Isohexide Glycidyl Ether Synthesis via Azeotropic Distillation

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Solution Overview

Problem

Existing methods for producing bis-anhydrohexitol ethers, such as isosorbide glycidyl ether, often use hazardous materials, solvents, or high-pressure conditions, resulting in compositions with high monofunctional and oligomeric content, which limits the formation of three-dimensional networks with high crosslinking density and glass transition temperature.

Innovation Solution

A process involving azeotropic distillation under reduced pressure, where a dianhydrohexitol is reacted with an organic halide, heated, and then treated with a basic reagent, minimizing the use of hazardous substances and optimizing for diepoxy derivatives, thereby increasing the crosslinking density and glass transition temperature of the resulting epoxy resins.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If conventional synthesis methods using hazardous materials and solvents are used, then the production process can be carried out, but the safety and environmental compliance deteriorate

Engineering Contradiction:

Improveproduction process feasibilityVSAvoidsafety and environmental compliance

Core Design Contradiction:

Ease of manufactureVSObject-affected harmful factors

Solution Approach 1:

The patent removes hazardous substances (benzene, toluene, sodium hydride, sodium metal) from the synthesis process entirely, replacing them with safe alternatives (water, atmospheric pressure conditions) while maintaining production feasibility

Inventive Principle:

Principle #2Taking out (Extraction)

Solution Approach 2:

The patent changes the reaction conditions from high temperature and pressure (200-300°C, 5 MPa) to atmospheric pressure and moderate temperature, eliminating the need for specialized high-pressure equipment and improving safety

Inventive Principle:

Principle #35Parameter changes

2Ease of manufacture

If high monofunctional and oligomeric content is present in the composition, then the synthesis is simpler, but the crosslinking density and glass transition temperature deteriorate

Engineering Contradiction:

Improvesynthesis simplicityVSAvoidcrosslinking density and glass transition temperature

Core Design Contradiction:

Ease of manufactureVSManufacturing precision

Solution Approach 1:

The patent optimizes reaction parameters (atmospheric pressure, moderate temperature, controlled reaction time) to favor the formation of diepoxy derivatives over monofunctional and oligomeric products, achieving high crosslinking density without complex synthesis procedures

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The patent employs azeotropic distillation to continuously remove water from the reaction system, shifting the equilibrium toward complete etherification and diepoxy derivative formation, thereby improving both selectivity and crosslinking density

Inventive Principle:

Principle #23Feedback

3Manufacturing precision

If azeotropic distillation is carried out under reduced pressure, then the selectivity for diepoxy derivatives improves, but the device complexity increases

Engineering Contradiction:

Improveselectivity for diepoxy derivativesVSAvoidvacuum system requirements

Core Design Contradiction:

Manufacturing precisionVSDevice complexity

Solution Approach 1:

Instead of using reduced pressure to facilitate azeotropic distillation, the patent performs distillation at atmospheric pressure, inverting the conventional approach and eliminating vacuum system requirements while maintaining high selectivity for diepoxy derivatives

Inventive Principle:

Principle #13The other way round (Inversion)

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 produces bis-anhydrohexitol ether compositions rich in diepoxy derivatives with low oligomer content, enhancing the chemical resistance, mechanical strength, and glass transition temperature of the materials, making them more suitable for applications in composite materials, coatings, and adhesives.

Implementation Method 1

azeotropic distillation carried out under reduced pressure

Methodology Applied

Scientific EffectAzeotropic distillation: Distillation

Implementation Method 2

azeotropic distillation carried out under reduced pressure

Methodology Applied

Scientific EffectReduced pressure distillation: Vacuum Distillation

Implementation Method 3

reacting a bis-anhydrohexitol and an alkyl carbonate in the presence of a basic catalyst

Methodology Applied

Scientific EffectBase-catalyzed etherification: Chemical Bonding

Implementation Method 4

heating in order to carry out the etherification reaction

Methodology Applied

Scientific EffectThermal activation: Heating

Data Source

PatentUS10174152B2Process for producing isohexide glycidyl ethers, products thus obtained, and uses thereof

Publication Date: 2019.01.08 ROQUETTE FRERES SA

AI summary

A process for producing bis-anhydrohexitol ether compositions and in particular isohexide glycidyl ether compositions, one of the originalities of which is azeotropic distillation carried out under reduced pressure. Such compositions are used to produce epoxy resins, the function thereof being to form a three-dimensional macromolecular network. The compositions obtained according to the process are rich in diepoxy derivatives of isosorbide to the detriment of monoepoxy derivatives, only the first participating in the formation of the three-dimensional network. The crosslinking density is therefore increased, thereby making it possible to obtain a material which is more chemically resistant and mechanically stronger and which has a higher glass transition temperature (Tg), compared with the same materials obtained with bis-anhydrohexitol ether compositions according to the prior art.