Fluorine substitution in 1,1,1-trihalomethanes

Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal

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2606538, C07C 1908

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active

040780074

ABSTRACT:
Fluorine is substituted for other halogen atoms on the 1-carbon atom of a compound which contains a 1,1,1-trihalomethyl group (trichloromethyl) by contacting said compound or a precursor thereof with liquid HF in the presence of a mixture of antimony pentahalide with at least an approximately equimolar amount of antimony trihalide. The antimony halides may be added as the chlorides and in situ converted to fluorides and/or chlorofluorides, which are believed to be the essential agents. Additional starting material and antimony pentahalide may be added in the course of the reaction which proceeds stepwise. When the reactant is 1,1,1,3-tetrachloropropane the reaction can be continued to produce 3-chloro-1,1,1-trifluoropropane which, upon reaction with alkali, yields 3,3,3-trifluoropropane, of known utility in making fluorosilicones. The reaction is also useful in the production of 2-chloro-1,1,1-trifluoroethane from 2-chloro-1,1,1-trihaloethanes and/or precursors thereof such as trichloroethylene, as well as in the production of trifluoromethane and chlorotrifluoromethane from chloroform and carbon tetrachloride, respectively.

REFERENCES:
tarrant et al., J. Am. Chem. Soc. 77, 2783-2787, (1955).
Henne et al., Chem. Abstracts, 45, 7948i, (1951).

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