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Carboxylic anhydrides or acid anhydrides are any class of organic compounds that have an -C(=O)-O-C(=O)- functional group. Anhydrides can be thought of as an oxygen atom flanked by two acyl groups. Anhydrides may be symmetrical or unsymmetrical (mixed) depending on the nature of the acyl groups present.
As a major industrial chemical, acetic anhydride has wide-spread applicability which includes the preparation of acetate esters, for example, cellulose acetate, and as precursors to various resins accomplished through copolymerization with styrene. Maleic anhydride, a cyclic anhydride, is a well-known dienophile for Diels-Alder reaction. Carboxylic anhydrides are excellent acylating agents. Acetic anhydride, owing to its low cost and high efficiency, is extensively used in organic synthesis as an acetylating agent for a variety of substrates including alcohols, amines and aromatics. Phthalic anhydrides are starting materials for the synthesis of phthalate esters which have utility as plasticizers. Napthalene-tetracarboxylic dianhydride is an important precursor to naphthalene diimides, which are often fluorescent. In paper production, alkyl succinic anhydride is employed as a sizing agent or for wet strength additives.