Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1992-02-09
1996-09-24
Wityshyn, Michael G.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 185, 536120, 536124, C07H 100, C07H 302, C07H 1504
Patent
active
055592198
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to a further development of the production of surface-active alkyl glycosides by the so-called direct synthesis method. In this process, the alkyl glycosides, i.e. acetals of sugars and monofunctional alcohols, are prepared by direct acid-catalyzed reaction of the alcohols with the sugars with elimination of water.
2. Statement of Related Art
More particularly, the present invention relates to a further development of a process of the type mentioned which is described, for example, in International patent application W090/03977 ("A Process for the Direct Production of Alkyl Glycosides"). In this document, the term alkyl glycosides is explained both in its broader form and, more particularly, in the narrower form used for practical purposes; those explanations also apply to the teaching of the present invention. The sugar components, hereinafter referred to as glycoses, comprise aldoses and also ketoses in the broadest sense. Aldoses are preferably used by virtue of their better reactivity. Glucose is particularly suitable by virtue of its ready accessibility and availability in industrial quantities, so that the invention is particularly concerned with the production of surface-active alkyl glucosides. The alkyl radical attached to the glucose by the acetal group is derived from monofunctional, preferably relatively long-chain alcohols, particular significance being attributed to corresponding alkyl radicals containing 8 to 20 carbon atoms. Particularly suitable alkyl radicals are derived from alcohols which have been obtained from natural materials, for example fats and/or oils of natural origin, although the invention is by no means limited to such alcohols. The term alkyl glycosides in this context encompasses compounds of the type mentioned in which the alkyl radicals are attached in acetal form to mononuclear and/or to polynuclear sugar residues.
Alkyl glycosides of the type mentioned, their production and their use, particularly as surface-active compounds, are the subject of numerous prior publications which are described in detail in applicants' above-cited earlier International application W090/03977. This earlier international application also relates to a process for the direct production of alkyl glycosides by acetalization of higher aliphatic primary alcohols with glycoses, particularly glucose, in the presence of an acidic catalyst, rapid removal of the water of reaction, neutralization of the catalyst with a base, removal of the alcohol excess by distillation and conversion of the reaction product into an aqueous paste and bleaching of this paste, the aliphatic alcohol being used in an excess to the glycose and the formation and removal of the water of reaction taking place in vacuo and reaction temperatures above 80.degree. C. being applied. The known process is essentially characterized in that a) mixtures of aliphatic primary alcohol, glycose and acidic catalyst are prepared and reacted at elevated temperature, either (i) part of the alcohol being initially introduced with the catalyst, the mixture being heated and a heated suspension of the glycose in the remaining quantity of alcohol being added continuously or in portions to the alcohol/catalyst mixture and the water of reaction formed being distilled off in vacuo, or (ii) a mixture of the entire alcohol and the glycose being initially introduced, heated and the acidic catalyst being added to the heated mixture, a vacuum subsequently being applied and the mixture being further heated until the reaction begins and the water of reaction being distilled off, b) the mixing ratios are selected so that the molar ratio of glycose to aliphatic alcohol is from 1:2 to 1:10 and preferably from 1:3 to 1:6, c) the reaction mixture is kept at that temperature and under that reduced pressure, preferably while mixing, until the water of reaction has been completely removed, d) the reaction mixture is subsequently cooled to approximately 90.degree. C., after which an organic
REFERENCES:
patent: 5043091 (1991-08-01), Joshi et al.
Eskuchen Rainer
Wollmann Joseph
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Drach John E.
Henkel Kommanditgesellschaft auf Aktien
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Millson Jr. Henry E.
White Everett
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