Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1994-05-06
1995-03-21
Evans, Joseph E.
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
568885, C07C 3120, C07C 3302, C07C 33025
Patent
active
053997921
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
This invention relates to a process for the production of unsaturated fatty alcohols by hydrogenation of deacidified and/or non-deacidified glyceride oils in the presence of zinc-chromium catalysts with formation of propane and 1,2-propylene glycol, the olefinic double bonds present in the starting material remaining largely intact.
STATEMENT OF RELATED ART
DE 25 13 377 B1 describes a process for the production of monounsaturated relatively high molecular weight fatty alcohols by catalytic hydrogenation of free, unsaturated fatty acids of relatively high molecular weight or esters thereof formed with monohydric alcohols of low molecular weight. The hydrogenation reaction is carried out on particulate zinc-containing catalysts of relatively low activity with no further addition of lower alcohols as diluents.
The readily volatile fatty acid methyl esters of unsaturated fatty acids are normally obtained from glyceride oils by transesterification with methanol.
Accordingly, the problem addressed by the present invention was to provide a process for the direct hydrogenation of the triglycerides, in which the transesterification step, i.e. the formation of methyl esters from the glyceride oils, would be eliminated.
DESCRIPTION OF THE INVENTION
The present invention relates to a process for the production of unsaturated fatty alcohols containing 6 to 22 carbon atoms, characterized in that deacidified and/or non-deacidified glyceride oils containing monounsaturated and/or polyunsaturated, predominantly linear and/or branched fatty acids containing 6 to 22 carbon atoms in the fatty acid residue are directly hydrogenated with a 30- to 100-fold excess of hydrogen on zinc-chromium catalysts of the spinel type under pressures of 50 to 300 bar and at temperatures of 200 to 350.degree. C. with formation of propane and 1,2-propylene glycol, the olefinic bonds remaining largely intact.
It is only in exceptional cases that commercial catalysts for the hydrogenation of unsaturated fatty acid methyl esters to unsaturated fatty alcohols are also suitable for the hydrogenation of non-deacidified glyceride oils. However, it has surprisingly been found that the zinc-chromium catalysts to be used in accordance with the invention also show excellent activity in the hydrogenation of glyceride oils having acid values of 0 to 10. According to the present invention, the hydrogenation reaction can be controlled through the choice of the reaction temperature and the additions of catalyst in such a way that hardly any glycerol and only a little propane-1,2-diol are formed in the production of the fatty alcohols, propane instead being predominantly formed as a cleavage product.
The catalyst is used in particulate form, i.e. in the form of pellets, extrudate or granules.
One preferred embodiment of the present invention is characterized by the use of glyceride oils obtained from olive oil, rapeseed oils poor and rich in erucic acid, fish oil, beef tallow and/or lard.
The selectivity of the reaction in regard to alcohol formation and also in regard to maintenance of the double bonds and the cis-configuration of the starting oil is very high in the process according to the invention. The selectivity of the catalyst can be increased by suitable additional doping agents and additives.
In one embodiment of the invention, zinc-chromium catalysts doped with aluminium, manganese, cadmium and/or vanadium are used. In one preferred embodiment, zinc-chromium catalysts containing 1 to 8% by weight and preferably 1.5 to 5% by weight of the doping agents mentioned above, based on the weight of the catalyst, are used. The selectivity of the catalyst can be further increased by this measure.
In another preferred embodiment of the invention, zinc-chromium catalysts additionally doped with additions of barium and alkali metals are used. According to the invention, zinc-chromium catalysts containing 0.1 to 3% by weight and preferably 0.5 to 2% by weight of barium and/or alkali metals, more particularly potassium (based on th
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Drach John E.
Evans Joseph E.
Henkel Kommanditgesellschaft auf Aktien
Jaeschke Wayne C.
Szoke Ernest G.
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