IP Library Granted Patent US 11,008,662
Granted Patent B2
US 11,008,662 · App. 15/843,717 · Granted May 18, 2021

Electrochemical and photoelectrochemical reduction of furfurals

Inventors: Kyoung-Shin Choi (Fitchburg, WI); John James Roylance (Madison, WI); Stephen Riley Kubota (Madison, WI)
Assignee: Wisconsin Alumni Research Foundation
C25B3/25C25B1/55C25B11/04Y02P20/133
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Quick Facts
Patent No.
US 11,008,662
App. No.
15/843,717
Granted
May 18, 2021
Kind
B2
Abstract

Electrochemical cells and photoelectrochemical cells for the reduction of furfurals are provided. Also provided are methods of using the cells to carry out the reduction reactions. Using the cells and methods, furfurals can be converted into furan alcohols or linear ketones.

Claims (14)

1. A method for the conversion of furfurals using an electrochemical cell comprising: an anode in an anode electrolyte solution; and a cathode comprising zinc in an acidic cathode electrolyte solution comprising a furfural, the method comprising: creating a potential difference between the anode and the cathode to provide a flow of electrons from the anode to the cathode, wherein the electrons at the cathode undergo reduction reactions at the cathode with chemical species consisting of the furfural and, optionally, water, and further wherein the reduction reactions between the electrons and the furfural form a linear ketone.

2. The method of claim 1 , wherein the furfural is furan-2-carbaldehyde and the linear ketone is 4-oxopentanal.

3. The method of claim 2 , further comprising reducing the 4-oxopentanal to form 5-hydroxy-2-pentanone.

4. The method of claim 1 , wherein the linear ketone is formed with a yield of at least 70%.

5. The method of claim 1 , wherein the linear ketone is formed with a yield of at least 80%.

6. A method for the conversion of furfurals using an electrochemical cell comprising: an anode in an anode electrolyte solution; and a cathode comprising zinc in an acidic cathode electrolyte solution comprising a furfural having a substituted furan ring, the method comprising: creating a potential difference between the anode and the cathode to provide a flow of electrons from the anode to the cathode, wherein the electrons at the cathode undergo reduction reactions with the furfural to form 2,5-hexanedione.

7. The method of claim 6 , further comprising dehydrating the 2,5-hexanedione to form 2,5-dimethylfuran.

8. The method of claim 6 , wherein the furfural is 5-hydroxymethylfurfural or 5-methylfurfural.

9. The method of claim 6 , wherein the furfural is 5-hydroxymethylfurfural.

10. The method of claim 9 , further comprising dehydrating the 2,5-hexanedione to form 2,5-dimethylfuran.

11. The method of claim 6 , wherein the furfural is the 5-methylfurfural.

12. The method of claim 11 , further comprising dehydrating the 2,5-hexanedione to form 2,5-dimethylfuran.

13. The method of claim 6 , wherein the 2,5-hexanedione is formed with a yield of at least 70%.

14. The method of claim 6 , wherein the 2,5-hexanedione is formed with a yield of at least 80%.

Assignments (2)
CONFIRMATORY LICENSE Recorded Aug 2, 2018
From: UNIVERSITY OF WISCONSIN-MADISON
To: UNITED STATES DEPARTMENT OF ENERGY
Reel/Frame 046688/0462 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 20, 2017
From: CHOI, KYOUNG-SHIN; ROYLANCE, JOHN; KUBOTA, STEPHEN
To: WISCONSIN ALUMNI RESEARCH FOUNDATION
Reel/Frame 044443/0739 →
Continuity (2)
Division 14620628 · Feb 12, 2015
Related Publication 20180105940A1 · Apr 19, 2018