Jump to content

2-Ethoxyethyl acetate

From Wikipedia, the free encyclopedia

This is an old revision of this page, as edited by Edgar181 (talk | contribs) at 21:49, 30 March 2018 (raw data such as this is not appropriate encylcopedia content). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

2-ethoxyethyl acetate
Names
IUPAC name
2-ethoxyethyl acetate
Other names
ethyglycol acetate, ethylene glycol mono ethyl ether acetate, 2-EEA, acetic acid,2-ethoxyethil ester, ethoxyethanol acetate, EGA, Cellosolve Acetate, Ethoxol Acetate, Oxidol Acetate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Structure 2-ethoxyethyl acetate

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]

Structure

  • Molecular weight: 132.16
  • Empirical formula: C6H12O3
  • IUPAC Name: 2-ethoxyethil acetate
  • Synonyms: ethyglycol acetate, ethylene glycol mono ethyl ether acetate, 2-EEA, acetic acid,2-ethoxyethil ester, ethoxyethanol acetate, EGA, Cellosolve Acetate, Ethoxol Acetate, Oxidol Acetate[3]

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.[4][5]

Physicochemical properties
Melting point < -62 °C
Boiling point 156 °C
Relative density 0.9730 at 20 °C
Vapour pressure 270 Pa at 20 °C
Surface tension 67.1 mN/m at 25 °C
Water solubility 229 g/l at 20 °C
Partition coefficient Log Pow 0.24 (experimental)
Flash point 51 °C (closed cup)
Flammability flammable
Ignition temperature 380 °C (DIN 51794)
Explosive properties not explosive
Oxidizing properties no oxidizing properties
Henry's law constant 0.16 Pa x m3 x mol−1

Reactivity

Chemical reactivity
Reactivity with Water No reaction
Reactivity with Common Materials No reaction
Stability During Transport Stable
Neutralizing Agents for Acids and Caustics Not pertinent
Polymerization Not pertinent
Inhibitor of Polymerization Not pertinent[5]

Safety data

H-code
H226 Flammable liquid and vapour
H302 + H312 + H332 Harmful if swallowed, harmful in contact with skin, harmful if inhaled
H360FD May damage fertility. Suspected of damaging the unborn child
P-code
P201 Obtain special instructions before use
P280 Wear protective gloves/protective clothing/eye protection/face protection
P308 + P313 IF exposed or concemed: Get medical advice/attention[6]

Metabolism

2-Ethoxyethyl acetate (EGEEA -ethylene glycol monoethyl ether acetate) is rapidly metabolized to 2-ethoxyethanol (EGEE -ethylene glycol monoethyl ether) in the blood, via hydrolyzation. 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. This two lasts 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.[7][8][9] 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.[8]

Kinetics

Absorption

The substance can be introduced into the body by inhalation of its vapour, through the skin and by ingestion.

Inhalation

2-ethoxyethyl acetate can be rapidly taken up by lungs, as a study involving male beagle dogs show. After 10 minutes of exposure, around 80% of the total inhaled amount started to be absorbed, while the other 20% was exhaled.[10]

Percutaneous absorption

The most significant pathway is percutaneous absorption, but this one only occurs when there is a direct skin contact with the solvent, for example when is used to clean instruments, floor or the skin itself, as was recorded during the study of twelve workers producing a new varnish on a factory.[11]

Also on the same beagle dogs, percutaneous absorption was measured. EEA was added to an undiluted compound and the mixture was applied on a shaved area on their thorax for 30 or 60 min. The percutaneous absorption rate was 110 nmol/cm2/min, estimated over a 60-min period. This value is similar to those for other lipid-soluble compounds.[10]

Oral administration

When exposing male Sprague-Dawley rats to oral administration, the main pathway of biotransformation was oxidation to EAA, with some subsequent conjugation of the acid metabolite with glycine.[12]

Excretion

Urinary excretion of EAA during and after exposure of different concentrations of 2-Ethoxyethyl acetate was measured in 10 healthy male volunteers. The half-life of the EAA molecules was 2.2 ± 0.1 hours. EAA reached maximal levels of concentration 3–4 hours after the exposure was finished. The decline after this was described assuming a half-life of 3.6 ± 1.8 hours. 3 hours after the first excretion peak, a second peak of excretion was noticed. On average, 22.2 ± 0.9% of the absorbed 2-ethoxyethyl acetate was recovered within 42 hours.[13]

