Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1996-05-09
1997-09-30
Ivy, C. Warren
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
C07C 2980, C07C 31125
Patent
active
056727810
DESCRIPTION:
BRIEF SUMMARY
This application is a 35 U.S.C. 371 National Stage filing of PCT/EP94/03348 published as WO95/11210 on Apr. 27, 1995.
BACKGROUND OF THE INVENTION
This invention relates to a process fort the production of fatty alcohols based on vegetable fats and oils with an iodine value in the range from 20 to 110, to fatty alcohols based on vegetable fats and oils with an iodine value of 20 to less than 95 and to the use of these products for the production surface-active formulations.
STATEMENT OF RELATED ART
Fatty compounds, particularly unsaturated fatty alcohols, are important intermediates for a large number of products of the chemical industry, for example for the production of surfactants and skin-care products. An overview of these intermediate products is provided, for example, by U. Ploog et al. in Seifen-ole-Fette-Wachse 109, 225 (1983). They are produced from more or less unsaturated fatty acid methyl esters which may be hydrogenated, for example, in the presence of chromium- or zinc-containing Chemie, Weinheim, 4th Edition, Vol. 11, pages 436 et seq.!.
The prior art in this field is an industrial process using animal fats and oils which has also been carried out by applicants and in which the unsaturated fatty alcohols accumulating after hydrogenation are distilled at a bottom temperature of, for example, 220.degree. to 250.degree. C. and under a reduced pressure of 1 to 20 mbar, as measured at the head of the column. Since the production of unsaturated fatty alcohols involves high costs, the distillation conditions were designed to minimize the loss of raw materials. In fact, a yield of around 90% of the theoretical (and hence a loss of 10%) was achieved in this way. Unfortunately, the products had a distinct odor. Another disadvantage was that the fatty alcohols of the prior art show unsatisfactory storage and low-temperature behavior.
Unsaturated fatty alcohols with iodine values of 20 to 95 are particularly preferred for applicational reasons because they have a particularly favorable solidification point for use in cosmetic products. Hitherto, unsaturated fatty alcohols with iodine values in the range mentioned have always been based on animal fats. The desired iodine value range is established by blending various products with different iodine value ranges. The iodine value range cannot be established by distillation-based processes because the iodine value or rather the iodine value range of fatty alcohols or fatty acids based on animal fats remains substantially constant during fractionation.
However, animal fats have the disadvantage that they are extremely heterogeneous. For example, animal fats contain nitrogen-containing compounds, such as amides or steroids, such as cholesterol for example, which are directly or indirectly responsible for the unpleasant odor of the products mentioned above. The nitrogen-containing compounds can enter into secondary reactions which adversely affects product stability, particularly oxidation stability, and leads to discolored products.
There is an urgent need in the cosmetic market in particular for purer raw materials of higher quality--a requirement which normally can only be satisfied by increasingly more expensive technical processes and additional purification steps. In the case of unsaturated fatty alcohols, there is a need above all for products with improved color and odor quality and more favorable low-temperature behavior. Added to this is the fact that, in recent years, consumer behavior has changed to the extent that consumers now attribute considerable importance to purely vegetable products.
Known vegetable fatty alcohols have iodine values below 20 or very high iodine values above 100. Fatty alcohols with iodine values in the applicationally preferred range of 20 to 95 mentioned above are not known. The blending of fatty alcohols with very different iodine values does not lead to satisfactory products.
The problem addressed by the present invention was to provide fatty alcohols based on vegetable fats and oils which would have iodine values
REFERENCES:
patent: 2004131 (1935-06-01), Reid
patent: 5043485 (1991-08-01), Fleckenstein et al.
patent: 5138106 (1992-08-01), Wilmott et al.
Seifen-Ole-Fette-Wasche 109, 225 (1983).
Ullmann's Enzyclopaedie der technischen Chemie, Verlag Chemie, Weinheim, 4th Edition, vol. 11, p. 436 et seq. (1976).
Rompp Chemie Lexikon, Thieme Verlag, Stuttgart, 9th Edition, vol. 3, p. 2305 (1990).
Katt, et al, "Indian Journal of Technology" (1967), vol. 5, No. 5, pp. 155-157, Reprint.
Demmering Guenther
Koehler Michael
Komp Horst-Dieter
Kubersky Hans-Peter
Schmid Karl-Heinz
Drach John E.
Henkel Kommanditgesellschaft auf Aktien
Ivy C. Warren
Jaeschke Wayne C.
Smith Lyman H.
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