Functional Silanes via Hydroxyl-Ene Reaction

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Current methods for synthesizing functional silanes are limited by slow reaction rates and low conversion efficiencies, hindering the development of novel functional silanes with diverse applications.

Innovation Solution

A hydroxyl-ene reaction method under water-free and oxygen-free conditions using an alkene-containing silane and an alcohol or polyhydroxy compound, with a catalyst, in the presence of organic solvents, to achieve high efficiency and control over silane structures.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If direct synthesis or nucleophilic substitution reaction is used to prepare functional silanes, then the existing functional silanes can be obtained, but the reaction rate is slow and conversion efficiency is low

Engineering Contradiction:
Improvereaction rateVSAvoidconversion efficiency
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The patent employs a hydroxyl-ene reaction mechanism that fundamentally changes the reaction parameters and pathway compared to traditional nucleophilic substitution. This new reaction mechanism enables significantly faster reaction rates and higher conversion efficiencies while maintaining product quality

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces specific catalysts as intermediaries to facilitate the hydroxyl-ene reaction between alkene-containing silanes and alcohols. These catalysts mediate the reaction process to achieve high conversion rates and eliminate the slow reaction rates characteristic of traditional methods

Inventive Principle:
Principle #24Intermediary (Mediator)

2Productivity

If water-free and oxygen-free conditions are maintained, then high conversion rates are achieved, but the operational complexity increases

Engineering Contradiction:
Improveconversion rateVSAvoidoperational simplicity
Core Design Contradiction:
ProductivityVSEase of operation

Solution Approach 1:

The patent creates and maintains an inert reaction environment by using water-free and oxygen-free conditions. This inert atmosphere prevents side reactions and ensures high conversion rates, while the systematic approach to maintaining these conditions makes the process manageable despite the apparent complexity

Inventive Principle:
Principle #39Inert atmosphere (Inert environment)

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 method enables fast reaction rates, high conversion rates, and the production of functional silanes with varied structures, enhancing their modification and application potential as coupling agents.

Implementation Method 1

A preparation method of functional silane, comprising: with substance A as the base material and B under water-free and oxygen-free condition, functional silanes are prepared. A is an alkene-containing silane and B is an alcohol or a polyhydroxy compound.

Methodology Applied
Scientific EffectHydroxyl-ene reaction: Chemical Bonding

Implementation Method 2

the reaction proceeds in the presence of a catalyst. Preferably, the catalyst is selected from inorganic bases, organic bases or metal complexes

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentUS11608348B2Preparation method of functional silanes
Publication Date: 2023.03.21 SHANDONG UNIV
  • US11608348B2 patent drawing
  • US11608348B2 patent drawing
  • US11608348B2 patent drawing

AI summary

A preparation method of functional silanes comprises: substance A and substance B are added in a three-necked bottle and a certain amount of solvent is added; the resultant mixture is stirred for 0.5-24 h in the presence of catalyst under an atmosphere of argon, resulting in the crude product; after removing the remaining solvent and catalyst, the residual product is purified by chromatographic column to obtain functional silanes; the substance A is an alkene-containing silane and the substance B is an alcohol; functional silanes with various structures can be prepared, and their structures can be controlled by regulating the ratio of substance A and substance B, thereby providing ideas for the preparation of different silanes and the structural design of silane coupling agents.