Hydrosilylation of Norbornane Olefins via Acidic Catalyst Addition

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Solution Overview

Problem

Current methods for producing hydrolysable silicon compounds with an alicyclic structure and carbonyl group, such as those used in semiconductor manufacturing, face challenges of low yield and purification difficulties due to incomplete reactions and poor reactivity.

Innovation Solution

A method involving a hydrosilylation reaction between a hydrosilane compound and a carbonyl group-containing alicyclic olefin compound, where an acidic compound or its precursor is gradually added in the presence of a platinum-based catalyst, enhancing reaction efficiency and yield.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional hydrosilylation reaction methods are used, then the reaction can proceed, but the reaction is incomplete and yield is low

Engineering Contradiction:
Improvereaction yieldVSAvoidreaction completeness
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The invention changes the chemical environment parameters by introducing acidic compounds or acidic compound precursors into the hydrosilylation reaction system. This parameter change activates the carbonyl group-containing alicyclic olefin compound, making it more reactive toward the hydrosilane compound, thereby completing the reaction more fully and increasing yield

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The acidic compound or acidic compound precursor acts as an intermediary substance that facilitates the reaction between the hydrosilane compound and the carbonyl group-containing alicyclic olefin compound. The intermediary activates the olefin compound, enabling more complete reaction and higher productivity

Inventive Principle:
Principle #24Intermediary (Mediator)

2Productivity

If conventional hydrosilylation reaction methods are used, then the reaction can proceed, but reactivity is poor and purification is difficult

Engineering Contradiction:
Improvereaction efficiencyVSAvoidpurification ease
Core Design Contradiction:
ProductivityVSEase of manufacture

Solution Approach 1:

By changing the reaction parameters through acidic compound addition, the reaction proceeds more completely with fewer unreacted starting materials remaining. This reduces the complexity of purification operations and makes the manufacturing process easier

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention converts the potential harm of incomplete reaction (which creates purification difficulties) into a benefit by using acidic compounds to drive the reaction to completion, thereby eliminating the need for complex purification steps

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

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 high-yield production of industrially useful silicon compounds with an alicyclic structure, facilitating mass production and improving industrial utility by completing reactions and reducing raw material leftovers.

Implementation Method 1

the hydrosilylation reaction between the hydrosilane compound (1) and the carbonyl group-containing alicyclic olefin compound (2) takes place while an acidic compound or acidic compound precursor is gradually added thereto in presence of a platinum-based catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentEP3640255B1Method for producing silicon compound, and silicon compound
Publication Date: 2021.10.13 SHIN ETSU CHEMICAL CO LTD
  • EP3640255B1 patent drawingFigure 1
  • EP3640255B1 patent drawingFigure 2
  • EP3640255B1 patent drawing

AI summary

The present invention provides a method for producing a silicon compound shown by the following general formula (3) through a hydrosilylation reaction between a hydrosilane compound shown by the following general formula (1) and a carbonyl group-containing alicyclic olefin compound shown by the following general formula (2), in which the hydrosilylation reaction takes place while an acidic compound or acidic compound precursor is gradually added in presence of a platinum-based catalyst. This provides a highly-efficient industrial method for producing an industrially useful, hydrolysable silicon compound having an alicyclic structure (particularly a norbornane ring) and a carbonyl group.