Polyvalent Alcohol Ester Synthesis via Swollen Cation Resin

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Solution Overview

Problem

Current methods for producing polyvalent alcohol esters, such as mono- and di-fatty acid esters, require high-temperature conditions, leading to the formation of harmful by-products and are inefficient in selectively synthesizing diesters, which complicates the separation process and increases production costs.

Innovation Solution

A method using a cation exchange resin as an acidic solid catalyst, swollen with the reaction raw materials, allows for the selective production of mono- or poly-fatty acid esters of polyvalent alcohols under mild conditions without solvents, enabling high-conversion ester synthesis and reducing separation loads.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If high-temperature conditions are used to achieve high conversion in esterification reaction, then conversion rate is improved, but harmful by-products (glycidol and 3-MCPD) are generated

Engineering Contradiction:
Improveconversion rateVSAvoidharmful by-products
Core Design Contradiction:
ProductivityVSObject-generated harmful factors

Solution Approach 1:

The patent changes the temperature parameter from high-temperature (conventional esterification requires high temperature for high conversion) to mild-temperature conditions by introducing a solid acid catalyst, thereby achieving high conversion without generating harmful by-products like glycidol and 3-MCPD that form at high temperatures

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent replaces the conventional homogeneous acid catalyst system with a solid acid catalyst system, substituting the chemical mechanism with a heterogeneous catalytic mechanism that enables mild reaction conditions and avoids harmful by-product formation

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

2Productivity

If severe conditions are used to synthesize diester, then diester yield is improved, but selectivity decreases and separation operation becomes necessary

Engineering Contradiction:
Improvediester yieldVSAvoidselectivity
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The patent changes the reaction conditions from severe (high temperature, long time) to mild conditions by using a solid acid catalyst, and optimizes parameters such as molar ratio of polyvalent alcohol to fatty acid (1:1 to 4:1), temperature (40-100°C), and reaction time to achieve both high diester yield and high selectivity without requiring separation operations

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs feedback control by monitoring the reaction progress and adjusting parameters such as molar ratio and reaction time based on the desired product distribution, allowing optimization of selectivity for diester while maintaining high yield through the solid acid catalyst system

Inventive Principle:
Principle #23Feedback

3Productivity

If homogeneous acid catalyst is used for esterification reaction, then reaction efficiency is improved, but separation operation and cost increase

Engineering Contradiction:
Improvereaction efficiencyVSAvoidseparation operation
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent extracts the catalyst from the homogeneous phase and places it in the solid phase, allowing easy separation by filtration or decantation. The solid acid catalyst can be removed from the reaction mixture by simple physical separation methods, eliminating the need for complex separation operations required when using homogeneous acid catalysts

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent substitutes the homogeneous acid catalyst system with a heterogeneous solid acid catalyst system, replacing the chemical separation complexity with simple physical separation, thereby reducing device complexity and operational costs while maintaining high reaction efficiency

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

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 enables selective production of esters with high selectivity and reduced catalyst activity degradation, allowing for single-stage synthesis of high molecular weight esters at lower costs and simplifying the separation process through filtration, thereby reducing production costs and environmental impact.

Implementation Method 1

a method using a cation exchange resin as an acidic solid catalyst, swollen with the reaction raw materials, allows for the selective production of mono- or poly-fatty acid esters

Methodology Applied
Scientific EffectAcid catalysis: Catalysis

Implementation Method 2

when, as a pretreatment, the cation exchange resin used as a catalyst is swollen with the reaction raw polyvalent alcohol or carboxylic acid compound

Methodology Applied
Scientific EffectAbsorption: Absorption (physical)

Data Source

PatentUS11691940B2Production method for polyvalent alcohol ester compounds
Publication Date: 2023.07.04 TOHOKU UNIV
  • US11691940B2 patent drawing
  • US11691940B2 patent drawing
  • US11691940B2 patent drawing

AI summary

A method for producing a polyvalent alcohol ester compound, characterized in that a polyvalent alcohol compound and a carboxylic acid compound are allowed to react in the presence of an acidic solid catalyst swollen with the polyvalent alcohol compound or the carboxylic acid compound without using a solvent to selectively produce a monocarboxylic acid ester or a polycarboxylic acid ester of a polyvalent alcohol. In this manner, a mono-fatty acid ester and a poly-fatty acid ester (e.g., di-fatty acid ester) of a polyvalent alcohol can be selectively and effectively produced from a polyvalent alcohol compound and a fatty acid compound.