Succinic anhydride

Succinic anhydride, is an organic compound with the molecular formula (CH2CO)2O. This colorless solid is the acid anhydride of succinic acid.

Succinic anhydride
Skeletal formula of succinic anhydride
Names
Preferred IUPAC name
Oxolane-2,5-dione[1]
Other names
3,4-Dihydrofuran-2,5-dione, Butanedioic anhydride[1]
Dihydrofuran-2,5-dione
Succinic acid anhydride
Succinyl oxide
Dihydro-2,5-furandione
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.003.246
KEGG
UNII
  • InChI=1S/C4H4O3/c5-3-1-2-4(6)7-3/h1-2H2 checkY
    Key: RINCXYDBBGOEEQ-UHFFFAOYSA-N checkY
  • InChI=1/C4H4O3/c5-3-1-2-4(6)7-3/h1-2H2
    Key: RINCXYDBBGOEEQ-UHFFFAOYAN
  • O=C1OC(=O)CC1
Properties
C4H4O3
Molar mass 100.073 g·mol−1
Appearance Colorless crystalline needles[2]
Density 1.23 g/cm3[2]
Melting point 119 to 120 °C (246 to 248 °F; 392 to 393 K)[3]
Boiling point 261 °C (502 °F; 534 K)[2]
Decomposes
-47.5·10−6 cm3/mol
Hazards
Flash point 147 °C (297 °F; 420 K)[4]
Lethal dose or concentration (LD, LC):
1510 mg/kg (oral, rat)[4]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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,[5] or thermally.[6]

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]

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.

See also

References
  1. "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.
  2. Record of CAS RN 108-30-5 in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 27 April 2010.
  3. 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.
  4. Chemical data
  5. 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); Collective Volume, vol. 2, p. 560
  6. Carlo 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.
  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. Gess, Jerome; Rend, Dominic (2005). "Alkenyl Succinic Anhydride (ASA)". TAPPI Journal. 4: 25–30.
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