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ethyl acetate

Product name ethyl acetate
Synonyms acetic acid ethyl ester
GOST 8981-78
CAS 141-78-6

Ethyl acetate CH3C(O)OC2H5 is a clear, colorless, flammable liquid with a fruity odor. It is fully miscible with benzene, toluene, chloroform, diethyl ether, ethanol, hexane, petroleum ether and other organic solvents. Ethyl acetate is boundedly soluble in water (12% wt), water dissolves in ethyl acetate up to 9.7% wt at room temperature. Ethyl acetate forms azeotropes with water (b.p. 70.4°C, 8.2% wt of water), ethyl alcohol (71.8°C and 30.8%), methanol (62.25°C and 44.0%), isopropanol (75.3°C and 21.0%), cyclohexane (72.8°C and 54.0%), carbon tetrachloride (74.7°C and 57.0%).

Ethyl acetate is a moderately polar solvent. It is relatively non-toxic and non-hygroscopic. It readily dissolves cellulose nitrates and acetates, synthetic varnishes, fats, oils and waxes.

Ethyl acetate is an ethyl ester of acetic acid. It possess typical chemical properties of esters. It easily hydrolyses in alkali media to form ethanol and acetic acid. Ethyl acetate can be interesterified under acid catalysis in the presence of other alcohol:

CH3C(O)OC2H5 + CH3 ⇄ CH3C(O)OCH3 + C2H5OH

Ethyl acetate possess a relatively low toxicity. This allows apply it as a solvent in food and pharmaceutical industries. Nevertheless its vapors irritate eyes and respiratory tract mucous membranes and contact with a skin may cause eczema and dermatitis.

Production.

There are several routes are used for manufacturing of ethyl acetate in industry.

  • By Tishchenko reaction from acetaldehyde. The process in conducted at 0-5°C in the presence of catalytic amounts of aluminium alcoholate. This process is characterized by high conversion of acetaldehyde (up to 98%) and high selectivity if reaction(97-98%):

    2CH3C(O)H → CH3C(O)OCH2CH3

  • By esterification of acetic acid with ethyl alcohol in the presence of acid catalysts (sulfuric acid, para-toluenesulfonic acid or ion-exchange resins). This process may be batch or continuous. The ratio of acid and alcohol is 1:1.1; water formed in the reaction is removed by distillation. It is important to achieve maximum conversion of acetic acid, which is costlier than ethyl alcohol. The conversion of reactants in this process is about 95%.

    CH3C(O)OH + CH3CH2OH → CH3C(O)OCH2CH3 + H2O

  • By liquid-phase oxidation of n-butane with oxygen of air in acetic acid manufacturing. Ethyl acetate is a by-product of this reaction.
  • By alkylation of acetic acid with ethylene at 150°C and pressure 7.7MPa in the presence of sulfuric acid or solid acid catalyst (Avada process). The molar ratio of acetic acid and ethylene is 1:3.89.

    CH3C(O)OH + CH2=CH2 → CH3C(O)OCH2CH3

Uses.

  • as one of the most popular solvents for nitrocellulose lacquers, varnishes and thinners. It shows high dilution ratios with both aromatic and aliphatic diluents;
  • as a solvent in paints and printing ink industry;
  • as a solvent in adhesives industry;
  • in flexible packaging industry at the screen printing stage;
  • in the treatment of aluminium foils and sheets;
  • in the manufacture of polyester films and BOPP films;
  • as an important component in extractants for the concentration and purification of antibiotics;
  • as a reactant in pharmaceutical industry;
  • as a solvent in making of artificial leather (in the mixture with ethanol);
  • in the manufacture of video/audio tapes and for cleaning of magnetic heads;
  • as an extracting agent in food industry (e.g. the decaffeination of coffee beans and tea leaves);
  • as a gelated agent in some explosives making;
  • in the preparation of synthetic fruit essences, flavours and perfumes;

Manufacturer(s) JSC Asha Chemical Plant
JSC Nizhne-Maltsevo Chemical Plant
JSC Omsky kauchuk
Chemical structure of ethyl acetate

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