Ester Synthesis via Vinyl Acetate Carbonylation

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Solution Overview

Problem

Existing methods for producing ester compounds, such as lactic acid ester and acetic acid ester, face inefficiencies in yield and production processes.

Innovation Solution

A method involving the reaction of vinyl acetate with a primary or secondary alcohol and carbon monoxide in the presence of specific catalysts, followed by an intermediate reduction step and subsequent reaction with an alcohol to produce lactic acid ester and acetic acid ester, utilizing catalysts like palladium chloride and organic phosphine ligands.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional methods are used for producing ester compounds, then the production process can be carried out with standard catalysts, but the yield and production efficiency are insufficient

Engineering Contradiction:
Improveproduction efficiencyVSAvoidyield
Core Design Contradiction:
ProductivityVSQuantity of substance

Solution Approach 1:

The patent changes the chemical parameters by introducing specific catalyst systems (palladium chloride combined with phosphine ligands like PPh3 or PCy3) and controlling reaction conditions (CO pressure, temperature, solvent type) to transform the carbonylation process, achieving both high yield and production efficiency that conventional methods cannot simultaneously achieve

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs a composite catalytic system combining palladium chloride with organic phosphine ligands (such as triphenylphosphine or tricyclohexylphosphine) to create a synergistic catalyst that significantly improves both the yield and production efficiency of the ester compound synthesis, overcoming the limitations of single-component catalysts

Inventive Principle:
Principle #40Composite materials

2Manufacturing precision

If standard catalytic systems are used, then the process is simpler, but the selectivity and yield of lactic acid ester and acetic acid ester are low

Engineering Contradiction:
ImproveselectivityVSAvoidcatalyst system complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent optimizes specific parameters including the molar ratio of PdCl2 to phosphine ligand (1:2 to 1:4), CO pressure (3-10 atm), and reaction temperature (60-100°C) to achieve high selectivity for lactic acid ester and acetic acid ester, where the precise control of these parameters enables superior manufacturing precision despite the complexity of the catalytic system

Inventive Principle:
Principle #35Parameter changes

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 method enables the efficient production of lactic acid ester and acetic acid ester with high yields, improving the overall process efficiency and selectivity.

Implementation Method 1

reacting vinyl acetate with methanol and carbon monoxide using a palladium catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

a catalytic system in which (a) a metal of Group VIIIB or a compound thereof and (b) a specific bidentate phosphine are combined

Methodology Applied
Scientific EffectLigand coordination: Chemisorption

Data Source

PatentUS20230192589A1Method for producing ester compound
Publication Date: 2023.06.22 RESONAC CORP
  • US20230192589A1 patent drawing
  • US20230192589A1 patent drawing
  • US20230192589A1 patent drawing

AI summary

What is provided is a production method in which a vinyl acetate is reacted with a primary or secondary alcohol represented by Formula (1) and carbon monoxide to produce a first ester compound represented by Formula (2), and the first ester compound is reacted with an alcohol to produce a lactic acid ester represented by Formula (3) and an acetic acid ester represented by Formula (4).