Hexafluoropropylene: Difference between revisions

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-{{chembox
+{{Chembox
-| verifiedrevid = 396492685
+| verifiedrevid = 420876606
-|   Name = Hexafluoropropylene
+| Name = Hexafluoropropylene
-|   ImageFileL1 = Hexafluoropropylene.svg
+| ImageFileL1 = Hexafluoropropylene.svg
-|   ImageSizeL1 = 100px
+| ImageSizeL1 = 125
+| ImageAltL1 = Structural formula of hexafluoropropylene
-|   ImageFileR1 = Hexafluoropropylene 3D.png
+| ImageFileR1 = Hexafluoropropylene 3D.png
-|  ImageSizeR1 = 120px
+| ImageSizeR1 = 125
-|   IUPACName = Hexafluoropropene
+| ImageAltR1 = Ball-and-stick model of the hexafluoropropylene molecule
-|   OtherNames = Perfluoropropene,<br /> Perfluoropropylene,<br /> freon R 1216,<br /> halocarbon R 1216,<br /> fluorocarbon 1216
+| PIN = 1,1,2,3,3,3-Hexafluoroprop-1-ene
-| Section1 = {{Chembox Identifiers
+| OtherNames = Perfluoropropene,<br /> Perfluoropropylene,<br /> freon R 1216,<br /> halocarbon R 1216,<br /> fluorocarbon 1216
-|   SMILES = F/C(F)=C(/F)C(F)(F)F
+|Section1={{Chembox Identifiers
-|   ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
+| 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
@@ Line 20: / Line 22: @@
 | CASNo_Ref = {{cascite|correct|CAS}}
 | CASNo = 116-15-4
+| UNII_Ref = {{fdacite|correct|FDA}}
-|   RTECS = UD0350000
+| UNII = TRW23XOS20
-  }}
+| RTECS = UD0350000
-| Section2 = {{Chembox Properties
-|   C=3|F=6
+| PubChem = 8302
+| UNNumber = 1858
-|   Appearance = Colorless, odorless gas
+| EINECS = 204-127-4
-|   Density = 1.332 g/ml, liquid at 20 °C
+ }}
-|   Solubility = Insoluble
+|Section2={{Chembox Properties
-|   MeltingPtC = -153
-|   BoilingPtC = -28
+| C=3 | F=6
+| Appearance = Colorless, odorless gas
-  }}
+| Density = 1.332 g/ml, liquid at 20 °C
-| Section7 = {{Chembox Hazards
+| Solubility = Insoluble
-|   ExternalMSDS =
+| MeltingPtC = -153
-|   MainHazards = Harmful ('''Xn''')
+| BoilingPtC = -28
-|   NFPA-H = 2
+ }}
-|   NFPA-F =
+|Section7={{Chembox Hazards
-|   NFPA-R =
+| ExternalSDS =
-|   FlashPt = Non flammable gas
+| MainHazards = Suffocation
-|   RPhrases = {{R20}}, {{R37}}
-|   SPhrases = {{S41}}
+| NFPA-H = 1
+| NFPA-F = 0
-  }}
+| NFPA-R = 1
-| Section8 = {{Chembox Related
+| FlashPt = Non flammable gas
-|   Function = [[alkene]]s
+| GHSPictograms = {{GHS04}}{{GHS07}}{{GHS08}}
-|   OtherFunctn = [[propylene]]
+| GHSSignalWord = Warning
-|   Function = organofluorides
+| HPhrases = {{H-phrases|280|332|335|351|371|373}}
-|   OtherFunctn = [[Hexafluoroacetone]],<br />[[Hexafluoro-2-propanol]]
+| 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 = [[alkene]]s;<br>organofluorides
+| OtherFunction = [[propylene]];<br>[[Hexafluoroacetone]], [[Hexafluoro-2-propanol]]
+ }}
 }}
-'''Hexafluoropropylene''' is a compound with the formula C<sub>3</sub>F<sub>6</sub>. It is a [[fluorocarbon]] [[alkene]] in which all of the hydrogen atoms in [[propylene]] are replaced by [[fluorine]] atoms. It is used as a chemical intermediate.<ref>{{cite journal
+'''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>
- |last=Lehmler |first=HJ
+==Preparation==
- |title=Synthesis of environmentally relevant fluorinated surfactants—a review
+Hexafluoropropylene can be produced by pyrolysis of [[tetrafluoroethylene]]:<ref name=Ullmann/><ref>{{cite journal
- |journal=Chemosphere |volume=58 |issue=11 |pages=1471–96 |month=March |year=2005
+| last=Lehmler |first=HJ
- |doi=10.1016/j.chemosphere.2004.11.078 |pmid=15694468 |pmc=2587313}}</ref>
+| 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:Organofluorides]]
+[[Category:Perfluoroalkenes]]
 {{organohalide-stub}}
-[[de:Hexafluorpropen]]
-[[ja:ヘキサフルオロプロペン]]
-[[zh:六氟丙烯]]