Chlorotrifluoroethylene: Difference between revisions

{{redirect|CTFE}}

| Watchedfields = changed

| verifiedrevid = 414432719

| ImageFileL1_Ref = {{chemboximage|correct|??}}

| PIN = 1-Chloro-1,2,2-trifluoroethene

| OtherNames = Chlorotrifluoroethene

| title = Handbook of Chemistry and Physics

| edition = 87 | volume =

| location = Boca Raton, Florida

| publisher = CRC Press

| isbn = 0-8493-0594-2 | pages = 3–126}}</ref>

|Section1={{Chembox Identifiers

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = AF215GW34G

| EC_number = 201-201-8

| RTECS = KV0525000

| UNNumber = 1082

|Section2={{Chembox Properties

| C=2 | F=3 | Cl=1

| Appearance = Colorless gas

| Odor = faint [[ether]]al odor

| MeltingPtC = -158.2

| BoilingPtC = -27.8

| Solubility = 4.01 g/100 mL

| SolubleOther = soluble in [[benzene]], [[chloroform]]

| RefractIndex = 1.38 (0 °C)

| MagSus = -49.1·10⁻⁶ cm³/mol

}}

|Section3={{Chembox Hazards

| MainHazards =

| NFPA-H = 3 | NFPA-F = 4 | NFPA-R = 3

| FlashPt =

| AutoignitionPt =

| ExploLimits = 24-40.3%

| GHSPictograms = {{GHS02}}{{GHS04}}{{GHS06}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|220|280|301|331}}

| PPhrases = {{P-phrases|210|261|264|270|271|301+310|304+340|311|321|330|377|381|403|403+233|405|410+403|501}}

}}

|Section8={{Chembox Related

| OtherAnions =

| OtherCations =

| OtherCompounds = [[Tetrafluoroethylene]] <br/> [[Bromotrifluoroethylene]] <br/> [[Trifluoroiodoethylene]] <br/> [[Dichlorodifluoroethylene]] <br/> [[Trichlorofluoroethylene]] <br/> [[Tetrachloroethylene]]

}}

'''Chlorotrifluoroethylene''' ('''CTFE''') is a [[chlorofluorocarbon]] with chemical formula CFCl=CF₂. 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>

==Production and reactions==

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>

:CFCl₂-CF₂Cl + Zn → CClF=CF₂ + ZnCl₂

In 2012, an estimated 1–10 million pounds were produced commercially in the United States.

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>

{{Use dmy dates|date=March 2018}}

[[Category:Heating, ventilation, and air conditioning]]

[[Category:Haloalkenes]]

[[Category:Organochlorides]]

{{organohalide-stub}}