Process for the production of highly sulfated fatty acids and fa

Details Process for the production of highly sulfated fatty acids and fa Process for the production of highly sulfated fatty acids and fa

1991-04-05

1994-04-19

Dees, Jose G.

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

Organic compounds

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

C07C30300

Patent

active

053046641

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to a process for the production of highly sulfated fatty acids, hydroxy fatty acids and/or oxalkylated hydroxy fatty acids.
The reaction of fatty acids and fatty acid esters with sulfuric acid or oleum to manufacture water-soluble products or those which have surface active properties is a wide-spread method in industry. Starting, for example, from castor oil, olive oil, soybean oil, sunflower oil, tallow, or various fish oils, as well as the natural fatty acids bonded therein and obtainable by saponification, and depending on certain reaction conditions so-called "sulfated oils" for many purposes could be manufactured.
A particularly known example of this family is sulfated castor oil which is commercially available until today under the name "Turkey-red oil".
According to a process described in DRP 561 715, it is possible to produce products with an extraordinary resistance to acids and salts by means of short-time sulfatation with large amounts of sulfuric acid under rapid cooling. Analytic tests revealed that these extraordinary wetting agents exhibited an amount of organically bonded sulfur which was substantially higher than could be achieved with other processes.
According to these results efforts were made to achieve a degree of sulfatation which is as high as possible. The degree of sulfatation indicates how much percent of the fatty acids within the examined product are actually sulfated; in this connection, it is arbitrarily assumed that the total amount of organically bonded sulfuric acid (calculated as SO.sub.3) is present in the form of ricinoleic acid monosulfuric acid ester (H. P. Kaufmann, Analyse der Fette und Fettprodukte [Analysis of the fats and fat products], Springer Verlag 1958, page 1495). Due to the properties with respect to application technology a sulfatation degree of at least 50 % was, and still is desirable. The terms "highly sulfated" or "high degree of sulfatation" will be used to this effect in the following.
According to known processes, increasing the sulfatation degree to values of more than 50 % requires the use of solvents, such as trichloroethylene. In this connection, the solvent on the one hand serves as diluent during sulfation, and, on the other hand, as agent to separate off the non-sulfated portions from the reaction product.
DE-OS 36 06 868 describes a possibility to separate the unsulfated portions from the sulfation mixture without having to use a solvent. According to this publication, foreign substances having a demulsifying effect are added during the production of unsaturated fatty-acid-low-alkyl-ester-sulfonates. It is recommended to use additions at 5 to 400 parts by weight of sorbitan- or glycerol fatty acid ester and 5 to 300 parts by weight of a low-molecular alcohol per 100 %-wt. sulfonated ester.
It is accordingly the object of the present invention to provide a process for the production of highly sulfated fatty acids, hydroxy fatty acids and/or oxalkylated hydroxy fatty acids, which on the one hand permits to avoid the use of solvents, the toxicity problems associated therewith, and the expenditure arising with respect to devices and equipment, and which, on the other hand, can do without the addition of foreign substances which may impair the end products' properties with respect to application technology.
This object is achieved by the process according to the present invention, in which--subsequent to the sulfation which is known per se--the reaction mixture comprising the sulfated esters as well as unsulfated starting products is neutralized. Then the neutral ester sulfate is diluted with water, in this connection the brine may optionally be separated off first. After addition of lye whose quantity is equimolar or submolar to the organically bonded sulfuric acid content, the alkaline solution obtained is hydrolyzed at temperatures between 20.degree. C. and 160.degree. C., preferably between 40.degree. and 90.degree. C., whereby a water-insoluble oil layer consisting of unsulfated esters separates out of the aqu

REFERENCES:
patent: 2127641 (1938-08-01), Cremer
patent: 4545939 (1985-10-01), Sekiguchi et al.

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