ĕthˈənōlˌ or ethyl alcohol, CH₃CH₂OH, a colorless liquid with characteristic odor and taste; commonly called grain alcohol or simply alcohol.

Properties

Ethanol is a monohydric primary alcohol. It melts at −117.3 degrees Celsius and boils at 78.5 degrees Celsius. It is miscible (i.e., mixes without separation) with water in all proportions and is separated from water only with difficulty; ethanol that is completely free of water is called absolute ethanol. Ethanol forms a constant-boiling mixture, or azeotrope, with water that contains 95% ethanol and 5% water and that boils at 78.15 degrees Celsius; since the boiling point of this binary azeotrope is below that of pure ethanol, absolute ethanol cannot be obtained by simple distillation. However, if benzene is added to 95% ethanol, a ternary azeotrope of benzene, ethanol, and water, with boiling point 64.9 degrees Celsius, can form; since the proportion of water to ethanol in this azeotrope is greater than that in 95% ethanol, the water can be removed from 95% ethanol by adding benzene and distilling off this azeotrope. Because small amounts of benzene may remain, absolute ethanol prepared by this process is poisonous.

Ethanol burns in air with a blue flame, forming carbon dioxide and water. It reacts with active metals to form the metal ethoxide and hydrogen, e.g., with sodium it forms sodium ethoxide. It reacts with certain acids to form esters, e.g., with acetic acid it forms ethyl acetate. It can be oxidized to form acetic acid and acetaldehyde. It can be dehydrated to form diethyl ether or, at higher temperatures, ethylene.

Preparation

Ethanol is the alcohol of beer, wines, and liquors. It can be prepared by the fermentation of sugar (e.g., from molasses), which requires an enzyme catalyst that is present in yeast; or it can be prepared by the fermentation of starch (e.g., from corn, rice, rye, or potatoes), which requires, in addition to the yeast enzyme, an enzyme present in an extract of malt. The concentration of ethanol obtained by fermentation is limited to about 10% (20 proof) since at higher concentrations ethanol inhibits the catalytic effect of the yeast enzyme. (The proof concentration of an alcoholic beverage is numerically double the percentage concentration.) For nonbeverage uses ethanol is more commonly prepared by passing ethylene gas at high pressure into concentrated sulfuric or phosphoric acid to form the corresponding ester; the acid-ester mixture is diluted with water and heated, forming ethanol by hydrolysis, and the alcohol is then removed from the mixture by distillation, usually with steam.

Uses

Ethanol is used extensively as a solvent in the manufacture of varnishes and perfumes; as a preservative for biological specimens; in the preparation of essences and flavorings; in many medicines and drugs; as a disinfectant and in tinctures (e.g., tincture of iodine); and as a fuel and gasoline additive (see gasohol). Many U.S. automobiles manufactured since 1998 have been equipped to enable them to run on either gasoline or E85, a mixture of 85% ethanol and 15% gasoline. E85, however, is not yet widely available. Denatured, or industrial, alcohol is ethanol to which poisonous or nauseating substances have been added to prevent its use as a beverage; a beverage tax is not charged on such alcohol, so its cost is quite low. Medically, ethanol is a soporific, i.e., sleep-producing; although it is less toxic than the other alcohols, death usually occurs if the concentration of ethanol in the bloodstream exceeds about 5%. Behavioral changes, impairment of vision, or unconsciousness occur at lower concentrations. See alcoholism.

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