Bisphosphite Catalyst Mixture for Hydroformylation Selectivity

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Solution Overview

Problem

Current hydroformylation processes face challenges in achieving good n/iso selectivity and yield, particularly in the use of bisphosphite ligands as catalysts for olefin reactions.

Innovation Solution

A mixture of bisphosphites with open and closed wing units is used as a catalyst mixture in hydroformylation reactions, comprising compounds (1A) and (1B) in specific mass ratios, along with a transition metal such as Rh, under controlled temperature and pressure conditions, to enhance selectivity and yield.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If a single bisphosphite ligand is used in hydroformylation, then the catalyst structure is simple, but the n/iso selectivity and yield are insufficient

Engineering Contradiction:
Improven/iso selectivityVSAvoidcatalyst composition complexity
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent combines multiple bisphosphite ligands (open-wing unit ligand and closed-wing unit ligand) into a single catalyst system. This merging of different ligand structures allows the catalyst to achieve both high n/iso selectivity and good yield, resolving the contradiction between simple catalyst structure and high manufacturing precision.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The invention uses a composite ligand system comprising both open-wing unit bisphosphite and closed-wing unit bisphosphite. This composite approach creates a catalyst with synergistic properties that neither ligand alone can achieve, simultaneously improving n/iso selectivity and yield without excessive complexity.

Inventive Principle:
Principle #40Composite materials

2Productivity

If conventional phosphine or phosphite ligands are used, then the catalyst is easy to prepare, but the hydroformylation yield and selectivity are limited

Engineering Contradiction:
Improvehydroformylation yieldVSAvoidcatalyst preparation complexity
Core Design Contradiction:
ProductivityVSEase of manufacture

Solution Approach 1:

The patent changes the chemical parameters of the ligand system by using bisphosphite ligands with specific open and closed wing units, rather than conventional phosphine or phosphite ligands. This parameter change in ligand structure enables superior hydroformylation performance in terms of both yield and selectivity.

Inventive Principle:
Principle #35Parameter changes

3Reliability

If ligands are used in excess, then the catalyst stability improves, but not all ligands are bound and free ligands remain in the reaction mixture

Engineering Contradiction:
Improvecatalyst stabilityVSAvoidunbound ligand content
Core Design Contradiction:
ReliabilityVSLoss of substance

Solution Approach 1:

The patent creates different local environments within the catalyst system by using ligands with distinct open and closed wing units. This local structural differentiation allows for optimized metal-ligand binding at the catalytic center while managing the presence of free ligands in the bulk solution, balancing catalyst stability with controlled ligand availability.

Inventive Principle:
Principle #3Local quality

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 described mixture achieves improved n/iso selectivity and yield in hydroformylation reactions, outperforming comparative mixtures in catalyzing the conversion of olefins to aldehydes, as demonstrated by catalysis experiments.

Implementation Method 1

Transition metal compounds from group VIII of the periodic table are frequently used as catalysts in these reactions

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

EP 0 213 639 A2 describes bisphosphite ligands and their use in transition metal complex-catalyzed reactions

Methodology Applied
Scientific EffectLigand coordination: Chemical Bonding

Data Source

PatentEP4074720B1Mixture of bisphosphites with an open and a closed volatile building block and its use as catalyst mixture in hydroformylation
Publication Date: 2023.07.19 EVONIK OXENO GMBH & CO KG
  • EP4074720B1 patent drawing
  • EP4074720B1 patent drawing
  • EP4074720B1 patent drawing

AI summary

Mixture of bisphosphites with an open and a closed wing component and its use as a catalyst mixture in hydroformylation.