Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1988-11-21
1991-01-15
Raymond, Richard L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
568814, 568885, 560105, 560265, C07D30720, C07C 31125, C07C 6708
Patent
active
049855727
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to the catalysed hydrogenation of carboxylic acids and their anhydrides to produce the corresponding alcohol and/or carboxylic acid ester and to catalysts for use in the aforesaid hydrogenations.
The hydrogenation of carboxylic acids to produce the corresponding alcohol in the presence of heterogeneous catalysts is known from, for example, U.S. Pat. Nos. 4,524,225, 4,104,478, GB-A-1534232, GB-A-1551741, DE-A-3221077 and EP-A-147219.
U.S. Pat. No. 4524225 describes the hydrogenation of C.sub.6 -C.sub.24 fatty acids by contacting the fatty acid with hydrogen at 100.degree. to 300.degree. C. and 100 to 3000 psig in the presence of a zerovalent metal selected from Cu, Cr, Ru, Pt, Pd, Rs and mixtures thereof dispersed on a support which may be alpha, theta or titanated alumina, titania, or AIPO.sub.4 or a mixture thereof.
U.S. Pat. No. 4,104,478 describes the production of C.sub.4 to C.sub.24 fatty alcohols by catalytically hydrogenating the corresponding fatty acid at 170.degree. to 250.degree. C. and 20 to 140 atmospheres over a catalyst system consisting of (a) 1 part wt. of activated Re, and (b) 0.25 to 1.5 parts of an extrinsic metal catalyst selected from Ru, Rh, Pt and Pd.
GB-A-1534232 describes the preparation of alcohols by catalytic hydrogenation of carboxylic acids at elevated temperature and pressure in the presence of water and/or solvents using a Pd/Re catalyst on a support, the catalyst having a Pd:Rs wt ratio of 0.01 to 5:1.
GB-A-1551741 describes the one-step preparation of 1,4-butanediol from maleic acid by hydrogenation in the presence of a catalyst containing (A) elments of Group VII, preferably Mn or Re, or their compounds, and (B) elements of Group VIII, preferably Ru, Rh, Pd, Os, Ir or Pt more preferably Pd or Pt or their compounds or mixtures thereof.
DE-A-3221077 describes the continuous production of ethanol by the hydrogenation of acetic acid at elevated pressure and temperature using a catalyst based on cobalt.
EP-A-147219, published after the priority date claimed for the subject application on an application claiming an earlier priority date, describes the hydrogenation of maleic acid using a Pd/Re/C catalyst.
Our copending European application publication No. 0198682 (BP Case No. 6347) provides a process for the production of an alcohol and/or a carboxylic acid ester from a C.sub.2 to C.sub.12 carboxylic acid by contacting the carboxylic acid at elevated temperature and pressure with hydrogen in the presence of a heterogeneous catalyst characterized in that the catalyst comprises a first component which is either molybdenum or tungsten and a second component which is a noble metal of Group VIII of the Periodic Table of the Elements.
Finally, our copending European application publication No. 0198681 (BP Case No. 5930) discloses a process for the production of either ethanol from acetic acid or propanol from propionic acid which process comprises contacting either acetic acid or propionic acid in the vapour phase with hydrogen at elevated temperature and a pressure in the range from 1 to 150 bar in the presence of a catalyst comprising as essential components (i) a noble metal of Group VIII of the Periodic Table of the Elements, and (ii) rhenium.
A problem associated with the use of heterogeneous hydrogenation catalysts in the aforesaid reactions is the co-production of unwanted alkanes, e.g. methene and ethane, by side-reactions, thereby decreasing the selectivity to desirable products.
We have now found that the problem of alkane formation can be reduced by the uss of alloyed catalysts.
Accordingly, in one aspect the present invention provides a process for the production from either a carboxylic acid or an anhydride thereof of the corresponding alcohol and/or carboxylic acid ester which process comprises reacting the carboxylic acid or anhydride thereof with hydrogen at elevated temperature in the presence as catalyst of a composition comprising an alloy of (i) at least one noble metal of Group VIII of the Periodic Table of the Elements, and (ii) at
REFERENCES:
patent: 4096156 (1978-01-01), Freudenberger et al.
patent: 4104478 (1978-01-01), Trivedi
patent: 4105674 (1978-08-01), De Thomas et al.
patent: 4524225 (1985-01-01), Qualeatti et al.
patent: 4777303 (1988-10-01), Kirtson et al.
patent: 4804791 (1989-02-01), Kirtson et al.
Kitson Melanie
Williams Peter S.
BP Chemicals Limited
Raymond Richard L.
Russell Mark W.
The British Petroleum Company p.l.c.
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