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Itaconic anhydride is the cyclic anhydride of itaconic acid (an unsaturated, dicarboxylic acid) and is obtained by the pyrolysis of citric acid. It is a colourless, crystalline solid, which dissolves in many polar organic solvents and hydrolyzes forming itaconic acid. [ 4 ]
Upon heating itaconic acid converts to its anhydride. [3] As a dicarboxylic acid, itaconic acid has two pKa's. At pH levels above 7, itaconic acid exists as its double negatively charged form, termed itaconate. [5] As an α,β-unsaturated carbonyl compound, itaconic acid is a good Michael acceptor. Thus, nucleophiles add across the C=C bond.
Citraconic acid can be produced, albeit inefficiently, by oxidation of xylene and methylbutanols. The acid displays the unusual property of spontaneously forming the anhydride, which, unlike maleic anhydride, is a liquid at room temperature. [2] Steps in conversion of citric acid to citraconic acid.
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Itaconic acid anhydride is isomerized to citraconic anhydride, which is hydrolyzed and the resulting acid further isomerized under acid-catalysis to give mesaconic acid. [ 1 ] Hydration of mesaconic acid, a conversion catalyzed by mesaconyl-C4-CoA hydratase, gives citramalic acid .
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Itaconic anhydride This page was last edited on 12 November 2022, at 04:44 (UTC). Text is available under the Creative Commons Attribution-ShareAlike 4.0 License ...