Bis-phosphine Catalyst for Hydroformylation n/i Ratio

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Solution Overview

Problem

Current catalysts used in hydroformylation reactions have a high selection ratio of normal aldehyde to iso aldehyde (n/i ratio), which limits the production of branched aldehyde derivatives in demand, and lack sufficient catalytic activity and stability.

Innovation Solution

A catalyst composition comprising two different monocoordinated phosphine ligands and a transition metal catalyst, specifically represented by Formulas 1, 2, and 3, is used to lower the n/i ratio while maintaining superior catalytic activity and stability, by reacting olefinic compounds with carbon monoxide and hydrogen.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If conventional catalysts are used for hydroformylation, then high n/i ratio is achieved, but demand for branched aldehyde derivatives cannot be met

Engineering Contradiction:
Improven/i ratioVSAvoidproduction of branched aldehyde derivatives
Core Design Contradiction:
Manufacturing precisionVSProductivity

Solution Approach 1:

The patent changes the chemical parameters of the catalyst system by introducing specific phosphine ligands (Formula 1 and Formula 2) with defined structural parameters (R1, R2, R3 as C1 or C2 alkyl or alkoxy groups). These parameter changes in the ligand structure directly alter the catalyst's selectivity, achieving n/i ratio of 2.5 or less while maintaining high productivity for branched aldehyde production

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite catalyst system combining transition metal (M) with two different phosphine ligands (L1 and L2) in specific molar ratios. This composite material approach, where the catalyst comprises M, L1, and L2 with defined compositional parameters, achieves synergistic effects that simultaneously improve selectivity (n/i ratio ≤ 2.5) and productivity for branched aldehyde derivatives

Inventive Principle:
Principle #40Composite materials

2Reliability

If catalyst stability is improved, then catalytic activity may be reduced

Engineering Contradiction:
Improvecatalyst stabilityVSAvoidcatalytic activity
Core Design Contradiction:
ReliabilityVSPower

Solution Approach 1:

The patent optimizes structural parameters of the phosphine ligands (Formula 1 and Formula 2) including the types of R1, R2, R3 substituents (C1 or C2 alkyl or alkoxy groups) and the cycloalkyl group Z (C5 to C10). These parameter changes in ligand structure simultaneously enhance catalyst stability and maintain high catalytic activity, resolving the trade-off between reliability and power

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The composite catalyst system combining transition metal M with two phosphine ligands L1 and L2 in specific proportions creates a synergistic effect. This composite material approach, with defined compositional parameters, achieves both high catalyst stability and sustained catalytic activity, overcoming the conventional trade-off between reliability and power

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 catalyst composition effectively lowers the n/i ratio, enhancing catalytic activity and stability, allowing for efficient production of branched aldehyde derivatives with a selection ratio of normal aldehyde to iso aldehyde of 2.5 or less, as demonstrated in Examples 1 to 4.

Implementation Method 1

reacting various olefins with carbon monoxide (CO) and hydrogen (H2), which are generally referred to as synthesis gases, in the presence of a homogeneous organometallic catalyst and a ligand

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentUS10300472B2Catalyst composition containing phosphorous-based ligand and method for hydroformylation using same
Publication Date: 2019.05.28 LG CHEM LTD
  • US10300472B2 patent drawing
  • US10300472B2 patent drawing
  • US10300472B2 patent drawing

AI summary

The present invention relates to a catalyst composition including a phosphorous-based ligand, and a hydroformylation method using the catalyst composition. More particularly, the present invention relates to a catalyst composition, which includes two different kinds of monocoordinated phosphine ligands and a transition metal catalyst, and a hydroformylation method using the catalyst composition. In accordance with the present invention, a catalyst composition lowering a selection ratio of normal aldehyde to iso aldehyde (n/i ratio), which are generated during hydroformylation of an olefinic compound, and exhibiting superior catalytic activity and stability, and a method of hydroformylating an olefinic compound using the catalyst composition are provided.