Hexafluoroacetone

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Hexafluoroacetone
Hexafluoropropanone 3D structure
1,1,1,3,3,3-hexafluoropropanone
IUPAC name 1,1,1,3,3,3-hexafluoro-
2-propanone
Other names perfluoroacetone
acetone hexafluoride
perfluoro-2-propanone
Identifiers
CAS number [684-16-2]
RTECS number UC2450000
SMILES O=C(C(F)(F)F)C(F)(F)F
Properties
Molecular formula C3F6O
Molar mass 166.02 g/mol
Appearance Colorless gas
Density 1.32 g/ml, liquid
Melting point

−129 °C (144 K)

Boiling point

−28 °C (245 K)

Solubility in water Reacts with water
Hazards
Main hazards Toxic (T),
Corrosive (C)
NFPA 704
0
3
2
 
R-phrases R14, R23/24/25,
R34, R60, R63
S-phrases S7/9, S26, S28,
S36, S45, S53
Flash point N/A
Related compounds
Related organofluorides Hexafluoro-2-propanol
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

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.

Contents

[edit] 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]

[edit] 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.

[edit] 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]

[edit] 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.