Process for the continuous production of partial glyceride sulfa

Details Process for the continuous production of partial glyceride sulfa Process for the continuous production of partial glyceride sulfa

1993-08-03

1994-05-17

Dees, Jose G.

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

Organic compounds

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

252353, C11D 128

Patent

active

053129326

DESCRIPTION:

BRIEF SUMMARY
This invention relates to a process for the continuous production of partial glyceride sulfates by reaction of partial glycerides with gaseous sulfur trioxide and subsequent neutralization of the reaction products with aqueous bases.
Sulfated partial glycerides, particularly monoglyceride sulfates are anionic surfactants which are distinguished by high foaming power, good cleaning performance and excellent dermatological compatibility (Anionic Surfactants, Pt. I, Surfactant Science Series, Vol. 7, W. M. Linfield (Ed.), Marcel Dekker Inc., New York 1976, page 219).
Monoglyceride sulfates are normally produced from glycerol which is first reacted with oleum (U.S. Pat. No. 2,693,479) or chlorosulfonic acid (JP 78/77014) to form the glycerol sulfate which is then transesterified in the presence of a triglyceride to form the monoglyceride sulfate (Lipidos 26, 19 (1966)). In addition, German application DE-A-38 21 446 discloses a process for the production of monoglyceride sulfates by reaction of glycerol with chlorosulfonic acid in an organic solvent, in which fatty acids or fatty acid esters are used for the transesterification. However, the sulfonation with oleum or chlorosulfonic acid leads to products of high electrolyte content and is therefore not advantageous.
It is known from Philipp. J. Sci. 311 (1965) that mixtures of triglycerides and glycerol can be transesterified in the presence of alkaline catalysts. It is also proposed in this document that the glycerol fatty acid partial esters obtained be sulfated with sulfuric acid or oleum.
The sulfation of glycerol with sulfur trioxide and the subsequent transesterification of the glycerol sulfate formed with triglycerides is known from U.S. Pat. No. 2,979,521. However, products having unsatisfactory degrees of sulfonation are obtained in this way.
The direct reaction of monoglycerides with sulfur trioxide in liquid su)fur dioxide (U.S. Pat. No. 3,634,287) or with oleum as the sulfonating agent (JP 50/70322) is also known. In addition, European patent application EP-A-0 267 518 discloses the reaction of partial glycerides with sulfur trioxide in nitrogen-containing solvents. The use of solvents is also a disadvantage for the industrial production of such partial glyceride sulfates because they cannot be left in the product, but instead have to be removed after the reaction in a very energy-and time-consuming step.
Accordingly, the problem addressed by the present invention was to provide a process for the production of partial glyceride sulfates which would be free from the disadvantages mentioned above.
The present invention relates to a process for the continuous production of partial glyceride sulfates, characterized in that technical partial glycerides are continuously reacted with gaseous sulfur trioxide, the acidic sulfonation products are subjected to ageing and are then neutralized with aqueous bases in the presence of a buffer.
The invention is based on the observation that partial glyceride sulfates having particularly high degrees of sulfonation are obtained by ageing the crude sulfonation products and using a buffer in the neutralization step.
Partial glycerides are known chemical substances which may be obtained by the relevant methods of organic preparative chemistry, for example by transesterification of triglycerides With glycerol. Monofatty acid and difatty acid glycerol esters and technical mixtures thereof based on aliphatic carboxylic acids containing 6 to 22 carbon atoms and 0, 1, 2 or 3 double bonds are suitable for the production of the partial glyceride sulfates. More specifically, the monoglycerides and diglycerides of caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, elaidic acid, petroselic acid, linoleic acid, linolenic acid, arachic acid, gadoleic acid, behenic acid or erucic acid may be used. It is preferred to use lauric acid monoglyceride and/or diglyceride.
As usual in oleochemistry, the fatty acid components of the partial glycerides may also be

REFERENCES:
patent: 2285773 (1942-06-01), Harris
patent: 2693479 (1954-11-01), Ross
patent: 2979521 (1961-04-01), Gray
patent: 3634287 (1972-01-01), Woo

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