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Ethyl acetate

From Wikipedia, the free encyclopedia
Ethyl ethanoate
Skeletal formula
Ball-and-stick model
Ethyl acetate
Preferred IUPAC name
Ethyl acetate
Systematic IUPAC name
Ethyl ethanoate
Other names
  • Acetic ester
  • Acetic ether
  • Ethyl ester of acetic acid
3D model (JSmol)
ECHA InfoCard 100.005.001 Edit this at Wikidata
E number E1504 (additional chemicals)
RTECS number
  • AH5425000
  • InChI=1S/C4H8O2/c1-3-6-4(2)5/h3H2,1-2H3 checkY
  • InChI=1/C3H8O2/c1-3-6-4(2)5/h3H2,1-2H3
  • O=C(OCC)C
Molar mass 88.106 g·mol−1
Appearance Colorless liquid
Odor nail polish-like, fruity
Density 0.902 g/cm3
Melting point −83.6 °C (−118.5 °F; 189.6 K)
Boiling point 77.1 °C (170.8 °F; 350.2 K)
8.3 g/100 mL (at 20 °C)
Solubility in ethanol, acetone, diethyl ether, benzene Miscible
log P 0.71[1]
Vapor pressure 73 mmHg (9.7 kPa) at 20 °C[2]
Acidity (pKa) 25
−54.10×10−6 cm3/mol
Viscosity 426 μPa·s (0.426 cP) at 25 °C
1.78 D
Occupational safety and health (OHS/OSH):
Main hazards
  • Flammable (F),
  • Irritant (Xi)
GHS labelling:
GHS02: Flammable GHS07: Exclamation mark[3]
H225, H319, H336[3]
P210, P233, P240, P305+P351+P338, P403+P235[3]
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
Flash point −4 °C (25 °F; 269 K)
Explosive limits 2.0–11.5%[2]
Lethal dose or concentration (LD, LC):
11.3 g/kg, rat
16,000 ppm (rat, 6 h)
12,295 ppm (mouse, 2 h)
1600 ppm (rat, 8 h)[4]
21 ppm (guinea pig, 1 h)
12,330 ppm (mouse, 3 h)[4]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 400 ppm (1400 mg/m3)[2]
REL (Recommended)
TWA 400 ppm (1400 mg/m3)[2]
IDLH (Immediate danger)
2000 ppm[2]
Related compounds
Related compounds
Supplementary data page
Ethyl acetate (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Ethyl acetate (systematically ethyl ethanoate, commonly abbreviated EtOAc, ETAC or EA) is the organic compound with the formula CH3CO2CH2CH3, simplified to C4H8O2. This colorless liquid has a characteristic sweet smell (similar to pear drops) and is used in glues, nail polish removers, and 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.[5]

Production and synthesis[edit]

Ethyl acetate was first synthesized by the Count de Lauraguais in 1759 by distilling a mixture of ethanol and acetic acid.[6]

In 2004, an estimated 1.3 million tonnes were produced worldwide.[5][7] The combined annual production in 1985 of Japan, North America, and Europe was about 400,000 tonnes. The global ethyl acetate market was valued at $3.3 billion in 2018.[8]

Ethyl acetate is synthesized in industry mainly via the classic Fischer esterification reaction of ethanol and acetic acid. This mixture converts to the ester in about 65% yield at room temperature:


The reaction can be accelerated by acid catalysis and the equilibrium can be shifted to the right by removal of water.

It is also prepared in industry using the Tishchenko reaction, by combining two equivalents of acetaldehyde in the presence of an alkoxide catalyst:


Silicotungstic acid is used to manufacture ethyl acetate by the alkylation of acetic acid by ethylene:[9]

C2H4 + CH3CO2H → CH3CO2C2H5


Ethyl acetate is used primarily as a solvent and diluent, being favored because of its low cost, low toxicity, and agreeable odor.[5] For example, it is commonly used to clean circuit boards and in some nail varnish removers (acetone is also used). Coffee beans and tea leaves are decaffeinated with this solvent.[10] It is also used in paints as an activator or hardener. Ethyl acetate is present in confectionery, perfumes, and fruits. In perfumes it evaporates quickly, leaving the scent of the perfume on the skin.

Ethyl acetate is an asphyxiant for use in insect collecting and study.[11] In a killing jar charged with ethyl acetate, the vapors will kill the collected insect quickly without destroying it. Because it is not hygroscopic, ethyl acetate also keeps the insect soft enough to allow proper mounting suitable for a collection. However, ethyl acetate is regarded as potentially doing damage to insect DNA, making specimens processed this way less than ideal for subsequent DNA sequencing.[12]

Laboratory uses[edit]

In the laboratory, mixtures containing ethyl acetate are commonly used in column chromatography and extractions.[13] Ethyl acetate is rarely selected as a reaction solvent because it is prone to hydrolysis, transesterification, and condensations.

