Ketene → Trifluoromethanesulfonic anhydride

HRID 992754Notes

Reaction equation

[F:1][C:2]([F:8])([F:7])[S:3]([OH:6])(=[O:5])=[O:4].C=C=O>>[S:3]([O:6][S:3]([C:2]([F:8])([F:7])[F:1])(=[O:5])=[O:4])([C:2]([F:8])([F:7])[F:1])(=[O:5])=[O:4]

Participants

Reactant 2

HCID 10038Ketene

HCID 62406Trifluoromethanesulfonic acid

Product 1

HCID 67749Trifluoromethanesulfonic anhydride

Procedure

Disclosed is a process for the preparation of trifluoromethanesulfonic acid anhydride by the steps of (1) forming a mixed anhydride comprising a trifluoromethanesulfonyl acyl residue and a carboxyl residue by contacting trifluoromethanesulfonic acid or a derivative thereof with a carboxyl compound selected from ketene, dialkyl ketenes, carboxylic acids, and derivatives of carboxylic acids and (2) subjecting the mixed anhydride to reactive distillation wherein the mixed anhydride undergoes disproportionation to produce triflic anhydride and a higher boiling carboxylic acid anhydride.

Workup

distillationdistillation wherein the mixed anhydride

Sources & evidence

ORD record: ord-ecc655a534bc4d258847c0b406a23da6
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06469206B2

Reaction notes

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