Group 8 Metal Catalysts Latent Activation Metathesis

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Solution Overview

Problem

Current olefin metathesis catalysts lack efficient methods for controlling initiation rates and maintaining catalyst activity over time, particularly in industrial applications such as Ring-Opening Metathesis Polymerization (ROMP) and cross-metathesis reactions, where latency and tunability are crucial for optimizing reaction conditions.

Innovation Solution

Development of Group 8 metal catalysts, specifically ruthenium or osmium-based, with modified alkylidene parts combined with ditopic or multitopic ligands, which can be easily activated using chemical or photo-activators, allowing for controlled initiation and high activity levels, and are stable in monomer solutions for extended periods.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of operation

If conventional olefin metathesis catalysts are used, then metathesis reactions can proceed, but the initiation rate cannot be controlled and catalyst activity decreases over time

Engineering Contradiction:
Improvecontrol of initiation rateVSAvoidcatalyst activity stability
Core Design Contradiction:
Ease of operationVSReliability

Solution Approach 1:

The patent applies dynamics by making the catalyst system adjustable and controllable. The use of latent catalyst precursors that can be activated on-demand, and the ability to modulate catalyst activity through ligand selection and reaction conditions, transforms a static catalyst system into a dynamic one where initiation rate and activity stability can be controlled according to process requirements.

Inventive Principle:
Principle #15Dynamics

Solution Approach 2:

The patent employs parameter changes by modifying catalyst structure (using Group 8 metals with specific ligands), changing reaction conditions (temperature, solvent, concentration), and adjusting catalyst precursor activation state. These parameter modifications enable control over initiation rate while maintaining catalyst activity stability throughout the reaction process.

Inventive Principle:
Principle #35Parameter changes

2Productivity

If catalysts are designed for high activity, then metathesis reactions proceed rapidly, but catalyst stability and latency are compromised

Engineering Contradiction:
Improvereaction rateVSAvoidcatalyst stability
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The patent applies preliminary action by preparing latent catalyst precursors in advance that remain stable and inactive during storage and handling. These precursors are designed to activate only when exposed to specific triggers (moisture, heat, light, or reaction with monomer), allowing the system to maintain high productivity during reaction while ensuring catalyst stability during storage and transport.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent uses intermediary substances such as latent precursor compounds and ligands that mediate between the stable stored state and the active catalytic state. These intermediaries protect the active metal center during storage while enabling controlled activation when needed, thus reconciling the conflict between high activity and stability.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Reliability

If Group 8 metal catalysts with modified alkylidene parts and ditopic ligands are used, then initiation rate can be controlled and activity maintained, but catalyst structure becomes more complex

Engineering Contradiction:
Improvecatalyst activity controlVSAvoidcatalyst structure
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent applies universality by designing ligands and catalyst structures that perform multiple functions simultaneously. The ditopic and multitopic ligands not only support the metal center but also control initiation rate, stabilize the catalyst, and can participate in activation mechanisms. This multi-functionality reduces the need for separate components, managing structural complexity while achieving reliable control.

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

4Productivity

If synthesis time is reduced to 4 hours or less, then productivity increases, but manufacturing precision and catalyst quality may be compromised

Engineering Contradiction:
Improvesynthesis timeVSAvoidcatalyst quality
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The patent applies preliminary action by pre-designing and pre-preparing stable precursor complexes that require minimal processing time to become active catalysts. The ligands and metal precursors are selected and pre-assembled in ways that ensure high-quality catalyst formation rapidly, allowing short synthesis times without compromising catalyst quality or activity.

Inventive Principle:
Principle #10Preliminary action

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

These catalysts enable efficient metathesis reactions with reduced synthesis time to 4 hours or less, maintaining high yields and allowing for easy separation from products, making them suitable for industrial-scale production of linear alpha-olefins and unsaturated polymers.

Implementation Method 1

Olefin metathesis is a catalytic process including, as a key step, a reaction between a first olefin and a first transition metal alkylidene complex, thus producing an unstable intermediate metallacyclobutane ring which then undergoes transformation into a second olefin and a second transition metal alkylidene complex

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

which can be easily activated using chemical or photo-activators, allowing for controlled initiation and high activity levels

Methodology Applied
Scientific EffectPhoto-activation: Photo-oxidation

Data Source

PatentEP3164409B1Group 8 transition metal catalysts and method for making same and process for use of same in metathesis reaction
Publication Date: 2021.09.01 GUANG MING INNOVATION CO (WUHAN)
  • EP3164409B1 patent drawingFigure 1~3
  • EP3164409B1 patent drawingFigure 4~5
  • EP3164409B1 patent drawingFigure 6~7

AI summary

Metal catalyst compounds are disclosed. The catalyst compound are represented by the formula (I-II and VII): wherein M is a Group 8 metal; X is an anionic ligand; L is a neutral two electron donor ligand; K 2 (A-E) is a ditopic or multitopic ligand. Also disclosed is an easy applicable catalyst synthesis and the application in different olefin metathesis processes, e.g. Reaction Injection Molding (RIM), rotational molding, vacuum infusion, vacuum forming, process for conversion of fatty acids and fatty acid esters or mixtures thereof, in –olefins, dicarboxylic acids or dicarboxylic esters, etc.