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 prop ...

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

refrigerant A refrigerant is a working fluid used in the heat pump and refrigeration cycle, 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. Ref ...

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 In polymer chemistry, polymerization (American English), or polymerisation (British English), is a process of reacting monomer molecules together in a chemical reaction to form polymer chains or three-dimensional networks. There are many for ...

to form

polychlorotrifluoroethylene Polychlorotrifluoroethylene (PCTFE or PTFCE) is a thermoplastic chlorofluoropolymer 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 a ...

or copolymerized to produce the plastic

ECTFE ECTFE (ethylenechlorotrifluoroethylene) is a copolymer of ethylene and chlorotrifluoroethylene. It is a semi-crystalline fluoropolymer (a partially fluorinated polymer) designed to provide chemical resistance in heavy-duty corrosion application ...

. PCTFE has the trade name Neoflon PCTFE from

Daikin Industries is a Japanese multinational corporation, multinational air conditioner, air conditioning manufacturing company headquartered in Osaka. It has operations in Japan, China, Australia, the United States, India, Southeast Asia, Europe, the Middle Eas ...

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 periodi ...

: :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 Hexafluorocyclobutene is the organofluorine compound with the formula (CF2)2(CF)2. A colorless gas, it is a precursor to a variety of compounds, including squaric acid. Hexafluorocyclobutene is prepared in two steps from chlorotrifluoroethylene. ...

References

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