Chlorotrifluoroethylene

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]

"CTFE" redirects here. For other uses, see CTFE (disambiguation).
Chlorotrifluoroethylene[1]
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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.093
EC Number
  • 201-201-8
RTECS number
  • KV0525000
UNII
UN number 1082
  • InChI=1S/C2ClF3/c3-1(4)2(5)6 checkY
    Key: UUAGAQFQZIEFAH-UHFFFAOYSA-N checkY
  • InChI=1/C2ClF3/c3-1(4)2(5)6
    Key: UUAGAQFQZIEFAH-UHFFFAOYAH
  • F/C(F)=C(/Cl)F
Properties
C2ClF3
Molar mass 116.47 g·mol−1
Appearance Colorless gas
Odor faint etheral odor
Density 1.54 g/cm3 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)
4.01 g/100 mL
Solubility soluble in benzene, chloroform
-49.1·10−6 cm3/mol
1.38 (0 °C)
Hazards
GHS labelling:
GHS02: FlammableGHS04: Compressed GasGHS06: Toxic
Danger
H220, H280, H301, H331
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 diamond
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 [77 °F], 100 kPa).
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Infobox references

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. 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.
  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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