Hexafluoroacetone

Hexafluoroacetone
Names
	IUPAC names 1,1,1,3,3,3-hexafluoro-; 2-propanone
	Other names perfluoroacetone; acetone hexafluoride; perfluoro-2-propanone
Identifiers
CAS Number	684-16-2 ;
3D model (JSmol)	Interactive image;
ChemSpider	13846015;
ECHA InfoCard	100.010.616
RTECS number	UC2450000;
CompTox Dashboard (EPA)	DTXSID9043778 ;
	InChI InChI=1/C3F6O/c4-2(5,6)1(10)3(7,8)9 Key: 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)	3 2
Flash point	N/A
Related compounds
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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 [(CF₃)₂CS]₂. This species is then oxidized by iodate to give (CF₃)₂CO.^[1]

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.

Reactivity

Hexafluoroacetone is a reactive substance, acting primarily as an electrophile. In water hexafluoroacetone is highly reactive as its equilibrium sharply favors (~10⁶) forming a gem-diol hydrate, unlike the identical unfavorable equilibrium with acetone (10^-3).^[2] This makes the equilibria of two chemicals differ by about a billion regarding this addition of water.^[2] 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.^[3]

References

^ 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.
^ ^a ^b Lemal DM. "Perspective on Fluorocarbon Chemistry" J Org Chem. 2004, volume 69, p 1-11. doi:10.1021/jo0302556
^ 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.

[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.

[Lemal2004-2] Lemal DM. "Perspective on Fluorocarbon Chemistry" J Org Chem. 2004, volume 69, p 1-11. doi:10.1021/jo0302556

[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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