Two-electron high potential and high capacity redox active molecules for energy storage applications

Patent metadata

Field	Value
Publication number	US-2017062863-A1
Application number	US-201514840935-A
Country	US
Kind code	A1
Filing date	Aug 31, 2015
Priority date	Aug 31, 2015
Publication date	Mar 2, 2017
Grant date	—

Abstract

A non-aqueous redox flow battery includes a catholyte including a compound of formula (I), a compound of formula (II), or a compound of formula (III):

wherein two R groups have the formula X, wherein X is X, wherein X is a group of formula IV-A or IV-B;

First claim

What is claimed is:

1 . A non-aqueous redox flow battery comprising:
a catholyte comprising a two-electron redox active compound represented by Formula I, II, III, or a mixture of two or more thereof;

wherein each R group is independently H, OR 20 , NO 2 , F, Cl, Br, I, alkyl, haloalkyl, aryl, amino, P(═O)R 20 R 21 , P(═O)(—OR 20 )(—OR 21 ), phosphate, —C(O)R 21 , —S(O) 2 R 21 , or X, wherein X is a group of formula IV-A or IV-B;

wherein
R 11 is H, alkyl, haloalkyl, or aryl;
each R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , and R 19 is independently H, F, Cl, Br, I, NO 2 , alkyl, or alkoxy; m is 0 to 12, n is 0 to 12, and p is 1 to 12;
each R 20 is H, alkyl, or aryl; and
each R 21 is alkyl, or aryl;

wherein the compound of formula I, II, or III has two independent R groups having formula X.

2 . The non-aqueous redox flow battery of claim 1 , wherein the active compound has the following structure:

3 . The non-aqueous redox flow battery of claim 1 , wherein the active compound has the following structure:

4 . The non-aqueous redox flow battery of claim 1 , wherein the active compound has the following structure:

5 . The non-aqueous redox flow battery of claim 1 , wherein the two R groups having formula X are the same.

6 . The non-aqueous redox flow battery of claim 1 , wherein m is 0.

7 . The non-aqueous redox flow battery of claim 1 , wherein m is 1 to 4, n is 0 to 4, and p is 1 to 4.

8 . The non-aqueous redox flow battery of claim 1 , wherein X is a moiety of formula IV-A, m is 0, and n is 0.

9 . The non-aqueous redox flow battery of claim 1 , wherein each X independently is —OCH 3 , —OCH 2 CH 3 , —(CH 2 ) 1-3 O(CH 2 CH 2 O) 1-3 CH 3 , or
—O(CH 2 CH 2 O) 1-3 CH 3 .

10 . The non-aqueous redox flow battery of claim 1 , wherein each X independently is —OCH 3 , —OCH 2 CH 3 , —CH 2 OCH 2 CH 2 OCH 3 , or
—OCH 2 CH 2 OCH 3 .

11 . The non-aqueous redox flow battery of claim 1 , wherein the active compound is represented by Formula I-A, I-B, or II-D, has the following structure:

wherein both X groups are independently —OCH 3 , —OCH 2 CH 3 , or —OCH 2 CH 2 OCH 3 .

12 . The non-aqueous redox flow battery of claim 1 , wherein each R group is independently H, F, Cl, Br, I, or alkyl.

13 . The non-aqueous redox flow battery of claim 1 , wherein the active compound is represented by one or more of the following formula;

or a mixture of two or more thereof.

14 . The non-aqueous redox flow battery of claim 1 , wherein the active compound is 1,4-dimethoxynaphthalene (DMN) or 2-ethyl-9,10-dimethoxyanthracene (EDMA).

15 . The non-aqueous redox flow battery of claim 1 further comprising a separator positioned between the anolyte and the catholyte.

16 . The non-aqueous redox flow battery of claim 1 , wherein the active compound is present in the catholyte at a concentration from about 0.001 M to about 5.0 M.

17 . The non-aqueous redox flow battery of claim 1 further comprising a solvent and an electrolyte salt.

18 . The non-aqueous redox flow battery of claim 1 further comprising an anode, wherein the anode comprises Li, Na, or Mg.

19 . The non-aqueous redox flow battery of claim 1 further comprising an anolyte, wherein the anolyte comprises viologen or quinoxaline.

20 . A method of operating a redox flow battery, the method comprising:
providing a redox flow battery comprising:
a catholyte comprising a two-electron redox active compound represented by Formula I, II, III, or a mixture of two or more thereof;

wherein each R group is independently H, OR 20 , NO 2 , F, Cl, Br, I, alkyl, haloalkyl, aryl, amino, P(═O)R 20 R 21 , P(═O)(—OR 20 )(—OR 21 ), phosphate, —C(O)R 21 , —S(O) 2 R 21 , or X, wherein X is a group of formula IV-A or IV-B;

wherein
R 11 is H, alkyl, haloalkyl, or aryl;
each R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , and R 19 is independently H, F, Cl, Br, I, NO 2 , alkyl, or alkoxy; m is 0 to 12, n is 0 to 12, and p is 1 to 12;
each R 20 is H, alkyl, or aryl; and
each R 21 is alkyl, or aryl;

wherein the compound of formula I, II, or III has two independent R groups having formula X; and

operating the redox flow battery at a voltage sufficient to access the second electron redox couple of the compound of formula I, II, or III.

Assignees

• Uchicago Argonne Llc

Inventors

• Huang Jinhua
• Zhang Lu
• Burrell Anthony K

Classifications

• H01M8/20

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

• H01M8/188 Primary

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

• H01M2300/0025

  Organic electrolyte · CPC title

• Y02E60/50

  Fuel cells · CPC title