Method for preparing organic carboxylic ester by using combined catalyst of aryl bidentate phosphine ligand
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Solution Overview
Problem
Existing catalysts for olefin hydroesterification, such as those using alkyl phosphine ligands, are unstable in air, leading to increased costs for industrial applications and a need for a more stable and efficient synthesis method.
Innovation Solution
A combined catalyst system comprising a palladium compound, an aryl bidentate phosphine ligand, and an acidic additive is used for olefin hydroesterification, with specific molar ratios and reaction conditions to produce organic carboxylic esters.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If alkyl phosphine ligands are used in the catalyst system, then high catalytic activity is achieved, but air stability deteriorates
Solution Approach 1:
The invention changes the chemical structure parameters of the phosphine ligand from alkyl groups to aryl groups (specifically substituted phenyl groups). This structural parameter change transforms the ligand from air-unstable alkyl phosphine to air-stable aryl phosphine, while maintaining catalytic activity through appropriate substituent selection (electron-donating or electron-withdrawing groups).
Solution Approach 2:
The invention creates a composite catalyst system combining palladium metal center with specially designed aryl bidentate phosphine ligands. The bidentate structure with two phosphine groups coordinated to palladium forms a stable chelate complex, and the aryl substituents provide both stability and tunable electronic properties for maintaining catalytic activity.
2Reliability
If complex catalyst systems are developed to improve stability, then air stability is improved, but device complexity increases
Solution Approach 1:
The invention applies local quality by introducing specific substituents at particular positions on the phenyl rings of the bidentate phosphine ligand. The substituents (electron-donating or electron-withdrawing groups) are placed at ortho, meta, or para positions to optimize both stability and catalytic activity without requiring complex overall structures. This localized modification achieves stability improvements with minimal increase in system complexity.
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 method achieves high conversion rates and selectivity for organic carboxylic esters, addressing the stability and efficiency issues of previous catalysts.
Implementation Method 1
subjecting a terminal olefin, carbon monoxide and an alcohol to a hydroesterification reaction in an organic solvent in the presence of a combined catalyst of a palladium compound, an aryl bidentate phosphine ligand and an acidic additive
Data Source
AI summary
Disclosed is a method for preparing an organic carboxylic ester by using a combined catalyst of an aryl bidentate phosphine ligand. The method includes subjecting a terminal olefin, carbon monoxide, and an alcohol to a hydroesterification reaction in the presence of a combined catalyst of a palladium compound, an aryl bidentate phosphine ligand, and an acidic additive, to generate an organic carboxylic ester having one more carbon atom than the terminal olefin.