Ketene → Trifluoromethanesulfonic anhydride

HRID 992756Notes

Reaction equation

HRID 992756 reaction equation
C=C=O.[OH:4][S:5]([C:8]([F:11])([F:10])[F:9])(=[O:7])=[O:6].[O:12](C(=O)C)[S:13]([C:16]([F:19])([F:18])[F:17])(=O)=[O:14].O(C(=O)C(C)C)S(C(F)(F)F)(=O)=O>>[S:5]([O:4][S:13]([C:16]([F:19])([F:18])[F:17])(=[O:14])=[O:12])([C:8]([F:11])([F:10])[F:9])(=[O:7])=[O:6]

Participants

5

Reactant 4

HCID 10038KeteneHCID 62406Trifluoromethanesulfonic acidHCID 13068595HCID 13068595, compoundHCID 13068596HCID 13068596, compound

Product 1

HCID 67749Trifluoromethanesulfonic anhydride

Procedure

The process of the present invention may be operated in a batch, continuous or semi-continuous manner. For example, the process may be carried out by first reacting a ketene and triflic acid in a reaction vessel equipped with a distillation column. This vessel containing the mixed anhydride then may be heated to effect reactive distillation of the contents of the reaction vessel and recover triflic anhydride from the upper section of the distillation column. The process for the coproduction of triflic anhydride and a carboxylic acid anhydride, e.g., acetic or isobutyric anhydride, preferably is carried out in a continuous or semi-continuous manner comprising the steps of: (1) introducing a ketene reactant such as ketene or dimethylketene and triflic acid to a reaction vessel wherein the ketene reactant and triflic acid react to form a product comprising a mixed anhydride, e.g., acetyl triflate or isobutyryl triflate; (2) removing product from the reaction vessel and introducing it into the mid-section of a reactive distillation column wherein the mixed anhydride disproportionates to form triflic anhydride and a carboxylic anhydride, e.g. acetic or isobutyric anhydride; (3) removing triflic anhydride from the upper section of the reactive distillation column; and (4) removing a carboxylic anhydride from the lower section of the reactive distillation column.

Workup

  1. customequipped with a distillation column
  2. temperaturemay be heated
  3. distillationdistillation of the contents of the reaction vessel
  4. customrecover triflic anhydride
  5. distillationfrom the upper section of the distillation column
  6. additionintroducing a ketene reactant such as ketene or dimethylketene and triflic acid to a reaction vessel wherein the ketene reactant and triflic acid
  7. customreact
  8. customto form a product
  9. custom(2) removing product from the reaction vessel
  10. additionintroducing it into the
  11. distillationmid-section of a reactive distillation column wherein the mixed anhydride

Sources & evidence

ORD record
ord-226c72fab7a84106b7717b5624fbd0f1
Source dataset
uspto-grants-2002_10
Patent number
US06469206B2

Reaction notes

Loading…