Cationic Si(II) Catalyst for Noble Metal-Free Hydrosilylation

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Solution Overview

Problem

The high cost and limited availability of noble metal catalysts in hydrosilylation reactions, along with the challenge of catalyst recovery and price fluctuations, necessitate the development of a noble metal-free hydrosilylation catalyst.

Innovation Solution

The use of cationic Si(II) compounds, specifically silyliumylidene cations, as catalysts in hydrosilylatable mixtures to facilitate hydrosilylation reactions without noble metals, where the cationic Si(II) group effectively catalyzes the formation of Si-C bonds.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If noble metal complexes (platinum, rhodium, or iridium) are used as hydrosilylation catalysts, then catalytic activity is achieved, but process cost increases significantly

Engineering Contradiction:
Improvecatalytic activityVSAvoidprocess cost
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent replaces expensive noble metal catalysts with a cheaper alternative - the cationic silylium species generated in situ from silicon(II) compound and carboxylic acid. This disposable-like approach uses readily available silicon compounds instead of precious metals, significantly reducing catalyst cost while maintaining catalytic functionality for hydrosilylation reactions

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

Solution Approach 2:

The patent changes the chemical nature of the catalyst from noble metal complexes to organosilicon-based cationic species. By altering the catalyst's chemical composition and electronic structure (using silicon(II) with specific ligands), the system achieves comparable catalytic activity without the cost associated with noble metals

Inventive Principle:
Principle #35Parameter changes

2Productivity

If precious metal catalysts are used, then hydrosilylation reaction proceeds efficiently, but material availability is limited and prices fluctuate

Engineering Contradiction:
Improvereaction efficiencyVSAvoidcatalyst availability
Core Design Contradiction:
ProductivityVSQuantity of substance

Solution Approach 1:

The invention substitutes scarce precious metals with abundant silicon-based compounds. Silicon is readily available and inexpensive compared to platinum, rhodium, or iridium, ensuring stable supply and consistent pricing while maintaining the ability to perform efficient hydrosilylation reactions

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

3Reliability

If noble metal catalysts are used, then catalytic function is provided, but catalyst recovery becomes difficult and expensive

Engineering Contradiction:
Improvecatalytic functionVSAvoidcatalyst recovery
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent extracts the essential catalytic function from noble metal complexes and transfers it to an organosilicon system. The silicon(II) compound with carboxylic acid ligand provides the necessary cationic silylium species for catalysis without requiring expensive metals, and the resulting system is easier to handle and recover

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The carboxylic acid ligand acts as an intermediary that stabilizes the silicon(II) center and enables catalyst formation. This ligand system allows the silicon-based catalyst to function effectively, providing noble metal-like activity through a different chemical mechanism that simplifies catalyst management and recovery

Inventive Principle:
Principle #24Intermediary (Mediator)

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 provides a cost-effective and sustainable solution for hydrosilylation, maintaining high catalytic activity and efficiency without the need for precious metal catalysts, as demonstrated by the examples of successful reactions with various substrates.

Implementation Method 1

The cationic Si(II) group is highly effective as a hydrosilylation catalyst. Surprisingly, it has now been found that silicon(II) compounds which are present in cationic form—so-called silyliumylidene cations—catalyze hydrosilylation reactions.

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentEP3440088B1Noble metal-free hydrosilylatable mixture
Publication Date: 2019.12.18 WACKER CHEMIE AG
  • EP3440088B1 patent drawing
  • EP3440088B1 patent drawing
  • EP3440088B1 patent drawing

AI summary

The invention relates to a hydrosilylatable mixture M containing: (A) a compound with at least one hydrogen atom directly bonded to Si, (B) a compound containing at least one carbon-carbon multiple bond, and (C) a compound containing at least one cationic Si(II) group. The invention also relates to a method for hydrosilylating the mixture M.