Acid anhydride

Acid anhydride

An acid anhydride is an organic compound that has two acyl groups bound to the same oxygen atom.GoldBookRef|title=acid anhydrides|url=] Most commonly, the acyl groups are derived from the same carboxylic acid, the formula of the anhydride being (RC(O))2O. Symmetrical acid anhydrides of this type are named by replacing the word "acid" in the name of the parent carboxylic acid by the word "anhydride".BlueBookRef|rec=R-5.7.7|pages=123–25] Thus, (CH3CO)2O is called "acetic anhydride." Mixed (or unsymmetrical) acid anhydrides, such as acetic formic anhydride (see below), are known.

Important acid anhydrides

Acetic anhydride is a major industrial chemical widely used for preparing acetate esters. The cyclic acid anhydride maleic anhydride is used in organic synthesis as dienophile in the Diels-Alder reaction. One or both acyl groups of an acid anhydride may also be derived from a sulfonic acid or a phosphonic acid. The mixed anhydride 1,3-bisphosphoglycerate is an intermediate in the formation of ATP via glycolysis. [Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. ISBN 1-57259-153-6.]


Acid anhydrides are prepared in industry by diverse means. Acetic anhydride is mainly produced by the carbonylation of methyl acetate. [Zoeller, J. R.; Agreda, V. H.; Cook, S. L.; Lafferty, N. L.; Polichnowski, S. W.; Pond, D. M. "Eastman Chemical Company Acetic Anhydride Process" Catalysis Today (1992), volume 13, pp.73-91. doi:10.1016/0920-5861(92)80188-S] Maleic anhydride is produced by the oxidation of butane. For pedogical and practical considerations, laboratory routes emphasize the dehydration of the corresponding acids. The conditions vary from acid to acid, but phosphorus pentoxide is a common dehydrating agent::2 CH3COOH + P4O10CH3C(O)OC(O)CH3 + "(HO)2P4O9"Acid chlorides are also effective precursors: [OrgSynth | author = Lewis I. Krimen | title = Acetic Formic Anhydride | collvol = 6 | collvolpages = 8| year = 1988 | prep = CV6P0008] :CH3C(O)Cl + HCO2Na → HCO2COCH3 + NaCl


Acid anhydrides are a source of reactive acyl groups, and their reactions and uses resemble those of acyl halides. In reactions with protic substrates, the reactions afford equal amounts of the acylated product and the carboxylic acid::RC(O)OC(O)R + HY → RC(O)Y + RCO2Hfor HY = H2O, HOR (alcohols), HNR'2 (ammonia, primary, secondary amines), aromatic ring (see Friedel-Crafts acylation).

Acid anhydrides tend to be less electrophilic than acyl chlorides, and only one acyl group is transferred per molecule of acid anhydride, which leads to a lower atom efficiency. The low cost, however, of acetic anhydride makes it a common choice for acetylation reactions. Furthermore, the avoidance of chlorocarbons is preferred from the environmental perspective.

Sulfur analogues

Sulfur can replace oxygen, either in the carbonyl group or in the bridge. In the former case, the name of the acyl group is enclosed in parentheses to avoid ambiguity in the name, e.g., (thioacetic) anhydride (CH3C(S)OC(S)CH3). When two acyl groups are attached to the same sulfur atom, the resulting compound is called a thioanhydride, e.g., acetic thioanhydride ((CH3C(O))2S).


Wikimedia Foundation. 2010.

Look at other dictionaries:

  • acid anhydride — rūgšties anhidridas statusas T sritis chemija apibrėžtis Apibrėžtį žr. priede. priedas( ai) Grafinis formatas atitikmenys: angl. acid anhydride rus. ангидрид кислоты ryšiai: sinonimas – anhidridas …   Chemijos terminų aiškinamasis žodynas

  • acid anhydride — an anhydride formed by dehydration of an acid or one that forms an acid upon hydration; if bimolecular, it can be composed of two molecules of the same acid (e.g., acetic anhydride or pyrophosphate), or it can be a mixed anhydride …   Medical dictionary

  • acid anhydride — Chem. See under anhydride (def. 1). * * * …   Universalium

  • acid anhydride — noun A class of organic compounds having two acyl groups bonded to the same oxygen atom. They react with water to give carboxylic acids. Syn: acyl anhydride …   Wiktionary

  • acid anhydride — Chem. See under anhydride (def. 1) …   Useful english dictionary

  • Acid anhydride hydrolases — are a class of hydrolase enzymes catalyzes the hydrolysis of a acid anhydride bond.They are classified under EC number 3.6.One well known member of this class is also* External links* …   Wikipedia

  • arsenic acid anhydride — arseno(V) oksidas statusas T sritis chemija formulė As₂O₅ atitikmenys: angl. arsenic acid anhydride; arsenic pentoxide; arsenic(V) oxide rus. мышьяка(V) оксид; мышьяковый ангидрид ryšiai: sinonimas – diarseno pentoksidas …   Chemijos terminų aiškinamasis žodynas

  • arsenous acid anhydride — arseno(III) oksidas statusas T sritis chemija formulė As₂O₃ atitikmenys: angl. arsenic trioxide; arsenic(III) oxide; arsenious oxide; arsenous acid anhydride; arsenous oxide; white arsenic rus. белый мышьяк; мышьяка пятиокись; мышьяка… …   Chemijos terminų aiškinamasis žodynas

  • nitric acid anhydride — azoto(V) oksidas statusas T sritis chemija formulė N₂O₅ atitikmenys: angl. nitric acid anhydride; nitrogen pentaoxide rus. азота пятиокись; азота(V) оксид; ангидрид азотной кислоты ryšiai: sinonimas – diazoto pentoksidas …   Chemijos terminų aiškinamasis žodynas

  • sulfurous acid anhydride — noun see sulfurous anhydride …   Useful english dictionary