Hexafluoroacetone
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| Hexafluoroacetone | |
|---|---|
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| General | |
| Systematic name | 1,1,1,3,3,3-hexafluoro- 2-propanone |
| Other names | perfluoroacetone acetone hexafluoride perfluoro-2-propanone |
| Molecular formula | C3F6O |
| SMILES | O=C(C(F)(F)F)C(F)(F)F |
| Molar mass | 166.02 g/mol |
| Appearance | Colorless gas |
| CAS number | [684-16-2] |
| Properties | |
| Density and phase | 1.32 g/ml, liquid |
| Solubility in water | Reacts with water |
| Melting point | −129 °C (144 K) |
| Boiling point | −28 °C (245 K) |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | Toxic (T), Corrosive (C) |
| NFPA 704 |
0
3
2
|
| Flash point | N/A |
| R-phrases | R14, R23/24/25, R34, R60, R63 |
| S-phrases | S7/9, S26, S28, S36, S45, S53 |
| RTECS number | UC2450000 |
| Supplementary data page | |
| Structure and properties |
n, εr, etc. |
| Thermodynamic data |
Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Related compounds | |
| Related Ketones | Acetone |
| 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 an organic 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).
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] (CF3)2CO adds ammonia to give (CF3)2C(OH)(NH2) which can be dehydrated with POCl3 to give (CF3)2CNH.[2]
[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 very reactive substance: it will react vigorously with water, forming corrosive acids. In the presence of humidity, reaction of hexafluoroacetone with most metals will generate white fumes of hydrogen gas. Hexafluoroacetone will also undergo violent reactions in the presence of alkali.
[edit] References
- ^ Van Der Puy, M. ; Anello, L. G. “Hexafluoroacetone” Organic Syntheses, Collective Volume 7, page 251
- ^ Middleton, W. J.; Carlson, H. D. "Hexafluoroacetoneimine" Organic Syntheses Collective Volume 6, page 664
