IP Library Granted Patent US 8,658,016
Granted Patent B2
US 8,658,016 · App. 13/541,933 · Granted Feb 25, 2014

Carbon dioxide capture and conversion to organic products

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Quick Facts
Patent No.
US 8,658,016
App. No.
13/541,933
Granted
Feb 25, 2014
Kind
B2
Abstract

Methods and systems for capture of carbon dioxide and electrochemical conversion of the captured carbon dioxide to organic products are disclosed. A method may include, but is not limited to, steps (A) to (C). Step (A) may introduce a solvent to a first compartment of an electrochemical cell. Step (B) may capture carbon dioxide with at least one of guanidine, a guanidine derivative, pyrimidine, or a pyrimidine derivative to form a carbamic zwitterion. Step (C) may apply an electrical potential between an anode and a cathode sufficient for the cathode to reduce the carbamic zwitterion to a product mixture.

Claims (21)

1. A method for electrochemical conversion of carbon dioxide, comprising:

(A) introducing a solvent to a first compartment of an electrochemical cell, the first compartment including an anode, the electrochemical cell including a second compartment containing a cathode;

(B) capturing carbon dioxide with at least one of 1,1,3,3-tetramethylguanidine, 1,5,7-triazabicyclo[4.4.0]dec-5-ene, 7-methyl-1,5,7triazabicyclo[4.4.0]dec-5-ene, 1,8-diazabicyclo[5.4.0]undec-7-ene, 1,5-diazabicyclo[4.3.0]non-5-ene, and 1,4,5,6-tetrahydropyrimidine to form a carbamic zwitterion;

(C) introducing the carbamic zwitterion to the second compartment via at least one of (i) forming the carbamic zwitterion in the second compartment or (ii) delivering the carbamic zwitterion to the second compartment; and

(D) applying an electrical potential between the anode and the cathode sufficient for the cathode to reduce the carbamic zwitterion to a product mixture, the product mixture including an organic product derived in part from the carbon dioxide.

2. The method of claim 1 , wherein capturing carbon dioxide with at least one of 1,1,3,3-tetramethylguanidine, 1,5,7-triazabicyclo[4.4.0]dec-5-ene, 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene, 1,8- diazabicyclo[5.4.0]undec-7-ene, 1,5-diazabicyclo[4.3.0]non-5-ene, and 1,4,5,6-tetrahydropyrimidine to form a carbamic zwitterion includes: capturing carbon dioxide in the second compartment with the at least one of 1,3,3-tetramethylguanidine, 1,5,7-triazabicyclo[4.4.0]dec-5-ene, 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene, 1,8-diazabicyclo[5.4.0]undec-7-ene, 1,5-diazabicyclo[4.3.0]non-5-ene, and 1,4,5,6-tetrahydropyrimidine to form the carbamic zwitterion, and wherein introducing the carbamic zwitterion to the second compartment via at least one of (i) forming the carbamic zwitterion in the second compartment or (ii) delivering the carbamic zwitterion to the second compartment includes: introducing the carbamic zwitterion to the second compartment via forming the carbamic zwitterion in the second compartment.

3. The method of claim 1 , wherein capturing carbon dioxide with at least one of 1,1,3,3-tetramethylguanidine, 1,5,7-triazabicyclo[4.4.0]dec-5-ene, 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene, 1,8-diazabicyclo[5.4.0]undec-7-ene, 1,5-diazabicyclo[4.3.0]non-5-ene, and 1,4,5,6-tetrahydropyrimidine to form a carbamic zwitterion includes: capturing the carbon dioxide in a mixing chamber with the at least one of 1,1,3,3-tetramethylguanidine, 1,5,7-triazabicyclo[4.4.0]dec-5-ene, 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene, 1,8-diazabicyclo[5.4.0]undec-7-ene, 1,5-diazabicyclo[4.3.0]non-5-ene, and 1,4,5,6-tetrahydropyrimidine to form the carbamic zwitterion in the mixing chamber, and wherein introducing the carbamic zwitterion to the second compartment via at least one of (i) forming the carbamic zwitterion in the second compartment or (ii) delivering the carbamic zwitterion to the second compartment includes: introducing the carbamic zwitterion to the second compartment via delivering the carbamic zwitterion from the mixing chamber to the second compartment.

4. The method of claim 1 , wherein applying an electrical potential between the anode and the cathode sufficient for the cathode to reduce the carbamic zwitterion to a product mixture includes:

applying the electrical potential between the anode and the cathode sufficient for the cathode to reduce the carbamic zwitterion to the product mixture and to regenerate the at least one of 1,1,3,3-tetramethylguanidine, 1,5,7-triazabicyclo[4.4.0]dec-5-ene, 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene, 1,8-diazabicyclo[5.4.0]undec-7-ene, 1,5-diazabicyclo[4.3.0]non-5-ene, and 1,4,5,6-tetrahydropyrimidine.

5. The method of claim 1 , wherein the solvent is at least one of water, methanol, acetonitrile, dimethylfuran, or a mixture of water and an organic solvent.

6. The method of claim 1 , wherein the organic product includes at least one of acetaldehyde, acetate, acetic acid, acetone, 1-butanol, 2-butanol, 2-butanone, carbon, carbon monoxide, a carbonate, ethane, ethanol, ethylene, formaldehyde, formate, formic acid, glycolate, glycolic acid, glyoxal, glyoxylic acid, graphite, isopropanol, lactate, lactic acid, methane, methanol, oxalate, oxalic acid, propanal, 1-propanol, and a polymer containing carbon dioxide.

7. A method for electrochemical conversion of carbon dioxide, comprising:

(A) introducing a solvent to a first compartment of an electrochemical cell, the first compartment including an anode, the electrochemical cell including a second compartment containing a cathode;

(B) capturing carbon dioxide with at least one of guanidine or a guanidine derivative to form a carbamic zwitterion;

(C) introducing the carbamic zwitterion to the second compartment via at least one of (i) forming the carbamic zwitterion in the second compartment or (ii) delivering the carbamic zwitterion to the second compartment; and

(D) applying an electrical potential between the anode and the cathode sufficient for the cathode to reduce the carbamic zwitterion to a product mixture, the product mixture including an organic product derived in part from the carbon dioxide.

8. A method for electrochemical conversion of carbon dioxide, comprising:

(A) introducing a solvent to a first compartment of an electrochemical cell, the first compartment including an anode, the electrochemical cell including a second compartment containing a cathode;

(B) capturing carbon dioxide with at least one of 1,8-diazabicyclo[5.4.0]undec-7-ene, 1,5-diazabicyclo[4.3.0]non-5-ene, and 1,4,5,6-tetrahydropyrimidine to form a carbamic zwitterion;

(C) introducing the carbamic zwitterion to the second compartment via at least one of (i) forming the carbamic zwitterion in the second compartment or (ii) delivering the carbamic zwitterion to the second compartment; and

(D) applying an electrical potential between the anode and the cathode sufficient for the cathode to reduce the carbamic zwitterion to a product mixture, the product mixture including an organic product derived in part from the carbon dioxide.

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 Jul 5, 2012
From: LAKKARAJU, PRASAD; TEAMEY, KYLE
To: LIQUID LIGHT, INC.
Reel/Frame 028491/0874 →