Electrochemical co-production of products with carbon-based reactant feed to anode

• US 8,845,876 B2
• Filed: 12/21/2012
• Issued: 09/30/2014
• Est. Priority Date: 07/26/2012
• Status: Active Grant

• Current Assignee: Avantium Knowledge Centre B.V. (Avantium NV)
• Original Assignee: Liquid Light, Inc. (Avantium NV)
• Inventors: Teamey, Kyle, Kaczur, Jerry J.
• Primary Examiner(s): Wong, Edna
• Application Number:
  US13/724,647
• Publication Number:
  US 20130105330A1
• Time in Patent Office: 648 Days
• Field of Search: 205/413, 205/431, 205/439, 205/440, 205/446, 205/448, 205/450, 205/455, 205/459, 205/462, 205/555, 205/460, 205/464
• US Class Current: 205/413
• CPC Class Codes: C07C 1/26 starting from organic compounds containing only halogen atoms as hetero-atoms
• CPC Class Codes: C07C 29/149 with hydrogen or hydrogen-containing gases
• CPC Class Codes: C07C 29/58 by elimination of halogen, e.g. by hydrogenolysis, splitting-off C07C29/124 takes precedence
• CPC Class Codes: C07C 51/02 from salts of carboxylic acids
• CPC Class Codes: C07C 51/15 by reaction of organic compounds with carbon dioxide, e.g. Kolbe-Schmitt synthesis
• CPC Class Codes: C07C 51/367 by introduction of functional groups containing oxygen only in singly bound form
• CPC Class Codes: C07C 67/08 by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
• CPC Class Codes: C25B 1/00 Electrolytic production of inorganic compounds or non-metals
• CPC Class Codes: C25B 1/24 Halogens or compounds thereof
• CPC Class Codes: C25B 13/08 based on organic materials
• CPC Class Codes: C25B 15/00 Operating or servicing cells
• CPC Class Codes: C25B 15/08 Supplying or removing reactants or electrolytes; Regeneration of electrolytes
• CPC Class Codes: C25B 3/00 Electrolytic production of organic compounds
• CPC Class Codes: C25B 3/23 Oxidation halogenation C25B3/27
• CPC Class Codes: C25B 3/25 Reduction
• CPC Class Codes: C25B 3/27 Halogenation
• CPC Class Codes: C25B 3/29 Coupling reactions
• CPC Class Codes: C25B 9/19 with diaphragms
• CPC Class Codes: C25B 9/23 comprising ion-exchange membranes in or on which electrode material is embedded
• CPC Class Codes: Y02P 20/10 Process efficiency
• CPC Class Codes: Y02P 20/129 : Energy recovery, e.g. by cogeneration, H2recovery or pressure recovery turbines
• CPC Class Codes: Y02P 20/133 : Renewable energy sources, e.g. sunlight
• CPC Class Codes: Y02P 20/582 : Recycling of unreacted starting or intermediate materials

Abstract

The present disclosure is a system and method for producing a first product from a first region of an electrochemical cell having a cathode and a second product from a second region of the electrochemical cell having an anode. The method may include a step of contacting the first region with a catholyte comprising carbon dioxide. The method may include another step of contacting the second region with an anolyte comprising a recycled reactant and at least one of an alkane, haloalkane, alkene, haloalkene, aromatic compound, haloaromatic compound, heteroaromatic compound or halo-heteroaromatic compound. Further, the method may include a step of applying an electrical potential between the anode and the cathode sufficient to produce a first product recoverable from the first region and a second product recoverable from the second region.

Claims

1. A method for producing a first product from a first region of an electrochemical cell having a cathode and a second product from a second region of the electrochemical cell having an anode, the method comprising the steps of:

contacting the first region with a catholyte comprising carbon dioxide;

contacting the second region with an anolyte comprising a recycled reactant and at least one of an alkane, haloalkane, alkene, haloalkene, aromatic compound, haloaromatic compound, heteroaromatic compound or halo-heteroaromatic compound, the recycled reactant includes a halide salt; and

applying an electrical potential between the anode and the cathode sufficient to produce the first product recoverable from the first region and the second product recoverable from the second region.

