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US4273947A Expired / Lapsed US ⏱️ 0.0 years remaining

Hydrogenation of fluorine-containing carboxylic acids

Assignee: Honeywell International Inc
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Filing: 1979-01-31
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Granted: 1981-06-16
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Expires: 1999-01-31
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Abstract

Abstract A process is described for the heterogeneous hydrogenation of fluorine-containing alkyl, cycloalkyl, and benzene carboxylic acids to the corresponding primary alcohols. The hydrogenation can be carried out in the liquid or vapor phase in the presence of a solid rhodium or iridium catalyst, employed as the metal, metallic oxide, or mixture thereof. In the liquid phase, the hydrogenation can be carried out batchwise under mild conditions of temperature and pressure, preferably at about 50 DEG -150 DEG C. and about 5-15 atmospheres, in an atmosphere containing hydrogen gas. A preferred embodiment is the hydrogenation of trifluoroacetic acid in the liquid phase to 2,2,2-trifluoroethanol, said alcohol being useful as an intermediate in the synthesis of the anesthetic, isoflurane, CF3CHClOCHF2.

Inventors

  • 👤 Miroslav Novotny

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-05 15:55
CPC Classifications
C; C07; C07C; C07C29/00; C07C29/132; C07C29/136; C07C29/147; C07C29/149; C07C2601/00; C07C2601/12; C07C2601/14

Claims Analysis

Total Claims: 8
Claim 1
Independent Claim 66 words
A process for hydrogenating the carboxy group in 2,2,2-trifluoroacetic acid to the primary alcohol group comprising the step of contacting said acid in the liquid phase with an atmosphere containing hydrogen gas in the presence of a supported or unsupported solid rhodium or iridium catalyst, employed as the metal, metallic oxide, or mixture thereof; at temperature of about 50°-150° C. and pressure of about 5-15 atmospheres.
Claim 2
Dependent Claim 66 words
A process for hydrogenating the carboxy group in 2,2,2-trifluoroacetic acid to the primary alcohol group comprising the step of contacting said acid in the liquid phase with an atmosphere containing hydrogen gas in the presence of a supported or unsupported solid rhodium or iridium catalyst, employed as the metal, metallic oxide, or mixture thereof; at temperature of about 50°-150° C. and pressure of about 5-15 atmospheres.
Claim 3
Dependent Claim 10 words
The process of claim 1 wherein said catalyst is unsupported.
Claim 4
Dependent Claim 14 words
The process of claim 1 wherein said catalyst is supported on carbon or alumina.
Claim 5
Dependent Claim 37 words
The process of claim 1 wherein said catalyst is selected from the group consisting of 5 weight percent rhodium on carbon, 5 weight percent rhodium on alumina, rhodium black, iridium black, rhodium oxide hydrate, or mixtures thereof.
Claim 6
Dependent Claim 28 words
The process of claim 1 wherein said catalyst, in supported or unsupported form, is present in an amount of about 0.001 to 20 weight percent of said acid.
Claim 7
Dependent Claim 15 words
The process of claim 4 wherein said catalyst is 5 weight percent rhodium on carbon.
Claim 8
Dependent Claim 30 words
The process of claim 6 wherein said catalyst is present in an amount of about 1-10 weight percent of said acid present and said atmosphere consists essentially of hydrogen gas.

References Cited (Backward Citations)

US2862977A Cited
US3356746A Cited
US3663629A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-06-15 1984-12-15 1985-06-16 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-06-15 1988-12-15 1989-06-16 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-06-15 1992-12-15 1993-06-16 $7700.00 Window Closed / Lapsed

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