Stable positive side material for all-organic flow battery

Patent metadata

Field	Value
Publication number	US-11245111-B2
Application number	US-201816161647-A
Country	US
Kind code	B2
Filing date	Oct 16, 2018
Priority date	Oct 17, 2017
Publication date	Feb 8, 2022
Grant date	Feb 8, 2022

Abstract

A quinone derivative with a high redox potential that does not undergo Michael addition or proto-desulfonation. This molecule addresses the key issues faced with the positive side material of an aqueous all-organic flow battery. This new molecule is 2,5-dihydroxy-4,6-dimethylbenzene-1,3-disulfonic acid (or the disulfonate salt thereof). This quinone derivative offers good solubility, electrochemical reversibility, and robustness to charge/discharge cycling. Quinones with reduced crossover are also 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 that includes a first organic compound, the first organic compound being a fully substituted sulfonated quinone, the positive electrode electrolyte flowing over and contacting the positive electrode;
a negative electrode;
a negative electrode electrolyte including water and a second redox couple, the negative electrode electrolyte flowing over and contacting the negative electrode; and
a polymer electrolyte membrane interposed between the positive electrode and the negative electrode, wherein the first organic compound is selected from the group consisting of compounds having formulae 1 and 2 with a reduction product H 2 Q 1 selected from compounds having formulae 1′ and 2′, respectively:

wherein R 1 , R 2 can be electron withdrawing groups or electron donating groups depending on a predetermined electrode potential.

2. The flow battery of claim 1 wherein R 1 , R 2 are each independently selected from the group consisting of —NO 2 , —N(R 3 ) 3 + X − , —CF 3 , CCl 3 , —CN, —SO 3 H, —PO 3 H 2 , —COOH, —OH, —O − M + , —SO 3 − M + , —PO 3 2− M + 2 , —COO − M + , —COOR 3 , F, Cl, and Br, where R 3 is H or C 1-10 alkyl, M + is a positively charged counter-ion.

3. The flow battery of claim 1 wherein R 1 , R 2 are each independently selected from the group consisting of C 1-10 alkyl, NH 2 , —NHR 2 , —N(R 2 ) 2 , —NHCOR 2 , —OR 2 , —CH 3 , —C 2 H 5 , and phenyl where R 2 is H or C 1-10 alkyl and M + is a positively charged counter-ion.

4. The flow battery of claim 1 wherein the first organic compound is selected from the group consisting of compounds having formulae 3 and a reduction product H 2 Q 1 is selected from compounds having formulae 3′:

wherein R 1 can be an electron withdrawing group or electron donating group depending on a predetermined electrode potential.

5. The flow battery of claim 4 wherein R 1 is —NO 2 , —N(R 3 ) 3 + X − , —CF 3 , CCl 3 , —CN, —SO 3 H, —PO 3 H 2 , —COOH, —OH, −O − M + , —SO 3 − M + , —PO 3 2− M + 2 , —COO − M + , —COOR 3 , F, Cl, Br, —CHO, or —COR 3 where R 3 is H or C 1-10 alkyl, M + is a positively charged counter-ion.

6. The flow battery of claim 4 wherein R 1 is C 1-10 alkyl, NH 2 , —NHR 2 , —N(R 2 ) 2 , —O − M + , —NHCOR 2 , —OR 2 , —CH 3 , —C 2 H 5 , or phenyl where R 2 is H or C 1-10 alkyl and M + is a positively charged counter-ion.

7. The flow battery of claim 1 wherein the first organic compound is selected from the group consisting of compounds having formulae 4 and a reduction product H 2 Q 1 is selected from compounds having formulae 4′:

wherein R 1 , R 2 can be electron withdrawing groups or electron donating groups depending on a predetermined electrode potential.

8. The flow battery of claim 7 wherein R 1 , R 2 are each independently selected from the group consisting of —NO 2 , —N(R 3 ) 3 + X − , —CF 3 , CCl 3 , —CN, —SO 3 H, —PO 3 H 2 , —COOH, —OH, —O − M + , —SO 3 − M + , —PO 3 2− M + 2 , —COO − M + , —COOR 3 , F, Cl, Br, —CHO, —COR 3 where R 3 is H or C 1-10 alkyl, M + is a positively charged counter-ion.

9. The flow battery of claim 4 wherein R 1 , R 2 are each independently selected C 1-10 alkyl, NH 2 , —NHR 2 , —N(R 2 ) 2 , —O − M + , —NHCOR 2 , —OR 2 , —CH 3 , —C 2 H 5 , or phenyl where R 2 is H or C 1-10 alkyl and M + is a positively charged counter-ion.

10. The flow battery of claim 1 wherein the second redox couple includes a sulfonated anthraquinone.

11. The flow battery of claim 1 wherein the second redox couple includes anthraquinones having formulae 5, 6, and 7 with H 2 Q 2 being reduced compounds thereof:

12. The flow battery of claim 1 wherein R 1 , R 2 are each C 1-10 alkyl.

13. The flow battery of claim 1 wherein R 1 , R 2 are each methyl, ethyl, propyl, or isopropyl.

14. The flow battery of claim 1 wherein first organic compound has the following formula:

15. The flow battery of claim 1 wherein first organic compound has the following formula:

Assignees

• Univ Southern California

Inventors

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

Classifications

• Y02E60/50

  Fuel cells · CPC title

• C07C2603/24

  Anthracenes; Hydrogenated anthracenes · CPC title

• C07C2603/50

  Pyrenes; Hydrogenated pyrenes · CPC title

• H01M4/60

  of organic compounds · CPC title

• H01M2300/0082

  Organic polymers · CPC title