Hexafluoroacetone trihydrate

Hexafluoroacetone trihydrate, also known as gem diol, hexafluoropropan-2,2- diol, is a covalent hydrate of the ketone. It could used as a structure stabilizer for peptides. It was a metabolite of aerosol propellant HFA-227 and is present in the urine. It was shown to undergo an efficient carbonyl-ene reaction with a variety of alkenes in the presence of molecular sieves under microwave heating and conventional heating producing hexafluoroisopropanol functionalized derivatives in high yields[1-2].

Hexafluoroacetone trihydrate was used to study the kinetics and thermodynamics of linkage isomerization of (acetone)pentaammineruthenium (III) and-ruthenium (II) complexes. It was used in a study to reconstitute the α-and β-polypeptides of both Rhodobacter sphaeroides and Rhodospirillum rubrum with bacteriochlorophyll a.

Hexafluoroacetone trihydrate (HFA3H2O) is used to produce Sevoflurane,a high quality anesthetic and Bisphenol AF, a crosslinker for fluoroelastomers. It can also be used to produce various high-end fluorinated products such as fluorinated polyimide, etc.

Hexafluoroacetone trihydrate forms crystalline 1:1 complexes with imidazole 3-oxides.

A spherical fluorinated alumina catalyst (30 g) (particle diameter: 2 to 4 mm) was charged into a reaction tube made of SUS316 (inner diameter: 16 mm, length: 460 mm). The reaction tube was heated to 140° C, and hexafluoro-1,2-epoxypropane (purity: 95%, impurity content: 5% hexafluoropropene) was fed into the reaction tube under the conditions of a feed rate of 50 Nml/min and a total pressure of 3 atmospheres. After 1 hour, the exit gas was analyzed by gas chromatography, with the result that the conversion of hexafluoro-1,2-epoxypropane was 100%. The exit gas was passed into the water, producing crude hexafluoroacetone trihydrate.

[1] Sridhar M, et al. A facile method for the preparation of hexafluoroisopropanol functionalized derivatives using hexafluoroacetone trihydrate via a carbonyl-ene reaction. Tetrahedron Letters, 2009; 50: 1777-1779.
[2] Kster U, et al. Biotransformation of the aerosol propellant 1,1,1,2,3,3,3-heptafluoropropane (HFA-227): lack of protein binding of the metabolite hexafluoroacetone. Drug Metabolism and Disposition , 1996.