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Hexafluoroacetone

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Hexafluoroacetone
Hexafluoropropanone 3D structure
1,1,1,3,3,3-hexafluoropropanone
Names
IUPAC names 1,1,1,3,3,3-hexafluoro-
2-propanone
Other names perfluoroacetone
acetone hexafluoride
perfluoro-2-propanone
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.010.616 Edit this at Wikidata
RTECS number
  • UC2450000
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3F6O/c4-2(5,6)1(10)3(7,8)9Key: VBZWSGALLODQNC-UHFFFAOYSA-N
  • InChI=1/C3F6O/c4-2(5,6)1(10)3(7,8)9Key: VBZWSGALLODQNC-UHFFFAOYAI
SMILES
  • FC(F)(F)C(=O)C(F)(F)F
Properties
Chemical 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
Occupational safety and health (OHS/OSH):
Main hazards Toxic (T),
Corrosive (C)
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability (red): no hazard codeInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazards (white): no code
3 2
Flash point N/A
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Hexafluoroacetone is a chemical compound with the formula CF3-CO-CF3. It is structurally similar to acetone, however its reactivity is markedly different. 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.

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 2. This species is then oxidized by iodate to give (CF3)2CO.

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, polyglycolide, polyacetals, and polyols or as a polymer adhesive.

Reactivity

Hexafluoroacetone is a reactive substance, acting primarily as an electrophile. In water hexafluoroacetone is highly reactive as its equilibrium sharply favors (~10) forming a gem-diol hydrate, unlike the identical unfavorable equilibrium with acetone (10). This makes the equilibria of two chemicals differ by about a billion regarding this addition of water. Hexafluoroacetone-hydrates are acidic and 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 phosphoryl chloride to give (CF3)2CNH.

References

  1. Van Der Puy, M. ; Anello, L. G. (1990). "Hexafluoroacetone". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 7, p. 251.
  2. ^ Lemal, David M. (2004). "Perspective on Fluorocarbon Chemistry". The Journal of Organic Chemistry. 69 (1): 1–11. doi:10.1021/jo0302556. PMID 14703372.
  3. Middleton, W. J.; Carlson, H. D. (1988). "Hexafluoroacetoneimine". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 6, p. 664.
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