Eletrochemical oxidation of 5-hydroxymethylfurfural using copper-based anodes

Patent metadata

Field	Value
Publication number	US-10669639-B2
Application number	US-201715695619-A
Country	US
Kind code	B2
Filing date	Sep 5, 2017
Priority date	Sep 5, 2017
Publication date	Jun 2, 2020
Grant date	Jun 2, 2020

Abstract

Electrochemical cells for the oxidation of 5-hydroxymethylfurfural are provided. Also provided are methods of using the cells to carry out the oxidation reactions. The electrochemical cells and methods use catalytic copper-based anodes to carry out the electrochemical oxidation reactions.

First claim

What is claimed is:

1. A method for the electrochemical oxidation of 5-hydroxymethylfurfural in an electrochemical cell comprising: an anode in an anode electrolyte solution; and a cathode in a cathode electrolyte solution, wherein the anode comprises copper, the anode electrolyte solution comprises the 5-hydroxymethylfurfural, and the 5-hydroxymethylfurfural makes up at least 50 mol. % of all aromatic compounds in the anode electrolyte solution before the electrochemical oxidation of the 5-hydroxymethylfurfural begins, and further wherein the pH of the anode electrolyte solution is at least 12, such that 5-hydroxymethylfurfural oxidation is favored over water oxidation, the method comprising: applying an anode potential to the anode that is sufficiently high to induce the electrochemical oxidation of the 5-hydroxymethylfurfural.

2. The method of claim 1 , wherein the 5-hydroxymethylfurfural is oxidized to 2,5-furandicarboxylic acid.

3. The method of claim 2 , wherein the 2,5-furandicarboxylic acid is formed at a yield of at least 75%.

4. The method of claim 2 , wherein the 2,5-furandicarboxylic acid is produced with a Faradaic efficiency of at least 75%.

5. The method of claim 2 , wherein the 2,5-furandicarboxylic acid is formed at a yield of at least 85%.

6. The method of claim 2 , wherein the 2,5-furandicarboxylic acid is produced with a Faradaic efficiency of at least 85%.

7. The method of claim 1 , wherein the anode comprises copper oxides, copper hydroxides, or a combination of copper oxides and copper hydroxides.

8. The method of claim 1 , wherein the anode comprises copper metal, and a surface of the copper metal is oxidized to form copper oxides, copper hydroxides, or a combination of copper oxides and copper hydroxides by applying an anode potential to the anode before or during the electrochemical oxidation of the 5-hydroxymethylfurfural.

9. The method of claim 1 , wherein the anode comprises a copper compound, and a surface of the copper compound is oxidized to form copper oxides, copper hydroxides, or a combination of copper oxides and copper hydroxides by applying an anode potential to the anode before or during the electrochemical oxidation of the 5-hydroxymethylfurfural.

10. The method of claim 9 , wherein the copper compound is a copper sulfide, a copper selenide, a copper telluride, a copper phosphide, or a combination of two or more thereof.

11. The method of claim 1 , wherein, in addition to the copper, the anode comprises at least one additional metal element.

12. The method of claim 11 , wherein the at least one additional metal element is nickel, cobalt, tin, silver, indium, or a combination of two or more thereof.

13. The method of claim 1 , wherein the anode comprises at least one non-metal element.

14. The method of claim 13 , wherein the at least one additional non-metal element is oxygen, sulfur, selenium, tellurium, phosphorus, nitrogen, a halogen, or a combination of two or more thereof.

15. The method of claim 1 , wherein the anode electrolyte solution has a pH of no greater than 13.

16. The method of claim 1 , wherein the anode is a copper foil, a copper mesh, a copper foam, or a copper plate.

17. The method of claim 1 , wherein the anode is nanostructured.

18. The method of claim 17 , wherein the anode comprises a nanocrystalline copper having a foam structure.

19. The method of claim 1 , wherein the 5-hydroxymethylfurfural makes up at least 70 mol. % of all aromatic compounds in the anode electrolyte solution before the electrochemical oxidation of the 5-hydroxymethylfurfural begins.

20. The method of claim 1 , wherein the 5-hydroxymethylfurfural is oxidized to 2,5-furandicarboxylic acid, and the 2,5-furandicarboxylic acid is formed at a yield of at least 75%.

21. The method of claim 20 , wherein the 2,5-furandicarboxylic acid is produced with a Faradaic efficiency of at least 75%.

Assignees

• Wisconsin Alumni Res Found

Inventors

• Choi Kyoung-Shin
• Nam Dohwan

Classifications

• C25B9/06

  Chemistry & Metallurgy · mapped topic

• C25B11/0452

  Chemistry & Metallurgy · mapped topic

• C25B11/04 Primary

  characterised by the material · CPC title

• C25B11/0415 Primary

  Chemistry & Metallurgy · mapped topic

• C25B11/0405

  Chemistry & Metallurgy · mapped topic