Patent GB-797948-A (GB)
Title: Process for the production of carbinols
IPC: C07C29/00
Filed: 1955-02-18
Abstract: Carbinols with chains of six or more carbon atoms are produced by catalytic hydrogenation of the corresponding fatty acids or their esters, especially the glycerides, or anhydrides, using colloidal copper as catalyst, at elevated temperature and at a pressure of at least 2 atmospheres in the presence of a protective colloid naturally occurring in fatty acids or esters, or a protective colloid comprising a synthetic polymerization and/or condensation resin which is of high molecular weight and soluble in fatty acids, or an ester or anhydride of such an acid.  The colloidal copper is produced by dissolving copper or its compounds, such as oxides, hydroxides, carbonates or organic salts, in the hot fatty acid to be hydrogenated and heating the solution in the presence of hydrogen.  Suitable protective colloids naturally occurring in naturally occurring oils, fats and fatty acids are stearins, phosphatides, albumens and mucins. Suitable polymerization resins are polymers and copolymers of styrenes or of vinyl compounds, for example vinyl esters of high fatty acids or vinyl ethers of acrylic compounds; esters of acrylic acid or methacrylic acid with high fatty alcohols; polymers and copolymers of caprolactam and other amides or of ethylene oxide or ethylene imide; and alkyd resins, phenoplasts and polyurethane resins which are soluble in hot fatty acids or their esters or anhydrides. A particularly suitable polymer is a copolymer of styrene and maleic anhydride.  Suitable starting materials are unpurified fats or oils of vegetable or animal origin, fatty acids obtained from these by hydrolysis, distillate fatty acids or synthetically produced fatty acids.  It is preferred to have present in the reaction mixture a small quantity of iron or manganese.  It is desirable to have present 1-4 per cent by weight of copper based on the material to be hydrogenated and the process is preferably carried out at 200-355 DEG C. and at pressures of 200-700 atm.  In the examples: (a) a first-fraction fatty acid obtained from coconut oil acids is mixed with a distillation residue of coconut alcohols and the mixture is hydrogenated in the presence of copper powder; (b) a technical paraffin oxidation fatty acid containing substantially C7-C9 molecules is treated as in (a); (c) undistilled coconut fatty acid is hydrogenated in the presence of a copper catalyst; (d) tallow oil fatty acid is hydrogenated in the presence of a copper catalyst; (e) a head sperm oil is saponified and hydrogenated in the presence of a copper catalyst; (f) train oil fatty acid is mixed with the distillation residues of coconut alcohols obtained according to the process of the invention and the mixture is hydrogenated in the presence of a copper catalyst; (g) undistilled fatty acids obtained by the saponification of castor oil are hydrogenated in the presence of a copper catalyst; (h) a mixture of crude coconut fatty acid and beef tallow fatty acid is hydrogenated in the presence of a copper catalyst; (j) a fatty acid obtained by the saponification of crude beef tallow is mixed with copper and the diester of the copolymer of styrene and maleic acid anhydride with tallow alcohols and the mixture is hydrogenated; (k) a fatty acid obtained from the refining of palm-kernel oil is mixed with copper and the coconut alcohol diester of a copolymer of styrene and maleic acid and the mixture is hydrogenated; (l) a fatty acid obtained by refining cotton seed oil is mixed with copper and diol obtained from distillation residues and the mixture is hydrogenated; (m) a fatty acid obtained as in (l) is mixed with copper and poly-octadecyl vinyl ether and the mixture is hydrogenated; (n) a fatty acid obtained by the saponification of beef tallow is mixed with copper and polyvinyl palmitate and the mixture is hydrogenated; (o) the process of (n) is repeated using a copolymer of a -methyl styrene and blown linseed oil as stabilizer; (p) the process of (n) is repeated using polycetyl acrylate as stabilizer; (q) crude sperm oil is reacted with sperm oil fatty acid containing copper hydroxide and the mixture is hydrogenated; and (r) pure stearic anhydride is reacted with stearic acid containing copper carbonate; polyvinyl palmitate is added and the mixture is hydrogenated.  In all cases carbinols are obtained as products. Specifications 356,606, 358,869, [both in Group IV], and 396,311, [Group III], are referred to.