Epoxy Compound Production via Organophosphorus Stabilizer

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Solution Overview

Problem

The production of epoxy compounds by reacting olefin compounds with hydrogen peroxide often results in excessive oxygen gas generation, posing safety concerns, especially in large-scale reactions, as existing methods are inadequate in controlling oxygen gas concentrations effectively.

Innovation Solution

A method involving a reaction medium with a pH range of 7.5 to 12.0, using an organophosphorus compound as a hydrogen peroxide stabilizer, alongside a nitrile compound and an alkaline substance, to reduce oxygen gas generation and stabilize the production of epoxy compounds.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If hydrogen peroxide is used in excess amount for epoxidation reaction, then epoxy compound production efficiency is improved, but oxygen gas generation increases causing safety hazards

Engineering Contradiction:
Improveepoxy compound production efficiencyVSAvoidoxygen gas concentration
Core Design Contradiction:
ProductivityVSObject-affected harmful factors

Solution Approach 1:

The patent introduces a phase transfer catalyst as an intermediary substance that mediates between hydrogen peroxide and the olefin substrate. This catalyst enables the reaction to proceed efficiently with reduced hydrogen peroxide excess, thereby decreasing oxygen gas generation while maintaining productivity. The phase transfer catalyst facilitates the reaction by transferring reactants between phases, allowing for better control of reagent consumption.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent changes the reaction parameters by optimizing the pH range (maintaining pH 7.5-12.0) and adjusting the molar ratio of hydrogen peroxide to olefin. By controlling these parameters, the reaction achieves high efficiency with minimal excess hydrogen peroxide, thus reducing oxygen gas generation to safe levels while maintaining high epoxy compound production.

Inventive Principle:
Principle #35Parameter changes

2Object-affected harmful factors

If nitrogen gas flow is used to decrease oxygen gas concentration in reactor, then safety is improved, but device complexity and operational cost increase for large-scale reactions

Engineering Contradiction:
Improveoxygen gas concentrationVSAvoidgas flow control system
Core Design Contradiction:
Object-affected harmful factorsVSDevice complexity

Solution Approach 1:

The patent converts the harmful effect of oxygen gas generation into a beneficial outcome by using the phase transfer catalyst to enable complete reaction of hydrogen peroxide. The catalyst ensures that hydrogen peroxide is consumed efficiently, converting the potential hazard of excess oxygen into a benefit of controlled, complete reaction that minimizes gas generation while maintaining safety.

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

3Strength

If crystalline epoxy resin is used for high heat resistance applications, then physical properties of cured product are improved, but molding flexibility is restricted

Engineering Contradiction:
Improveheat resistanceVSAvoidmolding application range
Core Design Contradiction:
StrengthVSAdaptability or versatility

Solution Approach 1:

The patent changes the physical state parameter of the epoxy resin from crystalline to liquid by modifying the molecular structure and reaction conditions. This parameter change enables the resin to be used in liquid molding applications while maintaining the high heat resistance properties, thus expanding the range of applicable molding techniques from only solid-state processes to include casting, coating, and other liquid-phase formulations.

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 allows for stable and safe production of epoxy compounds, enabling large-scale production by minimizing oxygen gas generation and improving the physical properties of the cured products, such as heat resistance and toughness.

Implementation Method 1

hydrogen peroxide is added in an excess amount relative to the olefin compound. At this time, an oxygen gas is generated from hydrogen peroxide

Methodology Applied
Scientific EffectDecomposition: Decomposition (biological)

Implementation Method 2

it is necessary that the oxygen gas concentration in a reactor be decreased to a concentration of lower explosion limit in terms of safety of a process... using a hydrogen peroxide stabilizer for decreasing an oxygen gas generated from hydrogen peroxide

Methodology Applied
Scientific EffectStabilization:

Implementation Method 3

A method for producing an epoxy compound by a reaction of an olefin compound with hydrogen peroxide

Methodology Applied
Scientific EffectOxidation: Oxidation

Data Source

PatentUS10005742B2Method for producing epoxy compound containing hydrogen peroxide stabilizer
Publication Date: 2018.06.26 NISSAN CHEM CORP

AI summary

The present invention provides a method for producing an epoxy compound by a reaction of an olefin compound with hydrogen peroxide, wherein the epoxy compound is stably and safely produced using a hydrogen peroxide stabilizer for reducing an oxygen gas generated from hydrogen peroxide. A method for producing an epoxy compound by a reaction of an olefin compound with hydrogen peroxide, wherein the reaction is carried out in the presence of an organophosphorus compound in such a reaction medium that the pH is maintained within a range of more than 7.5 and less than 12.0. The olefin compound may be 1,3,5-tris-(alkenyl)-isocyanurate. The alkenyl group in the olefin compound may be 3-butenyl group, 4-pentenyl group, 5-hexenyl group, 6-heptenyl group, or 7-octenyl group. The epoxy compound may be 1,3,5-tris-(epoxyalkyl)-isocyanurate. The reaction medium may be such a reaction medium that the pH is maintained within a range of 8.0 to 10.5.