Hexafluoropropylene → Carbon Dioxide

HRID 1285288Notes

Reaction equation

HRID 1285288 reaction equation
[S:1]([F:13])([O:4][C:5](F)(F)C(F)=C(F)F)(=[O:3])=[O:2].[F:14][C:15]([F:22])([F:21])[C:16]([F:20])=C(F)F.[B].B(OC)(OC)[O:25]C>>[C:15]([CH:16]([S:1]([F:13])(=[O:3])=[O:2])[F:20])([F:22])([F:21])[F:14].[C:5](=[O:4])=[O:25]

Participants

6

Reactant 4

HCID 8302HexafluoropropyleneHCID 8470Trimethyl borateHCID 2776028Pentafluoroallyl fluorosulphateHCID 5462311Boron

Product 2

HCID 280Carbon DioxideHCID 1606131,2,2,2-Tetrafluoroethanesulfonyl fluoride

Procedure

The starting material, perfluoroallyl fluorosulfate (FAF), CF2 =CFCF2OSO2F, may be prepared as described in U.S. Pat. No. 4,206,138 to D. C. England. England prepared FAF by reacting hexafluoropropylene with SO3 under anhydrous conditions in the presence of a small amount of a trivalent boron compound such as trimethyl borate at 0°-100° C. A possible byproduct is hexafluoropropylene sultone, ##STR2## which is difficult to separate from FAF by distillation. The sultone in the FAF mixture can be hydrolyzed with ice water to give CF3CFHSO2F+HF+CO2 (gas). This product, CF3CFHSO2F, is also difficult to separate from FAF by distillation, but it does not react with Br2 and can be separated from the Br2 adduct of FAF by distillation.

Workup

  1. customEngland prepared FAF
  2. customat 0°-100° C
  3. customto separate from FAF by distillation

Sources & evidence

ORD record
ord-b81dc8cf8c2a4abe81b6f5b411605a43
Source dataset
uspto-grants-1986_01
Patent number
US04567003

Reaction notes

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