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Ethyl acetate (systematically ethyl ethanoate, commonly abbreviated EtOAc, ETAC or EA) is the organic compound with the formula CH3–COO–CH2–CH3, simplified to C4H8O2. This colorless liquid has a characteristic sweet smell (similar to pear drops) and is used in glues, nail polish removers, decaffeinating 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.
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: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:
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 (acetone and acetonitrile are also used). Coffee beans and tea leaves are decaffeinated with this solvent. It is also used in paints as an activator or hardener.[citation needed] 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 fairly volatile at room temperature and has a boiling point of 77 °C (171 °F). Due to these properties, it can be removed from a sample by heating in a hot water bath and providing ventilation with compressed air.
Occurrence in wines
Ethyl acetate is the most common ester in wine, being the product of the most common volatile organic acid – acetic 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.
Entomological killing agent
In the field of entomology, ethyl acetate is an effective asphyxiant for use in insect collecting and study. 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