O-Xylene → Tetrafluorophthalic anhydride

HRID 1770007Notes

Reaction equation

HRID 1770007 reaction equation
[F:1][C:2]1[C:3]([F:16])=[C:4]([F:15])[C:5]([F:14])=[C:6]([C:11]([OH:13])=[O:12])[C:7]=1[C:8](O)=[O:9].C1(C)C(C)=CC=CC=1>O>[F:1][C:2]1[C:3]([F:16])=[C:4]([F:15])[C:5]([F:14])=[C:6]2[C:11](=[O:13])[O:12][C:8](=[O:9])[C:7]=12

Participants

4

Reactant 2

HCID 7237O-XyleneHCID 695443,4,5,6-Tetrafluorophthalic acid

Product 1

HCID 69545Tetrafluorophthalic anhydrideYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

350 g of crude tetrafluorophthalic acid are heated with 800 g of xylene using a water separator, until no further water passes over (5 hours). The resulting suspension is allowed to cool and the anhydride which has precipitated is filtered off. 301 g of tetrafluorophthalic anhydride are obtained, the mother liquor, which still contains about 5 g of tetrafluorophthalic anhydride, being used for further dehydrations. The tetrafluorophthalic anhydride is then purified by fractionation, whereupon it passes over as a colorless liquid (under 1 mbar/95° C.-105° C.) and solidifies as a colorless, crystalline mass of melting point 93°-94° C. 255 g (1.16 mol) of tetrafluorophthalic anhydride with a purity of >99% (GC, HPLC) are obtained in this manner.

Workup

  1. custompasses over (5 hours)
  2. temperatureto cool
  3. customthe anhydride which has precipitated
  4. filtrationis filtered off

Sources & evidence

ORD record
ord-5b4f6d519da54d50b5ac96fddc6682d0
Source dataset
uspto-grants-1995_01
Patent number
US05384413

Reaction notes

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