Girish Mahajan (Editor)

Succinic anhydride

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Formula
  
C4H4O3

Boiling point
  
261 °C

Molar mass
  
100.07 g/mol

Density
  
1.23 g/cm³

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Appearance
  
Colorless crystalline needles

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

Contents

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Preparation

Succinic anhydride Synthesis of SUCCINIC ANHYDRIDE PrepChemcom

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, or thermally.

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

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
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Maleic anhydride undergoes the Alder-ene reaction with olefins 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. Maleic anhydride undergoes a similar reaction with polyisobutylene to give polyisobutylenylsuccinic anhydride, a common building block chemical in the petroleum additives industry.

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References

Succinic anhydride Wikipedia