Industrially, succinic anhydride is prepared by catalytic hydrogenation of maleic anhydride.[6]
Reactions
Succinic anhydride hydrolyzes readily to give succinic acid:
(CH2CO)2O + H2O → (CH2CO2H)2
With alcohols (ROH), a similar reaction occurs, delivering the monoester:
(CH2CO)2O + ROH → RO2CCH2CH2CO2H
Succinic anhydride is used in acylations under Friedel-Crafts conditions, as illustrated by the industrial route to the drug Fenbufen.[7]
Related compounds
Chemical structure of an alkylsuccinic anhydride derived from octadecene
Maleic anhydride undergoes the Alder-ene reaction with alkenes to give alkenylsuccinic anhydrides. Such compounds are sizing agents in the paper industry. In this role, the anhydride is proposed to form an ester with the hydroxyl groups on the cellulose fibers.[8] Maleic anhydride undergoes a similar reaction with polyisobutylene to give polyisobutylenylsuccinic anhydride, a common building block chemical in the petroleum additives industry.
^ a b"Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 835. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
^McLean, Andrew; Adams, Roger (1936). "Succinic-α-d2,α'-d2 Acid and its Derivatives". J. Am. Chem. Soc. 58 (5): 804. doi:10.1021/ja01296a038.
^ a bChemical data
^Louis F. Fieser, E. L. Martin, R. L. Shriner, and H. C. Struck (1932). "Succinic Anhydride". Organic Syntheses. 12: 66{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 2, p. 560.
^ a bCarlo Fumagalli (2006). "Succinic Acid and Succinic Anhydride". Kirk-Othmer Encyclopedia of Chemical Technology. New York: John Wiley. doi:10.1002/0471238961.1921030306211301.a01.pub2. ISBN 9780471238966.