Organic compounds -- part of the class 532-570 series – Organic compounds – Fatty compounds having an acid moiety which contains the...
Patent
1992-07-24
1994-06-28
Dees, Jose G.
Organic compounds -- part of the class 532-570 series
Organic compounds
Fatty compounds having an acid moiety which contains the...
554163, C11C 306
Patent
active
053248473
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to olefinically unsaturated adducts of ethylene with polyunsaturated C.sub.18-22 fatty acids or esters thereof with C.sub.1-36 alkanols in molar ratios of ethylene to the fatty acids or fatty acid esters of 1:1 to 3:1 obtainable by reaction of the fatty acids or fatty acid esters with ethylene at elevated temperature and elevated pressure in the presence of compounds of transition metals from the group consisting of Ru, Rh, Pd, Ir and Pt as catalysts.
2. Statement of Related Art
Fatty acids branched in the alkyl chain of the Guerbet acid type, obtainable by "guerbetization" of the corresponding fatty alcohols and oxidation of the Guerbet alcohols to the corresponding acids, are technologically interesting intermediate products because they, or their alkyl esters, have distinctly reduced pour points comparison with the corresponding unbranched isomers. However, the production of Guerbet acids is technologically complicated and can only be carried out with unsatisfactory yields. Accordingly, there has been no shortage of attempts to produce corresponding fatty acid derivatives branched in the alkyl chain from fatty acids of esters thereof. A typical example of this is the layer-silicate-catalyzed dimerization of fatty acids. Unfortunately, considerable quantities of tirmeric fatty acids and methyl-branched fatty acids, so-called isofatty acids, are also formed in this reaction. Another, albeit complicated, process gives branched fatty acid derivatives from conjuene fatty acids in the trans-trans form with activated dienophiles under the conditions of a Diels-Alder reaction; for example, a branched C.sub.21 dicarboxylic acid can be obtained in this way from linoleic acid and acrylic acid, cf. U.S. Pat. Nos. 3,734,859, and 3,753,968, DE-B 2 253 930. Other branched fatty acid derivatives have been obtained by thermal or acid-catalyzed addition of activated enophiles onto unsaturated fatty acid derivatives. For example, maleic anhydride can be added onto oleic acid in the presence of an acid as catalyst in yields of up to 70%, of. Fat. Sci. Technol., 1, 1 (1988). However, the presence of more than one carboxyl group in the reaction products mentioned above has often proved to be troublesome.
Finally, attempts have also been made to add saturated hydrocarbons onto fatty acids by heat-initiated radical addition of saturated hydrocarbons onto fatty acids. The addition of cyclohexane onto oleic acid methyl ester at 340.degree. C./200 bar gives alkyl-branched fatty acids with 70% selectivity, but in a yield of only 2.8%, of. J.O. Metzget et al., Fat. Sci. Technol. 1 (1989), 18.
DESCRIPTION OF THE INVENTION
The present invention is directed to the provision of olefinically unsaturated adducts of ethylene with polyunsaturated fatty acids of the type mentioned at the beginning which can be readily obtained in high yields. The compounds provided in accordance with the invention are new products which, for example, differ in their chain length alone from the naturally occurring ethyl-branched fatty acids containing a total of 12 to 18 carbon atoms described in A. Smith etal. Biomed. Mass Spectrom., 6 (8), 347-349.
Suitable starting products for the production of the olefinically unsaturated adducts according to the invention are unsaturated fatty acids containing 18 to 22 carbon atoms and more than one olefinic double bond, such as linoleic acid, isomerized linoleic acid containing conjugated double bonds (so-called C.sub.18 :2-conjuene fatty acid), linolenic acid, arachidonic acid, docosadienoic acid, docosahexaenoic and eicosapentaenoic acid, which can be obtained in the form of technical mixtures with other fatty acids from renewable natural raw materials, for example from sunflower oil, tall oil or fish oil. As usual in oleochemistry, these polyunsaturated fatty acids are generally not used in the form of their pure compounds, but rather in the form of technical mixtures for the preparation of the adducts according to the invention. The a
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Behr Arno
Laufenberg Alfred
Barts Samuel
Dees Jos,e G.
Drach John E.
Henkel Kommanditgesellschaft auf Aktien
Jaeschke Wayne C.
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