Electrochemical co-production of chemicals employing the recycling of a hydrogen halide

• US 8,647,493 B2
• Filed: 12/21/2012
• Issued: 02/11/2014
• 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:
  US13/724,878
• Publication Number:
  US 20130134048A1
• Time in Patent Office: 417 Days
• Field of Search: 585/365, 585/400, 205/431, 205/440, 205/446, 205/448, 205/450, 205/462, 205/555, 205/618, 205/619, 423/481, 423/483
• US Class Current: 205/555
• 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. 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. The second product may be removed from the second region and introduced to a secondary reactor. The method may include forming the recycled reactant in the secondary reactor.

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, wherein the recycled reactant is a hydrogen halide, HX, where X is selected from the group consisting of F, Cl, Br, I, and mixtures thereof;

applying an electrical potential between the anode and the cathode sufficient to produce the first product from the first region and the second product from the second region, wherein the second product is X₂;

removing the second product from the second region;

introducing the second product and at least one of an alkane, an alkene or an aromatic compound to a secondary reactor;

producing the recycled reactant through a reaction of the second product and the at least one of an alkane, an alkene or an aromatic compound; and

recycling the recycled reactant produced through the reaction of the second product and the at least one of an alkane, an alkene or an aromatic compound at the secondary reactor to the second region.

2. The method according to claim 1, further comprising:

forming a halogenated organic compound in the secondary reactor.

3. The method according to claim 2, further comprising:

feeding the halogenated organic compound into a third reactor.

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

feeding water into the third reactor.

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

forming an alcohol and HX in the third reactor; and

recycling the HX into the second region.

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

forming HX and at least one of an alkene and an alkyne in the third reactor; and

recycling the HX into the second region.

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

forming HX and at least one of an alcohol, an alkene, an alkyne, an aldehyde, a ketone, an alkane, and mixtures thereof in the third reactor; and

recycling the HX into the second region.

8. The method according to claim 2, wherein the halogenated organic compound is bromoethane.

9. The method according to claim 1, wherein HX is HBr.

10. The method according to claim 9, wherein the second product is Br₂.

11. The method according to claim 1, wherein the anolyte and catholyte further comprise water, the first product includes acetic acid, and the X₂ is Br₂.

12. The method according to claim 1, wherein the catholyte further comprises a non-aqueous solvent, the first product includes a carboxylic acid, and the X₂ is Br₂.

13. The method according to claim 1, wherein the first region and the second region are separated by an ion permeable barrier that operates at a temperature of less than 600 degrees C.

14. The method according to claim 13, wherein the ion permeable barrier includes one of a polymeric or inorganic ceramic-based ion permeable barrier.

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

16. The method according to claim 1, wherein the catholyte is a liquid and the anolyte is a liquid.

17. The method according to claim 1, wherein said first product includes at least one of carbon monoxide, formic acid, formaldehyde, methanol, methane, oxalate, oxalic acid, glyoxylic acid, glyoxylate, glycolic acid, glyco late, glyoxal, glycolaldehyde, ethylene glycol, acetic acid, acetate, acetaldehyde, ethanol, ethane, ethylene, lactic acid, lactate, propionic acid, propionate, acetone, isopropanol, 1-propanol, 1,2-propylene glycol, propane, propylene, butane, butene, 1-butanol, 2-butanone, 2-butanol, a carboxylic acid, a carboxylate, a ketone, an aldehyde, and an alcohol.

18. The method according to claim 1, wherein the catholyte further comprises a solvent selected from the group consisting of water, methanol, ethanol, acetonitrile, propylene carbonate, ethylene carbonate, dimethyl carbonate, diethyl carbonate, dimethylsulfoxide, dimethylformamide, acetonitrile, acetone, tetrahydrofuran, N,N-dimethylacetaminde, dimethoxyethane, diethylene glycol dimethyl ester, butyrolnitrile, 1,2-difluorobenzene, γ

-butyrolactone, N-methyl-2-pyrrolidone, sulfolane, 1,4-dioxane, nitrobenzene, nitromethane, acetic anhydride, ionic liquids, and mixtures thereof.