Use of CO2 for the synthesis of cyclic glycocarbonates and linear polyglycocarbonates by polycondensation from glycans

Patent metadata

Field	Value
Publication number	US-10501576-B2
Application number	US-201615566473-A
Country	US
Kind code	B2
Filing date	Apr 13, 2016
Priority date	Apr 13, 2015
Publication date	Dec 10, 2019
Grant date	Dec 10, 2019

Abstract

Provided herein are methods for synthesizing cyclic carbonates, glycocarbonates, and polyglycocarbonates by reacting polyol glycans with carbon dioxide. Synthesis can include selective polycondensation of polyol glycan hydroxyl moieties.

First claim

What is claimed is:

1. A method for making glycocarbonates, the method comprising reacting a polyol glycan with carbon dioxide, wherein the glycan comprises a closed chain structure and selected from one or more of the group consisting of hexose, a pyranose moiety, a pyranoside, and a furanose moiety, or a derivative thereof selected from the group consisting of α-Methyl 3 and 4 di-O-methyl 2 and 6 dihydroxyls glucopyranoside, α-Methyl 2 and 4 di-O-methyl 3 and 6 dihydroxyls glucopyranoside, D-α-methyl mannopyranoside, and D-α-methyl galactopyranoside.

2. The method of claim 1 , wherein the polyol glycan comprises hexose.

3. The method of claim 1 , wherein the polyol glycan comprises the pyranose moiety or the furanose moiety.

4. The method of claim 1 , wherein the polyol glycan comprises the pyranoside.

5. The method of claim 1 , wherein the polyol glycan comprises a disaccharide moiety, an oligosaccharide moiety or a polysaccharide moiety.

6. The method of claim 1 , wherein the polyol glycan comprises one of the glycan derivatives selected from α-Methyl 3 and 4 di-O-methyl 2 and 6 dihydroxyls glucopyranoside and α-Methyl 2 and 4 di-O-methyl 3 and 6 dihydroxyls glucopyranoside.

7. The method of claim 1 , wherein reaction occurs in the presence of one or more solvents.

8. The method of claim 7 , wherein the solvents are one or more of dibromomethane, dimethylformamide, and an ionic liquid.

9. The method of claim 8 , wherein the ionic liquid comprises 1-Butyl-3-methylimidazolium hexafluorophosphate.

10. The method of claim 1 , further comprising selectively protecting one or more hydroxyl moieties of the polyol glycan before reacting, wherein the polyol glycan comprises at least three hydroxyl moieties.

11. The method of claim 10 , wherein protecting comprises methylating.

12. The method of claim 1 , wherein reacting is conducted in the presence of a catalyst.

13. The method of claim 12 , wherein the catalyst comprises 1,8-diazabicyclo[5.4.0]undec-7-ene.

14. The method of claim 1 , wherein the method is free of phosgene, phosgene derivatives, and isocyanates.

15. The method of claim 1 , wherein reacting is conducted at a pressure between about 1 bar and about 20 bar.

16. The method of claim 1 , wherein reacting is conducted at a temperature of between about 60° F. and 80° F.

17. The method of claim 1 , wherein the glycocarbonates comprise linear polyglycocarbonates.

18. The method of claim 1 , wherein the glycocarbonates comprise cyclic glycocarbonates.

19. The method of claim 1 , wherein the hydroxyl groups forming the carbonate moiety are trans relative to each other.

20. The method of claim 1 , wherein the hydroxyl groups forming the carbonate moiety are cis relative to each other.

Assignees

• Univ King Abdullah Sci & Tech

Inventors

• Gnanou Yves
• Pati Debasis
• Feng Xiaoshuang
• Hadjichristidis Nikolaos

Classifications

• C07H1/00

  Processes for the preparation of sugar derivatives · CPC title

• C08G64/0208

  saturated · CPC title

• C08G64/323 Primary

  and alcohols · CPC title

• C07H13/12

  by acids having the group -X-C(=X)-X-, or halides thereof, in which each X means nitrogen, oxygen, sulfur, selenium or tellurium, e.g. carbonic acid, carbamic acid · CPC title