Hexafluoroacetone
From Wikipedia, the free encyclopedia
| Hexafluoroacetone | |
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| 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
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| 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 |
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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.
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[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
- ^ Van Der Puy, M. ; Anello, L. G. (1990). "Hexafluoroacetone". Org. Synth.; Coll. Vol. 7: 251.
- ^ Middleton, W. J.; Carlson, H. D. (1988). "Hexafluoroacetoneimine". Org. Synth.; Coll. Vol. 6: 664.
