ester

ester

Chem any of a class of compounds produced by reaction between acids and alcohols with the elimination of water. Esters with low molecular weights, such as ethyl acetate, are usually volatile fragrant liquids; fats are solid esters

Collins Discovery Encyclopedia, 1st edition © HarperCollins Publishers 2005

ester

[′es·tər]

(organic chemistry)

The compound formed by the elimination of water and the bonding of an alcohol and an organic acid.

McGraw-Hill Dictionary of Scientific & Technical Terms, 6E, Copyright © 2003 by The McGraw-Hill Companies, Inc.

The following article is from The Great Soviet Encyclopedia (1979). It might be outdated or ideologically biased.

Ester

 

any of a number of organic compounds, such as C₂H₅OCOCH₃ or C₅H₁₁ONO, that are derived from acids by replacing the hydroxyl group (OH) with an alcohol, enol, or phenol radical (OR).

Esters are structural analogues of the salts of oxygen acids, but where a metal atom would be attached to the salt, a hydrocarbon group (R) is attached to the ester. The nomenclature for the salts and esters is similar; for example, NaOCOCH₃ is called sodium acetate, and C₂H₅OCOCH₃ is known as ethyl acetate. Like salts, esters form products of incomplete and complete replacement with dibasic and multibasic acids; thus, there are acid esters, such as monomethylsulfate (HOSO₂OCH₃), and complete (neutral) esters, such as dimethylsulfate (CH₃OSO₂OCH₃).

Esters differ greatly from salts in their properties, however. Typical organic compounds, esters are usually volatile liquids. In some instances, they have a fruity or flowery fragrance. Virtually insoluble in water, they are readily soluble in organic solvents. Esters are hydrolyzed by the action of water to form the corresponding alcohol and acid, in accordance with the general formula

RCOOR′ + H₂O ⇆ RCOOH + HOR′

The reaction is catalyzed by acids and even more so by bases. When alkaline catalysts are used, salts of acids are formed instead of free acids; the reaction is irreversible. Of the other reactions in which esters display acylating properties, the most common are transesterification, alcoholysis, and double exchange reactions. Some esters—for example, those formed by the lower aliphatic alcohols and such acids as sulfuric, trifluoroacetic, phosphoric, and phthalic acids—also have alkylating properties (seeDIMETHYL SULFATE and ).

Esters are usually obtained by esterification (see). They may also be formed by the acylation of alcohols by various acid derivatives (including acid halides and anhydrides), by the action of acid salts on alkyl halides, as in the reaction

C₂H₅I + AgONO → C₂H₅ONO + AgI

or by the action of acids on olefins, as in the reaction

HOSO₂OH + CH₂=CH₂ → HOSO₂OCH₂CH₃

Esters of glycerin and the higher carboxylic acids are the principal components of fats, and esters of the higher monohydric aliphatic alcohols and carboxylic acids are the main components of waxes. Other esters—mainly those of the terpene alcohols—are components of essential oils. Esters are used in technology as plastic monomers (acrylates and vinyl acetates), plasticizers for plastics (dioctyl and dibutyl phthalates), detergents (alkyl sulfates), solvents (amyl, butyl, and ethyl acetates), extraction agents and pesticides (esters of phosphoric acid), explosives (esters of nitric acid and polyhydric alcohols, such as nitroglycerin), pharmaceuticals (validol and aspirin), and fragrances (benzyl acetate and terpenyl acetate). Many esters of high molecular weight (including polyethylene terephthalate and cellulose acetates) are used in industry as plastics, lacquers, and synthetic fibers (seeALKYD RESINS and POLYESTER FIBER).

REFERENCES

Nesmeianov, A. N., and N. A. Nesmeianov. Nachala organicheskoi khimii, books 1–2. Moscow, 1969–70.
Chichibabin, A. E. Osnovnye nachala organicheskoi khimii, 7th ed., vol. 1. Moscow, 1963.

The Great Soviet Encyclopedia, 3rd Edition (1970-1979). © 2010 The Gale Group, Inc. All rights reserved.