Carbon dioxide capture and conversion to organic products

• US 8,658,016 B2
• Filed: 07/05/2012
• Issued: 02/25/2014
• Est. Priority Date: 07/06/2011
• Status: Active Grant

• Current Assignee: Avantium Knowledge Centre B.V. (Avantium NV)
• Original Assignee: Liquid Light, Inc. (Avantium NV)
• Inventors: Lakkaraju, Prasad, Teamey, Kyle
• Primary Examiner(s): Wong, Edna
• Application Number:
  US13/541,933
• Publication Number:
  US 20130008800A1
• Time in Patent Office: 600 Days
• Field of Search: 205/555, 205/431, 205/439, 205/440, 205/448, 205/450, 205/455, 205/462
• US Class Current: 205/439
• CPC Class Codes: B01D 2252/103 Water
• CPC Class Codes: B01D 2252/20 Organic absorbents
• CPC Class Codes: B01D 2252/2021 Methanol
• CPC Class Codes: B01D 2252/20415 Tri- or polyamines
• CPC Class Codes: B01D 2252/20463 containing a pyrimidine-ring
• CPC Class Codes: B01D 2252/30 Ionic liquids and zwitter-ions
• CPC Class Codes: B01D 53/1475 Removing carbon dioxide
• CPC Class Codes: B01D 53/965 including an electrochemical process step
• CPC Class Codes: C25B 3/25 Reduction
• CPC Class Codes: C25B 9/19 with diaphragms
• CPC Class Codes: Y02C 20/40 of CO2
• CPC Class Codes: Y02P 20/151 Reduction of greenhouse gas [GHG] emissions, e.g. CO2

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

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.