Unsaturated fatty compounds with improved low-temperature behavi

Details Unsaturated fatty compounds with improved low-temperature behavi Unsaturated fatty compounds with improved low-temperature behavi

1997-06-10

1999-06-29

Barts, Samuel

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

Organic compounds

Oxygen containing

568840, 568876, C07C 2704

Patent

active

059170972

DESCRIPTION:

BRIEF SUMMARY
FIELD OF THE INVENTION

This invention relates to unsaturated fatty compounds with improved low-temperature behavior which are obtained by splitting selected vegetable oils into fatty acids and glycerol, subjecting the resulting split fatty acids to fractional crystallization and hydrogenating the accumulating fraction of substantially unsaturated fatty acids, optionally after conversion into the methyl esters, with the double bonds intact to form the corresponding fatty alcohols. The invention also extends to derivatives of the unsaturated fatty alcohols, to processes for their production and to their use for the production of surface-active formulations. Finally, the invention relates to the use of selected vegetable oils for the production of unsaturated fatty alcohols.


DISCUSSION OF RELATED ART

Fatty compounds, more 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 cosmetic products. An overview of this subject was published, for example, by U. Ploog et al. in Seifen-Ole-Fette-Wachse 109, 225 (1983).
Unsaturated fatty alcohols cannot be produced on the basis of petrochemical raw materials and processes. Instead, they are produced from more or less unsaturated fatty acids or methyl esters thereof based on renewable raw materials which are hydrogenated with the double bonds intact, for example in the presence of chromium- and/or zinc-containing mixed oxide catalysts Weinheim, 4th Edition, Vol. 11, pages 436 et seq.!.
Basically, unsaturated fatty alcohols can be produced in three ways: removal of the water-containing glycerol, split fatty acids representing mixtures of saturated and unsaturated fatty acids are obtained. Since the co-hydrogenation of these acids is unable to influence the ratio of saturated and unsaturated components, it is only possible in this way to obtain fatty alcohols with a low iodine value below 85 which are less preferred. distillation. In contrast to (1), however, the split fatty acids can be converted by so-called rolling-up into a predominantly saturated fatty acid cut and a predominantly unsaturated fatty acid cut. Hydrogenation of the unsaturated fatty acid cut gives technical oleyl alcohols with an iodine value in the range from about 85 to 100. transesterification in which methyl esters with a comparatively low percentage content of saturated homologs are obtained. In this case, rolling-up is neither possible nor necessary because the hydrogenation directly yields highly unsaturated fatty alcohols (I.V.>100).
The three processes mentioned have long been commercially used for the production of unsaturated fatty alcohols. It is logical to use starting materials already having a high iodine value for the production of unsaturated fatty alcohols.
Examples of suitable starting products for process 1 are fats and oils with an iodine value of 40 to 70, such as for example beef tallow, lard, palm oil or palm stearin. Suitable starting materials for the production of highly unsaturated fatty alcohols by process 3 are, for example, rapeseed oil, olive oil, sunflower oil, linseed oil or peanut oil.
Starting materials such as coconut oil or palm kernel oil, for example, have not hitherto been considered for the production of unsaturated fatty alcohols with iodine values in the range from 90 to 100 because they contain too small a percentage of unsaturated species.
Unfortunately, the unsaturated commercial fatty alcohols obtainable by the processes described above have various disadvantages. Products with an iodine value below 80 are wax-like. Apart from their unfavorable solidification point, they do of course only have some of the advantages associated with the unsaturated structure. Highly unsaturated fatty alcohols (iodine value>100) contain a significant percentage of polyunsaturated homologs and, for this reason, are not stable to autoxidation. Although the products are liquid, they are difficult to incorporate in creamy or paste-like formulations.

REFERENCES:
patent: 3729520 (1973-04-01), Rutzen et al.
patent: 4338221 (1982-07-01), Qualeatti
patent: 5276204 (1994-01-01), Schmid et al.
patent: 5399792 (1995-03-01), Demmering et al.
Seifen-Ole-Fette-Wachse, vol. 109 (1983) pp. 225-230.
Ullmanns Encyklopaedie der technischen Chemie, Verlag Chemie, Weinheim,4th ed., vol. 11, pp. 436, et seq.
Fat Sci. Technol., vol. 89, 1987, p. 297.
Fat Sci. Technol, vol. 89, 1987, p. 237.

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