Hexafluoropropylene

Hexafluoropropylene is the fluoroalkene with the formula CF3CF=CF2. It is the perfluorocarbon counterpart to the hydrocarbon propylene. It is mainly used to produce copolymers with tetrafluoroethylene. Hexafluoropropylene is used as a chemical intermediate.[1]

Hexafluoropropylene
Structural formula of hexafluoropropylene
Ball-and-stick model of the hexafluoropropylene molecule
Names
Preferred IUPAC name
1,1,2,3,3,3-Hexafluoroprop-1-ene
Other names
Perfluoropropene,
Perfluoropropylene,
freon R 1216,
halocarbon R 1216,
fluorocarbon 1216
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.753
EC Number
  • 204-127-4
RTECS number
  • UD0350000
UNII
UN number 1858
  • InChI=1S/C3F6/c4-1(2(5)6)3(7,8)9 checkY
    Key: HCDGVLDPFQMKDK-UHFFFAOYSA-N checkY
  • InChI=1/C3F6/c4-1(2(5)6)3(7,8)9
    Key: HCDGVLDPFQMKDK-UHFFFAOYAV
  • F/C(F)=C(/F)C(F)(F)F
Properties
C3F6
Molar mass 150.023 g·mol−1
Appearance Colorless, odorless gas
Density 1.332 g/ml, liquid at 20 °C
Melting point −153 °C (−243 °F; 120 K)
Boiling point −28 °C (−18 °F; 245 K)
Insoluble
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Suffocation
GHS labelling:
GHS04: Compressed GasGHS07: Exclamation markGHS08: Health hazard
Warning
H280, H332, H335, H351, H371, H373
P201, P202, P260, P261, P264, P270, P271, P281, P304+P312, P304+P340, P308+P313, P309+P311, P312, P314, P403+P233, P405, P410+P403, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
1
0
1
Flash point Non flammable gas
Related compounds
Related alkenes;
organofluorides
 propylene;
Hexafluoroacetone, Hexafluoro-2-propanol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Preparation

Hexafluoropropylene can be produced by pyrolysis of tetrafluoroethylene:[1][2]

3 CF2=CF2 → 2 CF3CF=CF2

It can also be prepared from chlorodifluoromethane, or produced from various chlorofluorocarbons.[3]

References
  1. Siegemund, Günter; Schwertfeger, Werner; Feiring, Andrew; Smart, Bruce; Behr, Fred; Vogel, Herward; McKusick, Blaine; Kirschtitle=Fluorine Compounds, Organic, Peer (2016). Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a11_349.pub2.
  2. Lehmler, HJ (March 2005). "Synthesis of environmentally relevant fluorinated surfactants—a review". Chemosphere. 58 (11): 1471–96. Bibcode:2005Chmsp..58.1471L. doi:10.1016/j.chemosphere.2004.11.078. PMID 15694468.
  3. United States patent (expires 5-20-2020) 5043491A, James L. Webster, Elrey L. McCann, Douglas W. Bruhnke, Jan J. Lerou, "Multistep synthesis of hexafluoropropylene", published 1991-08-27, issued 1991-08-27, assigned to E. I. Du Pont de Nemours and Company
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