Electrochemical, dehydrogenation, epoxidation, substitution, and halogenation of hydrocarbons and hydrocarbon derivatives

Patent metadata

Field	Value
Publication number	US-11718920-B2
Application number	US-202117545805-A
Country	US
Kind code	B2
Filing date	Dec 8, 2021
Priority date	Dec 8, 2020
Publication date	Aug 8, 2023
Grant date	Aug 8, 2023

Abstract

A method of making alkenes and/or epoxides from alkanes and hydroxy-alkanes, respectively. In a reactor having an anode and a cathode separated by an ion exchange membrane, and containing a solution comprising water, halogen ions, and an alkane and/or a hydroxy-alkane, apply a potential across the anode and the cathode such that a halogenated intermediate is produced at the anode as an anolyte and hydroxyl ions are produced at the cathode as a catholyte; and combining the anolyte and the catholyte to yield an alkene and/or an epoxide.

First claim

What is claimed is:

1. A method of making epoxides, the method comprising:
in a reactor comprising an anode and a cathode separated by an ion exchange membrane, and containing a reactant comprising a hydroxy-alkane; and a solution comprising water and halogen ions, and;
(a) applying a potential across the anode and the cathode such that a halogenated intermediate is produced at the anode as an anolyte and hydroxyl ions are produced at the cathode as a catholyte; and
(b) combining the anolyte and the catholyte to yield an epoxide.

2. The method of claim 1 , wherein the anode, or the cathode, or both the anode and the cathode are polarizable electrodes.

3. The method of claim 1 , wherein the anode and the cathode comprise a material selected from the group consisting of boron-doped diamond (BDD), tetrahedral amorphous carbon, tetrahedral amorphous carbon nitride, and platinum.

4. The method of claim 1 , wherein the ion exchange membrane is an anion exchange membrane.

5. The method of claim 1 , wherein the hydroxy-alkane comprises a hydroxy-C2-C12-alkane.

6. The method of claim 1 , wherein the hydroxy-alkane comprises a hydroxy-C2-C6-alkane.

7. The method of claim 1 , wherein the hydroxy-alkane comprises a 1-hydroxy-C2-C12-alkane.

8. The method of claim 1 , wherein the hydroxy-alkane comprises a 1-hydroxy-C2-C6-alkane.

9. The method of claim 1 , wherein the halogen ions are selected from the group consisting of chloride ions and bromide ions.

10. The method of claim 9 , wherein the halogen ions are chloride ions.

11. The method of claim 9 , wherein the halogen ions are bromide ions.

12. The method of claim 9 , wherein the method occurs within a temperature range of about 20 to about 100° C.

13. The method of claim 9 , wherein the method occurs within a temperature range of about 20 to about 80° C.

14. The method of claim 1 , wherein the potential applied in step (a) is from about 0.8 V to about 4.0 V vs Ag/AgCl.

15. The method of claim 14 , wherein the potential applied in step (a) is from about 1.8 V to about 2.3 V.

16. The method of claim 1 , wherein the reactant comprises from about 0.001 M hydroxy-alkane to about 5.0 M hydroxy-alkane.

17. The method of claim 1 , wherein the solution comprises from about 0.1 M to about 2.0 M halogen ions.

18. A method of making ethylene oxide from ethanol, the method comprising:
in a reactor comprising an anode and a cathode separated by an anion exchange membrane, and containing a solution comprising water, chloride ions, and ethanol;
(a) applying a potential across the anode and the cathode such that 2-chloro-ethanol is produced at the anode as an anolyte and hydroxyl ions are produced at the cathode as a catholyte; and
(b) combining the anolyte and the catholyte to yield ethylene oxide.

19. The method of claim 18 , wherein the anode, or the cathode, or both the anode and the cathode are polarizable electrodes.

20. The method of claim 18 , wherein the anode and the cathode comprise a material selected from the group consisting of boron-doped diamond (BDD), tetrahedral amorphous carbon, tetrahedral amorphous carbon nitride, and platinum.

21. The method of claim 18 , wherein the method occurs within a temperature range of about 20 to about 80° C.

22. The method of claim 18 , wherein the potential applied in step (a) is from about 1.5 V to about 4.0 V vs Ag/AgCl.

23. The method of claim 18 , wherein the potential applied in step (a) is from about 1.8 V to about 2.3 V.

Assignees

• Wisconsin Alumni Res Found

Inventors

• Schreier Marcel
• Lucky Christine E

Classifications

• C25B3/07 Primary

  Oxygen containing compounds · CPC title

• C25B3/03

  Acyclic or carbocyclic hydrocarbons · CPC title

• C25B3/23

  Oxidation (halogenation C25B3/27) · CPC title

• C25B3/25

  Reduction · CPC title

• C25B11/042

  Electrodes formed of a single material · CPC title