Redox active liquid electrolytes for organic redox flow battery

Patent metadata

Field	Value
Publication number	US-11936081-B2
Application number	US-202117454810-A
Country	US
Kind code	B2
Filing date	Nov 13, 2021
Priority date	Feb 10, 2021
Publication date	Mar 19, 2024
Grant date	Mar 19, 2024

Abstract

A redox flow battery may include: a positive half-cell comprising a catholyte; a negative half-cell comprising an anolyte; and an ion permeable membrane, wherein the ion permeable membrane separates the catholyte and the anolyte, and wherein the catholyte, the anolyte, or both comprise a low-transition temperature material comprising: a redox-active phase; and an ionically conducting organic salt.

First claim

What is claimed is:

1. A low-transition temperature material composition comprising:
a hydrogen bond donor comprising urea;
a redox-active phase comprising maleimide; and
an ionically conducting organic salt comprising choline chloride,
wherein the low-transition temperature material has a melting point of less than 100° C.

2. The composition of claim 1 , wherein the redox-active phase further comprises at least one compound capable of undergoing a redox reaction wherein the at least one compound is selected from the group consisting of a cyclic polyols, dicarboxylic nitrogen heterocycles, and combinations thereof.

3. The composition of claim 1 , wherein the redox-active phase further comprises at least one organic compound selected from the group consisting of squaric acid, naphthalenediol, catechol, nitrocatechol, catechol and nitrocatechol substituted by one or more hydrocarboxyl groups with carbon numbers from C1-C10, dihydroxybenzaldehyde, nitrodihydroxybenzaldehyde, dihydroxybenzaldehyde and nitrodihydroxybenzaldehyde substituted by one or more hydrocarboxyl groups with carbon numbers from C1-C10, maleimide, imidazolidinone, p arab ani c acid, N-aminophthalimide, phthalimide, 2,3-naphthalenedicarboximide, 3-aminophthalhydrazide, urazole, and combinations thereof.

4. The composition of claim 1 , wherein the ionically conducting organic salt further comprises an additional quaternary ammonium salt capable of participating in a redox reaction with the redox-active phase.

5. The composition of claim 4 , wherein the ionically conducting organic salt further comprises a compound selected from the group consisting of: distearylammonium chloride; glycine betaine; alkyl dibenzylammonium chloride; dodecyl dimethylammonium chloride; benzalkonium chloride; ionic liquids containing alkylimidazolium, phosphonium or ammonium cations; ionic liquids containing bis(trifluorosulfonylimide), tetrafluoroborate, and/or hexafluorophosphate anions; and combinations thereof.

6. The composition of claim 1 , further comprising an additional hydrogen bond donor selected from the group consisting of ethylene glycol, glycerin, lactic acid, sulfuric acid, and combinations thereof.

7. The composition of claim 1 , wherein the redox-active phase further comprises benzene-1,2-diol.

8. A method of making a low-transition temperature material comprising:
combining a redox-active phase comprising maleimide, an ionically conducting organic salt comprising choline chloride, and urea to form a solid composite; and
melting the mixture to form the low-transition temperature material, wherein the low-transition temperature material has a melting point of less than 100° C.

9. The method of claim 8 , wherein the redox-active phase further comprises at least one compound capable of undergoing a redox reaction wherein the at least one compound is selected from the group consisting of a cyclic polyols, dicarboxylic nitrogen heterocycles, and combinations thereof.

10. The method of claim 8 , wherein the redox-active phase further comprises at least one organic compound selected from the group consisting of squaric acid, naphthalenediol, catechol, nitrocatechol, catechol and nitrocatechol substituted by one or more hydrocarboxyl groups with carbon numbers from C1-C10, dihydroxybenzaldehyde, nitrodihydroxybenzaldehyde, dihydroxybenzaldehyde and nitrodihydroxybenzaldehyde substituted by one or more hydrocarboxyl groups with carbon numbers from C1-C10, maleimide, imidazolidinone, parabanic acid, N-aminophthalimide, phthalimide, 2,3-naphthalenedicarboximide, 3-aminophthalhydrazide, urazole, and combinations thereof.

11. The method of claim 8 , wherein the ionically conducting organic salt further comprises an additional quaternary ammonium salt capable of participating in a redox reaction with the redox-active phase.

12. The method of claim 11 , wherein the conducting organic salt further comprises a compound selected from the group consisting of: distearylammonium chloride; glycine betaine; alkyl dibenzylammonium chloride; dodecyl dimethylammonium chloride; benzalkonium chloride; ionic liquids containing alkylimidazolium, phosphonium or ammonium cations; ionic liquids containing bis(trifluorosulfonylimide), tetrafluoroborate, and/or hexafluorophosphate anions; and combinations thereof.

13. The method of claim 8 , wherein the low-transition temperature material further comprises an additional hydrogen bond donor selected from ethylene glycol, glycerin, lactic acid, sulfuric acid, and combinations thereof.

Assignees

• Exxonmobil Technology & Engineering Company
• Exxon Mobil Tech And Engineering Company

Inventors

• Desai Divyaraj
• Harper Jr Michael R
• Elsen Heather A
• Saathoff Jonathan D
• Ertas Mehmet D
• Levine Steven W

Classifications

• H01M8/188 Primary

  by recharging of redox couples containing fluids; Redox flow type batteries · CPC title

• H01M4/368

  Liquid depolarisers · CPC title

• H01M4/60

  of organic compounds · CPC title

• H01M2300/0002

  Aqueous electrolytes · CPC title