Ester Mixture Composition Control via Boiling Point Segregation

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Solution Overview

Problem

Existing methods for producing ester mixtures struggle to achieve controlled compositions of mixed and unmixed esters, leading to uncontrollable deviations from statistical expectations, which complicates the production process and results in unfavorable properties for plasticizer applications.

Innovation Solution

A process involving the reaction of ester A(COOR)x+1 with a mixture of alcohols R1OH and R2OH, where the alcohol with a lower boiling point is heated to boiling, allowing for the controlled formation of ester mixtures with predetermined quantitative distributions of unmixed and mixed esters, thereby minimizing deviations from statistical expectations.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If ester mixtures are produced by esterifying acids with an alcohol mixture, then the process is simple, but the composition distribution of esters cannot be precisely controlled and deviates significantly from statistical expectations

Engineering Contradiction:
Improveprocess simplicityVSAvoidester composition control
Core Design Contradiction:
Ease of manufactureVSManufacturing precision

Solution Approach 1:

The process segments the esterification into two distinct stages: first producing unmixed esters with controlled composition, then adding mixed esters in precisely calculated amounts. This segmentation allows independent control of each ester type's formation, achieving both process simplicity and composition precision that cannot be obtained through simple one-step esterification with alcohol mixtures.

Inventive Principle:
Principle #1Segmentation

2Manufacturing precision

If separate esterification reactions are performed for each ester type and then blended, then precise composition control is achieved, but the production process becomes complex and time-consuming

Engineering Contradiction:
Improveester composition controlVSAvoidproduction process complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The invention merges the advantages of controlled separate esterification with the simplicity of mixture processing by performing one primary esterification reaction to produce unmixed esters, then adding pre-synthesized mixed esters in controlled amounts. This combination achieves precise composition control without requiring multiple separate esterification reactions and blending operations, thereby reducing equipment and time requirements.

Inventive Principle:
Principle #5Merging (Combining)

3Adaptability or versatility

If alcohol mixtures are used in esterification, then mixed esters are formed, but the distribution of alcohol residues in the ester mixture does not match the alcohol mixture composition

Engineering Contradiction:
Improvemixed ester formationVSAvoidalcohol residue distribution control
Core Design Contradiction:
Adaptability or versatilityVSManufacturing precision

Solution Approach 1:

The process incorporates feedback control by calculating the exact amounts of mixed esters needed based on the desired final composition, then adding precisely measured quantities. This feedback mechanism ensures that the alcohol residue distribution in the final ester mixture matches the target composition, correcting the inherent unpredictability of direct mixture esterification.

Inventive Principle:
Principle #23Feedback

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 process enables the production of ester mixtures with precise control over the composition, reducing processing complexity and improving the properties of plasticizers by aligning them with desired application requirements.

Implementation Method 1

the alcohol with a lower boiling point is heated to boiling

Methodology Applied
Scientific EffectBoiling: Boiling

Implementation Method 2

A(COOR)x+1 is reacted with a mixture of the alcohols R1OH and R2OH

Methodology Applied
Scientific EffectTransesterification: Chemical Transport Reactions

Data Source

PatentEP3059223B1Preparation of ester mixtures
Publication Date: 2023.06.28 EVONIK OXENO GMBH & CO KG
  • EP3059223B1 patent drawingFigure 1

AI summary

Ester mixtures comprising the esters A(COOR1)(COOR1)x, A(COOR1)(COOR2)x, A(COOR2)(COOR1)x and A(COOR2)(COOR2)x can be selectively prepared by processes in which acids A(COOH)x+1 or their derivatives are reacted with an amount (m1 + s1) of R1OH and an amount m2 of R2OH, wherein the reaction mixture is heated to boiling, the alcohol R1OH has a lower boiling point than the alcohol R2OH, A represents an aromatic, alicyclic or aliphatic residue, x is 1 or 2, and R1 and R2 independently represent substituted or unsubstituted aryl residues or linear or branched, substituted or unsubstituted alkyl residues with 3 to 20 carbon atoms, m1 and m2 being the molar equivalents of the esters in A(COOH)x+1 or their derivatives derivatives to be introduced correspond to alcohol residues OR1 and OR2 and s1 is greater than 0.