Process for the production of partial glyceride sulfates

Details Process for the production of partial glyceride sulfates Process for the production of partial glyceride sulfates

1993-06-02

1994-06-21

Richter, Johann

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

Organic compounds

Sulfate esters

558 20, 558 24, 558 26, 558 31, 558 32, 558 36, 558 39, 558 40, C07C40944

Patent

active

053229576

DESCRIPTION:

BRIEF SUMMARY
This invention relates to a process for the production of partial glyceride sulfates by reaction of mixtures consisting of triglycerides and glycerol 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 (US 2,693, 479) or chlorosulfonic acid (JP 78/77014) to form glycerol sulfate and then transesterified in the presence of a triglyceride to form the monoglyceride sulfate (Lipidos 26, 19 (1966)). In addition, German patent 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, sulfonation with oleum or chlorosulfonic acid gives products of high electrolyte content and, accordingly, is not advantageous.
It is known from Philipp. J. Sci. 311 (1965) that mixtures of triglyerides and glycerol can be transesterified in the presence of alkaline catalysts. In addition, it is proposed in the document in question to sulfate the glycerol fatty acid partial esters obtained with sulfuric acid or oleum.
The sulfation of glycerol with sulfur trioxide and 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.
In addition, processes for the production of partial glyceride sulfates which start out from monoglycerides are known, for example from U.S. Pat. No. 3,634,287 and from EP-A-O 0 267 518. However, partial glycerides, such as monoglycerides for example, are highly refined products, i.e. their production involves considerable time and energy, so that for economic reasons they are of only limited use for the production of partial glyceride sulfates.
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 production of partial glyceride sulfates by sulfonation of mixtures consisting of triglycerides and glycerol, characterized in that gaseous sulfur trioxide, temperature after sulfonation and buffer.
The invention is based on the observation that, by ageing the crude sulfonation products and using buffers in the neutralization step, partial glyceride sulfates are obtained in high yields even when raw materials in a low state of refinement are used.
The triglycerides used as starting materials for the production of the partial glyceride sulfates in accordance with the invention are natural or synthetic full esters of glycerol with aliphatic carboxylic acids containing 6 to 22 carbon atoms and 0, 1, 2 or 3 double bonds. More particularly, the triglycerides 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 are suitable for use in accordance with the invention. It is preferred to use glycerol trilaurate.
As usual in oleochemistry, the fatty acid components of the triglycerides may represent technical mixtures such as are typically encountered in natural fats and oils, for example in coconut oil, palm oil, rapeseed oil, sunflower oil, coriander oil or beef tallow. It is preferred to use hydrogenated or unhydrogenated palm kernel oil or coconut oil.
The triglycerides are used in admixture with glycerol for the sulfonation react

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
Anionic Surfactants, Pt.I, Surfactant Science Series vol. 7, W. M. Linfield (Ed.), Marcel Dekker Inc., New York, 1976, p. 219.
Lipidos 26, 19 (1966).
J. Falbe (ed.), "Surfactants in Consumer Products", Springer Verlag, Berlin-Heidelberg, 1987, p. 61.
Philipp, J. Sci.: "Sulfated Monoglyceride Detergents for the Philippines", 311 (1965).

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