Hexafluoroacetone

Chembox new
Name = Hexafluoroacetone
ImageFile = Hexafluoroacetone 3D.png ImageName = Hexafluoropropanone 3D structure
ImageFile1 = 1,1,1,3,3,3-hexafluoropropanone-chemical.png ImageName1 = 1,1,1,3,3,3-hexafluoropropanone
IUPACName = 1,1,1,3,3,3-hexafluoro-
2-propanone
OtherNames = perfluoroacetone
acetone hexafluoride
perfluoro-2-propanone
Section1 = Chembox Identifiers
SMILES = O=C(C(F)(F)F)C(F)(F)F
CASNo = 684-16-2
RTECS = UC2450000
Section2 = Chembox Properties
Formula = C₃F₆O
MolarMass = 166.02 g/mol
Appearance = Colorless gas
Density = 1.32 g/ml, liquid
Solubility = Reacts with water
MeltingPt = −129 °C (144 K)
BoilingPt = −28 °C (245 K)
Section7 = Chembox Hazards
ExternalMSDS =
MainHazards = Toxic (T),
Corrosive (C)
NFPA-H = 3
NFPA-F =
NFPA-R = 2 | Other=W
FlashPt = N/A
RPhrases = R14, R23/24/25,
R34, R60, R63
SPhrases = S7/9, S26, S28,
S36, S45, S53
Section8 = Chembox Related
Function = Ketones
OtherFunctn = Acetone
Function = organofluorides
OtherFunctn = Hexafluoro-2-propanol

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.

ynthesis 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. [OrgSynth | author = Van Der Puy, M. ; Anello, L. G. | title = Hexafluoroacetone | collvol = 7 | collvolpages = 251 | year = 1990 | prep = CV7P0251]

Uses

Hexafluoroacetone is mostly employed in organic synthesis, but it is also the mainchemical 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. [OrgSynth | author = Middleton, W. J.; Carlson, H. D. | title = Hexafluoroacetoneimine | collvol = 6 | collvolpages = 664 | year = 1988 | prep = CV6P0664]

References