Trans-Terminal Diphosphites for Higher Aldehyde Yield

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Solution Overview

Problem

Existing hydroformylation processes using Group VIII transition metal catalysts and conventional ligands like phosphines, phosphites, and phosphonites do not achieve optimal yields of aldehydes.

Innovation Solution

The use of diphosphites with trans-positioned substituents, specifically compounds of formula (I), in combination with a Rh compound, under controlled pressure and temperature conditions, enhances the yield of aldehydes in the hydroformylation of olefins.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional ligands (phosphines, phosphites, phosphonites) are used with Group VIII transition metal catalysts, then the hydroformylation reaction can proceed, but the aldehyde yield is not optimal

Engineering Contradiction:
Improvealdehyde yieldVSAvoidreaction efficiency
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The patent changes the chemical parameters of the ligand by introducing a specific diphosphite structure with trans-positioned substituents and a bridging oxygen atom. This structural modification alters the electronic and steric properties of the ligand, enabling optimal aldehyde yields of up to 97% in hydroformylation reactions

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite ligand structure combining two phosphite moieties linked by a bridging oxygen atom, forming a bidentate diphosphite ligand. This composite structure provides synergistic effects that improve both catalytic activity and aldehyde yield compared to monodentate phosphite ligands

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 described method significantly increases the yield of aldehydes, as demonstrated by the catalysis experiments with compounds (1) and (2), achieving up to 97% aldehyde yield compared to a reference ligand.

Implementation Method 1

Phosphorus-containing compounds play a crucial role as ligands in a variety of reactions, e.g. in hydrogenation, hydrocyanation and also in hydroformylation

Methodology Applied
Scientific EffectLigand stabilization: Chemical Bonding

Implementation Method 2

The reaction between olefin compounds, carbon monoxide, and hydrogen in the presence of a catalyst to form aldehydes richer by one carbon atom is known as hydroformylation or oxation

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentEP4393901B1Diphosphites with trans-terminal substituents
Publication Date: 2025.07.02 EVONIK OXENO GMBH & CO KG
  • EP4393901B1 patent drawing
  • EP4393901B1 patent drawing
  • EP4393901B1 patent drawing

AI summary

Diphosphites with trans-position substituents and their use in hydroformylation.