Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1989-12-01
1990-11-27
Raymond, Richard L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
568864, C07C 29147, C07D30708
Patent
active
049737171
DESCRIPTION:
BRIEF SUMMARY
Ths present invention relates in general to the production of alcohols and ethers by the catalysed hydrogenation of esters and in particular to the production of C.sub.4 alcohols and ethers by the catalysed hydrogenation of either the esters of C.sub.4 dicarboxylic acids or gamma-butyrolactone.
Alcohols and ethers are valuable industrial products which find wide useage as solvents.
The use of heterogeneous catalysts in the hydrogenation of esters is known.
A problem associated with the use of heterogeneous hydrogenation catalysts in ester hydrogenation reactions is the simultaneous co-production of unwanted alkanes, e.g. methane and ethane, by side reactions, thereby decreasing the overall selectivities to alcohols and/or ethers.
Our copending European application No. 88302891.2 (BP Case No. 6544) discloses the production of an alcohol and/or a carboxylic acid ester from a carboxylic acid or anhydride thereof by reacting the acid or anhydride 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 and (ii) at least one metal capable of alloying with the Group VIII noble metal, for example either silver, gold or copper, and optionally including a support and at least one of the metals rhenium, tungsten or molybdenum.
We have now found that the problem of alkane formation in ester hydrogenation can be substantially reduced by using the alloy catalyst of our aforesaid copending European application.
Accordingly, in one aspect the present invention provides a process for the production of an alcohol and/or an ether from a carboxylic acid ester which process comprises reacting the ester 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 least one metal capable of alloying with the aforesaid Group VIII noble metal.
Hydrogen is commercially available on a large scale and may be used with or without further purification. A desirable purification may be removal of carbon monoxide.
The process of the invention is applicable to the hydrogenation of carboxylic acid esters, which term includes not only the open-chain esters, for example ethyl acetate, but also cyclic internal esters, for example gamma-butyrolactone. Suitable open-chain carboxylic acid esters are esters of C.sub.1 to C.sub.24 acyclic mono- or di-, saturated or unsaturated, straight-or branched-chain carboxylic acids. Suitably the esters are alkyl esters, preferably lower, i.e. C.sub.1 to C.sub.4, alkyl esters. Suitable cyclic internal esters include C.sub.5 to C.sub.7 lactones. Examples of carboxylic acid esters useful herein include but are not in any way to be limited to methyl acetate, ethyl acetate, propyl acetate, butyl acetate, dimethyl maleate, dimethyl succinate, methyl methacrylate, methyl oxalate and gamma-butyrolactone.
As regards the catalyst composition, the noble metals of Group VIII of the Periodic Table of the Elements are palladium, platinum, rhodium, ruthenium, osmium and iridium. Of the aforesaid noble metals, palladium, rhodium and ruthenium are preferred. Metals capable of alloying with palladium include silver, gold, copper, nickel, rhodium, tin, cobalt, aluminium, manganese, gallium, iron, chromium and platinum, of which silver, gold and copper are preferred. Metals capable of alloying with ruthenium include iron, cobalt, manganese, germanium and rhenium.
Although a catalyst composition comprising an alloy of (i) at least one noble metal of Group VIII of the Periodic Table of the Elements, and (ii) at least one metal capable of alloying with the aforesaid Group VIII noble metal (hereinafter to be designated component (A)) may be used as catalyst in the hydrogenation of carboxylic acid esters, it is preferred to employ a catalyst incorporating one or more further components.
It is preferred to incorporate (as component (B)) at least one of the metals rhenium, tungsten or m
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BP Chemicals Limited
Raymond Richard L.
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