Hexafluoropropylene
{{Chembox
| verifiedrevid = 420876606
| Name = Hexafluoropropylene
| ImageFile =
| ImageFileL1 = Hexafluoropropylene.svg
| ImageSizeL1 = 125
| ImageAltL1 = Structural formula of hexafluoropropylene
| ImageFileR1 = Hexafluoropropylene 3D.png
| ImageFile2 = Liquified Hexafluoropropylene.png
| ImageSizeR1 = 125
| ImageAltR1 = Ball-and-stick model of the hexafluoropropylene molecule
| ImageSize2 = 200px
| PIN = 1,1,2,3,3,3-Hexafluoroprop-1-ene
| OtherNames = Perfluoropropene,
Perfluoropropylene,
freon R 1216,
halocarbon R 1216,
fluorocarbon 1216
| Section1 = {{Chembox Identifiers
| SMILES = F/C(F)=C(/F)C(F)(F)F
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 8001
| InChI = 1/C3F6/c4-1(2(5)6)3(7,8)9
| InChIKey = HCDGVLDPFQMKDK-UHFFFAOYAV
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C3F6/c4-1(2(5)6)3(7,8)9
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = HCDGVLDPFQMKDK-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 116-15-4
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = TRW23XOS20
| RTECS = UD0350000
| PubChem = 8302
| UNNumber = 1858
| EINECS = 204-127-4
}}
| Section2 = {{Chembox Properties
| C=3 | F=6
| Appearance = Colorless, odorless gas
| Density = 1.332 g/ml, liquid at 20 °C
| Solubility = Insoluble
| MeltingPtC = -153
| BoilingPtC = -28
}}
| Section7 = {{Chembox Hazards
| ExternalSDS =
| MainHazards = Suffocation
| NFPA-H = 1
| NFPA-F = 0
| NFPA-R = 1
| FlashPt = Non flammable gas
| GHSPictograms = {{GHS07}}{{GHS08}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|332|335|351|371|373}}
| PPhrases = {{P-phrases|201|202|260|261|264|270|271|281|304+312|304+340|308+313|309+311|312|314|403+233|405|410+403|501}}
}}
| Section8 = {{Chembox Related
| OtherFunction_label = alkenes;
organofluorides
| OtherFunction = propylene;
Hexafluoroacetone, Hexafluoro-2-propanol
}}
}}
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.{{Ullmann|first1=Günter |last1=Siegemund|first2=Werner|last2=Schwertfeger|first3=Andrew|last3=Feiring|first4=Bruce|last4=Smart|first5=Fred|last5=Behr|first6=Herward|last6=Vogel|first7=Blaine |last7=McKusick|first8=Peer|last8= Kirsch|title=Fluorine Compounds, Organic|year=2016|doi=10.1002/14356007.a11_349.pub2}}
Preparation
Hexafluoropropylene can be produced by pyrolysis of tetrafluoroethylene:{{cite journal
| last=Lehmler |first=HJ
| title=Synthesis of environmentally relevant fluorinated surfactants—a review
| journal=Chemosphere |volume=58 |issue=11 |pages=1471–96 |date=March 2005
| doi=10.1016/j.chemosphere.2004.11.078 |pmid=15694468 |bibcode=2005Chmsp..58.1471L
}}
:3{{nbsp}}CF2=CF2 → 2{{nbsp}}CF3CF=CF2
It can also be prepared from chlorodifluoromethane, or produced from various chlorofluorocarbons.
{{cite patent|country=United States|number=5043491A|title=Multistep synthesis of hexafluoropropylene|status=patent (expires 5-20-2020)|pubdate=1991-08-27|fdate=1989-12-19|pridate=1989-12-19|gdate=1991-08-27|inventor=James L. Webster, Elrey L. McCann, Douglas W. Bruhnke, Jan J. Lerou|assign1=E. I. Du Pont de Nemours and Company|url=https://patents.google.com/patent/US5043491A/en?q=~patent%2fUS5057634A}}