Chlorotrifluoroethene

Chlorotrifluoroethylene

Chlorotrifluoroethylene

Chemical compound

"CTFE" redirects here. For other uses, see CTFE (disambiguation).

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 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.[2]

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Production and reactions

Chlorotrifluoroethylene is produced commercially by the dechlorination of 1,1,2-trichloro-1,2,2-trifluoroethane with zinc:[3]

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.[4] Dichlorination of the latter gives hexafluorocyclobutene. It undergoes [2+2] cycloaddition to vinyl acetate.[5]

References

  1. [1]
    Lide, David R. (1998). Handbook of Chemistry and Physics (87 ed.). Boca Raton, Florida: CRC Press. pp. 3–126. ISBN 0-8493-0594-2.
  2. [2]
    Aetna Plastics Corp. - Products. Services ... Solutions, Aetna Plastics Corp., pp. PCTFE / Kel–F® / Neoflon®, archived from the original on 27 November 2022, retrieved 3 February 2012
  3. [3]
    Siegemund, Günter; Schwertfeger, Werner; Feiring, Andrew; Smart, Bruce; Behr, Fred; Vogel, Herward; McKusick, Blaine (2002). "Fluorine Compounds, Organic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a11_349. ISBN 978-3527306732.
  4. [4]
    Buxton, M. W.; Ingram, D. W.; Smith, F.; Stacey, M.; Tatlow, J. C. (1952). "The High-Temperature Dimerisation of Chlorotrifluoroethylene". Journal of the Chemical Society (Resumed): 3830. doi:10.1039/JR9520003830.
  5. [5]
    R. E. Putnam, B. C. Anderson, W. H. Sharkey (1963). "1-Chloro-1,4,4-Trifluorobutadiene". Organic Syntheses. 43: 17. doi:10.15227/orgsyn.043.0017.{{cite journal}}: CS1 maint: multiple names: authors list (link)


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