2. The method according to claim 1, wherein the halide salt is AX where A is selected from the group consisting of Li, Na, K and Cs and X is selected from the group consisting of F, Cl, Br and I.

3. The method according to claim 1, wherein the second product includes a halogenated compound.

4. The method according to claim 3, further comprising:

removing the halogenated compound from the second region; and

converting the halogenated compound to a different compound.

5. The method according to claim 1, wherein the catholyte further comprises a solvent selected from the group consisting of propylene carbonate, water, methanol, ethanol, acetonitrile, dimethylformamide, dimethylsulfoxide, and pyrrolidinone.

6. The method according to claim 1, wherein the catholyte and the anolyte are separated by an ion permeable barrier that operates at a temperature less than 600 degrees C.

7. The method according to claim 6, wherein the ion permeable barrier includes one of a polymeric or inorganic ceramic-based ion permeable barrier.

8. The method according to claim 1, wherein the catholyte is liquid phase and the anolyte is gas phase.

9. A method for producing a first product from a first region of an electrochemical cell having a cathode and a second product from a second region of the electrochemical cell having an anode, the method comprising the steps of:

contacting the first region with a catholyte comprising carbon dioxide;

contacting the second region with an anolyte comprising a recycled reactant and at least one of an alkane, haloalkane, alkene, haloalkene, aromatic compound, haloaromatic compound, heteroaromatic compound or halo-heteroaromatic compound, the recycled reactant includes a halide salt;

applying an electrical potential between the anode and the cathode sufficient to produce the first product recoverable from the first region and the second product recoverable from the second region, wherein the second product includes a halogenated compound;

removing the halogenated compound from the second region; and

converting the halogenated compound to a different compound.

10. The method according to claim 9, wherein the catholyte further comprises a solvent selected from the group consisting of propylene carbonate, water, methanol, ethanol, acetonitrile, dimethylformamide, dimethylsulfoxide, and pyrrolidinone.

11. The method according to claim 9, wherein the catholyte and the anolyte are separated by an ion permeable barrier that operates at a temperature less than 600 degrees C.

12. The method according to claim 11, wherein the ion permeable barrier includes one of a polymeric or inorganic ceramic-based ion permeable barrier.

13. The method according to claim 9, wherein the catholyte is liquid phase and the anolyte is gas phase.

14. The method according to claim 9, wherein the halide salt is AX where A is selected from the group consisting of Li, Na, K and Cs and X is selected from the group consisting of F, Cl, Br and I.

15. A method for producing a first product from a first region of an electrochemical cell having a cathode and a second product from a second region of the electrochemical cell having an anode, the method comprising the steps of:

contacting the first region with a catholyte comprising carbon dioxide;

contacting the second region with an anolyte comprising a recycled reactant and at least one of an alkane, haloalkane, alkene, haloalkene, aromatic compound, haloaromatic compound, heteroaromatic compound or halo-heteroaromatic compound; and

applying an electrical potential between the anode and the cathode sufficient to produce the first product recoverable from the first region and the second product recoverable from the second region, wherein the catholyte is liquid phase and the anolyte is gas phase.

16. The method of claim 15, wherein the recycled reactant includes a halide salt.

17. The method according to claim 16, wherein the halide salt is AX where A is selected from a group consisting of Li, Na, K and Cs and X is selected from the group consisting of F, Cl, Br and I.

18. The method according to claim 16, wherein the second product includes a halogenated compound.

19. The method according to claim 18, further comprising:

removing the halogenated compound from the second region; and

converting the halogenated compound to a different compound.

20. The method according to claim 15, wherein the catholyte further comprises a solvent selected from the group consisting of propylene carbonate, water, methanol, ethanol, acetonitrile, dimethylformamide, dimethylsulfoxide, and pyrrolidinone.

21. The method according to claim 15, wherein the catholyte and the anolyte are separated by an ion permeable barrier that operates at a temperature less than 600 degrees C.

22. The method according to claim 21, wherein the ion permeable barrier includes one of a polymeric or inorganic ceramic-based ion permeable barrier.