Electrochemical and photoelectrochemical oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid and 2,5-diformylfuran

Patent metadata

Field	Value
Publication number	US-11136679-B2
Application number	US-202016844437-A
Country	US
Kind code	B2
Filing date	Apr 9, 2020
Priority date	Jan 8, 2015
Publication date	Oct 5, 2021
Grant date	Oct 5, 2021

Abstract

Photoelectrochemical cells for the oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid and/or 2,5-diformylfuran are provided. Also provided are methods of using the cells to carry out the electrochemical and photoelectrochemical oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid and/or 2,5-diformylfuran.

First claim

What is claimed is:

1. A method for the photoelectrochemical oxidation of 5-hydroxymethylfurfural using a photoelectrochemical cell comprising:
an anode in an anode electrolyte solution comprising 5-hydroxymethylfurfural; and
a cathode in a cathode electrolyte solution;
wherein at least one of the anode and the cathode is a photoelectrode comprising a semiconductor,
the method comprising: exposing the at least one photoelectrode to radiation that is absorbed to produce electron-hole pairs, wherein holes are transported to an interface between the anode electrolyte solution and the anode where they induce the oxidation of the 5-hydroxymethylfurfural to form 2,5-furandicarboxylic acid, 2,5-diformylfuran or both, and electrons are transported to an interface between the cathode electrolyte solution and the cathode where they induce a reduction reaction.

2. The method of claim 1 , wherein the photoelectrochemical cell further comprises a TEMPO mediator immobilized on the anode or dissolved in the anode electrolyte solution, and further wherein oxidation of the 5-hydroxymethylfurfural to form 2,5-furandicarboxylic acid, 2,5-diformylfuran or both is mediated by the TEMPO mediator.

3. The method of claim 2 , wherein the anode electrolyte solution is a single-phase anode electrolyte solution.

4. The method of claim 3 , wherein the anode electrolyte solution serves as an oxygen donor and the TEMPO-mediated oxidation of the 5-hydroxymethylfurfural forms 2,5-furandicarboxylic acid at a yield of at least 90%.

5. The method of claim 3 , wherein the anode electrolyte solution is an aqueous electrolyte solution and the TEMPO-mediated oxidation of the 5-hydroxymethylfurfural forms 2,5-furandicarboxylic acid at a yield of at least 99%.

6. The method of claim 3 , wherein the anode electrolyte solution is an aqueous solution having a pH of less than 12 and the TEMPO-mediated oxidation of the 5-hydroxymethylfurfural forms 2,5-furandicarboxylic acid at a yield of at least 90%.

7. The method of claim 3 , wherein the anode electrolyte solution does not serve as an oxygen donor and the TEMPO-mediated oxidation of the 5-hydroxymethylfurfural forms 2,5-diformylfuran at a yield of at least 94%.

8. The method of claim 1 , wherein the anode is the photoelectrode and the semiconductor comprises n-type BiVO 4 .

Assignees

• Wisconsin Alumni Res Found

Inventors

• Choi Kyoung-Shin
• Cha Hyun Gil

Classifications

• H01G9/2027

  comprising an oxide semiconductor electrode · CPC title

• C25B11/081

  the element being a noble metal · CPC title

• C25B9/00

  Cells or assemblies of cells; Constructional parts of cells; Assemblies of constructional parts, e.g. electrode-diaphragm assemblies; Process-related cell features · CPC title

• C25B9/17

  Cells comprising dimensionally-stable non-movable electrodes; Assemblies of constructional parts thereof · CPC title

• C25B11/043

  Carbon, e.g. diamond or graphene · CPC title