Sulfate Ion → 2,3,4,5-Tetrafluorobenzoic acid

HRID 622250Notes

Reaction equation

HRID 622250 reaction equation
[F:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[C:8]([F:13])=[C:4](C(O)=O)[C:3]=1[C:14]([OH:16])=[O:15].S([O-])([O-])(=O)=O.S([O-])([O-])(=O)=O.[NH4+].[NH4+]>O>[F:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[C:8]([F:13])=[CH:4][C:3]=1[C:14]([OH:16])=[O:15]

Participants

5

Reactant 3

HCID 1117Sulfate IonHCID 695443,4,5,6-Tetrafluorophthalic acidHCID 6097028Ammonium Sulfate

Product 1

HCID 2975492,3,4,5-Tetrafluorobenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

In an autoclave having an inner volume of 1 liter, 150 g (0.630 mole) of 3,4,5,6-tetrafluorophthalic acid containing no sulfate ion, 29.1 g (0.220 mole) of ammonium sulfate, and 500 g of water were placed and heated and stirred for reaction at 160° C. for 21 hours [pH 1.74 at 30° C. at the time of charging]. After completion of the reaction, the reaction suspension was cooled to room temperature, filtered, washed with water, and then dried, to produce 2,3,4,5-tetrafluorobenzoic acid. Calculation from the amount obtained by filtration and the amount obtained by extraction as in Example 1 reveals that this example produced 2,3,4,5-tetrafluorobenzoic acid in a yield of 85.8 mole %.

Workup

  1. temperatureheated
  2. customAfter completion of the reaction
  3. temperaturethe reaction suspension was cooled to room temperature
  4. filtrationfiltered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-ce4085e226fa403b984e010b66f5bc9b
Source dataset
uspto-grants-1988_09
Patent number
US04769492

Reaction notes

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