Hexafluoropropylene oxide

Names
IUPAC name

2,2,3-Trifluoro-3-(trifluoromethyl)oxirane

Other names

trifluoro(trifluoromethyl)oxirane perfluoro(propylene oxide)

Identifiers

CAS Number

* 428-59-1 Y

3D model (JSmol)

* Interactive image
* Interactive image

Abbreviations  | HFPO
ChemSpider |

* 9499 N

PubChem CID

* 9883

UNII |

* JPY12AP87N Y

InChI

* InChI=1S/C3F6O/c4-1(2(5,6)7)3(8,9)10-1 N

Key: PGFXOWRDDHCDTE-UHFFFAOYSA-N 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
Density | 1300kg/m3 at 25 °C
Melting point |  −144 °C (−227 °F; 129 K)
Boiling point |  −27.4 °C (−17.3 °F; 245.8 K)
Solubility | nonpolar solvents
Vapor pressure | 660kPa at 25 °C

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

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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, which is a fluorinated analog of propylene oxide, HFPO is produced by Chemours 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 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.[2] The net polymerization reaction can be represented as:

n \+ 2 CF
3CFCF
2O → CF
3CF
2CF
2O(CF(CF
3)CF
2O)
nCF
2CF
3 \+ CO

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

3CFCF
2O → CF
3C(O)F + CF

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

In the presence of Lewis acids the compound rearranges to hexafluoroacetone (HFA), another important chemical intermediate. This rearrangement can be of concern during storage as the rearrangement be catalyzed by the material of the storage cylinder's walls and leads to unwanted formation of HFA during storage. As a result of this, 3M recommends using all HFPO shipped in carbon-steel containers within 90 days of shipping.[3]

Methanolysis affords methyl trifluoropyruvate, a reagent useful in organic synthesis:[4]

3CFCF
2O + 2 CH
3OH → CF
3C(O)CO
2Me + CH
3F + 2 HF

HFPO is a precursor to perfluoroalkyl ether sulfonic acids.[5]

## References

1. ↑ Siegemund, Günter; Schwertfeger, Werner; Feiring, Andrew; Smart, Bruce; Behr, Fred; Vogel, Herward; McKusick, Blaine; Kirsch, Peer (2016-01-28). "Fluorine Compounds, Organic" (in en). Ullmann's Encyclopedia of Chemical Technology. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA. pp. 1–56. doi:10.1002/14356007.a11_349.pub2. ISBN 978-3-527-30673-2.
2. ↑ "HEXAFLUOROPROPYLENE OXIDE | CAMEO Chemicals | NOAA". https://cameochemicals.noaa.gov/chemical/844#.
3. ↑ "Hexafluoropropylene Oxide Safety Data Sheet" (PDF). https://multimedia.3m.com/mws/mediawebserver?SSSSSuUn_zu8l00xlYtG4x2G4v70k17zHvu9lxtD7SSSSSS--.
4. ↑ 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. ISBN 978-0-471-93623-7.
5. ↑ Oppenheimer, Jossian; Hsung, Richard P.; Li, Hongyan; Lu, Ting; Wei, Yonggang (2007). "Hexafluoropropene Oxide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289x.rn00768. ISBN 978-0-471-93623-7.

## External links

* HFPO bulletin from Chemours
* Dyneon HFPO from 3M

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*[CID]: Compound ID