Naphthol Bisphosphite Ligands for Higher-Yield Hydroformylation

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Solution Overview

Problem

Existing hydroformylation processes face challenges in achieving high yields of aldehydes from olefins, particularly with existing bisphosphite compounds.

Innovation Solution

The use of novel bisphosphite compounds with a naphthol wing component, specifically structures (I) and (II), in combination with rhodium catalysts, to enhance the hydroformylation process.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If existing bisphosphite compounds are used in hydroformylation, then the process can proceed, but the yield of aldehydes is insufficient

Engineering Contradiction:

Improveyield of aldehydesVSAvoidefficiency of hydroformylation

Core Design Contradiction:

ProductivityVSReliability

Solution Approach 1:

The patent modifies the chemical structure of bisphosphite compounds by introducing a naphthol blade module with specific substituents (R1 = tBu, R2 = H or tBu) to change the electronic and steric parameters of the ligand. This structural parameter change enhances the ligand's ability to stabilize the rhodium catalyst and promote the hydroformylation reaction, thereby improving aldehyde yield from insufficient levels to 56-80% range.

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite catalytic system by combining rhodium compounds (Rh(acac)(CO)2, Rh(acac)(cod), or Rh4CO12) with the novel bisphosphite ligand in specific molar ratios (ligand to Rh from 2:1 to 10:1). This composite catalyst system synergistically combines the metal center's catalytic activity with the ligand's stabilizing and directing effects, achieving high productivity and reliability in hydroformylation.

Inventive Principle:

Principle #40Composite materials

2Productivity

If conventional ligands are used, then the catalyst system is simple, but the reaction efficiency and aldehyde yield are limited

Engineering Contradiction:

Improvehydroformylation efficiencyVSAvoidcomplexity of ligand structure

Core Design Contradiction:

ProductivityVSDevice complexity

Solution Approach 1:

The patent applies local quality modification by introducing specific functional groups (tert-butyl groups at R1 position, hydrogen or tert-butyl at R2 position) at particular locations on the naphthol blade module. These localized structural modifications create optimal electronic and steric environments at the metal-ligand interface, enhancing catalytic efficiency without requiring complete redesign of the entire ligand system.

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 novel compounds achieve improved yields of aldehydes, with yields ranging from 56% to 39% compared to comparative compounds, demonstrating enhanced efficiency in the hydroformylation reaction.

Implementation Method 1

the substance comprising Rh is selected from: Rh(acac)(CO) 2, Rh(acac)(cod) (Umicore, acac = acetylacetonate anion; cod = 1,5-cyclooctadiene), Rh 4 CO 12

Methodology Applied

Scientific EffectCatalysis: Catalysis

Data Source

PatentEP4663648A1Bis-phosphites with a naphthol blade module

Publication Date: 2025.12.17 EVONIK OXENO GMBH & CO KG

AI summary

Bisphosphites with a naphthol wing component and their use in hydroformylation.