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 = &minus;129 °C (144 K) | BoilingPt = &minus;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]]