Oxadisilacyclopentane Synthesis at Mild Temperature and High Yield

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Solution Overview

Problem

Existing methods for producing oxadisilacyclopentane compounds require high temperatures and complex operations, leading to high energy consumption and low industrial viability.

Innovation Solution

A method involving the reaction of azadisilacyclopentane compounds with water at mild temperatures (0 to 100°C) using an acid catalyst to suppress polymer formation, thereby efficiently producing oxadisilacyclopentane compounds.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If thermal decomposition is performed at high temperature (300°C or higher) to obtain desired oxadisilacyclopentane compound at practical reaction rate, then reaction rate is improved, but energy consumption increases significantly

Engineering Contradiction:
Improvereaction rateVSAvoidenergy consumption
Core Design Contradiction:
ProductivityVSUse of energy by moving object

Solution Approach 1:

The invention changes the reaction parameters by introducing a catalyst system comprising a metal compound and an organic carboxylic acid, which enables the reaction to proceed at lower temperatures (below 300°C) while maintaining practical reaction rates. This parameter change resolves the contradiction by decoupling high reaction rate from high energy consumption.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention introduces intermediary substances (metal compound catalyst and organic carboxylic acid) that mediate the reaction between 1,2-bis(chlorodimethylsilyl)ethane and water. These intermediaries lower the activation energy required for the reaction, enabling it to proceed at lower temperatures with acceptable reaction rates, thus reducing energy consumption while maintaining productivity.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Manufacturing precision

If magnesium is added as necessary to suppress side reaction, then product purity is improved, but operational complexity increases

Engineering Contradiction:
Improveproduct purityVSAvoidoperational complexity
Core Design Contradiction:
Manufacturing precisionVSEase of operation

Solution Approach 1:

The invention extracts the need for complex operational controls by replacing the stepwise magnesium addition process with a simpler catalyst system. The metal compound and organic carboxylic acid catalysts suppress side reactions without requiring continuous monitoring and adjustment of magnesium addition, thereby maintaining product purity while significantly simplifying operations.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The invention uses small amounts of metal compound and organic carboxylic acid as disposable catalysts that can be added once at the beginning of the reaction. These catalysts perform the function of suppressing side reactions throughout the reaction process without requiring repeated additions or complex operational interventions, unlike the magnesium approach.

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

3Quantity of substance

If two-step reaction with tin compound is used to obtain desired oxadisilacyclopentane compound, then product is obtained, but yield decreases and toxicity increases

Engineering Contradiction:
Improveproduct yieldVSAvoidtoxicity
Core Design Contradiction:
Quantity of substanceVSObject-affected harmful factors

Solution Approach 1:

The invention replaces toxic tin compounds with metal compounds (such as aluminum, zinc, or magnesium salts) and organic carboxylic acids that are less toxic and more environmentally friendly. These catalysts achieve the same purpose of facilitating the reaction and suppressing side reactions without the harmful effects associated with tin compounds, thereby improving both yield and safety.

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

Solution Approach 2:

The invention changes the chemical parameters by substituting tin-based reagents with metal compound/organic carboxylic acid catalyst systems. This parameter change results in both improved product yield (by avoiding the limitations of the two-step tin-based process) and reduced toxicity (by eliminating harmful tin compounds from the reaction system).

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 method allows for high-yield production of oxadisilacyclopentane compounds suitable for heat-resistant, electronic, and optical materials, reducing energy consumption and operational complexity.

Implementation Method 1

reacting an azadisilacyclopentane compound with water in the presence of a metal compound and an organic carboxylic acid

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

reacting an azadisilacyclopentane compound with water

Methodology Applied
Scientific EffectHydrolysis: Hydrolysis

Data Source

PatentEP4349841B1Method for producing oxadisilacyclopentane compound
Publication Date: 2026.03.25 SHIN ETSU CHEMICAL CO LTD
  • EP4349841B1 patent drawing
  • EP4349841B1 patent drawing
  • EP4349841B1 patent drawing

AI summary

Provided is a method for efficiently producing an oxadisilacyclopentane compound at a high yield, comprising reacting an azadisilacyclopentane compound with water, the azadisilacyclopentane compound having the following general formula (1): [R1 to R4 are each independently an unsubstituted monovalent hydrocarbon group having 1 to 4 carbon atoms, and R5 is a hydrogen atom, a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, or a group having the following general formula (2): (R1 to R4 are as defined above, m is an integer of 0 to 5, n is an integer of 1 to 5, and a broken line donates a valence bond.) the oxadisilacyclopentane compound having the following general formula (3): (R1 to R4 are as defined above.).]