Succinic anhydride

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Succinic anhydride
Skeletal formula of succinic anhydride
Ball-and-stick model of the succinic anhydride molecule
IUPAC name
Oxolane-2,5-dione [1]
Other names
Succinic acid anhydride
Succinyl oxide
108-30-5 YesY
ChEBI CHEBI:36595 YesY
ChemSpider 7634 YesY
Jmol 3D model Interactive image
KEGG C19524 N
PubChem 7922
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]
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).
N verify (what is YesYN ?)
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.


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. Maleic anhydride is used in multi-step synthesis of tetralone, 1-Naphthol, tetralin and naphthalene[7] as well as N-chloro– and N-Bromosuccinimide.[8] Citraconic anhydride is industrially manufactured by reacting succinic anhydride with formaldehyde.[9]

See also[edit]


  1. ^ CID 14718004 from PubChem
  2. ^ a b c 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. ^ a b 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. ^ a b 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. ^ Römpp Chemie Lexikon, 9. Auflage, Georg Thieme Verlag, 1995.
  8. ^ Hauptmann, S.; Graefe, J.; Remane, H.: Lehrbuch der Organischen Chemie, Deutscher Verlag für Grundstoffindustrie, Leipzig 1980, S. 407.
  9. ^ Lohbeck, K.; Haferkorn, H.; Fuhrmann, W.; Fedtke, N.: Maleic and Fumaric Acids in Ullmann's Encyclopedia of Industrial Chemistry,Wiley-VCH Verlag GmbH & Co KGaA, Weinheim 2005. doi:10.1002/14356007.a16_053.