SILP Catalyst for Hydroformylation Separation and Selectivity

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Solution Overview

Problem

Existing hydroformylation catalyst systems face challenges with catalyst separation, recycling, and stability, particularly due to ligand degradation and low selectivity for terminal alkenes, leading to reduced catalyst life and undesirable hydrogenation activity.

Innovation Solution

A catalytically active composition comprising a metal from Group 9 of the Periodic Table, such as rhodium, dissolved in an ionic liquid on a heterogeneous support with an asymmetrically substituted bisphosphite ligand, which enhances catalyst stability and selectivity for hydroformylation reactions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If heterogeneous catalysts are used for hydroformylation, then catalyst separation and recycling are simplified, but hydroformylation activity decreases and hydrogenation activity increases (undesirable)

Engineering Contradiction:
Improvecatalyst separation and recyclingVSAvoidhydroformylation activity
Core Design Contradiction:
Ease of manufactureVSProductivity

Solution Approach 1:

An ionic liquid is introduced as an intermediary phase that dissolves the homogeneous catalyst complex while being immobilized on a porous support. This creates a Supported Ionic Liquid Phase (SILP) system where the catalyst maintains its homogeneous-phase activity while the ionic liquid phase enables heterogeneous-phase separation and recycling.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The invention creates a composite catalyst system combining homogeneous catalyst complex dissolved in ionic liquid, which is then supported on porous material. This composite structure integrates the advantages of both homogeneous (high activity) and heterogeneous (easy separation) catalysts.

Inventive Principle:
Principle #40Composite materials

2Reliability

If ligand is used in large excess to stabilize the catalyst complex, then catalyst stability improves, but catalytic activity is suppressed due to formation of various transition metal complexes

Engineering Contradiction:
Improvecatalyst stabilityVSAvoidcatalytic activity
Core Design Contradiction:
ReliabilityVSProductivity

Solution Approach 1:

The invention changes the physical state and environment parameters by using an ionic liquid phase instead of traditional organic solvents. This alters the solvation properties and ligand-catalyst interactions, allowing optimal ligand-to-metal ratios without excessive ligand that would suppress activity.

Inventive Principle:
Principle #35Parameter changes

3Ease of manufacture

If purely heterogeneous catalysts are used, then catalyst separation is easy, but regioselectivity decreases and hydrogenation activity increases (undesirable)

Engineering Contradiction:
Improvecatalyst separationVSAvoidregioselectivity
Core Design Contradiction:
Ease of manufactureVSManufacturing precision

Solution Approach 1:

The ionic liquid phase acts as an intermediary that maintains the catalyst in a dissolved state similar to homogeneous catalysis, preserving the selective properties while enabling heterogeneous separation through the porous support structure.

Inventive Principle:
Principle #24Intermediary (Mediator)

4Productivity

If homogeneous catalyst systems are used, then hydroformylation activity and selectivity are high, but catalyst separation and recycling become difficult and complex

Engineering Contradiction:
Improvehydroformylation activity and selectivityVSAvoidcatalyst separation and recycling
Core Design Contradiction:
ProductivityVSEase of manufacture

Solution Approach 1:

The catalyst complex is localized within the ionic liquid phase that is immobilized on the porous support. This local confinement maintains the homogeneous-like catalytic environment while providing heterogeneous-phase separation capabilities.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The SILP catalyst creates a composite system where the ionic liquid phase and porous support work together to provide both homogeneous-phase catalytic activity and heterogeneous-phase separation properties.

Inventive Principle:
Principle #40Composite materials

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 composition achieves improved catalyst life, high stability, and enhanced selectivity for hydroformylation, allowing for efficient conversion of unsaturated compounds to n-terminal aldehydes with isomerization, while maintaining high activity and regioselectivity.

Implementation Method 1

a liquid catalyst solution is applied to a porous support material

Methodology Applied
Scientific EffectDissolution: Solvation

Implementation Method 2

The reactions between olefin compounds, carbon monoxide and hydrogen in the presence of a catalyst to produce aldehydes that are one carbon atom richer are known as hydroformylation

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentEP3038752B1Catalyst and method for the hydroformylation of unsaturated compounds by means of silp catalysis
Publication Date: 2017.07.19 EVONIK OPERATIONS GMBH
  • EP3038752B1 patent drawingFigure 1~2
  • EP3038752B1 patent drawingFigure 3
  • EP3038752B1 patent drawing

AI summary

The invention relates to a composition comprising: a) at least one support material; b) at least one ionic liquid; c) at least one metal selected from group IX of the periodic table of elements; d) at least one compound of formula (I) R'—A—R'' (I), wherein A, R' and R'' are each an organic radical, and R' and R" comprise the structural element —O—P(— O—)2 with trivalent P by which means they are covalently bonded to radical A, on the condition that R' ≠ R'', and e) optionally at least one organic amine. The invention also relates to a method for producing such a composition, to the use of said composition,and to a method for hydroformylation wherein the composition is used.