Catalytic production of 1,2,5,6-hexanetetrol from levoglucosenone

Patent metadata

Field	Value
Publication number	US-11247956-B2
Application number	US-201917049241-A
Country	US
Kind code	B2
Filing date	Apr 19, 2019
Priority date	Apr 20, 2018
Publication date	Feb 15, 2022
Grant date	Feb 15, 2022

Abstract

A method of making of 1,2,5,6-hexanetetrol (“tetrol”). The method includes the steps of contacting a reaction solution containing water as well as levoglucosenone, dihydrolevoglucosenone, and/or levoglucosanol, with a catalyst containing metal and acid functionalities, at temperature of from about 100° C. to about 175° C., and a hydrogen partial pressure of from about 1 bar to about 50 bar (about 0.1 MPa to about 5 MPa), and for a time wherein at least a portion of the reactant is converted into 1,2,5,6-hexanetetrol.

First claim

What is claimed is:

1. A method of making of 1,2,5,6-hexanetetrol, the method comprising:
contacting a solution comprising levoglucosenone, dihydrolevoglucosenone, or levoglucosanol, or mixtures thereof and water, with a catalyst containing metal sites and acid sites, at temperature of from about 100° C. to about 175° C., and a hydrogen partial pressure of from about 1 bar to about 50 bar (about 0.1 MPa to about 5 MPa), and for a time wherein at least a portion of the levoglucosenone, dihydrolevoglucosenone, or levoglucosanol, or mixtures thereof is converted into 1,2,5,6-hexanetetrol.

2. The method of claim 1 , wherein the catalyst comprises a metal selected from the group consisting of Ru, Rh, Pd, Os, Jr, Pt, Au, Ag, Cu, Co, Fe, and Ni.

3. The method of claim 1 , wherein the catalyst comprises a noble metal selected from the group consisting of Ru, Rh, Pd, and Pt.

4. The method of claim 1 , wherein the catalyst comprises a noble metal that is platinum.

5. The method of any one of claims 1 to 4 , wherein the pressure is from about 20 to about 45 bar.

6. The method of claim 5 , wherein the pressure is from about 30 to about 40 bar.

7. The method of claim 1 , wherein the acid catalyst comprises a mineral acid selected from the group consisting of sulfuric acid, hydrochloric acid, nitric acid, and phosphoric acid, and solid acidic supports selected from the group consisting of alumina, zirconia, titania, hafnia, silica, zirconia-phosphate, titania-phosphate, zirconia-tungsten, titania-tungsten, zeolites, and mixtures of these.

8. The method of claim 1 , wherein the catalyst comprises aluminum and silicon.

9. The method of claim 1 , wherein the catalyst comprises platinum deposited on a support.

10. The method of claim 1 , wherein the solution comprises levoglucosanol having a threo-to-erythro ratio of about 1.

11. The method of claim 1 , wherein the solution comprises levoglucosanol having a threo-to-erythro ratio of less than 1.

12. The method of claim 1 , wherein the solution comprises levoglucosanol having a threo-to-erythro ratio of greater than 1.

13. The method of claim 1 , wherein the method is conducted batch-wise or continuously.

Assignees

• Wisconsin Alumni Res Found

Inventors

• Krishna Siddarth H
• Huber George W
• Dumesic James A

Classifications

• B01J23/464

  Rhodium · CPC title

• B01J23/462

  Ruthenium · CPC title

• C07C29/132

  by reduction of an oxygen containing functional group · CPC title

• C07C29/172

  with the obtention of a fully saturated alcohol · CPC title

• B01J23/44

  Palladium · CPC title