Stabilizing Imino-Functional Silane via Bronsted-Lowry Base Neutralization
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Solution Overview
Problem
Imino-functional silanes undergo undesirable addition and deamination reactions during storage, leading to a reduction in product purity and stability, making them unsuitable for use as intermediates or adhesion promoters in clear compositions.
Innovation Solution
Adding a Bronsted-Lowry base with a conjugate acid pKa greater than 12 to imino-functional silanes to neutralize proton sources, thereby inhibiting self-addition and deamination reactions, and separating the base to collect the stabilized silane.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If imino-functional silane is stored without stabilization, then the silane can be used as an intermediate or adhesion promoter, but it undergoes addition and deamination reactions that reduce product purity and stability
Solution Approach 1:
A Bronsted-Lowry base is added to the imino-functional silane before storage to preemptively neutralize any acidic proton sources that could catalyze decomposition reactions. This preliminary stabilization prevents addition and deamination reactions during storage, maintaining both reliability and preventing substance loss.
Solution Approach 2:
The Bronsted-Lowry base acts as an intermediary substance that interacts with acidic impurities in the imino-functional silane system. By neutralizing these acids, the base mediates the prevention of catalyzed decomposition reactions, thereby preserving product purity and storage stability without requiring complex processing.
2Reliability
If a Bronsted-Lowry base is added to stabilize the imino-functional silane, then storage stability increases, but the system requires additional separation steps to remove the base
Solution Approach 1:
The patent employs volatile Bronsted-Lowry bases such as alkoxides that can be easily removed through simple distillation or evaporation. These bases serve their stabilization function during storage and then are readily eliminated, avoiding complex separation equipment while maintaining process simplicity.
Solution Approach 2:
The stabilization base is selected to undergo convenient phase transitions (such as evaporation or distillation) that enable easy separation from the imino-functional silane after stabilization. This phase change property allows removal of the base through simple heating or reduced pressure without requiring complex separation devices.
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 effectively prevents further reactions, preserving the original content of imino-functional silane, suppressing the formation of unwanted by-products, and significantly increasing storage stability.
Implementation Method 1
adding a Bronsted-Lowry base to an imino-functional silane to neutralize proton sources, thereby inhibiting self-addition and deamination reactions
Implementation Method 2
separating step (c) is preferably carried out by at least one of distilling the mixture of the imino-functional silane and the at least one Bronsted-Lowry base
Implementation Method 3
passing such mixture through an ion exchange resin or membrane
Data Source
AI summary
A method of stabilizing imino-functional silane involving adding thereto at least one Bromsted-Lowry base to inhibit, suppress or prevent the addition reactions of the imino- functional silane with itself to form a imino- and amino-functional silane and the subsequent deamination reactions to form conjugated carbon-carbon double bond-containing imino- functional silanes and stabilized imino-functional silanes containing the at least one Bronsted- Lowry base.