Methods and compositions for hydrodeoxygenation of carbohydrates and carbohydrate analogs

Patent metadata

Field	Value
Publication number	US-10882804-B2
Application number	US-201916547974-A
Country	US
Kind code	B2
Filing date	Aug 22, 2019
Priority date	Sep 14, 2018
Publication date	Jan 5, 2021
Grant date	Jan 5, 2021

Abstract

This disclosure provides embodiments directed to compositions, methods, and processes to produce compounds having the structure:

each of R1-R5 is selected from a hydroxyl group and hydrogen; and R1-R5 include at least one hydroxyl group and at least one hydrogen; and n=0-2. In particular, methods of the disclosure can include reacting a precursor, the precursor containing more oxygen (O) atoms than the compound, with a gas containing hydrogen (H 2 ) in the presence of a catalyst.

First claim

The invention claimed is:

1. A method for the production of a compound, the method comprising: reacting a precursor, the precursor comprising a carbohydrate or a carbohydrate derivative containing a greater number of oxygen atoms than the compound, with a gas containing H 2 in the presence of a catalyst, at a pressure less than about 40 bar; the compound comprising:

wherein each of R1-R5 is selected from the group consisting of: a hydroxyl group and hydrogen; and wherein R1-R5 comprise at least one hydroxyl group and at least one hydrogen; and wherein n=0-2, and
wherein the catalyst comprises a support comprising CeO 2 and the support is impregnated with both Re and Pd.

2. The method of claim 1 , wherein the compound is selected from one at least one of:

3. The method of claim 1 , wherein the carbohydrate or carbohydrate derivative is selected from the group consisting of: an aldose, a ketose, a sugar alcohol, and a sugar acid.

4. The method of claim 1 , the precursor comprising:

wherein, each of R10-R14 is selected from the group consisting of: a hydroxyl group, a carbonyl group, and a hydrogen; and wherein, n=0-2.

5. The method of claim 4 , wherein each of R10-R14 is selected from the group consisting of: a hydroxyl group, and a hydrogen.

6. The method of claim 4 , wherein each of R10-R14 is a hydroxyl group.

7. The method of claim 1 , wherein reacting the precursor with a gas occurs at a reaction temperature between about 100° C. to about 240° C.

8. The method of claim 7 , wherein the reaction temperature is between about 120° C. to about 200° C.

9. The method of claim 7 , wherein the reaction temperature is between about 130° C. to about 180° C.

10. The method of claim 7 , wherein the reaction pressure is between about 4 bar and about 25 bar.

11. The method of claim 1 , wherein reacting the precursor with a gas occurs at a catalyst loading between about 1 wt % to about 25 wt %.

12. The method of claim 11 , wherein the catalyst loading is between about 2 wt % and about 6 wt %.

13. The method of claim 1 , wherein the catalyst is impregnated with less than 10 wt % Re and less than 10 wt % Pd.

14. The method of claim 1 , wherein the catalyst is impregnated with less than 5 wt % Re and less than 3 wt % Pd.

15. The method of claim 1 , wherein the gas containing H 2 is greater than 90 vol % H 2 .

16. A process for converting a carbohydrate or carbohydrate derivative to a compound, the process comprising:
adding the carbohydrate or carbohydrate derivative to a reactor containing a catalyst;
reacting the carbohydrate or carbohydrate derivative with a gas containing hydrogen at a reaction pressure and a reaction temperature over a reaction time; and
purifying a portion of the compound from a product stream,
wherein, the reaction pressure is less than 40 bar, the reaction temperature is between about 120° C. to about 200° C., and the reactor is designed for batch reaction, and
wherein the catalyst comprises a support comprising CeO 2 and the support is impregnated with both Re and Pd.

17. The method of claim 16 , wherein the reaction pressure is less than 15 bar and the reaction time is less than 10 hours.

18. The method of claim 16 , wherein the precursor is derived from a lignocellulose containing material.

Assignees

• Univ South Carolina

Inventors

• Macqueen Blake H
• Barrow Elizabeth
• Lauterbach Jochen

Classifications

• B01J2235/15

  X-ray diffraction · CPC title

• B01J2235/00

  Indexing scheme associated with group B01J35/00, related to the analysis techniques used to determine the catalysts form or properties · CPC title

• B01J2523/74

  Rhenium · CPC title

• B01J2523/824

  Palladium · CPC title

• C07C29/60

  by elimination of -OH groups, e.g. by dehydration (C07C29/34 takes precedence) · CPC title