# US 2014/0194641 A1 · Method and System for the Electrochemical Co-Production of Halogen and Carbon Monoxide for Carbonylated Products

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- Number: US 2014/0194641 A1
- Document ID: US20140194641A1
- Status: Published application
- Kind: A1
- Application number: 14/203,158
- Filed: 2014-03-10
- Published: 2014-07-10
- Earliest claimed: 2012-07-26
- Assignees: Liquid Light, Inc.
- Applicants: Liquid Light, Inc.
- Inventors: Kyle Teamey; Jerry J. Kaczur; Robert Page Shirtum
- Web page: https://patentgrep.com/patent/US20140194641A1

## CPC

- C25B 3/00: Electrolytic production of organic compounds
- C07C 1/26: starting from organic compounds containing only halogen atoms as hetero-atoms
- C07C 29/149: with hydrogen or hydrogen-containing gases
- C07C 29/58: by elimination of halogen, e.g. by hydrogenolysis, splitting-off (C07C29/124 takes precedence)
- C07C 51/02: from salts of carboxylic acids
- C07C 51/15: by reaction of organic compounds with carbon dioxide, e.g. Kolbe-Schmitt synthesis
- C07C 51/367: by introduction of functional groups containing oxygen only in singly bound form
- C07C 67/08: by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
- C25B 1/00: Electrolytic production of inorganic compounds or non-metals
- C25B 1/24: Halogens or compounds thereof
- C25B 3/03: Acyclic or carbocyclic hydrocarbons
- C25B 3/07: Oxygen containing compounds
- C25B 3/11: Halogen containing compounds
- C25B 3/23: Oxidation (halogenation C25B3/27)
- C25B 3/25: Reduction
- C25B 3/27: Halogenation
- C25B 9/19: with diaphragms
- C25B 9/23: comprising ion-exchange membranes in or on which electrode material is embedded
- C25B 13/08: based on organic materials
- C25B 15/00: Operating or servicing cells
- C25B 15/08: Supplying or removing reactants or electrolytes; Regeneration of electrolytes
- C25B 15/083: {Separating products}
- C25B 3/29: Coupling reactions
- Y02P 20/10: Process efficiency
- Y02P 20/129: Energy recovery, e.g. by cogeneration, H2recovery or pressure recovery turbines
- Y02P 20/133: Renewable energy sources, e.g. sunlight
- Y02P 20/582: Recycling of unreacted starting or intermediate materials
- C25B: ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR (anodic or cathodic protection C23F13/00; single-crystal growth C30B)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## 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 including carbon dioxide and contacting the second region with an anolyte including a recycled reactant. The method may further include applying an electrical potential between the anode and the cathode sufficient to produce carbon monoxide recoverable from the first region and a halogen recoverable from the second region.

## Claims

### Claim 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 carbon monoxide; and
applying an electrical potential between the anode and the cathode sufficient to produce carbon monoxide recoverable from the first region and phosgene recoverable from the second region, the carbon monoxide recoverable from the first region being recycled as an input feed to the second region.

### Claim 2 (depends on 1)

The method according to claim 1, wherein the recycled reactant is HX, where X is selected from a group consisting of F, Cl, Br, I and mixtures thereof.

### Claim 3 (depends on 1)

The method according to claim 1, further comprising:
reacting the phosgene recovered from the second region with an additional reactant to form a third product and the recycled reactant.

### Claim 4 (depends on 3)

The method according to claim 3, wherein the additional reactant includes at least one of an amine, methyl amine, butyl amine, aniline, a diamine, di amino toluene, diamino benzene, 4,4′ methylene diphenyl diamine, hexamethylenediamine, meta-tetramethylxylylene-diamine, and toluenediamines, or at least one of an alcohol, methanol, and ethanol, and mixtures thereof.

### Claim 5 (depends on 3)

The method according to claim 3, wherein the third product includes an isocyanate, methyl isocyanate, butyl isocyanate, phenyl isocyanate, diisocyanate, methylene-diphenylisocyanate, phenyl-diisocyanate, hexamethylene-diisocyanate, toluene-diisocyanate, meta-tetramethylxylylene-diisocyanate, alkyl carbonate, dimethyl carbonate, ethylmethyl carbonate or diethyl carbonate.

### Claim 6 (depends on 1)

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

### Claim 7 (depends on 6)

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

### Claim 8 (depends on 1)

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

### Claim 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;
contacting the second region with an anolyte comprising a recycled reactant; and
applying an electrical potential between the anode and the cathode sufficient to produce hydrogen recoverable from the first region and a halogen recoverable from the second region, where the halogen includes at least one of F2, Cl2, Br2 or I2;
reacting the hydrogen recovered from the first region with carbon dioxide to produce water and carbon monoxide; and
reacting the carbon monoxide, the halogen recovered from the second region and an additional reactant to form a third product and the recycled reactant.

### Claim 10 (depends on 9)

The method according to claim 9, wherein the recycled reactant is HX, where X is selected from a group consisting of F, Cl, Br, I and mixtures thereof.

### Claim 11 (depends on 9)

The method according to claim 9, wherein the additional reactant includes at least one of an amine, methyl amine, butyl amine, aniline, diamine, di amino toluene, diamino benzene, 4,4′ methylene diphenyl diamine, hexamethylenediamine, meta-tetramethylxylylene diamine, and toluenediamines, or at least one of an alcohol, methanol, and ethanol, and mixtures thereof.

### Claim 12 (depends on 9)

The method according to claim 9, wherein the third product includes an isocyanate, methyl isocyanate, butyl isocyanate, phenyl isocyanate, diisocyanate, methylene-diphenylisocyanate, phenyl-diisocyanate, hexamethylene-diisocyanate, toluene-diisocyanate, meta-tetramethylxylylene-diisocyanate, alkyl carbonate, dimethyl carbonate, ethylmethyl carbonate or diethyl carbonate.

### Claim 13

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;
contacting the second region with an anolyte comprising a recycled reactant and carbon monoxide;
applying an electrical potential between the anode and the cathode sufficient to produce hydrogen recoverable from the first region and phosgene recoverable from the second region;
reacting the hydrogen recovered from the first region with carbon dioxide to produce water and carbon monoxide, the carbon monoxide being supplied as an input feed to the second region; and
reacting the phosgene recovered from the second region and an additional reactant to form a third product and the recycled reactant.

### Claim 14 (depends on 13)

The method according to claim 13, wherein the recycled reactant is HX, where X is selected from a group consisting of F, Cl, Br, I and mixtures thereof.

### Claim 15 (depends on 13)

The method according to claim 13, wherein the additional reactant includes at least one of an amine, methyl amine, butyl amine, aniline, diamine, di amino toluene, diamino benzene, 4,4′ methylene diphenyl diamine, hexamethylenediamine, meta-tetramethylxylylene diamine, and toluenediamines, or at least one of an alcohol, methanol, and ethanol, and mixtures thereof.

### Claim 16 (depends on 13)

The method according to claim 13, wherein the third product includes an isocyanate, methyl isocyanate, butyl isocyanate, phenyl isocyanate, diisocyanate, methylene-diphenylisocyanate, phenyl-diisocyanate, hexamethylene-diisocyanate, toluene-diisocyanate, meta-tetramethylxylylene-diisocyanate, alkyl carbonate, dimethyl carbonate, ethylmethyl carbonate or diethyl carbonate.
