Process for preparing alkylglucoside compounds from oligo- and/o

Details Process for preparing alkylglucoside compounds from oligo- and/o Process for preparing alkylglucoside compounds from oligo- and/o

1991-05-13

1992-08-11

Griffin, Ronald W.

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

Organic compounds

Carbohydrates or derivatives

536 185, 536120, 536124, C07H 1504, C07H 306, C08B 3000

Patent

active

051380463

DESCRIPTION:

BRIEF SUMMARY
The preparation of reaction products containing surface active alkylglucoside compounds has been described in numerous publications. As is well known, alkylglucosides are acetals obtained from sugars and monofunctional alcohols. The surfactant components are, more particularly, overwhelmingly monoglucoside containing reaction products of monofunctional aliphatic alcohols having 8 to 22, more particularly 12 to 18 carbon atoms and glucose as the monosaccharide. Depending on the method of preparation the corresponding reaction mixtures contain minor amounts of corresponding acetals which contain the residue of the longer-chained monofunctional alcohol bound to oligosaccharide residues. The term alkylglucoside is here intended to refer to the alkylmonoglucosides as well as alkyloligo- or alkylpolyglucosides, as well as corresponding alkenyl compounds, unless the particular structural differences are expressly mentioned.
The surface active alkylglucosides with C.sub.8-22, especially C.sub.12-18, alkyl or alkenyl groups belong to the category of non-ionic surfactants. Their molecular component which can be traced to the longer chained monofunctional alcohols leads back to corresponding alcohols of natural and/or synthetic origin. The saccharide starting material which is of most value in practice consists of the polyanhydroglucose compounds which are abundently available in nature, the individual glucose units of these are present in an alpha-glucosidic linkage. The most important starting material of natural origin of this kind is starch, which is produced worldwide by crop plants of all kinds, such as potatoes, maize, tapioca, rice, wheat and the like. Powdered starches and their partial degradation products, for example in the form of a corresponding, usually highly concentrated glucose syrup, are available as comparatively cheap starting materials.
Within the framework of the numerous attempts to produce alkylglucoside compounds useful for washing or cleansing, the problems of this category of substance have become known to those skilled in the art. It is difficult to obtain alkylmonoglucosides of this kind with the degree of purity required in practice, i.e. with light colours and a high colour constancy in an alkaline medium. The high susceptibility of the polyanhydroglucose starting material to the high temperatures and pressures required during processing under the influence of catalysts has hitherto stood in the way of the discovery of a method in which alkylglucoside-containing reaction products can be prepared, for example from powdered starch, on an industrial scale in a single operation.
The relevant literature on the preparation of the desired alkylglucosides with a detergent action is concerned particularly with two auxiliary elements which are used in varying ways in the course of different kinds of synthesis. First of all, it is proposed that the polyanhydroglucose components should not be used as they are, but that this starting material of natural origin should first be degraded into the monosaccharide, i.e. glucose. The glucose can then be subjected to acetalisation as an anhydrous material or as a glucose hydrate.
The second auxiliary method used in practice makes use of the fact that lower monofunctional alcohols, particularly those with a carbon atom content of up to 6, and particularly C.sub.3-5, lead comparatively easily to the desired acetalisation of the monosaccharide. The acetals of the monosaccharide thus formed, however, have only inadequate surfactant properties. They are converted by re-acetalisation with the longer chained alcohols in the range from C.sub.12-18 into the desired alkylglucoside reaction products having surface active properties. Even this apparently relatively easy method of manufacture involves, in practice, numerous restrictive problems of the kind mentioned above. Hitherto, the recovery of light coloured, colour-fast alkylglucosides, particularly those which are colour-fast in an alkaline medium, has involved such high expenditure that for reasons of cost alon

REFERENCES:
patent: 2390507 (1945-12-01), Cantor
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patent: 4721780 (1988-01-01), McDaniel, Jr. et al.
patent: 4889925 (1989-12-01), Schmid et al.
patent: 4990605 (1991-02-01), Lueders

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