Iron Tridentate Ligand Catalysts for Ester Hydrogenation

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Solution Overview

Problem

Current hydrogenation processes for reducing esters, lactones, ketones, or aldehydes to their corresponding alcohols or diols lack effective and diverse catalysts, particularly those using iron complexes with tridentate ligands, which are needed for broader substrate compatibility and enhanced selectivity.

Innovation Solution

The use of iron complexes with tridentate ligands containing an amino or imino group and two phosphino groups as catalysts or pre-catalysts in hydrogenation processes, which activate molecular hydrogen to reduce carbonyl or carboxylic functional groups in the presence of a base, allowing for a range of substrates and improved selectivity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If ruthenium/amino-phosphine complexes are used as catalysts for ester hydrogenation, then high catalytic performance is achieved, but the cost increases and toxicity problems arise

Engineering Contradiction:
Improvecatalytic performanceVSAvoidtoxicity and cost
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent replaces expensive and toxic ruthenium metal with iron, which is abundant, inexpensive, and less toxic. The iron complexes with tridentate ligands serve as effective catalysts for ester hydrogenation, achieving the desired catalytic performance while eliminating the harmful effects associated with ruthenium.

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

Solution Approach 2:

The patent changes the metal center parameter from ruthenium to iron, fundamentally altering the catalyst's properties. This substitution maintains catalytic activity while improving environmental compatibility and reducing cost, demonstrating a successful parameter change strategy.

Inventive Principle:
Principle #35Parameter changes

2Adaptability or versatility

If conventional catalysts are used for hydrogenation, then limited substrate scope is covered, but broader substrate compatibility is needed

Engineering Contradiction:
Improvesubstrate scopeVSAvoidcatalytic effectiveness
Core Design Contradiction:
Adaptability or versatilityVSReliability

Solution Approach 1:

The iron complex catalyst with tridentate ligand structure demonstrates universal applicability across multiple substrate types including esters, lactones, ketones, and aldehydes. The catalyst maintains high effectiveness while broadening the substrate scope, achieving multi-functionality in hydrogenation reactions.

Inventive Principle:
Principle #6Universality (Multi-functionality)

Solution Approach 2:

The patent employs a composite catalytic system combining iron metal center with tridentate ligands containing nitrogen and phosphorus donor atoms. This composite structure enhances the catalyst's versatility and effectiveness across diverse substrates while maintaining selectivity.

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

This approach enables efficient hydrogenation of various substrates, such as esters, lactones, ketones, and aldehydes, providing high conversion rates and selectivity, making it suitable for pharmaceutical, agrochemical, and perfumery industries, while avoiding the use of expensive and toxic metals like ruthenium.

Implementation Method 1

The development of useful catalysts or catalytic systems for the hydrogenation of an ester functional group represents still an important need in chemistry

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

hydrogenation processes, in which molecular hydrogen is used

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Data Source

PatentUS10053475B2Hydrogenation of esters with Fe/tridentate ligands complexes
Publication Date: 2018.08.21 FIRMENICH SA
  • US10053475B2 patent drawing
  • US10053475B2 patent drawing
  • US10053475B2 patent drawing

AI summary

The present invention relates to the field of catalytic hydrogenation and, more particularly, to the use of Fe complexes with tridentate ligands, having one amino or imino coordinating group and two phosphino coordinating groups, in hydrogenation processes for the reduction of ketones, aldehydes, esters or lactones into the corresponding alcohol or diol, respectively.