Organic compounds -- part of the class 532-570 series – Organic compounds – Fatty compounds having an acid moiety which contains the...
Patent
1992-11-19
1994-11-15
Dees, Jose' G.
Organic compounds -- part of the class 532-570 series
Organic compounds
Fatty compounds having an acid moiety which contains the...
554162, 554163, C11C 306
Patent
active
053649494
DESCRIPTION:
BRIEF SUMMARY
This invention relates to a process for the production of branched fatty acids and esters thereof by reaction of unsaturated fatty acids and esters thereof with aliphatic, non-activated olefins in the presence of layer silicates and active carbon.
Branched fatty acids are distinguished from linear fatty acids by lower pour points, lower volatility, better oxidation stability, higher wetting power and easier compoundability. Accordingly, they are important raw materials for the production of surface-active agents, for example surfactants, lubricants, rolling and drawing oils, textile auxiliaries and cosmetics.
One method of producing branched fatty acids and esters thereof is based on the Guerbet reaction [Soap, Cosm. Chem. Spec., 52, (1987)] which, by dimerization of alcohols, gives beta-branched alcohols which in turn can be reacted by oxidation to form alpha-branched acids. However, this process involved considerable preparative effort.
A well-known process for the production of branched fatty acids is based on the thermal treatment of unsaturated fatty acids, more particularly tall oil fatty acid, with montmorillonite and water or homogeneous ruthenium catalysts [Fette, Seifen, Anstrichm., 72, 667 (1970), J. Am. Oil. Chem. Soc., 56, 782 (1979), Rev. Fr. Corps, Gras 33, 431 (1986)]. However, the reaction mixture obtained in this process essentially contains high molecular weight dimeric, trimeric and tetrameric fatty acids while the percentage content of branched monomeric fatty acids, for example isostearic acid, is comparatively low and can only be removed from the mixture at considerable cost. Accordingly, the dimerization of fatty acids is of only limited value for the economic production of branched fatty acids.
It is known from U.S. Pat. No. 2,361,018 (1944) that drying oils can be activated with activated olefins, for example cyclopentadiene, dicyclopentadiene or indene, to form branched fatty acids which are used in the paint industry. The Dieis-Alder and ene reactions of unsaturated fatty acids and other activated olefins, such as for example acrolein, acrylic acid, crotonaldehyde, crotonic acid, maleic anhydride, maleic acid or methyl vinyl ketone, are reported in Fette, Seifen, Anstrichm., 63, 633 (1961) and in Fat Sci. Techn. 90, 1 (1988). The reaction of butadiene with unsaturated fatty acids is described in J. Chem. Soc. Chem. Comm., 7, 251 (1974). According to the teaching of published Japanese patent application JP 53/34708, erucic acid ester can be reacted with ethylene in the presence of tungsten hexachloride and organoaluminium compounds. However, all the processes mentioned above can only be carried out with considerable outlay on equipment.
Finally, a simple process for the production of branched fatty acid esters thereof is known from Fette, Seifen, Anstrichm., 65, 105 (1963). In this process, unsaturated fatty acids are reacted with short-chain C.sub.2-4 olefins in a diene reaction. However, the process only gives satisfactory yields where ethylene and propylene are used. With increasing chain length both of the unsaturated fatty acids and of the olefin used, the yields obtained are so poor that the process is unsuitable for industrial application.
Accordingly, the problem addressed by the present invention was to provide a process for the production of branched fatty acids and esters thereof which would be free from the disadvantages mentioned above.
The present invention relates to a process for the production of branched fatty acids and esters thereof by reaction of unsaturated fatty acids or esters thereof with aliphatic non-activated olefins in the presence of layer silicates and active carbon.
It has surprisingly been found that the reaction of unsaturated fatty acids with aliphatic non-activated olefins takes place in a short time and gives comparatively high yields. The present invention also includes the observation that the reaction in the presence of layer silicates and active carbon leads to distinctly smaller percentage contents of oligomeric secondary products than mi
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Soap/Cosm./Chem. Spec., 1987, pp. 52-56.
J. Am. Oil Chem. Soc., 56, 1979, pp. 782-785.
Rev. Fr. Corps Gras, 33, pp. 431-435, 1986.
Fette, Seifen, Anstrichm, 63, 1961, pp. 633-635.
Fat. Sci. Techn., 90, 1988, pp. 1-5.
Fette, Seifen, Anstrichm, 65, 1963, pp. 105-108.
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JP 53/34708, Abstract only, Mar. 31, 1978.
Eierdanz Horst
Neuss Michael
Barts Samuel
Dees Jos,e G.
Henkel Kommanditgesellschaft auf Aktien
Jaeschke Wayne C.
Millson Jr. Henry E.
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