IP Library Granted Patent US 8,444,844
Granted Patent B1
US 8,444,844 · App. 13/724,768 · Granted May 21, 2013

Electrochemical co-production of a glycol and an alkene employing recycled halide

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Quick Facts
Patent No.
US 8,444,844
App. No.
13/724,768
Granted
May 21, 2013
Kind
B1
Abstract

The present disclosure is a method and system for electrochemically co-producing a first product and a second product. The system may include a first electrochemical cell, a first reactor, a second electrochemical cell, at least one second reactor, and at least one third reactor. The method and system for for co-producing a first product and a second product may include co-producing a glycol and an alkene employing a recycled halide.

Claims (40)

1. A method for co-producing a first product and a second product, the method comprising the steps of:

contacting a first region of a first electrochemical cell having an cathode with a catholyte comprising carbon dioxide;

contacting a second region of a first electrochemical cell having an anode with an anolyte comprising a MX where M is at least one cation and X is selected from a group consisting of F, Cl, Br, I, and mixtures thereof;

applying an electrical potential between the anode and the cathode sufficient to produce M-carboxylate recoverable from the first region of the first electrochemical cell and a halogen recoverable from the second region of the first electrochemical cell;

reacting the M-carboxylate with HX via a secondary reactor to produce a carboxylic acid and MX, the MX being recycled to an input of the second region of the first electrochemical cell;

contacting a first region of a second electrochemical cell having a cathode with a catholyte comprising the carboxylic acid;

contacting a second region of a second electrochemical cell having an anode with an anolyte comprising HX;

applying an electrical potential between the anode of the second electrochemical cell and the cathode of the second electrochemical cell sufficient to produce at least one of another carboxylic acid, an aldehyde, a ketone, a glycol or an alcohol recoverable from the first region of the second electrochemical cell and a halogen recoverable from the second region of the second electrochemical cell;

reacting the halogen from the second region of the first electrochemical cell and from the second region of the second electrochemical cell with an alkane, aromatic compound, or other carbon compound to produce a halogenated compound and HX, the HX being recycled back to the second region of the second electrochemical cell and to the input of the secondary reactor; and

reacting the halogenated compound via at least one reactor to produce at least one of an alkene, alkyne, alcohol, phenol, aldehyde, ketone, unsaturated carbon compound, or longer-chain alkane, and HX, the HX being recycled back to the second region of the second electrochemical cell and to the input of the secondary reactor.

2. The method according to claim 1 , wherein the halogen includes at least one of F 2 , Cl 2 , Br 2 , or I 2 .

3. The method according to claim 1 , wherein the halogen is reacted with at least one of methane, ethane, propane, butane, isobutane, benzene, toluene, or xylene.

4. The method according to claim 1 , wherein the M-carboxylate is M oxalate.

5. The method according to claim 1 , wherein at least one of glyoxylic acid, glyoxal, glycolic acid, glycolaldehyde, acetic acid, acetaldehyde, ethanol, ethane, ethylene, or ethylene glycol is recoverable from the first region of the second electrochemical cell.

6. The method according to claim 1 , wherein the cathode and the anode of the first electrochemical cell and the cathode and the anode of the second electrochemical cell, 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 of the second electrochemical cell is liquid phase and the anolyte of the second electrochemical cell is gas phase.

9. The method according to claim 1 , wherein at least one of:

the catholyte and the anolyte of the first electrochemical cell; and

the catholyte and the anolyte of the second electrochemical cell;

is non-aqueous.

10. The method according to claim 1 , wherein reacting the recovered halogen from the second region of the first electrochemical cell and the second region of the second electrochemical cell with an alkane, aromatic compound, or other carbon compound is performed by at least a single reactor.

11. The method according to claim 1 , wherein reacting the recovered halogen from the second region of the first electrochemical cell and the second region of the second electrochemical cell with an alkane, aromatic compound, or other carbon compound is performed by at least two reactors.

12. A method for co-producing a first product and a second product, the method comprising the steps of:

applying an electrical potential between a cathode of a first region of a first electrochemical cell, including a catholyte comprising carbon dioxide, and an anode of a second region of a first electrochemical cell, the second region including an anolyte comprising MX, where M is at least one cation and X is selected from a group consisting of F, Cl, Br, I, and mixtures thereof, sufficient to produce M-carboxylate recoverable from the first region of the first electrochemical cell and a halogen recoverable from the second region of the first electrochemical cell;

reacting the M-carboxylate with HX via a secondary reactor to produce a carboxylic acid and MX, the MX being recycled to an input of the second region of the first electrochemical cell;

applying an electrical potential between a cathode of a first region of a second electrochemical cell, including a catholyte comprising the carboxylic acid, and an anode of a second region of a second electrochemical cell, including an anolyte comprising HX, sufficient to produce at least one of another carboxylic acid, an aldehyde, a ketone, a glycol or an alcohol recoverable from the first region of the second electrochemical cell and a halogen recoverable from the second region of the second electrochemical cell;

reacting the halogen from the second region of the first electrochemical cell and from the second region of the second electrochemical cell with an alkane, aromatic compound, or other carbon compound, to produce a halogenated compound and HX, the HX being recycled back to the second region of the second electrochemical cell and to the input of the secondary reactor; and

reacting the halogenated compound via at least a third reactor to produce at least one of an alkene, alkyne, alcohol, aldehyde, ketone, or longer-chain alkane, and HX, the HX being recycled back to the second region of the second electrochemical cell and to the input of the secondary reactor.

13. The method according to claim 12 , wherein the halogen includes at least one of F 2 , Cl 2 , Br 2 , or I 2 .

14. The method according to claim 12 , wherein the alkane, aromatic compound, or other carbon compound includes at least one of methane, ethane, propane, or butane.

15. The method according to claim 12 , wherein the M-carboxylate is M-oxalate.

16. The method according to claim 12 , wherein at least one of glyoxylic acid, glyoxal, glycolic acid, glycolaldehyde, acetic acid, acetaldehyde, ethanol, ethane, ethylene, or ethylene glycol is recoverable from the first region of the second electrochemical cell.

17. The method according to claim 12 , wherein the cathode and the anode of the first electrochemical cell and the cathode and the anode of the second electrochemical cell, are separated by an ion permeable barrier that operates at a temperature less than 600 degrees C.

18. The method according to claim 17 , wherein the ion permeable barrier includes one of a polymeric or inorganic ceramic-based ion permeable barrier.

19. The method according to claim 12 , wherein the catholyte of the second electrochemical cell is liquid phase and the anolyte of the second electrochemical cell is gas phase.

20. The method according to claim 12 , wherein at least one of:

the catholyte and the anolyte of the first electrochemical cell; and

the catholyte and the anolyte of the second electrochemical cell;

are non-aqueous.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 27, 2017
From: AVANTIUM HOLDING B.V.
To: AVANTIUM KNOWLEDGE CENTRE B.V.
Reel/Frame 041214/0698 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 13, 2017
From: ARES CAPITAL CORPORATION
To: AVANTIUM HOLDING B.V.
Reel/Frame 041033/0406 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 7, 2016
From: LIQUID LIGHT, INC.
To: ARES CAPITAL CORPORATION
Reel/Frame 040644/0921 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 2, 2013
From: TEAMEY, KYLE; KACZUR, JERRY J.; COLE, EMILY BARTON
To: LIQUID LIGHT, INC.
Reel/Frame 030130/0790 →