Chlorotrifluoroethylene: Difference between revisions
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{{redirect|CTFE}} |
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{{Chembox |
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| verifiedrevid = |
| verifiedrevid = 414432719 |
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| ImageFileL1_Ref = {{chemboximage|correct|??}} |
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| ImageFileL1 = Chlortrifluorethen.svg |
| ImageFileL1 = Chlortrifluorethen.svg |
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| ImageSizeL1 = 120px |
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| ImageNameL1 = Structural formula of chlorotrifluoroethylene |
| ImageNameL1 = Structural formula of chlorotrifluoroethylene |
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| ImageFileR1 = Chlorotrifluoroethylene-3D-balls.png |
| ImageFileR1 = Chlorotrifluoroethylene-3D-balls.png |
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| ImageSizeR1 = 105px |
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| ImageNameR1 = Ball-and-stick model of chlorotrifluoroethylene |
| ImageNameR1 = Ball-and-stick model of chlorotrifluoroethylene |
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| PIN = 1-Chloro-1,2,2-trifluoroethene |
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| OtherNames = |
| OtherNames = Chlorotrifluoroethene |
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| Reference = <ref name="hand"> |
| Reference = <ref name="hand"> |
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{{cite book | last = Lide | first = David R. | year = 1998 |
{{cite book | last = Lide | first = David R. | year = 1998 |
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| title = Handbook of Chemistry and Physics |
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| edition = 87 | volume = |
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| location = Boca Raton, Florida |
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| publisher = CRC Press |
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| isbn = 0-8493-0594-2 | pages = 3–126}}</ref> |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 6345 |
| ChemSpiderID = 6345 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 79-38-9 |
| CASNo = 79-38-9 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = AF215GW34G |
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| PubChem = 6594 |
| PubChem = 6594 |
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| EC_number = 201-201-8 |
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| RTECS = KV0525000 |
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| UNNumber = 1082 |
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| SMILES = F/C(F)=C(/Cl)F |
| SMILES = F/C(F)=C(/Cl)F |
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|Section2={{Chembox Properties |
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| C=2 | F=3 | Cl=1 |
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| Formula = CF<sub>2</sub>CClF |
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| MolarMass = 116.469 g/mol |
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| Odor = faint [[ether]]al odor |
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| Density = 1.54 g/cm<sup>3</sup> at −60°C |
| Density = 1.54 g/cm<sup>3</sup> at −60°C |
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| MeltingPtC = -158.2 |
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| BoilingPtC = -27.8 |
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| Solubility = |
| Solubility = 4.01 g/100 mL |
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|SolubleOther = |
| SolubleOther = soluble in [[benzene]], [[chloroform]] |
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| RefractIndex = 1.38 (0 °C) |
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| MagSus = -49.1·10<sup>−6</sup> cm<sup>3</sup>/mol |
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| Autoignition = }} |
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| NFPA-H = 3 | NFPA-F = 4 | NFPA-R = 3 |
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| AutoignitionPt = |
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| ExploLimits = 24-40.3% |
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| GHSPictograms = {{GHS02}}{{GHS04}}{{GHS06}} |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|220|280|301|331}} |
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| PPhrases = {{P-phrases|210|261|264|270|271|301+310|304+340|311|321|330|377|381|403|403+233|405|410+403|501}} |
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}} |
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|Section8={{Chembox Related |
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| OtherAnions = |
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| OtherCations = |
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| OtherCompounds = [[Tetrafluoroethylene]] <br/> [[Bromotrifluoroethylene]] <br/> [[Trifluoroiodoethylene]] <br/> [[Dichlorodifluoroethylene]] <br/> [[Trichlorofluoroethylene]] <br/> [[Tetrachloroethylene]] |
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'''Chlorotrifluoroethylene''' ('''CTFE''') is a [[chlorofluorocarbon]] with chemical formula CFCl=CF<sub>2</sub>. It is commonly used as a [[refrigerant]] in cryogenic applications. CTFE has a carbon-carbon [[double bond]] and so can be [[polymerization|polymerized]] to form [[polychlorotrifluoroethylene]] or copolymerized to produce the plastic [[ECTFE]]. PCTFE has the trade name Neoflon PCTFE from [[Daikin Industries]] in Japan, and it used to be produced under the trade name Kel-F from [[3M Corporation]] in Minnesota.<ref>{{citation|url=http://www.aetnaplastics.com/products/d/pctfe|title=Aetna Plastics Corp. - Products. Services ... Solutions|publisher=Aetna Plastics Corp.|pages=PCTFE / Kel–F® / Neoflon®|access-date=3 February 2012|archive-date=27 November 2022|archive-url=https://web.archive.org/web/20221127215032/https://www.aetnaplastics.com/products/d/pctfe|url-status=dead}}</ref> |
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{{For|compiler feature|Compile time function execution}} |
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==Production and reactions== |
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'''CTFE''', or '''chlorotrifluoroethylene''' is a [[chlorofluorocarbon]] with chemical formula [[Carbon|C]][[Fluorine|F]]<sub>2</sub>[[Carbon|C]][[Chlorine|Cl]][[Fluorine|F]]. It is commonly used as a [[refrigerant]] in cryogenic applications. CTFE can be [[polymer|polymerised]] to produce the plastic [[ECTFE]]. |
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Chlorotrifluoroethylene is produced commercially by the dechlorination of [[1,1,2-trichloro-1,2,2-trifluoroethane]] with [[zinc]]:<ref name=Ull>{{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|title=Fluorine Compounds, Organic|year=2002|doi=10.1002/14356007.a11_349}}</ref> |
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:CFCl<sub>2</sub>-CF<sub>2</sub>Cl + Zn → CClF=CF<sub>2</sub> + ZnCl<sub>2</sub> |
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In 2012, an estimated 1–10 million pounds were produced commercially in the United States. |
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The thermal dimerization of chlorotrifluoroethylene gives 1,2-dichloro-1,2,3,3,4,4-hexafluorocyclobutane.<ref>{{cite journal |doi=10.1039/JR9520003830|title=The High-Temperature Dimerisation of Chlorotrifluoroethylene|year=1952|last1=Buxton|first1=M. W.|last2=Ingram|first2=D. W.|last3=Smith|first3=F.|last4=Stacey|first4=M.|last5=Tatlow|first5=J. C.|journal=Journal of the Chemical Society (Resumed)|page=3830}}</ref> Dechlorination of the latter gives [[hexafluorocyclobutene]]. It undergoes [2+2] cycloaddition to [[vinyl acetate]].<ref>{{cite journal |doi=10.15227/orgsyn.043.0017|title=1-Chloro-1,4,4-Trifluorobutadiene |journal=Organic Syntheses |year=1963 |volume=43 |page=17|author=R. E. Putnam, B. C. Anderson, W. H. Sharkey }}</ref> |
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==References== |
==References== |
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{{reflist}} |
{{reflist}} |
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{{Use dmy dates|date=March 2018}} |
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[[Category:Heating, |
[[Category:Heating, ventilation, and air conditioning]] |
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[[Category:Organofluorides]] |
[[Category:Organofluorides]] |
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[[Category:Refrigerants]] |
[[Category:Refrigerants]] |
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[[Category:Haloalkenes]] |
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[[Category:Organochlorides]] |
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[[de:Chlortrifluorethen]] |
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[[nl:Chloortrifluoretheen]] |