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{{Chembox
{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
| verifiedrevid = 420876606
! {{chembox header}} | Hexafluoropropylene
| Name = Hexafluoropropylene
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Hexafluoropropylene.gif|200px|Hexafluoropropylene 3D structure]]
| ImageFileL1 = Hexafluoropropylene.svg
| ImageSizeL1 = 125
|-
| ImageAltL1 = Structural formula of hexafluoropropylene
! {{chembox header}} | General
| ImageFileR1 = Hexafluoropropylene 3D.png
|-
| ImageSizeR1 = 125
| [[IUPAC nomenclature|Systematic name]]
| ImageAltR1 = Ball-and-stick model of the hexafluoropropylene molecule
| Hexafluoropropene
| PIN = 1,1,2,3,3,3-Hexafluoroprop-1-ene
|-
| OtherNames = Perfluoropropene,<br /> Perfluoropropylene,<br /> freon R 1216,<br /> halocarbon R 1216,<br /> fluorocarbon 1216
| Other names
|Section1={{Chembox Identifiers
| Perfluoropropene,<br/> Perfluoropropylene,<br/> freon R 1216,<br/> halocarbon R 1216,<br/> fluorocarbon 1216
| SMILES = F/C(F)=C(/F)C(F)(F)F
|-
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| [[Chemical formula|Molecular formula]]
| ChemSpiderID = 8001
| CF<sub>3</sub>CF=CF<sub>2</sub>
| InChI = 1/C3F6/c4-1(2(5)6)3(7,8)9
|-
| InChIKey = HCDGVLDPFQMKDK-UHFFFAOYAV
| [[Simplified molecular input line entry specification|SMILES]]
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| FC(F)=C(F)C(F)(F)F
| StdInChI = 1S/C3F6/c4-1(2(5)6)3(7,8)9
|-
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| [[Molar mass]]
| StdInChIKey = HCDGVLDPFQMKDK-UHFFFAOYSA-N
| 150.02 g/mol
| CASNo_Ref = {{cascite|correct|CAS}}
|-
| CASNo = 116-15-4
| Appearance
| UNII_Ref = {{fdacite|correct|FDA}}
| Colorless, odorless gas
| UNII = TRW23XOS20
|-
| RTECS = UD0350000
| [[CAS registry number|CAS number]]
| PubChem = 8302
| [116-15-4]
| UNNumber = 1858
|-
| EINECS = 204-127-4
! {{chembox header}} | Properties
}}
|-
|Section2={{Chembox Properties
| [[Density]] and [[Phase (matter)|phase]]
| C=3 | F=6
| 1.332 g/ml, liquid at 20 °C
| Appearance = Colorless, odorless gas
|-
| Density = 1.332 g/ml, liquid at 20 °C
| [[Solubility]] in [[Water (molecule)|water]]
| Insoluble
| Solubility = Insoluble
| MeltingPtC = -153
|-
| BoilingPtC = -28
<!-- | Other solvents e.g. [[ethanol]], [[acetone]] -->
}}
<!-- | solubility info on other solvents -->
|Section7={{Chembox Hazards
<!-- |- -->
| ExternalSDS =
| [[Melting point]]
| MainHazards = Suffocation
| &minus;153 °C (120 K)
| NFPA-H = 1
|-
| NFPA-F = 0
| [[Boiling point]]
| NFPA-R = 1
| &minus;28 °C (245 K)
| FlashPt = Non flammable gas
|-
| GHSPictograms = {{GHS04}}{{GHS07}}{{GHS08}}
! {{chembox header}} | Hazards
| GHSSignalWord = Warning
|-
| HPhrases = {{H-phrases|280|332|335|351|371|373}}
| [[Material safety data sheet|MSDS]]
| 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}}
| [[Hexafluoropropylene (data page)#Material Safety Data Sheet|External MSDS]]
}}
|-
|Section8={{Chembox Related
| Main [[Worker safety and health|hazard]]s
| OtherFunction_label = [[alkene]]s;<br>organofluorides
| Harmful ('''Xn''')
| OtherFunction = [[propylene]];<br>[[Hexafluoroacetone]], [[Hexafluoro-2-propanol]]
|-
}}
| [[NFPA 704]]
}}
| {{nfpa|2|0|0}}
|-
| [[Flash point]]
| Non flammable gas
|-
| [[List of R-phrases|R-phrases]]
| {{R20}}, {{R37}}
|-
| [[List of S-phrases|S-phrases]]
| {{S41}}
|-
| [[RTECS]] number
| UD0350000
|-
! {{chembox header}} | [[Hexafluoropropylene (data page)|Supplementary data page]]
|-
| [[Hexafluoropropylene (data page)#Structure and properties|Structure and<br/>properties]]
| [[Refractive index|''n'']], [[Dielectric constant|ε<sub>r</sub>]], etc.
|-
| [[Hexafluoropropylene (data page)#Thermodynamic properties|Thermodynamic<br/>data]]
| Phase behaviour<br>Solid, liquid, gas
|-
| [[Hexafluoropropylene (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Related [[alkene]]s
| [[propylene]]
|-
| Related organofluorides
| [[Hexafluoroacetone]],<br/>[[Hexafluoro-2-propanol]]
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br/>[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-
|}


'''Hexafluoropropylene''' in a compound with the formula C<sub>3</sub>F<sub>6</sub>. It is a fluorinated [[alkene]] in which all of the hydrogen atoms in [[propylene]] are replaced by fluorine atoms. It is used as a chemical intermediate.
'''Hexafluoropropylene''' is the [[fluoroalkene]] with the formula CF<sub>3</sub>CF=CF<sub>2</sub>. 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.<ref name=Ullmann>{{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= Kirschtitle=Fluorine Compounds, Organic|year=2016|doi=10.1002/14356007.a11_349.pub2}}</ref>


==Preparation==
[[Category:Organofluorides]]
Hexafluoropropylene can be produced by pyrolysis of [[tetrafluoroethylene]]:<ref name=Ullmann/><ref>{{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
}}</ref>
:3{{nbsp}}CF<sub>2</sub>=CF<sub>2</sub> → 2{{nbsp}}CF<sub>3</sub>CF=CF<sub>2</sub>
It can also be prepared from [[chlorodifluoromethane]], or produced from various [[chlorofluorocarbons]].<ref name="dupontsynth">
{{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}}
</ref>


==References==
<references/>


[[Category:Perfluoroalkenes]]
{{organic-compound-stub}}

{{organohalide-stub}}

Latest revision as of 11:39, 5 April 2023

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 Edit this at Wikidata
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 diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 0: Will not burn. E.g. waterInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
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 ?)

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[edit]

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[edit]

  1. ^ 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.
  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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