5242. Itaconic Acid

Nomenclature

CAS number: 97-65-4
Methylenesuccinic acid; propylenedicarboxylic acid.
C5H6O4; mol wt 130.10.
C 46.16%, H 4.65%, O 49.19%.

Description and references

Obtained by dry distillation of citric acid and subsequent treatment of the anhydride with water. Produced on a large scale by submerged aerobic fermentation using Aspergillus terreus and low cost carbohydrates from beet or cane: Kane et al., US 2385283 (1945 to Pfizer). Synthesis from propargyl chloride, carbon monoxide, nickel carbonyl and water: Chiusoli, US 3025320 (1962 to Montecatini).

Chemical structure

Properties

Hygroscopic crystals; characteristic odor. d 1.63. mp 162-164° with decompn. Also reported as mp 172° [Kinoshita, Acta Phytochim. 5, 273 (1931)]. One gram dissolves in 12 ml water, 5 ml alcohol; very slightly sol in benzene, chloroform, ether, carbon disulfide, petr ether. Keep well closed.