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N-Phenylphthalimide → Phthalic Anhydride

HRID 65605
Notes
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Reaction equation

HRID 65605 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=O.[C:9]1([N:15]2[C:19](=[O:20])[C:18]3=CC=CC=[C:17]3[C:16]2=[O:25])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O>[C:4]1(=[O:6])[O:7][C:1](=[O:8])[C:2]2=[CH:14][CH:9]=[CH:10][CH:11]=[C:3]12.[C:9]1([N:15]2[C:19](=[O:20])[CH:18]=[CH:17][C:16]2=[O:25])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 68215N-PhenylphthalimideHCID 444266Maleic Acid

Product 2

HCID 6811Phthalic AnhydrideHCID 13662N-Phenylmaleimide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 2.32 parts of maleic acid, 2.23 parts of N-phenyl phthalimide and 20 parts of water is heated under sealed conditions for 2 hours at 180° C. The reaction mixture is then allowed to cool to ambient conditions and distilled under vacuum. Maleic anhydride is initially recovered followed by phthalic anhydride and N-phtnyl maleimide. There is obtained a yield of 16% by weight of phthalic anhydride and 14.1% by weight of N-phenylmaleimide.

Workup

  1. temperatureto cool to ambient conditions
  2. distillationdistilled under vacuum
  3. customMaleic anhydride is initially recovered

Sources & evidence

ORD record
ord-d29f888cbcaa45d6800b090bb8a32222
Source dataset
uspto-grants-1978_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04128574

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes