Acetic Acid → Tetrafluorophthalic anhydride

HRID 622264Notes

Reaction equation

HRID 622264 reaction equation
C(N1[C:8](=[O:9])[C:7]2=[C:10]([F:17])[C:11]([F:16])=[C:12]([F:15])[C:13]([F:14])=[C:6]2[C:5]1=[O:18])(C)C.S(=O)(=O)(O)[OH:20].C(O)(=O)C>O>[F:17][C:10]1[C:11]([F:16])=[C:12]([F:15])[C:13]([F:14])=[C:6]2[C:5](=[O:18])[O:9][C:8](=[O:20])[C:7]=12

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 142741834,5,6,7-Tetrafluoro-2-(propan-2-yl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 69545Tetrafluorophthalic anhydrideYield 66.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 500 ml three neck distillation flask were placed 47 g (0.18 mol) of N-isopropyl-tetrafluorophthalimide, 71 ml of concentrated sulfuric acid, 43 ml of acetic acid, and 13 ml of water, and the mixture was reacted for 5 hours at 140° to 150° C. with stirring. After cooling, the reaction mixture was extracted three times with 200 ml of toluene, and the toluene layers thus formed were collected and concentrated by distillation under a reduced pressure to provide 26.3 g (yield 66.4%) of tetrafluorophthalic anhydride as white crystals.

Workup

  1. distillationIn a 500 ml three neck distillation flask
  2. customthe mixture was reacted for 5 hours at 140° to 150° C.
  3. temperatureAfter cooling
  4. extractionthe reaction mixture was extracted three times with 200 ml of toluene
  5. customthe toluene layers thus formed
  6. customwere collected
  7. concentrationconcentrated by distillation under a reduced pressure

Sources & evidence

ORD record
ord-47d579934062463994cdee766542ddea
Source dataset
uspto-grants-1988_09
Patent number
US04769493

Reaction notes

Loading…