Chemistry:Bromotrifluoroethylene
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| Names | |
|---|---|
| IUPAC name
bromotrifluoroethene
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| Other names
trifluorovinyl bromide, trifluorobromoethylene
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| Identifiers | |
| UN number | 2419 |
| Properties | |
| C2BrF3 | |
| Molar mass | 160.921 g·mol−1 |
| Appearance | colourless gas |
| Odor | moldy,[1] phosgene-like[2] |
| Boiling point | –2.5°C[2] |
| Hazards | |
| Main hazards | spontaneous polymerisation, flammable[3] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Bromotrifluoroethylene (BTFE) is a halogenated ethylene derivative with the chemical formula F
2CCBrF. It is a highly flammable colourless gas with a musty odour resembling phosgene. It can polymerise spontaneously.[3]
Preparation
Bromotrifluoroethylene can be prepared from chlorotrifluoroethylene with high yields:[3][4]
- [math]\ce{ F2C=CClF + HBr -> CF2BrCHClF + Zn -> CF2=CHF + ZnBrCl }[/math]
- [math]\ce{ CF2=CHF + Br2 -> CF2BrCHBrF + KOH -> CF2CHBr + KBr + H2O }[/math]
It was first prepared by the Belgian chemist Frédéric Swarts in 1899.[5]
Reactions and uses
Bromotrifluoroethylene forms metal complexes with substituted phosphine compounds and platinum(II).[6]
BTFE can polymerise on standing. Spontaneous polymerisation may be inhibited by addition of tributylamine.[4] UV light and heat may accelerate polymerisation.[4] It participates in various co-polymerisation reactions.[2] BTFE telomers are oily liquids sold under the tradename BFC oil. The telomers can be prepared with fluorotrichloromethane or tetrachloromethane as telogens. If tetrachloromethane is used for the telomerisation, it will have -CCl3 terminals.[5] It is a useful reagent for the synthesis of trifluorovinyl compounds.[3]
References
- ↑ Hazardous Substance Fact Sheet, New Jersey Department of Health PDF
- ↑ 2.0 2.1 2.2 Yaws, C. L., Braker, W. (2001). Matheson gas data book. Page 69
- ↑ 3.0 3.1 3.2 3.3 Arthur J. Elliott, Bromotrifluoroethylene in Kirk-Othmer Encyclopedia of Chemical Technology
- ↑ 4.0 4.1 4.2 Fluorine chemistry: a comprehensive treatment (1995), pages 479–480
- ↑ 5.0 5.1 Industrial Polymers and Radiation: Proceedings of the Symposium Held at Sardar Patel University, Vallabh Vidyanagar, Gujarat, February 12–14, 1979.
- ↑ V.A. Mukhedkar, B.J. Kavathekar, A.J. Mukhedkar, Reactions of metal complexes Rearrangement reactions of bromotrifluoroethylene-bis(substituted phosphine)-platinum (II), Journal of Inorganic and Nuclear Chemistry, Volume 37, Issue 2, February 1975, Pages 483-485
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