Titanium Catalyst Ligand Design for Esterification Efficiency

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Existing methods for esterification of carboxylic acids with alcohols in the presence of titanium catalysts require long reaction times and large amounts of catalyst, resulting in low conversion rates and yields, leading to inefficient product manufacturing processes.

Innovation Solution

The use of titanium organic catalysts with at least two alkoxy and two aryloxy groups, which exhibit higher catalytic activity and stability, allowing for reduced catalyst amounts and reaction times while increasing conversion rates and yields.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional titanium catalysts are used in esterification, then the reaction can proceed, but long reaction times and large amounts of catalyst are required, resulting in low conversion rates and yields

Engineering Contradiction:
Improvereaction rateVSAvoidreaction time
Core Design Contradiction:
ProductivityVSLoss of time

Solution Approach 1:

The patent modifies the catalyst structure by changing the ligand environment of titanium from conventional single-donor ligands to bidentate ligands (such as acetylacetonate and salicylaldimine). This structural parameter change increases the catalytic activity and stability of the titanium complex, enabling faster reaction rates and higher conversion rates while reducing the required catalyst amount and reaction time

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite catalyst systems by combining titanium with specific organic ligands (bidentate ligands) to form titanium-organic complex catalysts. This composite approach leverages the synergistic effect between the metal center and the organic ligands, resulting in enhanced catalytic performance with higher activity, better stability, and improved selectivity compared to conventional titanium catalysts

Inventive Principle:
Principle #40Composite materials

2Productivity

If conventional titanium catalysts are used, then esterification can occur, but large amounts of catalyst are required, leading to increased costs and reduced efficiency

Engineering Contradiction:
Improveconversion rateVSAvoidcatalyst amount
Core Design Contradiction:
ProductivityVSQuantity of substance

Solution Approach 1:

By changing the catalyst structure to incorporate bidentate ligands, the patent increases the catalytic activity per unit of titanium. This structural modification allows the same conversion rate to be achieved with significantly less catalyst, improving both economic efficiency and process sustainability

Inventive Principle:
Principle #35Parameter changes

3Productivity

If mineral acids are used as catalysts, then esterification proceeds efficiently, but equipment corrosion increases and neutralization costs rise

Engineering Contradiction:
Improvereaction efficiencyVSAvoidequipment corrosion
Core Design Contradiction:
ProductivityVSObject-affected harmful factors

Solution Approach 1:

The patent introduces titanium-organic complex catalysts as an intermediary substance that mediates the esterification reaction without the corrosive effects of mineral acids. These organic-based titanium catalysts provide the necessary catalytic activity while being non-corrosive to equipment and eliminating the need for costly neutralization steps, thus resolving the contradiction between reaction efficiency and equipment protection

Inventive Principle:
Principle #24Intermediary (Mediator)

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 significantly enhances the efficiency of the esterification process by achieving higher product yields and conversion rates with less catalyst, improving the overall performance of the manufacturing equipment.

Implementation Method 1

esterification of carboxylic acids with alcohols in the presence of a catalyst based on titanium organic compounds

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentEP3194357B1Process for preparing carboxylic acid esters in the presence of a titanium-containing catalyst
Publication Date: 2019.05.08 PUBLIC JOINT STOCK COMPANY SIBUR HOLDING
  • EP3194357B1 patent drawingFigure 1
  • EP3194357B1 patent drawingFigure 2
  • EP3194357B1 patent drawingFigure 3

AI summary

The present invention relates to a process for preparing carboxylic acid esters, comprising esterification of a carboxylic acid with an alcohol in the presence of a titanium-containing catalyst selected from compounds of a general formula, Tin(OR)x(OR')xOy, wherein n is an integer from 1 to 4; у is an integer from 0 to 6; x can be the same or different and is an integer from 2 to 8; R is a linear or branched C1-C18alkyl, C3-C18cycloalkyl, R' is aryl optionally comprising an electron-donor substituent; or a mixture thereof, with the proviso that if n is 1, then x is 2 and у is 0; and if n>1, then the compounds comprise at least two alkoxy groups and two aryloxy groups. The present invention also relates to a process for preparing carboxylic acid esters, wherein a compound of general formula (I) or (II), wherein q represents an integer of 1 to 4; Y is independently R or R'; or a mixture thereof, with the proviso that the compounds comprise at least two alkoxy groups and two aryloxy groups, is used as a catalyst. The claimed process allows to reduce the amount of a used catalyst and the time of the process duration, while increasing the conversion rate of initial reagents and the yield of a target product.