Alkenyl glycosides and their preparation

US9266918B2 · US · B2

Patent metadata
FieldValue
Publication numberUS-9266918-B2
Application numberUS-201414202863-A
CountryUS
Kind codeB2
Filing dateMar 10, 2014
Priority dateMar 14, 2013
Publication dateFeb 23, 2016
Grant dateFeb 23, 2016

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Abstract

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An alkenyl glycoside is prepared by reacting a metathesis-derived unsaturated fatty alcohol containing 10 to 30 carbon atoms with either (1) a reducible monosaccharide or composition hydrolyzable to a reducible monosaccharide, or (2) a hydrocarbyl glycoside produced by reacting an alcohol containing up to 6 carbon atoms with a reducible monosaccharide or composition hydrolyzable to a reducible monosaccharide. Each of these reactions is performed in the presence of an acid catalyst and under conditions sufficient to form the alkenyl glycoside or hydrocarbyl glycoside. The preferred alkenyl glycosides are 9-decen-1-yl glycoside; 9-dodecen-1-yl glycoside; 9-tridecen-1-yl glycoside; 9-pentadecen-1-yl glycoside; 9-octadecen-yl glycoside; or 9-octadecen-1,18-diyl glycoside.

First claim

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We claim: 1. A method for preparing an alkenyl glycoside, comprising reacting an unsaturated fatty alcohol with a reducible monosaccharide or a composition hydrolyzable to a reducible monosaccharide, wherein the reacting is performed in the presence of an acid catalyst and under conditions sufficient to form the alkenyl glycoside or hydrocarbyl glycoside, and wherein the unsaturated fatty alcohol is 9-decen-1-ol, 9-dodecen-1-ol, 9-tridecen-1-ol, 9-pentadecen-1-ol, or 9-octadecen-1,18-diol. 2. The method of claim 1 wherein the reducible monosaccharide is at least one of glucose, mannose, galactose, talose, allose, ribose, or any and the monohydrate forms of any thereof. 3. The method of claim 1 wherein the reducible monosaccharide is glucose. 4. The method of claim 1 wherein the composition hydrolyzable to a reducible monosaccharide comprises at least one of starch, maltose, sucrose, lactose, melibose, raffinose methyl glucosides, butyl glucosides, or anhydro sugars. 5. The method of claim 1 wherein the mole ratio of the metathesis-derived unsaturated fatty alcohol to reducible monosaccharide or composition hydrolyzable to a reducible monosaccharide is in the range of from 3:1 to 10:1. 6. The method of claim 1 wherein the mole ratio of the metathesis-derived unsaturated fatty alcohol to reducible monosaccharide or composition hydrolyzable to a reducible monosaccharide is in the range of from 5:1 to 7:1. 7. The method of claim 1 , wherein the unsaturated fatty alcohol is 9-decen-1-ol. 8. The method of claim 1 , wherein the unsaturated fatty alcohol is 9-dodecen-1-ol. 9. The method of claim 1 , wherein the unsaturated fatty alcohol is 9-tridecen-1-ol. 10. The method of claim 1 , wherein the unsaturated fatty alcohol is 9-pentadecen-1-ol. 11. The method of claim 1 , wherein the unsaturated fatty alcohol is 9-octadecen-1,18-diol.

Assignees

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Classifications

  • C07H15/10Primary

    containing unsaturated carbon-to-carbon bonds · CPC title

  • Processes for the preparation of sugar derivatives · CPC title

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What does patent US9266918B2 cover?
An alkenyl glycoside is prepared by reacting a metathesis-derived unsaturated fatty alcohol containing 10 to 30 carbon atoms with either (1) a reducible monosaccharide or composition hydrolyzable to a reducible monosaccharide, or (2) a hydrocarbyl glycoside produced by reacting an alcohol containing up to 6 carbon atoms with a reducible monosaccharide or composition hydrolyzable to a reducible …
Who is the assignee on this patent?
Elevance Renewable Sciences
What technology area does this patent fall under?
Primary CPC classification C07H15/10. Mapped technology areas include Chemistry & Metallurgy.
When was this patent published?
Publication date Tue Feb 23 2016 00:00:00 GMT+0000 (Coordinated Universal Time) (B2). Legal status and post-grant events are not shown on this page.
What related patents are in patentsdb?
We list 8 related publications on this page (citations in our corpus or others sharing the same primary CPC).