Separation process
US-2024287118-A1 · Aug 29, 2024 · US
US9266918B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-9266918-B2 |
| Application number | US-201414202863-A |
| Country | US |
| Kind code | B2 |
| Filing date | Mar 10, 2014 |
| Priority date | Mar 14, 2013 |
| Publication date | Feb 23, 2016 |
| Grant date | Feb 23, 2016 |
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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.
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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.
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