Materials for high-performance aqueous organic redox flow batteries

Patent metadata

Field	Value
Publication number	US-10833345-B2
Application number	US-201715723071-A
Country	US
Kind code	B2
Filing date	Oct 2, 2017
Priority date	Sep 30, 2016
Publication date	Nov 10, 2020
Grant date	Nov 10, 2020

Abstract

Quinones and related compounds for use in flow batteries are provided. Many of these compounds are found to mitigate the effects of crossover in a flow battery. Other structure for improving battery performance is provided.

First claim

What is claimed is:

1. A flow battery comprising:
a positive electrode;
a positive electrode electrolyte including water and a first redox couple, the positive electrode electrolyte flowing over and contacting the positive electrode, the first redox couple including an organic compound having formula I and a reduction product of the organic compound, the organic compound having formula I being reduced during discharge:
a negative electrode; and
a negative electrode electrolyte including water and a second redox couple, the negative electrode electrolyte flowing over and contacting the positive electrode, the second redox couple also includes the organic compound having formula I, the reduction product of the organic compound having formula I being oxidized during discharge:

wherein:
p is 0, 1, 2, 3, or 4;
o is 0, 1, 2, or 3;
r is 0, 1, 2, or 3;
R 1 and R 2 are each independently —SO 3 H, —SO 3 Na, —SO 3 K, —CO 2 H, —OH, —OCH 3 , C 1-10 alkyl, —(CH 2 CH 2 O) n OCH 3 , —NH 2 , N(CH 3 ) 2 , —I, —Cl, —Br, —F, —CF 3 , —CF 2 H, —NO 2 , —CCl 3 , —CN, —PO 3 H 2 , —PO 3 2− M + 2 , —COO − M + , —COOR, —CHO, —O − M + , —NHR, —N(R) 2 , —NHCOR, —OR, phenyl, —COR, C 6-10 aryl, pyridinyl, imidazoyl, or pyrroyl,
R 3 is —SO 3 H, —SO 3 Na, —SO 3 K, —CO 2 H, —OH, —OCH 3 , C 1-10 alkyl, —(CH 2 CH 2 O) n OCH 3 , —NH 2 , —N(CH 3 ) 2 , —I, —Cl, —Br, —F, —CF 3 , —CF 2 H, —NO 2 , —CCl 3 , —CN, —PO 3 H 2 , —PO 3 2− M + 2 , —COO − M + , —COOR, —CHO, —O − M + , —COR, C 6-10 aryl, pyridinyl, imidazoyl, or pyrroyl;
R is H or C 1-10 alkyl;
M + is Na + or K + ;
X is —(CH 2 ) n , —(CH 2 OCH 2 ) n , C 4-15 branched alkyl chains or other substituted alkyl chains; and
n is 1 to 10; and
wherein the first redox couple and the second redox couple include the same organic compound having formula I.

2. The flow battery of claim 1 wherein R 3 is —SO 3 H, —CF 3 , or —NO 2 .

3. The flow battery of claim 1 wherein R 3 is —SO 3 H, —SO 3 Na, —SO 3 K, —CO 2 H, —OH, —I, —Cl, —Br, —F, —CF 3 , —NO 2 , —CCl 3 , —CN, —PO 3 H 2 , —PO 3 2− M + 2 , —COOH, —COO − M + , —COOR, —CHO, —O − M + or —COR where R is H or C 1-10 alkyl and M + is Na + or K + .

4. The flow battery of claim 1 wherein R 1 and R 2 are each independently C 1-10 alkyl, —NH 2 , —O − M + , —NHR, —N(R) 2 , —NHCOR, —OR or phenyl.

5. The flow battery of claim 1 wherein R 1 R 2 , and R 3 are each independently —SO 3 H, —CO 2 H, —OH, —PO 3 H 2 , —PO 3 2− M+ 2 , —COOH, —COO − M + , —O − M + pyridinyl, imidazoyl, or pyrroyl.

6. The flow battery of claim 1 further comprising an ion exchange membrane interposed between the positive electrode and the negative electrode.

7. The flow battery of claim 6 wherein the ion exchange membrane has an equivalent weight greater between 1000 and 2000 with respect to sulfonic acid groups.

8. The flow battery of claim 1 wherein R 1 and R 2 are each independently —SO 3 H, —SO 3 Na, —SO 3 K, —CO 2 H, —OH, —OCH 3 , C 1-10 alkyl, —(CH 2 CH 2 O) n OCH 3 , —NH 2 , N(CH 3 ) 2 , —I, —Cl, —Br, —F, —CF 3 , —CF 2 H, —NO 2 , —CCl 3 , —CN, —PO 3 H 2 , —PO 3 2− M + 2 , —COO − M + , —COOR, —CHO, —O − M + , —NHCOR 2 , —OR, phenyl, or —COR.

9. The flow battery of claim 8 wherein R 3 is —SO 3 H, —SO 3 Na, —SO 3 K, —CO 2 H, —OH, —OCH 3 , C 1-10 alkyl, —(CH 2 CH 2 O) n OCH 3 , —NH 2 , —N(CH 3 ) 2 , —I, —Cl, —Br, —F, —CF 3 , —CF 2 H, —NO 2 , —CCl 3 , —CN, —PO 3 H 2 , —PO 3 2− M + 2 , —COO − M + , —COOR, —CHO, —O − M + , or —COR.

10. The flow battery of claim 1 wherein R 1 , R 2 and R 3 are each independently —SO 3 H, —SO 3 Na, —SO 3 K, —CO 2 H, —OH, —OCH 3 , C 1-10 alkyl, —(CH 2 CH 2 O) n OCH 3 , —NH 2 , N(CH 3 ) 2 , —I, —Cl, —Br, —F, —CF 3 , —CF 2 H, —NO 2 , —CCl 3 , —CN, —PO 3 H 2 , —PO 3 2− M + 2 , —COO − M + , —COOR, —CHO, —O − M + , —OR, phenyl, or —COR.

11. The flow battery of claim 1 wherein R 1 , R 2 and R 3 are each independently —SO 3 H, —SO 3 Na, —SO 3 K, —CO 2 H, —OH, —OCH 3 , C 1-10 alkyl, —(CH 2 CH 2 O) n OCH 3 , —CF 3 , —CF 2 H, —NO 2 , —CCl 3 , —CN, —PO 3 H 2 , —PO 3 2− M + 2 , —COO − M + , —COOR, —CHO, —O − M + , —OR, phenyl, or —COR.

12. The flow battery of claim 11 wherein R 3 is —SO 3 H, —CF 3 , or —NO 2 .

13. The flow battery of claim 12 further comprising an ion exchange membrane interposed between the positive electrode and the negative electrode.

14. The flow battery of claim 13 wherein the ion exchange membrane has an equivalent weight greater between 1000 and 2000 with respect to sulfonic acid groups.

Assignees

• Univ Southern California

Inventors

• Narayan Sri
• Prakash Surya G
• Aniszfeld Robert
• Yang Bo
• Hoober-Burkhardt Lena
• Krishnamoorthy Sankarganesh
• Murali Advaith
• Nirmalchandar Archith

Classifications

• H01M2300/0082

  Organic polymers · CPC title

• H01M4/96

  Carbon-based electrodes · CPC title

• H01M8/20

  Indirect fuel cells, e.g. fuel cells with redox couple being irreversible (H01M8/18 takes precedence) · CPC title

• Y02E60/50

  Fuel cells · CPC title

• H01M2250/10

  Fuel cells in stationary systems, e.g. emergency power source in plant · CPC title