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	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; Kirsch, Peer (2016). "Fluorine Compounds, Organic". 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; Kirsch, Peer (2016). "Fluorine Compounds, Organic". 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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