Organic compounds -- part of the class 532-570 series – Organic compounds – Fatty compounds having an acid moiety which contains the...
Patent
1991-02-28
1994-05-17
Dees, JoseG.
Organic compounds -- part of the class 532-570 series
Organic compounds
Fatty compounds having an acid moiety which contains the...
554 56, 554 68, 554156, 554 61, C07C23102
Patent
active
053129334
DESCRIPTION:
BRIEF SUMMARY
CROSS REFERENCE TO RELATED APPLICATIONS
This application is related to Federal Republic of Germany Application No. P3921342.0, filed Jun. 29, 1989, and International Application No. PCT/EP90/00996, filed Jun. 22, 1990, both of which are incorporated herein by reference.
BACKGROUND OF THE INVENTION
1. Field of the Invention
The invention relates to a method of producing difatty acid diamides of symmetrical composition and/or the corresponding pure fatty acids from fatty acids or fatty acid esters.
2. Technology Review
Difatty acid diamides are compounds with a wide range of technical applications that are used, among other things, as auxiliary materials in plastics processing, as lubricants, or as fluxing agents for solders. Such difatty acid diamides are chiefly made by reacting activated fatty acid mixtures of commercial oils with diamines. The diamides resulting from these kinds of reaction are not uniform compounds in chemical terms. They are rather mixtures of difatty acid diamides as they form according to the various possibilities of combination, depending on the fatty acid composition of the raw materials used. When starting from natural fats and oils, which contain three different kinds of fatty acids, mixtures of six different difatty acid diamides thus result according to the rules of combination, some of which are symmetrical, i.e. are composed of two like fatty acid residues, and others are unsymmetrical. Such difatty acid diamide mixtures of heterogeneous composition can therefore only be used in cases where heterogeneity is not troublesome or is even advantageous. In contrast, pure diolecic acid diamides for example can be used to advantage as lubricating agents for plastics as used, for example, for the sheathing of cables.
Separating fatty acid mixtures usually requires considerable efforts. This is due, among other things, to the structural similarity of the fatty acid molecules to be separated or the reactivity of the frequently preset double bonds. Separation is the more difficult higher purity when purity is required of the end product. Particular problems arise when separating fatty acids of identical chain length which differ only with respect to the number of double bonds. This applies, for example, to the technically very interesting C.sub.18 carboxylic acids, stearic acid, oleic acid, linoleic acid and linolenic acid. Isolating oleic acid from natural fats is thus very toilsome, because absolute separation from other saturated and unsaturated fatty acids is extremely difficult to achieve. Accordingly, the classical method of producing pure oleic acid by low-temperature crystallization of the fatty acids of olive oil or their methyl esters involves much effort and great losses. However, oleic acid is a very good example by which to demonstrate that a higher content of this constituent, e.g., in cosmetic products like sun lotion, improves the quality of these products considerably.
SUMMARY OF THE INVENTION
The present invention provides for a process of producing symmetrically structured difatty acid diamides comprising reacting mixtures of fatty acids or their esters with diamines, possibly in a suitable solvent and with or without the addition of catalysts and antioxidants; and, separating the symmetrical difatty acid diamides from the resulting reaction mixture by techniques based on differential solubility and, if desired, further purifying said diamides by recrystallization. The invention also provides for a process of isolating a fatty acid from a mixture of fatty acids wherein the difatty acid diamides produced in the process of the invention are saponified to yield the corresponding free fatty acids.
DETAILED DESCRIPTION OF THE INVENTION
An object of the present invention was to provide a method by which it is possible to obtain symmetrically structured difatty acid diamides of such great purity that on one hand they are suitable basic materials for producing high-quality materials such as plastics, as described in the simultaneously filed patent application U.S. Se
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Ach Alexander
Best Bernd
Frische Rainer
Gross-Lannert Renate
Schneider Judith
Battelle-Institut e.V.
Carr Deborah D.
Dees Jose'G.
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