Hexafluoroacetone
3939550
172321592
2007-11-18T18:41:50Z
Smokefoot
698909
repair OS links per RM
{{Chembox new
| Name = Hexafluoroacetone
| ImageFile = Hexafluoroacetone 3D.png
<!-- | ImageSize = 200px -->
| ImageName = Hexafluoropropanone 3D structure
| ImageFile1 = 1,1,1,3,3,3-hexafluoropropanone-chemical.png
<!-- | ImageSize1 = 200px -->
| ImageName1 = 1,1,1,3,3,3-hexafluoropropanone
| IUPACName = 1,1,1,3,3,3-hexafluoro-<br />2-propanone
| OtherNames = perfluoroacetone<br /> acetone hexafluoride<br /> 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 = C<sub>3</sub>F<sub>6</sub>O
| 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'''),<br />Corrosive ('''C''')
| NFPA-H = 3
| NFPA-F =
| NFPA-R = 2 | Other=<s>W</s>
| FlashPt = N/A
| RPhrases = {{R14}}, {{R23/24/25}},<br />{{R34}}, {{R60}}, {{R63}}
| SPhrases = {{S7/9}}, {{S26}}, {{S28}},<br />{{S36}}, {{S45}}, {{S53}}
}}
| Section8 = {{Chembox Related
| Function = [[Ketone]]s
| OtherFunctn = [[Acetone]]
| Function = organofluorides
| OtherFunctn = [[Hexafluoro-2-propanol]]
}}
}}
'''Hexafluoroacetone''' is a [[chemical compound]] with the [[chemical formula|formula]] CF<sub>3</sub>-CO-CF<sub>3</sub>. 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 [[water (molecule)|H<sub>2</sub>O)]], which is a gem-diol.
==Synthesis and reactions==
(CF<sub>3</sub>)<sub>2</sub>CO 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 [(CF<sub>3</sub>)<sub>2</sub>CS]<sub>2</sub>. This species is then oxidized by iodate to give (CF<sub>3</sub>)<sub>2</sub>CO.<ref>{{OrgSynth | author = Van Der Puy, M. ; Anello, L. G. | title = Hexafluoroacetone | collvol = 7 | collvolpages = 251 | year = 1990 | prep = CV7P0251}}</ref>
==Uses==
Hexafluoroacetone is mostly employed in [[organic synthesis]], but it is also the main
chemical intermediate used in the production of [[hexafluoro-2-propanol|hexafluoroisopropanol]], as well as [[polymethyl methacrylate]]s and [[polyester]]s for textile coating. Hexafluoroacetone can be employed as a solvent for acetal resins, [[polyamide]]s 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, (CF<sub>3</sub>)<sub>2</sub>CO adds [[ammonia]] to give (CF<sub>3</sub>)<sub>2</sub>C(OH)(NH<sub>2</sub>) which can be dehydrated with POCl<sub>3</sub> to give (CF<sub>3</sub>)<sub>2</sub>CNH.<ref>{{OrgSynth | author = Middleton, W. J.; Carlson, H. D. | title = Hexafluoroacetoneimine | collvol = 6 | collvolpages = 664 | year = 1988 | prep = CV6P0664}}</ref>
==References==
<references/>
[[Category:Organofluorides]]
[[Category:Ketones]]