Hexafluoroacetone

Hexafluoroacetone is a chemical compound with the formula CF₃-CO-CF₃. It comes in the form of a colourless, hygroscopic, nonflammable, highly reactive gas characterized by a musty odour. The most common form of this substance is hexafluoroacetone sesquihydrate (1.5 H₂O), which is a gem-diol.

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Synthesis and reactions

(CF₃)₂CO is prepared in a two step process from perfluoropropene. In the first step KF catalyzes the reaction of the alkene with elemental sulfur to give the 1,3-dithete [(CF₃)₂CS]₂. This species is then oxidized by iodate to give (CF₃)₂CO.^[1]

Uses

Hexafluoroacetone is mostly employed in organic synthesis, but it is also the main chemical intermediate used in the production of hexafluoroisopropanol, as well as polymethyl methacrylates and polyesters for textile coating. Hexafluoroacetone can be employed as a solvent for acetal resins, polyamides and polyglycolide or as a polymer adhesive.

Reactivity

Hexafluoroacetone is a reactive substance, acting primarily as an electrophile. It will react vigorously with water, irreversibly forming a hydrate. Such hydrates are acidic that react with most metals to generate hydrogen. Hexafluoroacetone violently reacts in the presence of alkali. Related to its tendency to hydrate, (CF₃)₂CO adds ammonia to give (CF₃)₂C(OH)(NH₂) which can be dehydrated with POCl₃ to give (CF₃)₂CNH.^[2]

References

1. ^ Van Der Puy, M. ; Anello, L. G. (1990). "Hexafluoroacetone". Org. Synth.; Coll. Vol. 7: 251. 
2. ^ Middleton, W. J.; Carlson, H. D. (1988). "Hexafluoroacetoneimine". Org. Synth.; Coll. Vol. 6: 664.