Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1994-05-13
1996-01-02
Wityshyn, Michael G.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 41, 536 185, C07H 1504, C07H 1508, C07H 100
Patent
active
054809797
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to a process for the production of alkyl and/or alkenyl oligoglycosides by acetalization of glycoses with fatty alcohols at elevated temperature in the presence of sulfomonocarboxylic acids as acidic catalysts, removal of the water of reaction and subsequent working up.
2. Statement of Related Art
Surface-active alkyl oligoglycosides, more particularly alkyl oligoglucosides, have long been known as valuable raw materials for the production of detergents and cosmetic products. They are normally produced either by direct acetalization of glycose with fatty alcohols ("direct synthesis") or via the intermediate stage of butyl glycosides which are subjected to transacetalization with fatty alcohols ("butanol route"), the water of reaction and any butanol being continuously removed from the reaction equilibrium. Working up of the crude alkyl oligoglycosides comprises neutralization of the products, removal of the excess fatty alcohol and, optionally, bleaching and conversion into paste form. EP 0 319 616 A1 and WO 90/03977 are cited as representative of the extensive prior art available.
The acetalization of glycoses or the transacetalization of glycosides with fatty alcohols always takes place in the presence of acidic catalysts. Typical examples of such catalysts are sulfuric acid [U.S. Pat. No. 3,974,138], alkyl benzenesulfonic acid [U.S. Pat. No. 5,003,057], p-toluenesulfonic acid [EP 0 301 298 A1]or sulfosuccinic acid [EP 0 415 192 ].
However, the use of the above-mentioned catalysts involves technical difficulties. Where sulfuric acid is used, partial carbonization of the glycose can occur; alkyl benzenesulfonic acid shows unsatisfactory catalytic activity; the use of p-toluenesulfonic acid results in incomplete yields and sulfosuccinic acid is not satisfactorily biodegradable.
Accordingly, the problem addressed by the present invention was to provide new catalysts for the acetalization of glycoses and for the transacetalization of glycosides with fatty alcohols which would be free from the disadvantages mentioned above.
DESCRIPTION OF THE INVENTION
The present invention relates to a process for the production of alkyl and/or alkenyl oligoglycosides by acetalization of glycose with fatty alcohols at elevated temperature in the presence of acidic catalysts, removal of the water of reaction and working up of the reaction mixture, characterized in that the reaction is carried out in the presence of sulfomonocarboxylic acids containing 2 to 8 carbon atoms, carboxylic anhydrides thereof and/or mixed cyclic carboxylic/sulfonic anhydrides thereof as acidic catalysts.
It has surprisingly been found that the use of sulfomonocarboxylic acids in the acetalization reaction leads not only to high yields and small quantities of unwanted secondary products, more particularly polyglycose, but also to short reaction times and, hence, to advantageous utilization of existing plant capacity. In addition, the sulfocarboxylic acids may readily be incorporated in fatty alcohols and, hence, are easy to dose. Finally, the catalysts are distinguished by high ecological and toxicologial compatibility.
Sulfomonocarboxylic acids are known substances which may be obtained by the relevant methods of preparative organic chemistry. In one known method, for example, short-chain hydroxycarboxylic acids are sulfated and then reacted with bisulfite. In addition, short-chain aliphatic carboxylic acids or benzoic acid may be initially introduced in inert solvents and sulfonated with sulfuric acid, chlorosulfonic acid or sulfur trioxide [Rec. trav. chim. 43, 297, 420 (1924); 71, 814 (1952)].
Sulfomonocarboxylic acids suitable as catalysts in accordance with the invention contain 2 to 8 and preferably 2 to 4 carbon atoms. Typical examples are sulfoacetic acid, sulfopropionic acid, sulfobutyric acid, sulfovaleric acid, sulfocaproic acid, sulfocaprylic acid, sulfocapric acid or sulfobenzoic acid. The sulfomonocarboxylic acids may also be used in the form of their carbo
REFERENCES:
patent: 3974138 (1976-08-01), Lew
patent: 5003057 (1991-03-01), McCurry et al.
D. S. Kemp et al, "Organic Chemistry" published 1980 by Worth Publishers, Inc. (New York, N.Y.), pp. 285-314.
Chemical Abstracts; vol. 91, No. 19, Nov. 5, 1979, Columbus, Ohio, Abs. No. 157440v Rec. trav.chim. 43, 297, 420 (1924); 71, 814 (1952).
Hill Karlheinz
Schulz Paul
Weuthen Manfred
Drach John E.
Henkel Kommanditgesellschaft auf Aktien
Jaeschke Wayne C.
Ortiz Daniel S.
White Everett
LandOfFree
Process for the production of alkyl and/or alkenyl oligoglycosid does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Process for the production of alkyl and/or alkenyl oligoglycosid, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for the production of alkyl and/or alkenyl oligoglycosid will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-236101