Custom Ionic Liquid Electrolytes for Decarboxylation

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Solution Overview

Problem

Conventional electrochemical decarboxylation processes face limitations due to the lack of a universal electrolyte that provides high conductivity, electrochemical stability, and specific solubility requirements for carboxylic acids, leading to low efficiency and high side product formation, which hampers the commercial application and environmental benefits of the process.

Innovation Solution

The development of custom ionic liquid electrolytes tailored for specific decarboxylation processes, designed to enhance the solubility of carboxylic acids, stability, and separation of hydrocarbon products, using cations and anions that can be modified to meet the requirements of the specific reaction, such as pyridinium, imidazolium, and phosphonium-based ionic liquids.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional polar organic solvents are used as electrolytes, then the electrochemical decarboxylation process can proceed, but the solubility of carboxylic acids is limited and the electrolyte undergoes electrochemical oxidation leading to low efficiency and high side product formation

Engineering Contradiction:
Improveefficiency of electrochemical decarboxylationVSAvoidelectrochemical stability of electrolyte
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The patent changes the fundamental parameters of the electrolyte system by transitioning from conventional polar organic solvents to ionic liquids. This parameter change enables the electrolyte to maintain electrochemical stability while achieving high carboxylic acid solubility, thereby resolving the contradiction between productivity and reliability.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs composite ionic liquid electrolyte systems that combine multiple ionic liquid components with specific cation-anion combinations. These composite materials provide both high conductivity and electrochemical stability, simultaneously improving efficiency and reliability of the decarboxylation process.

Inventive Principle:
Principle #40Composite materials

2Manufacturing precision

If conventional polar organic solvents are used as electrolytes, then the process can be performed, but the solubility of carboxylic acid precursors is limited and product selectivity is low due to high side product formation

Engineering Contradiction:
Improveproduct selectivityVSAvoidside product formation
Core Design Contradiction:
Manufacturing precisionVSObject-generated harmful factors

Solution Approach 1:

The patent creates an inert electrochemical environment using ionic liquids that are resistant to oxidation. This inert environment prevents the electrolyte from undergoing electrochemical oxidation, thereby eliminating the source of side products and improving product selectivity.

Inventive Principle:
Principle #39Inert atmosphere (Inert environment)

Solution Approach 2:

By changing the electrolyte parameters to ionic liquids with appropriate viscosity and conductivity, the patent optimizes the reaction environment to favor main reaction pathways while suppressing side reactions, thereby improving manufacturing precision and reducing harmful factors.

Inventive Principle:
Principle #35Parameter changes

3Object-affected harmful factors

If conventional polar organic solvents are used as electrolytes, then the decarboxylation reaction can proceed, but the environmental benefits are counterbalanced by the use of these solvents

Engineering Contradiction:
Improveenvironmental impactVSAvoidavailability of electrolyte
Core Design Contradiction:
Object-affected harmful factorsVSEase of manufacture

Solution Approach 1:

The patent changes the physical and chemical parameters of the electrolyte to ionic liquids, which have negligible vapor pressure and high thermal stability. This eliminates the environmental hazards associated with conventional volatile organic solvents while maintaining ease of manufacture through established ionic liquid synthesis routes.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs ionic liquids that can be reused multiple times without significant degradation, replacing the conventional practice of using disposable or single-use organic solvents. This improves environmental sustainability while the scalability of ionic liquid production maintains ease of manufacture.

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

4Adaptability or versatility

If a universal electrolyte is used, then the process can be applied broadly, but no single polar organic solvent meets all requirements for high conductivity, electrochemical stability, and specific solubility

Engineering Contradiction:
Improveapplicability to various carboxylic acidsVSAvoidelectrochemical stability
Core Design Contradiction:
Adaptability or versatilityVSReliability

Solution Approach 1:

The patent develops ionic liquid electrolyte systems that can universally accommodate various carboxylic acid substrates while maintaining electrochemical stability. The modular structure of ionic liquids allows them to serve multiple functions: providing conductivity, stability, and tunable solubility for different substrates.

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

Solution Approach 2:

The patent employs dynamic tuning of ionic liquid properties by selecting different cation-anion combinations to match specific carboxylic acid substrates. This dynamic adaptability allows the electrolyte system to maintain optimal performance across diverse applications while preserving electrochemical stability.

Inventive Principle:
Principle #15Dynamics

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

This approach improves the applicability and efficiency of electrochemical decarboxylation by enabling the synthesis of a variety of organic compounds at moderate conditions without catalysts, increasing product selectivity, and facilitating the separation of products from the electrolyte, thus making the process more economically and environmentally sustainable.

Implementation Method 1

Custom ionic liquid electrolytes tailored for specific decarboxylation processes, designed to enhance the solubility of carboxylic acids, stability

Methodology Applied
Scientific EffectIonic conduction: Conduction (electrical)

Implementation Method 2

The electrochemical decarboxylation disclosed in this patent removes CO2 from the carboxylic acid and creates a high energy radical or carbocation

Methodology Applied
Scientific EffectElectrochemical oxidation: Oxidation

Data Source

PatentUS10145019B2Custom ionic liquid electrolytes for electrolytic decarboxylation
Publication Date: 2018.12.04 ENLIGHTEN INNOVATIONS INC
  • US10145019B2 patent drawing
  • US10145019B2 patent drawing
  • US10145019B2 patent drawing

AI summary

Methods, equipment, and reagents for preparing organic compounds using custom electrolytes based on different ionic liquids in electrolytic decarboxylation reactions are disclosed.