Transesterification Process for Controlled Ester Mixture Distribution

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Solution Overview

Problem

Existing processes for producing ester mixtures face challenges in controlling the distribution of ester compositions, leading to uncontrollable deviations from statistical expectations, requiring multiple costly and time-consuming steps, and resulting in ester mixtures with unfavorable properties for high-temperature applications and polymer compatibility.

Innovation Solution

A process involving the reaction of ester A(COOR1)(COOR1)x with less than 1 mole equivalent of alcohol R2OH, where R1OH has a lower boiling point than R2OH, allowing for the removal of more than 90% of R1OH before catalyst destruction, resulting in a controlled composition of unmixed and mixed esters with predetermined quantitative distribution.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If ester mixtures are produced by esterifying acids with an alcohol mixture, then mixed esters are formed, but the distribution of esters cannot be specifically adjusted and deviates uncontrollably from statistical expectations

Engineering Contradiction:
Improveability to adjust ester distributionVSAvoidcontrol of ester composition
Core Design Contradiction:
Adaptability or versatilityVSManufacturing precision

Solution Approach 1:

The patent applies preliminary action by first producing pure unmixed esters (e.g., C8-diesters and C9-diesters) through controlled esterification reactions before combining them to form the final ester mixture. This preliminary production of pure components allows for precise control over the final ester distribution, eliminating the uncontrollable deviations that occur when attempting to produce mixed esters directly in a single step.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent segments the ester production process into separate reactions: first producing C8-diesters and C9-diesters independently through controlled esterification, then combining them to create the desired ester mixture. This segmentation allows each ester type to be produced with controlled composition, and their combination yields the target distribution without the statistical deviations observed in direct mixture esterification.

Inventive Principle:
Principle #1Segmentation

2Manufacturing precision

If multiple separate esterification reactions are performed to control ester distribution, then manufacturing precision improves, but equipment and time expenditure increases

Engineering Contradiction:
Improvecontrol of ester compositionVSAvoidproduction efficiency
Core Design Contradiction:
Manufacturing precisionVSProductivity

Solution Approach 1:

The patent merges the production of multiple esters into a single controlled esterification reaction by using an alcohol mixture containing both C8-alcohol and C9-alcohol in specific ratios. This allows simultaneous formation of C8-diesters, C9-diesters, and mixed esters in one reactor, eliminating the need for multiple separate esterification reactions while maintaining precise control over the final ester distribution through the initial alcohol composition.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The patent changes the parameters of the esterification reaction by controlling the composition and ratio of alcohols in the alcohol mixture feedstock. By adjusting the C8-alcohol to C9-alcohol ratio in the feed, the process directly controls the final distribution of esters in the product, achieving precise manufacturing control without requiring multiple reaction steps or complex post-reaction adjustments.

Inventive Principle:
Principle #35Parameter changes

3Temperature

If high-temperature applications use esters with high heat resistance, then thermal stability improves, but polymer compatibility deteriorates

Engineering Contradiction:
Improveheat resistanceVSAvoidpolymer compatibility
Core Design Contradiction:
TemperatureVSReliability

Solution Approach 1:

The patent creates a composite ester mixture containing multiple ester types (C8-diesters, C9-diesters, and mixed esters) in specific proportions. This composite composition combines the high heat resistance properties of longer-chain esters with the good polymer compatibility of shorter-chain esters, achieving a balanced plasticizer system that simultaneously provides both thermal stability and compatibility with polymers like PVC.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent applies local quality by creating an ester mixture where different ester components serve different functional roles: C8-diesters and C9-diesters provide heat resistance, while the mixed esters and shorter-chain components provide polymer compatibility. Each ester type contributes its specific properties to the overall system, allowing the plasticizer to exhibit both high heat resistance and good polymer compatibility simultaneously.

Inventive Principle:
Principle #3Local quality

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 achieves ester mixtures with reduced deviations from statistical expectations, improving heat resistance, compatibility, and volatility, while reducing equipment and time expenditure, enabling the production of ester mixtures with specific properties for various applications.

Implementation Method 1

Process for the preparation of ester mixtures by transesterification

Methodology Applied
Scientific EffectTransesterification: Chemical Bonding

Implementation Method 2

allowing for the removal of more than 90% of R1OH before catalyst destruction

Methodology Applied
Scientific EffectEvaporation: Evaporation

Implementation Method 3

where R1OH has a lower boiling point than R2OH

Methodology Applied
Scientific EffectDistillation: Distillation

Data Source

PatentEP3059222B1Process for the preparation of ester mixtures by transesterification
Publication Date: 2018.06.27 EVONIK OPERATIONS GMBH
  • EP3059222B1 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 the ester A(COOR1)(COOR1)x is reacted with less than 1 mol equivalent, based on the number of its ester functional groups, of the alcohol R2OH and heated to boiling, wherein the alcohol R1OH has a lower boiling point at a given pressure than the alcohol R2OH at the same pressure, and 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.