Converting Hydroquinone Waste to 1,2,4-Trihydroxybenzene for Flow Batteries

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Flow batteries face sub-optimal energy storage performance and limited cycle life due to the lack of commercially viable technologies, with hydroquinone byproducts from catechol synthesis posing waste disposal issues and not being utilized in the flow battery industry.

Innovation Solution

A three-step process to convert hydroquinone into 1,2,4-trihydroxybenzene, which can then be incorporated into metal catecholate complexes, enhancing solubility and reducing waste disposal issues by providing a high-value product for flow batteries.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If hydroquinone byproduct is separated and discarded from catechol synthesis, then catechol purity is improved, but material waste and disposal costs increase

Engineering Contradiction:
Improvecatechol purityVSAvoidhydroquinone waste
Core Design Contradiction:
Manufacturing precisionVSLoss of substance

Solution Approach 1:

The patent converts the harmful waste byproduct (hydroquinone) into a beneficial product (1,2,4-trihydroxybenzene) that can be used as a ligand for metal coordination complexes in flow batteries. This transforms the waste disposal problem into a value-added product generation process, simultaneously achieving waste reduction and economic benefit.

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

Solution Approach 2:

Instead of discarding hydroquinone as waste, the patent recovers it by converting it into 1,2,4-trihydroxybenzene through a chemical transformation process. This allows the material to be reused in a different application (flow battery electrolytes), thereby eliminating waste while maintaining catechol synthesis efficiency.

Inventive Principle:
Principle #34Discarding and recovering

2Ease of manufacture

If conventional catechol synthesis is used, then production cost is reduced, but hydroquinone waste disposal issues arise

Engineering Contradiction:
Improveproduction costVSAvoidwaste disposal issues
Core Design Contradiction:
Ease of manufactureVSObject-generated harmful factors

Solution Approach 1:

The patent creates a multi-functional process where hydroquinone serves dual purposes: it is both a byproduct of catechol synthesis and a precursor for 1,2,4-trihydroxybenzene production. This integrated approach allows the same material to be utilized in two different value chains, eliminating waste disposal issues while maintaining manufacturing efficiency.

Inventive Principle:
Principle #6Universality (Multi-functionality)

Solution Approach 2:

The patent transforms the harmful waste stream (hydroquinone) into a beneficial product (1,2,4-trihydroxybenzene ligand) that has specific applications in flow battery systems. This conversion eliminates the harmful effect of waste disposal while creating additional economic value from the same feedstock.

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

3Reliability

If metal catecholate complexes are used in flow batteries, then energy storage performance is improved, but solubility limitations and cycle life issues persist

Engineering Contradiction:
Improveenergy storage performanceVSAvoidsolubility and cycle life
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent introduces substitution at specific positions on the catecholate ligand structure (using 1,2,4-trihydroxybenzene) to improve solubility properties. This localized modification maintains the essential metal coordination chemistry while adding functional groups that enhance aqueous solubility and stability, thereby improving both performance and reliability.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent modifies the chemical parameters of the catecholate ligand by using 1,2,4-trihydroxybenzene substitution patterns, which changes the solubility characteristics and electrochemical stability of the metal complexes. These parameter changes enable improved cycle life and performance in flow battery applications.

Inventive Principle:
Principle #35Parameter changes

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 process allows for the production of high-yield, economically viable metal catecholate complexes with improved solubility, addressing waste disposal and performance limitations in flow batteries.

Implementation Method 1

oxidizing hydroquinone in a first reaction to form p-benzoquinone

Methodology Applied
Scientific EffectOxidation: Oxidation

Implementation Method 2

converting the p-benzoquinone in a second reaction to form 1,2,4-triacetoxybenzene

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Implementation Method 3

deacetylating the 1,2,4-triacetoxybenzene in a third reaction to form 1,2,4-trihydroxybenzene

Methodology Applied
Scientific EffectHydrolysis: Hydrolysis

Data Source

PatentUS10065977B2Concerted processes for forming 1,2,4-trihydroxybenzene from hydroquinone
Publication Date: 2018.09.04 LOCKHEED MARTIN ADVANCED ENERGY STORAGE LLC
  • US10065977B2 patent drawing
  • US10065977B2 patent drawing
  • US10065977B2 patent drawing

AI summary

Flow batteries incorporating an active material with one or more catecholate ligands can have a number of desirable operating features. Commercial syntheses of catechol produce significant quantities of hydroquinone as a byproduct, which presently has limited value in the battery industry and can represent a significant waste disposal issue at industrial production scales. Using a concerted, high-yield process, low-value hydroquinone can be transformed into high-value 1,2,4-trihydroxybenzene, which can be a desirable ligand for active materials of relevance in the flow battery industry. Methods for forming 1,2,4-trihydroxybenzene can include: oxidizing hydroquinone in a first reaction to form p-benzoquinone, converting the p-benzoquinone in a second reaction to form 1,2,4-triacetoxybenzene, deacetylating the 1,2,4-triacetoxybenzene in a third reaction to form 1,2,4-trihydroxybenzene, and isolating the 1,2,4-trihydroxybenzene after performing the first reaction, the second reaction and the third reaction consecutively.