Hexafluoropropylene

Hexafluoropropylene
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
CAS Number	116-15-4 ;
3D model (JSmol)	Interactive image;
ChemSpider	8001 ;
ECHA InfoCard	100.003.753
EC Number	204-127-4;
PubChem CID	8302;
RTECS number	UD0350000;
UNII	TRW23XOS20 ;
UN number	1858
CompTox Dashboard (EPA)	DTXSID2026949 ;
	InChI InChI=1S/C3F6/c4-1(2(5)6)3(7,8)9 Key: HCDGVLDPFQMKDK-UHFFFAOYSA-N ; InChI=1/C3F6/c4-1(2(5)6)3(7,8)9 Key: HCDGVLDPFQMKDK-UHFFFAOYAV;
	SMILES F/C(F)=C(/F)C(F)(F)F;
Properties
Chemical formula	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)
Solubility in water	Insoluble
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Suffocation
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H280, H332, H335, H351, H371, H373
Precautionary statements	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)	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). verify (what is ?) Infobox references

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]

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

^ ^a ^b 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. ISBN 978-3527306732.
^ 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.
^ 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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[Ullmann-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. ISBN 978-3527306732.

[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.

[dupontsynth-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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