Hydroxyalkylamino glycosides and process of preparation
AssigneeBASF Wyandotte Corporation
InventorWilliam K. Langdon
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Abstract
Glycosides are prepared by reacting a monosaccharide or a compound hydrolyzable to a monosaccharide with 3-chloro-1,2-propanediol in the presence of an acid catalyst producing a 2-hydroxy-3-chloropropyl glycoside. The glycoside is then reacted with a base and an amine having at least one alkyl group that contains 8 to 30 carbon atoms to produce an alkali soluble surfactant.
Claims12
A compound having the formula ##EQU5## wherein M is selected from the group consisting of ##EQU6## wherein R is selected from the group consisting of hydrogen or hydrocarbon ranging from CH.sub.3 -C.sub.18 H.sub.37, R' is selected from the group consisting of hydrocarbon ranging from C.sub.8 H.sub.17 to C.sub.18 H.sub.37, R" is selected from the group consisting of benzyl or hydrocarbon ranging from CH.sub.3 to C.sub.18 H.sub.37, the moieties C.sub.6 H.sub.11 O.sub.5 and C.sub.6 H.sub.10 O.sub.5 represent glycosyl units and m is a number from 0 to 20.
A process for the preparation of 2-hydroxy-3 alkylaminopropyl glycoside which comprises reacting glucose or a polysaccharide that is hydrolyzable to glucose with from about 0.5 mole to about 1.2 mole of 3-chloro-1,2-propanediol per mole of anhydroglucose unit based on said glucose or said polysaccharide in the presence of an acid catalyst, followed by a reaction with a quantity of an alkali metal hydroxide or an alkaline earth metal hydroxide sufficient to react with the hydrochloric acid formed in the reaction and a quantity of amine selected from the group consisting of primary, secondary, tertiary, saturated, unsaturated, alicyclic, arylalkyl and aryl amines containing from about 8 to about 30 carbon atoms equivalent to the amount of 3-chloro-1,2-propanediol.
Dependencies are inferred from the claim text.