Electrochemical breaking of C—C bonds

Patent metadata

Field	Value
Publication number	US-12442090-B2
Application number	US-202217959744-A
Country	US
Kind code	B2
Filing date	Oct 4, 2022
Priority date	Oct 4, 2021
Publication date	Oct 14, 2025
Grant date	Oct 14, 2025

Abstract

Electrochemical systems and methods for cleaving C—C bonds are disclosed. In performing the method, a reactant adsorption electrical potential, a C—C bond breaking electrical potential, and a desorption electrical potential are sequentially applied to an electrode pair contacting a composition initially containing a target chemical reactant, such as a polymer or alkane. As a result of performing the method, one or more desired chemical products, such as smaller alkane-containing molecules, are released from the electrode into the region between the electrode pairs. The method may be performed at ambient temperatures using renewable electricity.

First claim

The invention claimed is:

1. A method for producing one or more desired chemical products from one or more chemical reactants comprising one or more sp 3 -hybridized C—C bonds, the method comprising:
(a) contacting a feedstock comprising an electrolyte and at least one reactant comprising at least one sp 3 -hybridized C—C bond to at least one pair of separated electrodes and applying a reactant adsorption electrical potential to the at least one electrode pair, whereby at least a portion of the at least one reactant is adsorbed to at least one electrode of the at least one electrode pair;
(b) applying a C—C bond breaking electrical potential to the at least one electrode pair, whereby the at least one sp 3 -hybridized C—C bond in the one or more adsorbed reactants is broken, thereby yielding one or more desired chemical products formed from the breaking of the at least one sp 3 -hybridized C—C bond; and
(c) applying a desorption electrical potential to the at least one electrode pair, whereby the one or more desired chemical products are released from the at least one electrode into the region between the at least one electrode pair;
wherein steps (a), (b), and (c) are conducted at a temperature of between about 0° C. and below 100.0° C.;
wherein the at least one reactant comprises a saturated hydrocarbon or a polymer whose backbone comprises carbon atoms; and
wherein the desired chemical products are C 1 -C 10 linear, branched, or cyclic alkanes.

2. The method of claim 1 , wherein steps (a), (b), and (c) are conducted at a temperature of between about 0.0° C. and 50° C.

3. The method of claim 1 , wherein steps (a), (b), and (c) are conducted at a temperature of between about 4° C. and about 30° C.

4. The method of claim 1 , wherein steps (a), (b), and (c) are conducted at a temperature of between about 15° C. and about 30° C.

5. The method of claim 1 , wherein steps (a), (b), and (c) are conducted at a temperature of between about 15° C. and about 30° C., and without an externally applied source of heat other than the applied electrical potentials.

6. The method of claim 1 , wherein steps (a), (b), and (c) are conducted within a flow cell, wherein the feedstock is continuously flowed through the flow cell.

7. The method of claim 1 , wherein the feedstock is in the gas phase.

8. The method of claim 1 , wherein steps (a), (b) and (c) are repeated through multiple cycles.

9. The method of claim 8 , wherein the electrical potentials of steps (a), (b) and (c) are applied to the at least one electrode pair through multiple continuous alternating electrical potential cycles.

10. The method of claim 9 , wherein the alternating electrical potential cycles occur at a rate of 0.001 Hz to 10,000.0 Hz.

11. The method of claim 1 , wherein the reactant adsorption electrical potential applied to the at least one electrode pair is positive of potential zero charge (PZC) of the feedstock and any catalyst included on the at least one electrode pair.

12. The method of claim 11 , wherein the applied reactant adsorption electrical potential applied is between about 0.05 V and about 1.2 V relative to a reversible hydrogen electrode.

13. The method of claim 1 , wherein the at least one electrode pair comprise a conductive carbon support.

14. The method of claim 1 , wherein the at least one electrode pair comprise one or more metals.

15. The method of claim 14 , wherein the one or more metals are selected from the group consisting of Pt, Au, Ag, Cu, Fe, Rh, Ni, Pd, Ir, Co, V, Cr, Sn, Ti, W, and alloys, sulfides, nitrides, oxides, and carbides thereof.

16. The method of claim 15 , wherein the at least one electrode pair comprise a compound alloy selected from the group consisting of CoMo sulfide, NiMo sulfide, Mn oxide/SnO 2 , Co oxide/SnO 2 , MoV mixed metal oxide (MMO), TeNb MMO, and W-doped MoVMn.

17. The method of claim 1 , wherein the at least one reactant comprises the polymer whose backbone comprises carbon atoms, and wherein the polymer is obtained from recycled plastic or waste plastic.

18. The method of claim 1 wherein the at least one reactant is selected from the group consisting of ethane, propane, butane, pentane, octane, an addition polymer, and a condensation polymer.

19. The method of claim 18 , wherein the addition polymer or condensation polymer is selected from the group consisting of low-density polyethylene (LDPE), high-density polyethylene (HDPE), polyvinyl chloride, and polystyrene.

20. The method of claim 1 , wherein the desired chemical products are selected from the group consisting of methane, ethane, propane, and butane.

21. The method of claim 1 , wherein in step (c) the desorption electrical potential is less than 0.2 volts relative to a reversible hydrogen electrode (RHE).

22. The method of claim 1 , wherein in step (c) desorption occurs without generating hydrogen.

23. The method of claim 1 , wherein the electrolyte comprises an acid.

24. The method of claim 1 , wherein the feedstock has a pH of between 0 and 2.

25. A method for producing one or more desired chemical products from one or more chemical reactants comprising one or more sp 3 -hybridized C—C bonds, the method comprising:
(a) contacting a feedstock comprising an electrolyte and at least one reactant comprising at least one sp 3 -hybridized C—C bond to at least one pair of separated electrodes and applying a reactant adsorption electrical potential to the at least one electrode pair, whereby at least a portion of the at least one reactant is adsorbed to at least one electrode of the at least one electrode pair;
(b) applying a C—C bond breaking electrical potential to the at least one electrode pair, whereby the at least one sp 3 -hybridized C—C bond in the one or more adsorbed reactants is broken, thereby yielding one or more desired chemical products formed from the breaking of the at least one sp 3 -hybridized C—C bond; and
(c) applying a desorption electrical potential to the at least one electrode pair, whereby the one or more desired chemical products are released from the at least one electrode into the region between the at least one electrode pair;
wherein steps (a), (b), and (c) are conducted at a temperature of between about 0° C. and below 100.0° C.;
wherein the at least one reactant comprises a saturated hydrocarbon or a polymer whose backbone comprises carbon atoms;
wherein the desired chemical products are C 1 -C 10 linear, branched, or cyclic alkanes; and
wherein steps (a), (b), and (c) are conducted within a flow cell, wherein the feedstock is continuously flowed through the flow cell.

Assignees

• Wisconsin Alumni Res Found

Inventors

• Schreier Marcel
• Lucky Christine
• Bakshi Harshal

Classifications

• C25B11/02 Primary

  characterised by shape or form · CPC title

• C25B11/089

  Alloys · CPC title

• C25B11/065

  Carbon · CPC title

• C25B15/083

  Separating products · CPC title

• C25B9/15

  Flow-through cells · CPC title