Water → 3,4,5,6-Tetrafluorophthalic acid

HRID 622261Notes

Reaction equation

HRID 622261 reaction equation
[F:1][C:2]1[C:3]([F:15])=[C:4]([F:14])[C:5]([F:13])=[C:6]2[C:11](=[O:12])[O:10][C:8](=[O:9])[C:7]=12.[OH2:16]>Cl.S(=O)(=O)(O)O>[F:1][C:2]1[C:3]([F:15])=[C:4]([F:14])[C:5]([F:13])=[C:6]([C:11]([OH:10])=[O:12])[C:7]=1[C:8]([OH:16])=[O:9]

Participants

5

Reactant 2

HCID 962WaterHCID 69545Tetrafluorophthalic anhydride

Product 1

HCID 695443,4,5,6-Tetrafluorophthalic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 1118Sulfuric AcidCatalyst

Procedure

In the second step, high-purity tetrafluorophthalic acid can be obtained by first isolating tetrafluorophthalic anhydride formed as a reaction intermediate, or separating the product in solution from the reaction system, and hydrolyzing the product under acidic or neutral conditions, and this embodiment is particularly preferred. For example, by hydrolyzing the N-substituted tetrafluorophthalimide under acid conditions (e.g., H2SO4 concentration: from about 50 to 98%) and, after cooling, extracting the product with an aprotic solvent (e.g., toluene, benzene, chlorobenzene, xylene, etc.), a solution of tetrafluorophthalic anhydride can be obtained. Furthermore, by removing the solvent from the extract thus obtained, tetrafluorophthalic anhydride can be isolated. In this case, the tetrafluorophthalic anhydride may be purified by distillation, if desired, under a reduced pressure. Then, by hydrolyzing the tetrafluorophthalic anhydride thus obtained under acid or neutral conditions, tetrafluorophthalic acid can be obtained. In the hydration reaction, water is generally used in an amount of from 1 to 5000 mols per mol of the tetrafluorophthalic anhydride and the reaction temperature is usually from about 0° to 100° C. The reaction can be conducted by adding an acid (e.g., hydrochloric acid and sulfuric acid) as a catalyst. This technique of isolating tetrafluorophthalic anhydride or separating it as a solution is preferred, since the purification of tetrafluorophthalic acid, which is the desired product, can be easily performed and high-purity tetrafluorophthalic acid can be obtained.

Workup

  1. customcan be obtained
  2. customis usually from about 0° to 100° C
  3. customThe reaction
  4. customThis technique of isolating tetrafluorophthalic anhydride or separating it as a solution
  5. customis preferred, since the purification of tetrafluorophthalic acid, which

Sources & evidence

ORD record
ord-3627f60a419f4888a9d6c92609374b01
Source dataset
uspto-grants-1988_09
Patent number
US04769493

Reaction notes

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