Bisphosphite Ligand Selectivity in Non-Conjugated Diene Hydroformylation

Resolve Bottlenecks,
Find Innovative SolutionsGenerate Solutions

Solution Overview

Problem

Conventional hydroformylation reactions using phosphorus compounds face challenges with non-conjugated dienes having carbon-carbon double bonds, leading to reduced selectivity and increased formation of undesirable products due to internal hydroformylation and isomerization reactions, particularly when the dienes have 6 or more carbon atoms.

Innovation Solution

A method involving a bisphosphite with a specific structure, represented by formula (I), is used in conjunction with a group 8 to 10 metal compound to selectively hydroformylate the carbon-carbon double bond at the molecular end of non-conjugated dienes, suppressing internal hydroformylation and isomerization reactions, while maintaining high heat stability and catalytic activity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If conventional phosphorus compounds are used in hydroformylation reaction of non-conjugated dienes, then the reaction can proceed, but selectivity decreases due to internal hydroformylation and isomerization reactions

Engineering Contradiction:

Improveselectivity of hydroformylationVSAvoidinternal hydroformylation and isomerization side reactions

Core Design Contradiction:

Manufacturing precisionVSObject-generated harmful factors

Solution Approach 1:

The patent changes the chemical parameters of the phosphorus compound by developing a novel bisphosphite structure with specific substituents (electron-donating or electron-withdrawing groups at defined positions) to optimize catalyst selectivity. This structural parameter change suppresses internal hydroformylation and isomerization while maintaining end hydroformylation activity

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite catalyst system combining group 8-10 metal compounds with the specifically designed bisphosphite ligand. This composite structure synergistically enhances selectivity for end hydroformylation while suppressing unwanted side reactions, achieving better performance than conventional phosphorus compounds

Inventive Principle:

Principle #40Composite materials

2Reliability

If conventional phosphorus compounds are used, then hydroformylation reaction occurs, but catalyst stability and activity deteriorate over time

Engineering Contradiction:

Improvecatalyst stabilityVSAvoidcatalytic activity duration

Core Design Contradiction:

ReliabilityVSDuration of action of moving object

Solution Approach 1:

The patent modifies the chemical parameters of the phosphorus compound by introducing a stable bisphosphite structure with specific substituents that enhance catalyst stability. This structural change prevents catalyst decomposition and maintains high catalytic activity over extended reaction periods, solving the stability-duration problem

Inventive Principle:

Principle #35Parameter changes

3Productivity

If conventional phosphorus compounds are used, then reaction proceeds, but undesirable by-products are formed reducing yield

Engineering Contradiction:

Improvealdehyde yieldVSAvoidundesirable by-products

Core Design Contradiction:

ProductivityVSObject-generated harmful factors

Solution Approach 1:

The patent changes the chemical parameters of the phosphorus compound to create a novel bisphosphite structure that selectively promotes end hydroformylation while suppressing internal hydroformylation and isomerization. This parameter change reduces by-product formation and increases desired aldehyde yield

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The patent converts the potential harm of having multiple double bonds in non-conjugated dienes into a benefit by designing a catalyst that selectively targets only the terminal double bond. The internal double bonds remain unaffected, transforming what could be a source of side reactions into a feature that maintains molecular integrity and increases product yield

Inventive Principle:

Principle #22Blessing in disguise (Convert harm into benefit)

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 allows for high selectivity in producing the desired aldehyde, suppressing internal hydroformylation and isomerization, and maintaining long-term catalytic activity and industrial stability, making it suitable for various chemical reactions.

Implementation Method 1

reacting a non-conjugated diene having a carbon-carbon double bond in an end thereof and having from 6 to 20 carbon atoms with carbon monoxide and hydrogen in the presence of a bisphosphite having a specified structure and a group 8 to 10 metal compound

Methodology Applied

Scientific EffectCatalysis: Catalysis

Data Source

PatentEP2003138B1Method for producing aldehyde using bisphosphite and group 8-10 metal compound, and such bisphosphite

Publication Date: 2013.10.09 KURARAY CO LTD

AI summary

A bisphosphite represented by the general formula (I): (in the formula, A represents an alkylene group which may have a substituent, a cycloalkylene group which may have a substituent, a phenylene group which may have a substituent, or a naphthylene group which may have a substituent; and R1 represents a hydrogen atom or an alkyl group) and a method for producing an aldehyde including reacting a non-conjugated diene having a carbon-carbon double bond in a molecular end and having from 6 to 20 carbon atoms with a carbon monoxide and hydrogen in the presence of such a bisphosphite and a group 8 to 10 metal compound, are provided.