Succinic anhydride
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| Names | |||
|---|---|---|---|
| IUPAC name
Oxolane-2,5-dione [1] | |||
| Other names
Succinic acid anhydride Succinyl oxide Dihydro-2,5-furandione | |||
| Identifiers | |||
108-30-5  | |||
| ChEBI | CHEBI:36595 | ||
| ChemSpider | 7634 | ||
| Jmol interactive 3D | Image | ||
| KEGG | C19524  | ||
| PubChem | 7922 | ||
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| 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): | |||
| LD50 (Median dose) |
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). | |||
| verify (what is ?) | |||
| 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]
Related compounds
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
- ↑ CID 14718004 from PubChem
- 1 2 3 Record of CAS RN 108-30-5 in the GESTIS Substance Database of the IFA, accessed on 27 April 2010
- ↑ 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.
- 1 2 Chemical data
- ↑ 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
- 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