Occurrence in wines[edit]

Ethyl acetate is the most common ester in wine, being the product of the most common volatile organic acidacetic acid, and the ethyl alcohol generated during the fermentation. The aroma of ethyl acetate is most vivid in younger wines and contributes towards the general perception of "fruitiness" in the wine. Sensitivity varies, with most people having a perception threshold around 120 mg/L. Excessive amounts of ethyl acetate are considered a wine fault.


Ethyl acetate is only weakly Lewis basic, like a typical carboxylic acid ester.

Ethyl acetate hydrolyses to give acetic acid and ethanol. Bases accelerate the hydrolysis, which is subject to the Fischer equilibrium mentioned above. In the laboratory, and usually for illustrative purposes only, ethyl esters are typically hydrolyzed in a two-step process starting with a stoichiometric amount of a strong base, such as sodium hydroxide. This reaction gives ethanol and sodium acetate, which is unreactive toward ethanol:

CH3CO2C2H5 + NaOH → C2H5OH + CH3CO2Na

In the Claisen condensation, anhydrous ethyl acetate and strong bases react to give ethyl acetoacetate:[14]

Preparation of ethyl acetoacetate.
Preparation of ethyl acetoacetate.


Physical Properties[edit]

Vapor pressure of ethyl acetate
Heat of evaporation of ethyl acetate

Under normal conditions, ethyl acetate exists as a colorless, low-viscosity, and flammable liquid. Its melting point is -83 °C, with a melting enthalpy of 10.48 kJ·mol−1. At atmospheric pressure, the compound boils at 77 °C. The vaporization enthalpy at the boiling point is 31.94 kJ·mol−1. The vapor pressure function follows the Antoine equation:


  • is the vapor pressure in bars,
  • is the absolute temperature in Kelvin, and
  • , , and are constants.

This function is valid within the temperature range of 289 K (16 °C) to 349 K (76 °C).

The enthalpy of vaporization in kJ/mol is calculated according to the empirical equation by Majer and Svoboda [15]


  • is the reduced temperature, and = 523.2 K is the critical temperature.
  • = 54.26 kJ/mol and = 0.2982 are constants.
Compilation of Key Thermodynamic Properties
Property Type Value Remarks References
Standard Enthalpy of Formation
-480.57 kJ·mol−1
-445.43 kJ·mol−1
as liquid
as gas
Standard Entropy
259.4 J·mol−1·K−1
362.75 J·mol−1·K−1
as liquid
as gas
Combustion Enthalpy -2235.4 kJ·mol−1 [19]
Heat Capacity 168.94 J·mol−1·K−1 (25 °C)
1.92 J·g−1·K−1 (25 °C)
113.64 J·mol−1·K−1 (25 °C)
1.29 J·g−1·K−1 (25 °C)
as liquid
as gas
Critical Temperature 523.2 K [15]
Critical Pressure 38.82 bar [21]
Critical Density 3.497 mol·L−1 [22]
Acentric Factor 0.36641 [23]

The table above summarizes the most important thermodynamic properties of ethyl acetate under various conditions.


The LD50 for rats is 5620 mg/kg,[24] indicating low acute toxicity. Given that the chemical is naturally present in many organisms, there is little risk of toxicity.

Overexposure to ethyl acetate may cause irritation of the eyes, nose, and throat. Severe overexposure may cause weakness, drowsiness, and unconsciousness.[25] Humans exposed to a concentration of 400 ppm in 1.4 mg/L ethyl acetate for a short time were affected by nose and throat irritation.[26] Ethyl acetate is an irritant of the conjunctiva and mucous membrane of the respiratory tract. Animal experiments have shown that, at very high concentrations, the ester has central nervous system depressant and lethal effects; at concentrations of 20,000 to 43,000 ppm (2.0–4.3%), there may be pulmonary edema with hemorrhages, symptoms of central nervous system depression, secondary anemia and liver damage. In humans, concentrations of 400 ppm cause irritation of the nose and pharynx; cases have also been known of irritation of the conjunctiva with temporary opacity of the cornea. In rare cases exposure may cause sensitization of the mucous membrane and eruptions of the skin. The irritant effect of ethyl acetate is weaker than that of propyl acetate or butyl acetate.[27]


