Succinic anhydride

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Succinic anhydride
Skeletal formula of succinic anhydride
Ball-and-stick model of the succinic anhydride molecule
Names
IUPAC name
Oxolane-2,5-dione [1]
Other names
Succinic acid anhydride
Succinyl oxide
Dihydro-2,5-furandione
Identifiers
108-30-5 YesY
ChEBI CHEBI:36595 YesY
ChemSpider 7634 YesY
Jmol 3D model Interactive image
KEGG C19524 N
PubChem 7922
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[edit]

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]

Use[edit]

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]

References[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.