Novel methods of isomerizing carbohydrates

Patent metadata

Field	Value
Publication number	US-2016368941-A1
Application number	US-201515121422-A
Country	US
Kind code	A1
Filing date	Mar 4, 2015
Priority date	Mar 4, 2014
Publication date	Dec 22, 2016
Grant date	—

Abstract

The invention provides a method of isomerizing a sugar into fructose using a calcium salt and an organic base. In certain embodiments, the sugar is glucose and/or mannose.

First claim

What is claimed:

1 . A method of isomerizing a sugar into fructose, wherein the sugar is selected from the group consisting of glucose and mannose, the method comprising contacting an aqueous solution of the sugar with a calcium salt and an organic base to form a system, wherein fructose is formed in the system.

2 . The method of claim 1 , wherein the system is free of organic solvents.

3 . The method of claim 1 , wherein the system comprises one or more water-soluble organic solvents.

4 . The method of claim 1 , wherein the calcium salt comprises one or more anions selected from the group consisting of chloride, bromide, iodide, nitrate, bicarbonate, sulfate bisulfate, phosphate, hydrogen phosphate, dihydrogen phosphate, and aliphatic, cycloaliphatic, aromatic, araliphatic, heterocyclic, carboxylic and sulfonic classes of organic anions.

5 . The method of claim 1 , wherein the organic base is aromatic or aliphatic.

6 . The method of claim 5 , wherein the aliphatic organic base is at least one selected from the group consisting of trimethylamine, triethylamine, tri-n-propylamine, diisopropylethylamine, N-alkyl-pyrrolidine, N-alkyl-morpholine, and N-alkyl-piperidine.

7 . The method of claim 1 , wherein the reaction is run from about 0° C. to about 100° C.

8 . The method of claim 7 , wherein the reaction is run from about 20° C. to about 50° C.

9 . The method of claim 1 , wherein the sugar, calcium salt and organic base are in solution.

10 . The method of claim 1 , wherein at least one selected from the group consisting of the calcium salt and the organic base is not in solution.

11 . The method of claim 10 , wherein at least one selected from the group consisting of the calcium salt and the organic base is a solid.

12 . The method of claim 10 , wherein at least one selected from the group consisting of the calcium salt and the organic base is immobilized on a solid support or permeable membrane.

13 . The method of claim 10 , wherein the calcium salt and the organic base are each independently immobilized on a solid support or permeable membrane.

14 . The method of claim 1 , wherein the reaction is run for a period ranging from about 5 minutes to about 4 weeks.

15 . The method of claim 14 , wherein the reaction is run for a period of about 3 days.

16 . The method of claim 14 , wherein the reaction is run for a period of about 2 weeks.

17 . The method of claim 1 , wherein the reaction is run under a pressure that is higher or lower than atmospheric pressure.

18 . The method of claim 1 , wherein the sugar, calcium salt and organic base are contacted in the presence of microwave irradiation.

19 . The method of claim 1 , wherein the reaction is quenched by a method comprising precipitation, filtration, decantation, crystallization, solvent extraction, resin extraction, resin neutralization or chromatography.

20 . The method of claim 1 , wherein the fructose is isolated from the system using a method comprising precipitation, filtration, decantation, crystallization, solvent extraction, resin extraction or chromatography.

21 . The method of claim 1 , wherein the system comprising fructose is further subjected to a process comprising precipitation, filtration, decantation, crystallization, solvent extraction, resin extraction or chromatography.

Assignees

• Univ Yale

Inventors

• Shrader Alanna Schepartz
• Zwicker Aaron
• Miller Scott

Classifications

• C07H1/00

  Processes for the preparation of sugar derivatives · CPC title

• C07H3/02 Primary

  Monosaccharides · CPC title