فارسی

Ethyl acetate (systematically, ethyl ethanoate, commonly abbreviated EtOAc or EA) is the organic compound with the formula CH3COOCH2CH3.

This colorless liquid has a characteristic sweet smell (similar to pear drops) and is used in glues, nail polish removers, and cigarettes (see list of additives in cigarettes). Ethyl acetate is the ester of ethanol and acetic acid; it is manufactured on a large scale for use as a solvent.

 

Production

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:

CH3CH2OH + CH3COOH CH3COOCH2CH3 + H2O

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:

2 CH3CHO → CH3COOCH2CH3

Uses

Ethyl acetate is used primarily as a solvent and diluent, being favored because of its low cost, low toxicity, and agreeable odor.

For example, it is commonly used to clean circuit boards and in some nail varnish removers.Coffee beans and tea leaves are decaffeinated with this solvent. 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 only the scent of the perfume on the skin.

 

Laboratory uses

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

Ethyl acetate is very volatile and has a low boiling point of 77 °C. Due to these properties, it can be removed from a sample by heating in a hot water bath and providing ventilation with compressed air.

Properties

Molecular Formula C4H8O2
Molar Mass 88.105 g/mol
Appearance colorless liquid
Density 0.897 g/cm³, liquid
Melting Point −83.6 °C, 190 K, -118 °F
Boiling Point 77.1 °C, 350 K, 171 °F
Solubility in Water 8.3 g/100 mL (20 °C)
Solubility in Ethanol,
acetone, diethyl ether,
benzene
Miscible
Refractive Index (nD) 1.3720
Viscosity 0.426 cP at 25 °C
  Ethyl Acetate        

Specification

MSDS
         
   
   
               

Ethyl Acetate

IUPAC name

Ethyl acetate

Systematic name

Ethyl ethanoate

Other names

Ethyl ester
Acetic ester
Ester of ethanol

   

Hazards

MSDS MSDS(PDF)
R-phrases R11, R36, R66, R67
S-phrases S16, S26, S33
Main Hazards Flammable (F),
Irritant (Xi)
NFPA

Flash Point −4 °C
LD50 11.3 g/kg, rat
               
   
   
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