Electrochemical and photoelectrochemical reduction of furfurals

Patent metadata

Field	Value
Publication number	US-2016237576-A1
Application number	US-201514620628-A
Country	US
Kind code	A1
Filing date	Feb 12, 2015
Priority date	Feb 12, 2015
Publication date	Aug 18, 2016
Grant date	—

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.

First claim

What is claimed is:

1 . A method for the electrochemical reduction of a furfural to a furan alcohol in an electrochemical cell comprising: an anode in an anode electrolyte solution; and a cathode in a cathode electrolyte solution, wherein the cathode electrolyte solution comprises a furfural and the cathode comprises a material that is catalytically active for the reduction of the furfural to the furan alcohol, 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 the furan alcohol at a yield of at least 80%.

2 . The method of claim 1 , wherein the furfural is 5-hydroxymethylfurfural and the furan alcohol is 2,5-bis(hydroxymethyl)furan.

3 . The method of claim 2 , wherein the 2,5-bis(hydroxymethyl)furan is formed at a yield of at least 98%.

4 . The method of claim 3 , wherein the material that is catalytically active for the reduction of the furfural is silver.

5 . The method of claim 3 , wherein the material that is catalytically active for the reduction of the furfural is silver and the silver has a dendritic fractal morphology.

6 . The method of claim 1 , wherein the furfural is 5-methylfurfural and the furan alcohol is 5-methylfurfuryl alcohol.

7 . The method of claim 1 , wherein the furfural is furan-2-carbaldehyde and the furan alcohol is 2-furanmethanol.

8 . The method of claim 1 , wherein the material that is catalytically active for the reduction of the furfural is silver.

9 . The method of claim 8 , wherein the silver has a dendritic fractal morphology.

10 . The method of claim 1 , wherein the material that is catalytically active for the reduction of the furfural is indium.

11 . The method of claim 1 , wherein the cathode electrolyte solution has a pH in the range from about 9 to about 9.5.

12 . A method for the photoelectrochemical reduction of a furfural to a furan alcohol in a photoelectrochemical cell comprising: an anode in an anode electrolyte solution; and a cathode in a cathode electrolyte solution comprising a furfural, 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 electrons are transported to the electrolyte-cathode interface where they undergo reduction reactions with the furfural to form the furan alcohol and holes are transported to the electrolyte-anode interface where they induce an oxidation reaction.

13 . The method of claim 12 , wherein the furan alcohol is formed at a yield of at least 90%.

14 . The method of claim 13 , wherein the furfural is 5-hydroxymethylfurfural and the furan alcohol is 2,5-bis(hydroxymethyl)furan.

15 . The method of claim 13 , wherein the furfural is 5-methylfurfural and the furan alcohol is 5-methylfurfuryl alcohol.

16 . The method of claim 13 , wherein the furfural is furan-2-carbaldehyde and the furan alcohol is 2-furanmethanol.

17 . The method of claim 13 , wherein the cathode comprises silver having a dendritic fractal morphology.

18 . The method of claim 13 , wherein the cathode is a photocathode comprising a p-type semiconductor material partially coated with silver.

19 . 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 with the furfural to form a linear ketone.

20 . The method of claim 19 , wherein the linear ketone is 2,5-hexanedione

21 . The method of claim 19 , further comprising dehydrating the 2,5-hexanedione to form 2,5-dimethylfuran.

22 . The method of claim 19 , wherein the furfural is 5-hydroxymethylfurfural or 5-methylfurfural and the linear ketone is 2,5-hexanedione.

23 . The method of claim 19 , wherein the furfural is furan-2-carbaldehyde and the linear ketone is 4-oxopentanal.

24 . The method of claim 23 , further comprising reducing the 4-oxopentanal to form 5-hydroxy-2-pentanone.

25 . A method for the photoelectrochemical reduction of a furfural to a linear ketone in a photoelectrochemical cell comprising: an anode in an anode electrolyte solution; and a cathode comprising zinc in an acidic cathode electrolyte solution comprising a furfural, 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 electrons are transported to the electrolyte-cathode interface where they undergo reduction reactions with the furfural to form the linear ketone and holes are transported to the electrolyte-anode interface where they induce an oxidation reaction.

Assignees

• Wisconsin Alumni Res Found

Inventors

• Choi Kyoung-Shin
• Roylance John James

Classifications

• C25B11/042

  Electrodes formed of a single material · CPC title

• C25B3/07

  Oxygen containing compounds · CPC title

• C25B3/05

  Heterocyclic compounds · CPC title

• C25B3/25 Primary

  Reduction · CPC title

• C25B3/04 Primary

  Chemistry & Metallurgy · mapped topic