Hydrogenation of halogen-containing carboxylic anhydrides

Details Hydrogenation of halogen-containing carboxylic anhydrides Hydrogenation of halogen-containing carboxylic anhydrides

1979-09-18

1981-03-10

Lone, Werren B.

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

C07C 3138

Patent

active

042555949

ABSTRACT:
A process is described for the heterogeneous hydrogenation of haloalkyl, halocycloalkyl or haloaryl carboxylic anhydrides to the corresponding primary alcohols. In the haloalkyl or halocycloalkyl carboxylic anhydrides at least one halogen is in the alpha-position relative to the carboxylic anhydride grouping. The hydrogenation can be carried out in the liquid or vapor phase in the presence of a supported or unsupported catalyst comprising a member of the group consisting of rhodium, iridium, metal oxides thereof, or mixtures thereof. In the liquid phase, the hydrogenation can be carried out batchwise under mild conditions of temperature and pressure, preferably at about 50.degree.-150.degree. C. and about 5-15 atmospheres, in an atmosphere containing hydrogen gas. A preferred embodiment is the hydrogenation of trifluoroacetic anhydride in the liquid phase to 2,2,2-trifluoroethanol, said alcohol being useful as an intermediate in the synthesis of the anesthetic, isoflurane, CF.sub.3 CHClOCHF.sub.2.

REFERENCES:
patent: 3314987 (1967-04-01), Case et al.
patent: 3356746 (1967-12-01), Anello et al.
patent: 3356746 (1967-12-01), Anello et al.
patent: 4072726 (1978-02-01), Nychka et al.
Swart, "Compt. Rend" 197 1261 (1933).
Chem Abstract, vol. 28, pp. 1987, Swarts.

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