Naphthol Bisphosphite Ligands for Higher Hydroformylation Yield

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Solution Overview

Problem

Existing hydroformylation processes face challenges in achieving high yields of aldehyde production from olefins.

Innovation Solution

The use of bisphosphites with a naphthol outer unit, specifically compounds of formula (I) and (II), in combination with rhodium catalysts, to enhance the hydroformylation process.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional ligands are used in hydroformylation, then the process is simple, but the yield of aldehyde production is insufficient

Engineering Contradiction:
Improveyield of aldehyde productionVSAvoidcomplexity of phosphorus-containing compound structure
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent applies composite materials by designing bisphosphite ligands that combine a naphthol outer unit with specific substituent patterns (R1 groups at positions 2 and 7). This composite molecular structure integrates multiple functional elements - the naphthol core provides structural rigidity and electronic properties, while the alkyl substituents modulate steric and electronic characteristics. The resulting composite ligand structure achieves superior catalytic performance with yields of 56% or more in hydroformylation reactions, resolving the contradiction between simplicity and productivity by creating an optimized composite molecular architecture.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent employs parameter changes by systematically varying the substituent parameters (R1 groups) on the naphthol outer unit of the bisphosphite ligand. Different alkyl substituents (such as methyl, tert-butyl) at specific positions modify the electronic and steric parameters of the ligand, which in turn tune the catalytic activity and yield. This parameter optimization approach allows achieving high productivity (56%+ yield) while maintaining reasonable structural complexity through controlled modification of specific molecular parameters.

Inventive Principle:
Principle #35Parameter changes

2Productivity

If existing hydroformylation processes are used, then the process conditions are standard, but the aldehyde yield remains below 56%

Engineering Contradiction:
Improvealdehyde yieldVSAvoidconsistency of catalytic performance
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The patent applies local quality by introducing specific substituents (R1 groups) at localized positions (2 and 7) on the naphthol outer unit of the bisphosphite ligand. These localized structural modifications create specific electronic and steric environments at the catalytic active site, which enhances the consistency and reliability of catalytic performance. The local substitution pattern ensures reproducible high yields of 56% or more by creating a well-defined local chemical environment that stabilizes the catalytic cycle and reduces variability in reaction outcomes.

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 proposed compounds achieve improved yields of aldehyde production, with yields ranging from 48% to 56% in catalytic experiments.

Implementation Method 1

adding a substance comprising Rh; converting the olefin to an aldehyde

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentUS20250382314A1Bisphosphites with a naphthol outer unit
Publication Date: 2025.12.18 EVONIK OXENO GMBH & CO KG
  • US20250382314A1 patent drawing
  • US20250382314A1 patent drawing
  • US20250382314A1 patent drawing

AI summary

Bisphosphites with a naphthol outer unit and the use thereof in hydroformylation.