Onium Salt Catalyst for High-Purity Epoxy Production

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Solution Overview

Problem

Conventional methods for producing epoxy compounds with low heavy metal and nitrogen-containing compound content are cumbersome and inefficient, often requiring complex purification processes and resulting in residual impurities that affect the quality of epoxy resins used in electronic and optical materials.

Innovation Solution

A method involving an onium salt with substituents convertible to active hydrogen-containing functional groups is used in the epoxidation reaction, allowing for easy separation and removal of catalyst components, resulting in a high-purity epoxy compound with reduced heavy metal and nitrogen content.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If conventional epoxidation methods using ammonium salts or pyridinium salts with long-chain alkyl groups are employed, then the epoxidation reaction can proceed effectively, but the catalyst components become very difficult to separate and purify from the epoxy compound, resulting in high residual heavy metal and nitrogen content

Engineering Contradiction:
Improvepurity of epoxy compoundVSAvoidcomplexity of purification process
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent changes the chemical structure parameters of the onium salt catalyst by replacing long-chain alkyl groups with short-chain alkyl groups or hydrogen atoms. This parameter change fundamentally alters the solubility and separation characteristics of the catalyst, enabling easy removal through simple washing with water or dilute acid without requiring complex purification processes, thus achieving high-purity epoxy compounds with very low heavy metal and nitrogen content

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent extracts the harmful long-chain alkyl groups from the onium salt catalyst structure and replaces them with removable short-chain groups or hydrogen atoms. This extraction approach allows the catalyst components to be easily separated and removed from the reaction mixture through simple washing operations, leaving the epoxy compound with minimal residual impurities

Inventive Principle:
Principle #2Taking out (Extraction)

2Productivity

If palladium catalyst is used for condensing allyl alcohol to form allyl ether, then the epoxy compound can be produced, but the residual palladium contacts with peroxide to decompose it, requiring cumbersome purification processes

Engineering Contradiction:
Improveproduction efficiency of epoxy compoundVSAvoidsimplicity of purification process
Core Design Contradiction:
ProductivityVSEase of manufacture

Solution Approach 1:

The patent employs a disposable onium salt catalyst system where the catalyst is designed to be easily removed and discarded after a single use. The short-chain alkyl group modification enables the catalyst to be completely washed away with water or dilute acid, eliminating the need for complex recovery processes and making the overall manufacturing process simpler and more efficient

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

3Reliability

If onium salts with long-chain alkyl groups are used as catalysts, then the epoxidation reaction proceeds well, but the onium salt has high distribution factor to organic solvent, making separation and purification of epoxy compound from catalyst components extremely difficult

Engineering Contradiction:
Improveeffectiveness of epoxidation reactionVSAvoidease of separation and purification
Core Design Contradiction:
ReliabilityVSEase of operation

Solution Approach 1:

The patent changes the hydrophobicity parameter of the onium salt by replacing long-chain alkyl groups with short-chain groups or hydrogen atoms. This parameter change reduces the distribution factor of the catalyst to organic solvents, fundamentally improving the ease of separation and purification operations while maintaining the catalytic effectiveness of the epoxidation reaction

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

This approach simplifies the production of epoxy compounds with very low heavy metal and nitrogen content, improving the purity and quality of epoxy resins for electronic and optical applications without the need for cumbersome purification processes.

Implementation Method 1

reacting hydrogen peroxide with a compound having a carbon-carbon double bond in the presence of at least either a tungsten compound or a molybdenum compound and an onium salt... This epoxidation reaction generates only water as a byproduct

Methodology Applied
Scientific EffectOxidation: Oxidation

Implementation Method 2

an onium salt having 20 or more carbon atoms and containing one or more substituents convertible to an active hydrogen-containing functional group... allowing for easy separation and removal of catalyst components

Methodology Applied
Scientific EffectHydrolysis: Hydrolysis

Data Source

PatentUS10730846B2Method of producing epoxy compound and catalyst composition for epoxidation reaction
Publication Date: 2020.08.04 MITSUBISHI CHEM CORP
  • US10730846B2 patent drawing
  • US10730846B2 patent drawing
  • US10730846B2 patent drawing

AI summary

A method of producing an epoxy compound, which comprises reacting hydrogen peroxide with a compound having a carbon-carbon double bond, in the presence of at least one of a tungsten compound and a molybdenum compound; and an onium salt comprising 20 or more carbon atoms and one or more of substituents convertible to a functional group containing an active hydrogen or a salt thereof.