Alkoxycarbonylation Two-Phase System Catalyst Separation

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Solution Overview

Problem

Existing alkoxy carbonylation processes for producing aliphatic esters face inefficiencies, high energy requirements, and challenges in catalyst separation from the product.

Innovation Solution

A two-phase reaction system using an organophosphorous ligand-modified metal complex catalyst, where aliphatic olefins and alcohols react in separate aqueous and organic phases, allowing for efficient ester production with low catalyst concentrations and easy energy-saving catalyst separation.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If a homogeneous reaction system is used for alkoxycarbonylation, then reaction efficiency is improved, but catalyst separation from product becomes difficult and energy-consuming

Engineering Contradiction:
Improvereaction efficiencyVSAvoidenergy consumption for catalyst separation
Core Design Contradiction:
ProductivityVSLoss of energy

Solution Approach 1:

The reaction system is divided into two distinct phases: an aqueous phase containing the water-soluble metal complex catalyst and an organic phase containing the olefin and alcohol reactants. This segmentation allows the catalyst to remain in the aqueous phase while products form in the organic phase, enabling easy phase separation and catalyst recovery without energy-intensive distillation processes.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

Water-soluble organophosphorus ligands act as intermediaries that modify the metal complex catalyst to enhance its water solubility. These ligands serve as the connecting element between the hydrophobic catalyst core and the hydrophilic aqueous environment, allowing the catalyst to function in the two-phase system while maintaining ease of separation.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Productivity

If high catalyst concentrations are used to achieve high conversions, then reaction yield is improved, but catalyst separation complexity increases

Engineering Contradiction:
Improvereaction yieldVSAvoidcatalyst separation complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

By segmenting the system into two immiscible phases with the catalyst confined to the aqueous phase, the invention enables effective catalyst separation even at low concentrations. The phase boundary acts as a natural separation mechanism, eliminating the need for complex separation equipment or processes regardless of catalyst concentration.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The invention changes the solubility parameter of the catalyst by introducing water-soluble organophosphorus ligands. This parameter change allows the catalyst to operate at low concentrations in the aqueous phase while maintaining high conversion efficiency, and the altered solubility characteristics enable simple phase-based separation rather than complex purification procedures.

Inventive Principle:
Principle #35Parameter changes

3Reliability

If thermal separation operations are used to separate catalyst from product, then separation completeness is improved, but product quality deteriorates and energy consumption increases

Engineering Contradiction:
Improveseparation completenessVSAvoidproduct quality
Core Design Contradiction:
ReliabilityVSManufacturing precision

Solution Approach 1:

The invention utilizes liquid-liquid phase separation instead of thermal separation. The two phases (aqueous and organic) naturally separate based on density and immiscibility, allowing complete catalyst separation without applying heat that could degrade the ester product. This phase transition approach maintains product quality while achieving thorough separation.

Inventive Principle:
Principle #36Phase transitions

Solution Approach 2:

The water-soluble organophosphorus ligands continue to act as intermediaries during the separation process, ensuring the catalyst remains in the aqueous phase throughout the reaction and separation. This intermediary function guarantees complete separation without requiring harsh thermal conditions that would compromise product quality.

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 enables high-yield production of aliphatic esters from a wide variety of aliphatic olefins, even those with multiple double bonds, while significantly reducing energy consumption and simplifying catalyst separation.

Implementation Method 1

water-soluble organophosphorus ligands, wherein the water-soluble organophosphorus ligand serves to enhance the water solubility of the metal complex catalyst

Methodology Applied
Scientific EffectSolubility enhancement through ligand modification: Solvation

Implementation Method 2

two-phase reaction system consisting of an aqueous phase at least comprising water-soluble metal complex catalysts and water-soluble organophosphorus ligands, and an organic phase at least comprising the aliphatic olefins and one or more aliphatic C1 to C8 monoalcohols

Methodology Applied
Scientific EffectPhase separation: Liquid-Liquid Extraction

Implementation Method 3

alkoxycarbonylation of aliphatic olefins in the presence of carbon monoxide over an organophosphorus ligand-modified metal complex catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentEP4549427A1Alkoxycarbonylation in a 2-phase reaction system
Publication Date: 2025.05.07 OQ CHEM GMBH
  • EP4549427A1 patent drawing
  • EP4549427A1 patent drawing
  • EP4549427A1 patent drawing

AI summary

The present invention relates to a process for the preparation of aliphatic esters by alkoxycarbonylation of aliphatic olefins in the presence of carbon monoxide over an organophosphorus ligand-modified metal complex catalyst, wherein the aliphatic olefins are reacted in a two-phase reaction system consisting of an aqueous phase comprising at least water-soluble metal complex catalysts from a transition metal of groups 8-10 and water-soluble organophosphorus ligands, and an organic phase comprising at least the aliphatic olefins and one or more aliphatic C1 to C8 monoalcohols.