Inhalation

A fast decline in the post-exposure breath concentrations of the beagle dogs was noticed, which means that the compound was rapidly removed from the blood. The breath concentration of EEA was 7 ppm at 10 min and decreased to 2 ppm after 3 hours of post-exposure. Blood elimination half-life ended being 7.9 hours. However, this compound was slowly excreted. Only 20% of the dose appeared in urine after 4 hours. After 24 hours, no more than 61% had already been excreted.[10]

Percutaneous absorption

In the case of the workers from the varnish factory, the concentration of the compound and its metabolites in the urine didn’t correlate with the concentrations of exposure. Urine samples were taken before and after the shift in which they suffered the exposure. The average post shift concentration of EAA was 167,8 mg/l. The relatively high concentrations found in the samples before the exposure can be explained by the long half-lives of this metabolite.[11]

Again in the dogs case, after exposure to [14C]EEA, urinary excretion of radioactivity was similar after 4 and 8 hours, and was still substantial after 24 hours. No measurable concentrations of radioactivity were detected in the blood of dogs exposed for 60 min to [14C]EEA. The amount of compound absorbed was similar both after 30 and 60-min of exposures.[10]

Oral administration

The two major metabolites that were produced by the tested male Sprague-Dawley rats, EAA and 2-Ethoxyacetyl glycine, represented 73–76% of the orally administered dose and were eliminated in the urine[12]


Symptoms

It can cause a slight skin and eye irritation after exposion.[14]

Uses

Although 2-ethoxyethyl acetate is characterized as toxic and use is limited due to health concerns, it has been used to dissolve polyester and short oil alkyd resins.[15] It has also been used in coatings, dyes, insecticides, soaps and cosmetics.[10] It is also a solvent for nitro-cellulose and is being used for the same applications as ethyl glycol[15][14]

In automobile lacquers it was used to reduce evaporation ant impart high gloss.[16]

References

  1. ^ 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)
  2. ^ 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)
  3. ^ "The PubChem Project". pubchem.ncbi.nlm.nih.gov. Retrieved 2018-03-29.
  4. ^ 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)
  5. ^ a b "2-Ethoxyethyl acetate, SUMMARY RISK ASSESSMENT". 2005. {{cite journal}}: Cite journal requires |journal= (help)
  6. ^ "2-ethoxyethyl acetate SDS". SIGMA-ALDRICH. {{cite web}}: Cite has empty unknown parameter: |dead-url= (help)
  7. ^ "Chemical Sampling Information | 2-Ethoxyethyl acetate". www.osha.gov. Retrieved 2018-03-29.
  8. ^ a b "Selected Alkoxyethanols: 2-Ethoxyethanol and 2-Eropoxyethanol" (PDF). Concise International Chemical Assessment Document 67. World Health Organization. 2009.
  9. ^ 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.
  10. ^ a b c d e 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.
  11. ^ a b Angerer J, Lichterbeck E, Begerow J, Jekel S, Lehnert G (1990-02-01). "Occupational chronic exposure to organic solvents". International Archives of Occupational and Environmental Health. 62 (2): 123–126. doi:10.1007/BF00383588.
  12. ^ a b Cheever KL, Plotnick HB, Richards DE, Weigel WW (August 1984). "Metabolism and excretion of 2-ethoxyethanol in the adult male rat". Environmental Health Perspectives. 57: 241–8. PMC 1568278. PMID 6437805.
  13. ^ Groeseneken D, Veulemans H, Masschelein R, Van Vlem E (July 1987). "Ethoxyacetic acid: a metabolite of ethylene glycol monoethyl ether acetate in man" (PDF). British Journal of Industrial Medicine. 44 (7): 488–93. PMC 1007866. PMID 3620374.
  14. ^ 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)
  15. ^ a b JETLAG. "Ethyl glycol acetate - Coating Terms - Kansai Altan". www.kansaialtan.com (in Turkish). Retrieved 2018-03-29.
  16. ^ 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)
Retrieved from "https://en.wikipedia.org/enwiki/w/index.php?title=2-Ethoxyethyl_acetate&oldid=833326254"