  1. ^ "ethyl acetate MSDS".
  2. ^ a b c d e NIOSH Pocket Guide to Chemical Hazards. "#0260". National Institute for Occupational Safety and Health (NIOSH).
  3. ^ a b c Record of Ethyl acetate in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 7 December 2020.
  4. ^ a b "Ethyl acetate". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  5. ^ a b c Riemenschneider, Wilhelm; Bolt, Hermann M. "Esters, Organic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a09_565.pub2. ISBN 978-3527306732.
  6. ^ Parker, Joseph (1832). "The Edinburgh Encyclopaedia". The Edinburgh Encyclopaedia. 5.
  7. ^ Dutia, Pankaj (August 10, 2004). "Ethyl Acetate: A Techno-Commercial Profile" (PDF). Chemical Weekly: 184. Retrieved 2009-03-21.
  8. ^ ""Global Ethyl Acetate Market to be valued at $3.3 billion in 2018" reports Visiongain". Visiongain. 2019-09-05. Retrieved 2019-09-05.
  9. ^ Misono, Makoto (2009). "Recent progress in the practical applications of heteropolyacid and perovskite catalysts: Catalytic technology for the sustainable society". Catalysis Today. 144 (3–4): 285–291. doi:10.1016/j.cattod.2008.10.054.
  10. ^ ico.org Archived 2007-04-29 at the Wayback Machine
  11. ^ Littledyke, M.; Cherrett, J. M. (June 1976). "Direct ingestion of plant sap from cut leaves by the leaf-cutting ants Atta cephalotes (L.) and acromyrmex octospinosus (reich) (Formicidae, Attini)". Bulletin of Entomological Research. 66 (2): 205–217. doi:10.1017/S0007485300006647. ISSN 1475-2670.
  12. ^ Cilia, G.; Flaminio, S.; Quaranta, M. (2022). "A novel and non-invasive method for DNA extraction from dry bee specimens". Scientific Reports. 12 (1): 11679. Bibcode:2022NatSR..1211679C. doi:10.1038/s41598-022-15595-8. PMC 9270346. PMID 35804181.
  13. ^ Tan, Wei Wen; Wu, Bin; Wei, Ye; Yoshikai, Naohiko (2018). "Copper and Secondary Amine-Catalyzed Pyridine Synthesis from O-Acetyl Oximes and α,β-Unsaturated Aldehydes". Organic Syntheses. 95: 1–14. doi:10.15227/orgsyn.095.0001.
  14. ^ Inglis, J. K. H.; Roberts, K. C. (1926). "Ethyl Acetoacetate". Org. Synth. 6: 36. doi:10.15227/orgsyn.006.0036.
  15. ^ a b V. Majer, V. Svoboda: Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation. Blackwell Scientific Publications, Oxford 1985, ISBN 0-632-01529-2.
  16. ^ a b K. B. Wiberg, L. S. Crocker, K. M. Morgan: Thermochemical studies of carbonyl compounds. 5. Enthalpies of reduction of carbonyl groups. In: J. Am. Chem. Soc. 113, 1991, pp. 3447–3450. doi:10.1021/ja00009a033.
  17. ^ G. S. Parks, H. M. Huffman, M. Barmore: Thermal data on organic compounds. XI. The heat capacities, entropies and free energies of ten compounds containing oxygen or nitrogen. In: J. Am. Chem. Soc. 55, 1933, S. 2733–2740, doi:10.1021/ja01334a016.
  18. ^ a b D. R. Stull, Jr.: The Chemical Thermodynamics of Organic Compounds. Wiley, New York, 1969.
  19. ^ M. E. Butwill, J. D. Rockenfeller: Heats of combustion and formation of ethyl acetate and isopropyl acetate. In: Thermochim. Acta. 1, 1970, pp. 289–295. doi:10.1016/0040-6031(70)80033-8.
  20. ^ Pintos, M.; Bravo, R.; Baluja, M.C.; Paz Andrade, M.I.; Roux-Desgranges, G.; Grolier, J.-P.E. (1988). "Thermodynamics of alkanoate + alkane binary mixtures. Concentration dependence of excess heat capacities and volumes". Can. J. Chem. 66 (5): 1179–1186. doi:10.1139/v88-193.
  21. ^ D. Ambrose, J. H. Ellender, H. A. Gundry, D. A. Lee, R. Townsend: Thermodynamic properties of organic oxygen compounds. LI. The vapour pressures of some esters and fatty acids. In: J. Chem. Thermodyn. 13, 1981, S. 795–802. doi:10.1016/0021-9614(81)90069-0
  22. ^ S. Young, G. L. Thomas: The vapour pressures, molecular volumes, and critical constants of ten of the lower esters. In: J. Chem. Soc. 63, 1893, S. 1191.
  23. ^ J. Schmidt: Auslegung von Sicherheitsventilen für Mehrzweckanlagen nach ISO 4126-10. In: Chem. Ing. Techn. 83, 2011, pp. 796–812. doi:10.1002/cite.201000202
  24. ^ Hazard Ethyl Acetate MSDS "Ethyl Acetate MSDS Number: E2850".
  25. ^ Mackison, F. W.; Stricoff, R. S.; Partridge, L. J. Jr., eds. (January 1981). NIOSH/OSHA – Occupational Health Guidelines for Chemical Hazards. DHHS (NIOSH) Publication No. 81–123. Washington, DC: U.S. Government Printing Office.
  26. ^ Clayton, G.D.; Clayton, F.E., eds. (1993–1994). Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology (4th ed.). New York, NY: John Wiley & Sons. p. 2981.
  27. ^ Encyclopedia of Occupational Health and Safety, Geneva, Switzerland: International Labour Office, 1983, p. 782

External links[edit]