Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1993-07-29
1994-08-30
Tsang, Cecilia
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
549252, C07D30760
Patent
active
053429656
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
This invention relates to a process for the production of branched fats by addition of maleic anhydride onto unsaturated fatty acids or esters thereof in the presence of rhodium and/or platinum catalysts.
STATEMENT OF RELATED ART
Branched fats are distinguished from linear fats by lower pour points, lower volatility, better oxidation stability, higher wetting power and easier blendability. Accordingly, they are important raw materials for the production of surface-active compositions, such as for example surfactants, lubricants, rolling and drawing oils, cosmetics, textile and paper auxiliaries [DE-A1-28 28 384].
A proven process for the production of branched fats is the addition of maleic anhydride (MA) onto unsaturated fatty acids or esters thereof ("maleicization"). If monounsaturated fats are used, the reaction takes place as a so-called "ene reaction" [Fat Sci. Technol., 90, 1 (1988)]. If, by contrast, fats containing two or more double bonds are used, a Diels-Alder reaction takes place. Both reactions are carried out in the absence of catalysts at temperatures above 200.degree. C. and lack selectivity [Oil and Soap, 18/19, 23 (1942); J. Am. Oil. Chem. Soc., 25, 254 (1948)].
DESCRIPTION OF THE INVENTION
Object of the Invention
The problem addressed by the present invention was to provide a process for the production of branched fats which would be free from the disadvantages mentioned above.
SUMMARY OF THE INVENTION
The present invention relates to a process for the production of branched fats by addition of maleic anhydride onto unsaturated fatty acids or lower alkyl esters thereof, characterized in that maleic anhydride is reacted with fatty acids containing 16 to 24 carbon atoms and 1, 2, 3, 4 or 5 double bonds or esters thereof with alcohols containing 1 to 4 carbon atoms in the presence of at least one rhodium and/or platinum catalyst.
It has surprisingly been found that the maleicization of fatty acids or fatty acid esters in the presence of rhodium salts gives high yields of addition products, even at comparatively low temperatures.
Suitable starting materials for the production of the branched fats are fatty acids containing 16 to 24 carbon atoms and 1, 2, 3, 4 or 5 double bonds and esters thereof with alcohols containing 1 to 4 carbon atoms. Typical examples are palmitoleic acid, oleic acid, elaidic acid, petroselic acid, chaulmoogric acid, ricinoleic acid, linoleic acid, linolenic acid, gadoleic acid, arachidonic, erucic acid or clupanodonic acid and methyl, ethyl, propyl or butyl esters thereof. Oleic acid or oleic acid methyl ester is preferably used.
As usual in oleochemistry, the fatty acids or their esters may also be present in the form of the technical cuts which are formed in the pressure hydrolysis or transesterification of natural fats and oils, such as for example cottonseed oil, peanut oil, rapeseed oil, linseed oil, soybean oil, coriander oil, sunflower oil, chaulmoogra oil, beef tallow or fish oil. Fatty acid fractions predominantly containing unsaturated fatty acids, i.e. more than 50% by weight unsaturated fatty acids in addition to saturated fatty acids, may also be used in the process according to the invention.
The maleic anhydride and the unsaturated fatty acids or their esters may be used in a molar ratio of 1:1 to 4:1 and preferably in a molar ratio of 2:1.
The rhodium catalysts may be homogeneous or heterogeneous, i.e. may be soluble or insoluble in the reaction mixture. In the context of the process according to the invention, homogeneous rhodium catalysts, which are preferably used, are the halides, acetyl acetonates, acetates and formates of rhodium in its oxidation state III. Mixtures of the salts mentioned may also be used. Suitable heterogeneous catalysts are elemental rhodium on inorganic support materials, for example active carbon.
DESCRIPTION OF PREFERRED EMBODIMENTS
Platinum catalysts are understood to be the halides, acetyl acetonates, acetates and formates of platinum in its oxidation states II and IV.
The rhodium an
REFERENCES:
patent: 2569420 (1951-09-01), Kosmin
The Reaction of Nonconjugated Unsaturated Fatty Acid Esters with Maleic Anhydride, W. G. Bickford, P. Krauczunas and D. H. Wheeler, Oil and Soap, 18/19, 23-27 (1942).
Polymerization of Drying Oils. III. Some Observations on Reaction of Maleic Anhydride with Methyl Oleate and Methyl Linoleate, H. M. Teeter, M. J. Geerts, and J. C. Cowan, J. Am. Oil. Chem. Soc., 25, 158 (1948).
Autoxidation of Fats. II. Preparation and Oxidation of Methyl Oleate-Maleic Anhydride Adduct, W. G. Bickford, G. S. Fisher, Lillian Kyame, and C. E. Swift, J. Am. Oil. Chem. Soc., 25, 254 (1948).
Addition of Maleic Anhydride to Esters of Mono-unsaturated Fatty Acids, Krister Holmberg and Jan-Allan Johansson, Acta Chem. Scand., B36, 481 (1982).
Fat Sci. Technol., 90, 1 (1988).
Reaction of Maleic Anhydride with cis-Isolated Unsaturated Fatty Acid Esters, by Prof. Dr. A. E. Rheineck and Dr. T. H. Khoe, Fette, Seifen, Anstrichmtt., 71, 644 (1969).
Behr Arno
Handwerk Hans-Peter
Henkel Kommanditgesellschaft auf Aktien
Jaeschke Wayne C.
Szoke Ernest G.
Tsang Cecilia
Wisdom, Jr. Norvell E.
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