Chlorotrifluoroethylene (CTFE) is a

chlorofluorocarbon Chlorofluorocarbons (CFCs) and hydrochlorofluorocarbons (HCFCs) are fully or partly halogenated hydrocarbons that contain carbon (C), hydrogen (H), chlorine (Cl), and fluorine (F), produced as volatile derivatives of methane, ethane, and pro ...

with chemical formula CFCl=CF₂. It is commonly used as a

refrigerant A refrigerant is a working fluid used in the refrigeration cycle of air conditioning systems and heat pumps where in most cases they undergo a repeated phase transition from a liquid to a gas and back again. Refrigerants are heavily regulate ...

in cryogenic applications. CTFE has a carbon-carbon

double bond In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist betw ...

and so can be polymerized to form

polychlorotrifluoroethylene Polychlorotrifluoroethylene (PCTFE or PTFCE) is a thermoplastic chloro fluoropolymer with the molecular formula , where ''n'' is the number of monomer units in the polymer molecule. It is similar to polytetrafluoroethene (PTFE), except that it is ...

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.

Production and reactions

Chlorotrifluoroethylene is produced commercially by the dechlorination of 1,1,2-trichloro-1,2,2-trifluoroethane with

zinc Zinc is a chemical element with the symbol Zn and atomic number 30. Zinc is a slightly brittle metal at room temperature and has a shiny-greyish appearance when oxidation is removed. It is the first element in group 12 (IIB) of the periodic t ...

: :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. Dichlorination of the latter gives hexafluorocyclobutene.

References

Heating, ventilation, and air conditioning Organofluorides Refrigerants {{organohalide-stub