Succinic anhydride

Preparation

In the laboratory, this material can be prepared by dehydration of succinic acid. Such dehydration can occur with the help of acetyl chloride or phosphoryl chloride, or thermally.

Industrially, succinic anhydride is prepared by catalytic hydrogenation of maleic anhydride.

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.

Related compounds

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. Maleic anhydride undergoes a similar reaction with polyisobutylene to give polyisobutylenylsuccinic anhydride, a common building block chemical in the petroleum additives industry.

Drugs List

Succinic anhydride is used in the synthesis of the following list of agents:

1. Haloperidol
2. Oxaprozin
3. Procodazole
4. Endixaprine
5. Clofilium phosphate
6. Indolidan
7. Lometraline
8. McN 4612-z
9. Fenbufen
10. Furobufen
11. NNC 38-1049
12. Piretanide
13. Pirisudanol
14. Cinazepam
15. Bucloxic acid
16. Exatecan
17. Blarcamesine
18. Ibutilide
19. Diclomezine
20. Domipizone
21. Daminozide
22. Trepibutone
23. Benfurodil hemisuccinate
24. Tepoxalin
25. Menbutone
26. Florantyrone
27. Artesunate
28. Suxibuzone
29. Sunepitron
30. Prizidilol
31. Xemilofiban
32. Sulfasuccinamide
33. Succisulfone

References

References

1. (2014). "Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)". [[Royal Society of Chemistry.
2. (1936). "Succinic-α-d₂,α'-d₂ Acid and its Derivatives". J. Am. Chem. Soc..
3. {{GESTIS
4. [http://www.chemicalland21.com/specialtychem/perchem/SUCCINIC%20ANHYDRIDE.htm Chemical data]
5. [[Louis F. Fieser]], E. L. Martin, R. L. Shriner, and H. C. Struck. (1932). "Succinic Anhydride".
6. Carlo Fumagalli. (2006). "Succinic Acid and Succinic Anhydride".
7. Castillo, Rafael; Suárez-Herrera, Margarita; Aparicio, Mayra; Hernández-Lui, Francisco; Hernández, Alicia (1995). "An Improved Synthesis of Fenbulen". Organic Preparations and Procedures International. 27 (5): 550–552. doi:10.1080/00304949509458497.
8. (2005). "Alkenyl Succinic Anhydride (ASA)". TAPPI Journal.