Mononuclear Ruthenium Complex Catalyst for Selective Hydrosilylation

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Solution Overview

Problem

Current catalysts for hydrosilylation, hydrogenation, and reductive reactions, particularly those involving Pt, Pd, and Rh, face issues such as side reactions, low selectivity, high costs, and the need for expensive noble metals, while existing ruthenium catalysts lack superior reactivity, selectivity, and require high temperatures and harsh conditions.

Innovation Solution

A mononuclear ruthenium complex with ruthenium-silicon bonds, specifically designed to catalyze hydrosilylation, hydrogenation, and reductive reactions of carbonyl compounds under mild conditions, utilizing a formula that includes various ligands and crosslinking substituents to enhance catalytic activity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If Pt, Pd, or Rh compounds are used as catalysts for hydrosilylation reaction, then catalytic activity is achieved, but side reactions and internal rearrangement occur, and selectivity is low

Engineering Contradiction:
Improvecatalytic activityVSAvoidselectivity
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The patent changes the chemical parameters of the catalyst by replacing noble metals (Pt, Pd, Rh) with ruthenium and modifying the ligand environment with specific phosphine ligands and silane substituents. This parameter change in catalyst composition resolves the contradiction by maintaining catalytic activity while improving selectivity and preventing side reactions.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite catalyst system combining ruthenium metal center with organic ligands containing phosphine groups and silane substituents. This composite structure allows the catalyst to maintain high activity while achieving superior selectivity for terminal olefin addition and preventing internal rearrangement.

Inventive Principle:
Principle #40Composite materials

2Productivity

If Pt, Pd, or Rh compounds are used as catalysts, then hydrosilylation reaction proceeds, but the cost is very high due to expensive noble metal elements

Engineering Contradiction:
Improvecatalytic activityVSAvoidcost
Core Design Contradiction:
ProductivityVSEase of manufacture

Solution Approach 1:

The patent replaces expensive noble metal catalysts (Pt, Pd, Rh) with a cheaper ruthenium-based catalyst system. The ruthenium complex with modified phosphine ligands provides comparable catalytic activity at lower cost, making the process economically viable without sacrificing productivity.

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

Solution Approach 2:

The patent changes the metallic component parameter from expensive noble metals to more affordable ruthenium, while optimizing the ligand environment to maintain catalytic performance. This parameter substitution resolves the cost contradiction while preserving catalytic activity.

Inventive Principle:
Principle #35Parameter changes

3Productivity

If existing Ru catalysts are used for hydrogenation and reductive reactions, then reaction can proceed, but high temperature and harsh conditions are required

Engineering Contradiction:
Improvereaction capabilityVSAvoidreaction condition severity
Core Design Contradiction:
ProductivityVSTemperature

Solution Approach 1:

The patent modifies the catalyst parameters by incorporating specific phosphine ligands and silane substituents on the ruthenium center. These structural modifications enable the catalyst to function effectively under milder temperature conditions and less harsh reaction environments while maintaining high reaction capability for hydrogenation and reductive processes.

Inventive Principle:
Principle #35Parameter changes

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 mononuclear ruthenium complex achieves high catalytic activity in hydrosilylation, hydrogenation, and reductive reactions, allowing for selective addition reactions at room temperature to 100°C, efficient hydrogenation under mild conditions, and effective reduction of carbonyl compounds with silanes or polysiloxanes, reducing the need for expensive noble metals and harsh conditions.

Implementation Method 1

a mononuclear ruthenium complex having formula (1) [...] having catalytic activity to three reactions: hydrosilylation reaction, hydrogenation reaction, and reductive reaction of carbonyl compounds

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

hydrogenation reaction of olefins

Methodology Applied
Scientific EffectHydrogenation: Hydrogenation

Implementation Method 3

reductive reaction of carbonyl compounds in the presence of relatively low cost ruthenium catalysts

Methodology Applied
Scientific EffectReduction: Reduction

Data Source

PatentEP2963046B1Mononuclear ruthenium complex and organic synthesis reaction using same
Publication Date: 2018.10.17 SHIN ETSU CHEMICAL CO LTD
  • EP2963046B1 patent drawingFigure 1~3
  • EP2963046B1 patent drawingFigure 4~6
  • EP2963046B1 patent drawing

AI summary

Provided is a mononuclear ruthenium complex that comprises a ruthenium-silicon bond that is represented by formula (1) and that exhibits excellent catalyst activity in each of a hydrosilylation reaction, a hydrogenation reaction, and reduction of a carbonyl compound. In formula (1), R1-R6 either independently represent an alkyl group, an aryl group, an aralkyl group or the like that may be substituted with a hydrogen atom or X, or represent a crosslinking substituent in which at least one pair comprising one of R1-R3 and one of R4-R6 is combined. X represents a halogen atom, an organoxy group, or the like. L represents a two-electron ligand other than CO and phosphine. When a plurality of L are present, the plurality of L may be the same as or different from each other. When two L are present, the two L may be bonded to each other. n and m independently represent an integer of 1 to 3 with the stipulation that n+m equals 3 or 4.