Onium Salt Purification via Amine-Carboxylic Acid Salt Formation

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Solution Overview

Problem

Existing methods for producing quaternary ammonium carboxylates result in low cellulose solubility due to the presence of carboxylic acid associates, which form with the produced quaternary ammonium carboxylate, limiting its effectiveness as a cellulose solvent.

Innovation Solution

A method involving the production of an onium salt by reacting an onium salt with a carboxylic acid, followed by the addition of an amine to form an amine-carboxylic acid salt, which is then separated to obtain an onium salt free or with reduced carboxylic acid content, enhancing cellulose solubility.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Quantity of substance

If quaternary ammonium carboxylate is produced by reacting quaternary ammonium carbonate with carboxylic acid, then the onium salt can be obtained, but carboxylic acid remains in the product forming associates that reduce cellulose solubility

Engineering Contradiction:
Improveonium salt productionVSAvoidcarboxylic acid content
Core Design Contradiction:
Quantity of substanceVSManufacturing precision

Solution Approach 1:

The patent extracts the harmful carboxylic acid from the product mixture by reacting with a base to form a water-soluble carboxylate salt, which is then removed through liquid-liquid extraction or filtration, leaving the pure onium salt

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent introduces a base as an intermediary substance that reacts with carboxylic acid to form an intermediate carboxylate salt, which serves as a removable species that facilitates the separation of the onium salt from unreacted carboxylic acid

Inventive Principle:
Principle #24Intermediary (Mediator)

2Reliability

If carboxylic acid is present in the onium salt, then the onium salt can be produced, but cellulose solubility is reduced due to associate formation

Engineering Contradiction:
Improvecellulose solubilityVSAvoidcarboxylic acid associate
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent converts the harmful carboxylic acid into a beneficial removable species by reacting it with a base to form a water-soluble carboxylate salt, which can be easily separated from the onium salt through liquid-liquid extraction or filtration

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

Solution Approach 2:

The base acts as an intermediary that transforms the harmful carboxylic acid into a removable carboxylate salt intermediate, enabling effective separation and purification of the onium salt to achieve high cellulose solubility

Inventive Principle:
Principle #24Intermediary (Mediator)

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 method achieves an onium salt with minimal carboxylic acid content, significantly improving cellulose solubility, making it effective as a cellulose solvent.

Implementation Method 1

adding an amine to the mixture containing the onium salt and the carboxylic acid to generate an amine-carboxylic acid salt

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Implementation Method 2

separating the onium salt from the amine-carboxylic acid salt generated in step (2)

Methodology Applied
Scientific EffectPhase separation: Liquid-Liquid Extraction

Data Source

PatentUS20250109090A1Method for producing onium salt and method for purifying onium salt
Publication Date: 2025.04.03 KOEI CHEMICAL CO LTD
  • US20250109090A1 patent drawing
  • US20250109090A1 patent drawing
  • US20250109090A1 patent drawing

AI summary

The present invention provides a method for producing an onium salt that is free of carboxylic acid or an onium salt with a decreased carboxylic acid content to such an extent that sufficient solubility of cellulose in the onium salt is achieved. The method for obtaining an onium salt from a mixture containing the onium salt and a carboxylic acid includes the following steps (1), (2) and (3): step (1) of obtaining a mixture containing an onium salt and a carboxylic acid, step (2) of adding an amine to the mixture containing the onium salt and the carboxylic acid to form an amine-carboxylic acid salt formed of the amine and the carboxylic acid, and step (3) of separating the onium salt from the amine-carboxylic acid salt produced in step (1) to obtain the onium salt.