Process for the production of alkyl glycosides

Details Process for the production of alkyl glycosides Process for the production of alkyl glycosides

1992-02-24

1997-12-16

Kight, John

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

Organic compounds

Carbohydrates or derivatives

536 185, 536120, 502168, C07G 300, C07H 1504, B01J 3100

Patent

active

056986840

DESCRIPTION:

BRIEF SUMMARY
This invention relates to a new improved process for the production of C.sub.1-30 alkyl glycosides using an acid as catalyst.
Processes for the production of alkyl glycosides using a catalyst have been known for more than 50 years. Thus, Austrian patent 135 333 describes the production of lauryl glucoside and cetyl glucoside from acetobromoglucose and the appropriate fatty alcohol in the presence of a base. The direct synthesis from glucose and lauryl alcohol using hydrogen chloride as acidic catalyst is also described therein.
U.S. Pat. No. 3,547,828 describes a process from the production of surface-active alkyl glycosides, in which a saccharide is initially reacted with a lower alcohol, such as butanol, in the presence of an acidic catalyst to form a lower alkyl glycoside which then reacts with a higher alcohol to form the higher surface-active alkyl glycoside (transacetalization). Suitable acidic catalysts are mineral acids, such as sulfuric acid, hydrochloric acid and nitric acid, p-toluenesulfonic acid and methanesulfonic acid.
According to the reaching of U.S. Pat. No. 3,598,865, C.sub.8-25 alkyl glycosides are prepared by the acid-catalyzed reaction of monosaccharide or oligo- or polysaccharide hydrolyzable to monosaccharide with a C.sub.8-25 alcohol in the presence of a lower alcohol. The acidic catalyst is sulfuric acid, hydrochloric acid, phosphoric acid, phosphorous acid, toluenesulfonic acid or boron trifluoride.
U.S. Pat. No. 3,839,318 describes a process for the production of alkyl glycosides by direct acid-catalyzed reaction of a higher alcohol with a saccharide. Mineral acids, such as sulfuric acid and hydrochloric acid, and sulfoacid ion exchanger resins are mentioned as suitable catalysts.
According to European patent application 132 043, the acid form of an anionic surfactant, such as alkyl hydrogen sulfate, alkyl sulfonic acid and alkyl benzenesulfonic acid, is used as acidic catalyst in the production of alkyl glycosides obtained by reaction of a glycose unit with an alcohol (direct synthesis).
The problem addressed by the present invention is to extend the catalytst potential to the production of alkyl glycosides.
The present invention relates to a process for the production of alkyl glycosides corresponding to the general formula RO(G).sub.n, where G is a glycose unit, n is a number of 1 to 10 and R is an aliphatic C.sub.1-30 radical, using sulfosuccinic acid as catalyst.
The alkyl glycosides obtainable in accordance with the invention using sulfosuccinic acid as catalyst may be represented by the general formula RO(G).sub.n. In this formula, the aliphatic radical R is derived from a C.sub.1-30 alcohol. The higher aliphatic alcohols are preferably obtained by reduction of natural fats, so that in the context of the present disclosure the term alkyl in alkyl glycoside encompasses saturated and ethylenically unsaturated radicals and mixtures thereof, including those of different chain length in admixture with one another. Preferred aliphatic radicals are alkyl radicals of linear and primary C.sub.8-22 and, more particularly, C.sub.12-18 alcohols. Sulfosuccinic acid is also suitable for the production of alkyl glycosides of which the alkyl radical is derived form synthetic primary alcohols, more particularly from so-called oxoalcohols which are obtained by oxosynthesis or hydroformylation and which have a certain percentage content, generally 20 to 40%, of branched isomers with a 2-methyl radical. Typical alkyl glycosides which may be produced by the process according to the invention are those in which alkyl consists of octyl, nonyl, decyl, undecyl, dodecyl, 2-methyl undecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl and mixtures thereof.
The glycose unit G emanates from the usual aldoses or ketoses, such as for example glucose, fructose, mannose, glactose, arabinose and ribose, or from oligo- and poly-saccharides which may be degraded to monosaccharides by hydrolysis. Among the monosaccharides, the aldoses and, more particularly, glucose are preferably used b

REFERENCES:
patent: 3598865 (1971-08-01), Lew
patent: 4713447 (1987-12-01), Letton
patent: 5003057 (1991-03-01), McCurry et al.
Chemical Abstracts, vol. 91, No. 19, issued 5 Nov. 1979, Hagiwara et al, "Alkylphenols" see p. 612, column 1, Abstract No. 157440v, Jpn. Kokai Tokkyo Koho 79/84,537 (cl. C07C 39/06), 5 Jul. 1979, Appl. 77/152,243, 16 Dec. 1977.

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