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Chlorotrifluoroethylene

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"CTFE" redirects here. For other uses, see CTFE (disambiguation).
Chlorotrifluoroethylene
Structural formula of chlorotrifluoroethylene
Structural formula of chlorotrifluoroethylene
Ball-and-stick model of chlorotrifluoroethylene
Ball-and-stick model of chlorotrifluoroethylene
Names
Preferred IUPAC name 1-Chloro-1,2,2-trifluoroethene
Other names Chlorotrifluoroethene
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.093 Edit this at Wikidata
EC Number
  • 201-201-8
PubChem CID
RTECS number
  • KV0525000
UNII
UN number 1082
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2ClF3/c3-1(4)2(5)6Key: UUAGAQFQZIEFAH-UHFFFAOYSA-N
  • InChI=1/C2ClF3/c3-1(4)2(5)6Key: UUAGAQFQZIEFAH-UHFFFAOYAH
SMILES
  • F/C(F)=C(/Cl)F
Properties
Chemical formula C2ClF3
Molar mass 116.47 g·mol
Appearance Colorless gas
Odor faint etheral odor
Density 1.54 g/cm at −60°C
Melting point −158.2 °C (−252.8 °F; 115.0 K)
Boiling point −27.8 °C (−18.0 °F; 245.3 K)
Solubility in water 4.01 g/100 mL
Solubility soluble in benzene, chloroform
Magnetic susceptibility (χ) -49.1·10 cm/mol
Refractive index (nD) 1.38 (0 °C)
Hazards
GHS labelling:
Pictograms GHS02: FlammableGHS06: Toxic
Signal word Danger
Hazard statements H220, H301, H331
Precautionary statements P210, P261, P264, P270, P271, P301+P310, P304+P340, P311, P321, P330, P377, P381, P403, P403+P233, P405, P410+P403, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneInstability 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g. hydrogen peroxideSpecial hazards (white): no code
3 4 3
Explosive limits 24-40.3%
Related compounds
Related compounds Tetrafluoroethylene
Bromotrifluoroethylene
Trifluoroiodoethylene
Dichlorodifluoroethylene
Trichlorofluoroethylene
Tetrachloroethylene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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.

Production and reactions

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

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. Dechlorination of the latter gives hexafluorocyclobutene. It undergoes cycloaddition to vinyl acetate.

References

  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. 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. 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. 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. 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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