Synthesis of carbohydrate-based surfactants

Patent metadata

Field	Value
Publication number	US-9499575-B2
Application number	US-201314041251-A
Country	US
Kind code	B2
Filing date	Sep 30, 2013
Priority date	Nov 16, 2012
Publication date	Nov 22, 2016
Grant date	Nov 22, 2016

Abstract

The present invention provides carbohydrate-based surfactants and methods for producing the same. Methods for producing carbohydrate-based surfactants include using a glycosylation promoter to link a carbohydrate or its derivative to a hydrophobic compound.

First claim

What is claimed is:

1. A method for producing a carbohydrate-based surfactant, said method consisting essentially of contacting a carbohydrate comprising a protecting group with a hydrophobic compound in the presence of a catalytic amount of a glycosylation promoter under conditions sufficient to form a covalent bond between said carbohydrate and said hydrophobic compound to produce a carbohydrate-based surfactant, wherein said hydrophobic compound comprises a functional group selected from the group consisting of an amine group, a hydroxyl group and a thiol group, and wherein the functional group of said hydrophobic compound covalently links said hydrophobic compound to said carbohydrate and wherein said glycosylation promoter is selected from the group consisting of bismuth (III) compound, a scandium (III) compound, an indium (III) compound and a mixture thereof.

2. The method of claim 1 , wherein said glycosylation promoter comprises a bismuth (III) compound.

3. The method of claim 2 , wherein said bismuth (III) compound comprises bismuth trifluoromethanesulfonate, bismuth halide, or a mixture thereof.

4. The method claim 1 , wherein the amount of glycosylation promoter used in the reaction is about 0.25 equivalent or less.

5. The method of claim 1 , wherein said hydrophobic compound is a hydrocarbon compound of the formula R x —X, wherein R x is a hydrocarbon and X is —OH, —NH 2 , or —SH.

6. The method of claim 5 , wherein R x is a C 6 -C 30 hydrocarbon.

7. The method of claim 6 , wherein R x is a C 6 -C 18 hydrocarbon.

8. The method of claim 1 further comprising a step of removing said protecting group to produce said carbohydrate-based surfactant.

9. The method of claim 1 , wherein said protecting group is a hydroxyl protecting group.

10. The method of claim 9 , wherein said hydroxyl protecting group comprises an ester.

11. The method of claim 9 , wherein said hydroxyl protecting group comprises acetate, benzoylate or a combination thereof.

Assignees

• Univ Arizona

Inventors

• Pemberton Jeanne E
• Polt Robin L
• Maier Raina M
• Coss Clifford S

Classifications

• C07H1/00

  Processes for the preparation of sugar derivatives · CPC title

• C07H15/04

  attached to an oxygen atom of the saccharide radical · CPC title

• C07H15/14 Primary

  attached to a sulfur, selenium or tellurium atom of a saccharide radical · CPC title

• C07H15/06 Primary

  being a hydroxyalkyl group esterified by a fatty acid · CPC title

• C07F3/003

  without C-Metal linkages · CPC title