Succinic anhydride

Succinic anhydride
Skeletal formula of succinic anhydride
Ball-and-stick model of the succinic anhydride molecule
Names
Preferred IUPAC name
Oxolane-2,5-dione[1]
Other names
3,4-Dihydrofuran-2,5-dione[1]
Butanedioic anhydride[1]
Succinic anhydride[1]
Dihydrofuran-2,5-dione
Succinic acid anhydride
Succinyl oxide
Dihydro-2,5-furandione
Identifiers
108-30-5 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:36595 YesY
ChemSpider 7634 YesY
ECHA InfoCard 100.003.246
KEGG C19524 N
PubChem 7922
UNII 6RF4O17Z8J N
Properties
C4H4O3
Molar mass 100.07 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
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

Succinic anhydride, also called dihydro-2,5-furandione and butanedioic anhydride , is an organic compound with the molecular formula C4H4O3. This colorless solid is the acid anhydride of succinic acid.

Preparation

In the laboratory, this material can be prepared by dehydration of succinic acid. Such dehydration can occur with the aid of acetyl chloride or phosphoryl chloride,[5] or thermally.[6]

Industrially, succinic anhydride is prepared by catalytic hydrogenation of maleic anhydride.[6]

Maleic anhydride undergoes the Alder-ene reaction with olefins to give alkenyl succinic anhydrides that are sizing agents in the paper industry. It undergoes a similar reaction with polyisobutylene to give polyisobutylenyl succinic anhydride, a common building block chemical.

See also

References

  1. 1 2 3 4 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. 1 2 3 Record of CAS RN 108-30-5 in the GESTIS Substance Database of the IFA, 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. 1 2 Chemical data
  5. ↑ Louis F. Fieser, E. L. Martin, R. L. Shriner, and H. C. Struck (1932). "Succinic Anhydride". Org. Synth. 12: 66.; Coll. Vol., 2, p. 560
  6. 1 2 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
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