Process for the production of oligomeric fatty acids and lower a

Details Process for the production of oligomeric fatty acids and lower a Process for the production of oligomeric fatty acids and lower a

1993-10-04

1995-08-15

Dees, Jose G.

Organic compounds -- part of the class 532-570 series

Organic compounds

Fatty compounds having an acid moiety which contains the...

554 25, 554167, 554159, C09F 706

Patent

active

054420814

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/EP92/006761 filed Mar. 20, 1992.


BACKGROUND OF THE INVENTION

1. Field of the Invention
This invention relates to a process for the production of oligomeric fatty acids and lower alkyl esters thereof by oligomerization of fatty acids or lower alkyl esters thereof in the presence of Lewis acids.
2. Statement of Related Art
Oligomeric fatty acids and their esters, i.e. technical mixtures of acyclic and cyclic di-, tri- and oligocarboxylic acids or esters, are important products which are used for the production of adhesives, paints, fibers, corrosion inhibitors and lubricants.
Among the oligomeric fatty acids, the dimer fatty acids are particularly important. They are normally obtained by oligomerization of unsaturated fatty acids at temperatures of 180.degree. to 250.degree. C. in the presence of aluminas, for example montmorillonites (Fette, Seifen, Anstrichmittel, 72, 667 (1970)). However, the process is attended by the disadvantage that achieving satisfactory oligomerization yields requires not only comparatively high catalyst concentrations, but also drastic reaction conditions which involve high energy consumption.
It is known from Rev. Fr. Corps. Gras, 33, 431 (1986) that the oligomerization of linoleic acid can also be carried out in the presence of ruthenium or nickel on active carbon supports. Although the process manages with low catalyst concentrations, high yields of oligomers are only obtained at temperatures above 200.degree. C.
Finally, it is reported in Fette, Seifen, Anstrichmittel, S80, 186 (1978) that linoleic acid esters can be quantitatively oligomerized at only 80.degree. C. in the presence of rhodium/olefin complexes and tin(II) chloride. This process has the disadvantage that the production of rhodium/olefin complexes involves significant outlay on equipment. In addition, the use of homogeneous rhodium catalysts is economically unfavorable.


DESCRIPTION OF THE INVENTION

Accordingly, the problem addressed by the present invention was to provide a new process for the oligomerization of fatty acids or fatty acid esters which would not have any of the disadvantages mentioned above.
The present invention relates to a process for the production of oligomeric fatty acids and lower alkyl esters thereof, characterized in that fatty acids containing 16 to 24 carbon atoms and 2, 3, 4 or 5 double bonds or lower alkyl esters thereof are oligomerized with C.sub.1-4 alcohols at elevated temperature in the presence of at least one Lewis acid.
It has surprisingly been found that the oligomerization of unsaturated fatty acids and lower alkyl esters thereof does not require the presence of noble metals or their complexes, but instead takes place with satisfactory oligomer yields and selectivities under comparatively mild conditions, even in the presence of readily obtainable Lewis acids. Accordingly, the process according to the invention represents a clear advance over the prior art both in terms of handling and in terms of profitability.
Suitable starting materials for the oligomerization are fatty acids containing 16 to 24 carbon atoms and 2, 3, 4 or 5 double bonds and lower alkyl esters thereof. Typical examples are linoleic acid, linolenic acid, arachidonic acid or clupanodonic acid and, for example, methyl esters thereof. The corresponding conjuene fatty acids, which are obtained from the fatty acids mentioned by isomerization of the double bonds in the presence of alkali (Rompp's Chemielexikon, 9th Edition, Thieme Verlag, Stuttgart, 1990, page 2322) may also be used in the oligomerization reaction. The term "conjuenes" is jargon for multiple unsaturated organic compounds whose double-bonds remain in conjugation. Examples: diene, triene, polyene. Accordingly those fatty acids combine as conjuene fatty acids, whose double-bonds (e.g. linoleic-, linolenic-, arachidonic-, clupanodonic acid) are conjugated under alkali influence. Linoleic acid, conjuene fatty acid based on linoleic acid and methyl esters thereof are preferably used.
As usual in oleochemistry, the

REFERENCES:
patent: 3341570 (1967-09-01), Barie
patent: 3865855 (1975-02-01), Linn et al.
Rev. Fr. Corps. Gras. 33, 431 (1986).
Fette, Seifen, Anstrichmittel, 80, 186 (1978).
Rompp's Chemielexikon, 9th Ed., Thieme Verlag, Stuttgart, 1990 S.2322.
Fette, Seifen, Anstrichmittel, 72, 667 (1970).

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