Chlorotrifluoroethylene

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

Chlorotrifluoroethylene ^[1]

Structural formula of chlorotrifluoroethylene Ball-and-stick model of chlorotrifluoroethylene
Names
Preferred IUPAC name 1-Chloro-1,2,2-trifluoroethene
Other names Chlorotrifluoroethene
Identifiers
CAS Number	79-38-9  Y
3D model (JSmol)	Interactive image
ChemSpider	6345  Y
ECHA InfoCard	100.001.093
EC Number	201-201-8
PubChem CID	6594
RTECS number	KV0525000
UNII	AF215GW34G  Y
UN number	1082
CompTox Dashboard (EPA)	DTXSID3026485
InChI InChI=1S/C2ClF3/c3-1(4)2(5)6 Y Key: UUAGAQFQZIEFAH-UHFFFAOYSA-N Y InChI=1/C2ClF3/c3-1(4)2(5)6 Key: UUAGAQFQZIEFAH-UHFFFAOYAH
SMILES F/C(F)=C(/Cl)F
Properties
Chemical formula	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)
Solubility in water	4.01 g/100 mL
Solubility	soluble in benzene, chloroform
Magnetic susceptibility (χ)	-49.1·10−6 cm3/mol
Refractive index (nD)	1.38 (0 °C)
Hazards
GHS labelling:
Pictograms
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)	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). Y  verify  (what is  YN ?) Infobox references

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]

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.

Addition of iodine monochloride to chlorotrifluoroethylene gives iododichlorotrifluoroethane:

CF₂=CFCl + ICl → ClCF₂−CFCl(I)

The latter is a precursor to hexafluorobutadiene. ^[4]

Thermal dimerization of chlorotrifluoroethylene gives 1,2-dichloro-1,2,3,3,4,4-hexafluorocyclobutane. ^[5] Dechlorination of the latter gives hexafluorocyclobutene. It undergoes [2+2] cycloaddition to vinyl acetate. ^[6]

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   978-3-527-30673-2.
4. Haszeldine, R. N. (1952). "849. Fluoro-olefins. Part I. The Synthesis of Hexafluorobuta-1:3-diene". Journal of the Chemical Society (Resumed): 4423. doi:10.1039/jr9520004423.
5. 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.
6. 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.