2170-03-8

WHITE TO CREAM CRYSTALLINE POWDER

Itaconic anhydride is used in immobilization of β-glucosidase. It undergoes estrification to obtain suitable monomers for emulsion polymerization itaconates.

Tetrahedron Letters, 25, p. 6027, 1984 DOI: 10.1016/S0040-4039(01)81751-2

Crystallise the anhydride from CHCl3/pet ether. It can be distilled under reduced pressure. Distillation at atmospheric pressure, or prolonged distillation causes rearrangement to citraconic anhydride (2-methylmaleic anhydride). If the material (as seen in the IR spectrum) contains much free acid, then heat with acetyl chloride or SOCl2, evaporate and distil at as high a vacuum as possible. The crude anhydride deposits crystals of itaconic acid on standing probably due to hydrolysis by H2O — store it in sealed ampoules under dry N2. [Skinner et al. Org Synth Coll Vol II 368 1943, IR: Nagai Bull Chem Soc Jpn 37 369 1964, Kelly & Segura J Am Chem Soc 56 2497 1934, Beilstein 17/11 V 66.]