Stable Quinone Derivative for All-Organic Flow Battery

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Solution Overview

Problem

Existing organic redox flow batteries face challenges with degradation reactions such as Michael addition and proto-desulfonation, which affect the sustainability and cost-effectiveness of energy storage solutions, particularly in grid-scale applications.

Innovation Solution

A quinone derivative, 2,5-dihydroxy-4,6-dimethylbenzene-1,3-disulfonic acid (DHDMDS), is developed, offering high redox potential, solubility, electrochemical reversibility, and robustness to charge/discharge cycling, thereby avoiding these degradation issues.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Use of energy by moving object

If quinone-type molecules are used in all-organic flow batteries, then energy storage performance is improved, but degradation reactions (Michael addition and proto-desulfonation) occur reducing stability

Engineering Contradiction:
Improveenergy storage performanceVSAvoidmolecular stability
Core Design Contradiction:
Use of energy by moving objectVSReliability

Solution Approach 1:

The patent modifies the chemical structure of quinone molecules by introducing specific substituents (electron-donating groups like alkyl or aryl groups at positions 2 and 5, and sulfonate groups at positions 1 and 3) to change the electronic and steric parameters of the molecule. These parameter changes raise the redox potential above +0.35 V vs. SHE and prevent degradation reactions, thereby simultaneously improving energy storage performance and molecular stability.

Inventive Principle:
Principle #35Parameter changes

2Productivity

If conventional quinone molecules are used, then solubility and electrochemical activity are achieved, but degradation through Michael addition and proto-desulfonation reduces durability

Engineering Contradiction:
Improveelectrochemical activityVSAvoiddurability
Core Design Contradiction:
ProductivityVSDuration of action of stationary object

Solution Approach 1:

The patent creates composite molecular structures combining electron-donating groups (alkyl or aryl) with sulfonate groups on the quinone core. This composite structure achieves both high solubility in aqueous electrolytes and high electrochemical activity (redox potential > +0.35 V vs. SHE) while the specific arrangement of these groups prevents degradation reactions, thereby improving both productivity and duration of action.

Inventive Principle:
Principle #40Composite materials

3Quantity of substance

If metal-based battery systems are used, then energy storage capacity is achieved, but cost and environmental sustainability are compromised

Engineering Contradiction:
Improveenergy storage capacityVSAvoidcost and sustainability
Core Design Contradiction:
Quantity of substanceVSEase of manufacture

Solution Approach 1:

The patent replaces expensive and environmentally problematic metal-based electrolytes with organic quinone molecules that can be synthesized from abundant, renewable carbon resources. The designed quinone structures (with molecular formulas such as C14H14O8S2 for the oxidized form) provide sufficient energy storage capacity while being inexpensive to manufacture and environmentally sustainable, effectively replacing metal-based systems with cheaper organic alternatives.

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

The DHDMDS molecule provides a stable and cost-effective solution for energy storage, maintaining capacity over multiple cycles and resisting proto-desulfonation, enhancing the sustainability and eco-friendliness of redox flow batteries.

Implementation Method 1

2,5-dihydroxy-4,6-dimethylbenzene-1,3-disulfonic acid (DHDMDS), is developed, offering high redox potential, solubility, electrochemical reversibility

Methodology Applied
Scientific EffectRedox reactions: Redox Reactions

Implementation Method 2

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.

Methodology Applied
Scientific EffectProto-desulfonation resistance:

Data Source

PatentUS11245111B2Stable positive side material for all-organic flow battery
Publication Date: 2022.02.08 UNIV OF SOUTHERN CALIFORNIA
  • US11245111B2 patent drawing
  • US11245111B2 patent drawing
  • US11245111B2 patent drawing

AI summary

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.