Hexafluoropropylene oxide

Hexafluoropropylene oxide
Names
	IUPAC name 2,2,3-Trifluoro-3-(trifluoromethyl)oxirane
	Other names trifluoro(trifluoromethyl)oxirane
Identifiers
CAS Number	428-59-1 ;
3D model (JSmol)	Interactive image; Interactive image;
Abbreviations	HFPO
ChemSpider	9499 ;
ECHA InfoCard	100.006.411
PubChem CID	9883;
UNII	JPY12AP87N ;
CompTox Dashboard (EPA)	DTXSID6029177 ;
	InChI InChI=1S/C3F6O/c4-1(2(5,6)7)3(8,9)10-1 Key: PGFXOWRDDHCDTE-UHFFFAOYSA-N ; InChI=1/C3F6O/c4-1(2(5,6)7)3(8,9)10-1 Key: PGFXOWRDDHCDTE-UHFFFAOYAQ;
	SMILES C1(C(O1)(F)F)(C(F)(F)F)F; FC(F)(F)C1(F)OC1(F)F;
Properties
Chemical formula	C3F6O
Molar mass	166.02 g/mol
Appearance	colourless gas
Boiling point	-27.4 °C
Solubility in water	nonpolar solvents
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Hexafluoropropylene oxide (HFPO) is an intermediate used in industrial organofluorine chemistry; specifically it is a monomer for fluoropolymers. This colourless gas is the epoxide of hexafluoropropylene, that is fluorinated analog of propylene oxide, HFPO is produced by DuPont and 3M and as a precursor to the lubricant Krytox and related materials. It is generated by oxidation of perfluoropropylene, e.g. with oxygen as well as other oxidants.[1]

Reactivity

Fluoride catalyzes the formation of the perfluorinated polyethers such as Krytox. The initial step entails nucleophilic attack at the middle carbon to give the perfluoropropoxide anion, which in turn attacks another monomer. This process generates a polymer terminated by an acyl fluoride, which is hydrolyzed to the carboxylic acid which is decarboxylated with fluorine. The net polymerization reaction can be represented as:

n+2 CF₃CFCF₂O → CF₃CF₂CF₂O(CF(CF₃)CF₂O)_nCF₂CF₃ + CO

Upon heating above 150 °C, HFPO decomposes to trifluoroacetyl fluoride and difluorocarbene:

CF₃CFCF₂O → CF₃C(O)F + CF₂

The epoxide of tetrafluoroethylene is even more unstable with respect to trifluoracetyl fluoride.

In the presence of Lewis acids the compound rearranges to hexafluoroacetone, another important chemical intermediate.

Methanolysis affords methyl trifluoropyruvate, a reagent useful in organic synthesis:[2]

CF₃CFCF₂O + 2 MeOH → CF₃C(O)CO₂Me + MeF + 2 HF

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References

Günter Siegemund, Werner Schwertfeger, Andrew Feiring, Bruce Smart, Fred Behr, Herward Vogel, Blaine McKusick "Fluorine Compounds, Organic" Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2016. doi:10.1002/14356007.a11_349.pub2
Ruth Figueroa, Richard P. Hsung, Gang Li, Jin Haek Yang (2007). "Methyltrifluoropyruvate". e-EROS Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. doi:10.1002/047084289X.rn00769.CS1 maint: uses authors parameter (link)

External links

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[1] Günter Siegemund, Werner Schwertfeger, Andrew Feiring, Bruce Smart, Fred Behr, Herward Vogel, Blaine McKusick "Fluorine Compounds, Organic" Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2016. doi:10.1002/14356007.a11_349.pub2

[2] Ruth Figueroa, Richard P. Hsung, Gang Li, Jin Haek Yang (2007). "Methyltrifluoropyruvate". e-EROS Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. doi:10.1002/047084289X.rn00769.CS1 maint: uses authors parameter (link)