplies. Vinyl chloride is a common contaminant found near landfills. In the past VCM was used as a refrigerant.

Ethylene oxide Chemical compound

Ethylene oxide is an organic compound with the formula C
2H
4O. It is a cyclic ether and the simplest epoxide: a three-membered ring consisting of one oxygen atom and two carbon atoms. Ethylene oxide is a colorless and flammable gas with a faintly sweet odor. Because it is a strained ring, ethylene oxide easily participates in a number of addition reactions that result in ring-opening. Ethylene oxide is isomeric with acetaldehyde and with vinyl alcohol. Ethylene oxide is industrially produced by oxidation of ethylene in the presence of silver catalyst.

Diethyl ether Organic chemical compound

Diethyl ether, or simply ether, is an organic compound in the ether class with the formula (C
2H
5)
2O, sometimes abbreviated as Et
2O. It is a colorless, highly volatile, sweet-smelling, extremely flammable liquid. It is commonly used as a solvent in laboratories and as a starting fluid for some engines. It was formerly used as a general anesthetic, until non-flammable drugs were developed, such as halothane. It has been used as a recreational drug to cause intoxication. It is a structural isomer of butanol.

Ethyl acetate Chemical compound

Ethyl acetate is the organic compound with the formula CH3−COO−CH2−CH3, simplified to C4H8O2. This colorless liquid has a characteristic sweet smell and is used in glues, nail polish removers, and in the decaffeination process of tea and coffee. Ethyl acetate is the ester of ethanol and acetic acid; it is manufactured on a large scale for use as a solvent.

Methyl acetate 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 considered a VOC in the USA.

Ethylbenzene Chemical compound

Ethylbenzene is an organic compound with the formula C6H5CH2CH3. It is a highly flammable, colorless liquid with an odor similar to that of gasoline. This monocyclic aromatic hydrocarbon is important in the petrochemical industry as an intermediate in the production of styrene, the precursor to polystyrene, a common plastic material. In 2012, more than 99% of ethylbenzene produced was consumed in the production of styrene.

2-Butoxyethanol Chemical compound

2-Butoxyethanol is an organic compound with the chemical formula BuOC2H4OH (Bu = CH3CH2CH2CH2). 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, the study also reported a positive association below the level of statistical significance with a higher risk of obese asthma and increased child BMI.

Ethyl acetoacetate Chemical compound

The organic compound ethyl acetoacetate (EAA) is the ethyl ester of acetoacetic acid. It is a colorless liquid. It is widely used as a chemical intermediate in the production of a wide variety of compounds. It is used as a flavoring for food.

Glycol ethers are a group of solvents based on alkyl ethers of ethylene glycol or propylene glycol commonly used in paints and cleaners. These solvents typically have a higher boiling point, together with the favorable solvent properties of lower-molecular weight ethers and alcohols. The word "Cellosolve" was registered in 1924 as a United States trademark by Carbide & Carbon Chemicals Corp. for "Solvents for Gums, Resins, Cellulose Esters, and the Like". The first one was ethyl cellosolve, with the name now generic for glycol ethers.

2-Ethoxyethanol Chemical compound

2-Ethoxyethanol, also known by the trademark Cellosolve or 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.

2-Methoxyethanol Chemical compound

2-Methoxyethanol, or methyl cellosolve, is an organic compound with formula C
3H
8O
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:

1,3-Propanediol is the organic compound with the formula CH2(CH2OH)2. This 3-carbon diol is a colorless viscous liquid that is miscible with water.

Dimethyl carbonate 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 more recently as a solvent that is exempt from the restrictions placed on most volatile organic compounds (VOCs) in the US. Dimethyl carbonate is often considered to be a green reagent.

Ethyl acrylate 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.

Acetic acid 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 (also written as CH3CO2H, C2H4O2, or HC2H3O2). Vinegar is no less than 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water and other trace elements.

Isopropyl alcohol (IUPAC name propan-2-ol and also called isopropanol or 2-propanol) is a colorless, flammable chemical compound (chemical formula CH3CHOHCH3) with a strong odor. As an isopropyl group linked to a hydroxyl group, it is the simplest example of a secondary alcohol, where the alcohol carbon atom is attached to two other carbon atoms. It is a structural isomer of 1-propanol and ethyl methyl ether.

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.
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