Mercaptoalkylalkoxysilane Production via pH Control and Phase Transfer Catalysis

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Solution Overview

Problem

Existing processes for producing sulfur-containing organosilicon compounds, such as mercaptoalkylalkoxysilanes, face issues with low yields, inefficiency, and environmental concerns due to the formation of undesirable co-products and side reactions.

Innovation Solution

A process involving the reaction of an alkali metal or ammonium sulfide with a haloalkyl silane in an aqueous medium, using an acidic gas to maintain pH below 10 and an alkylguanidinium salt phase transfer catalyst to enhance yield and purity, effectively suppressing by-product formation.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional synthetic processes are used to produce sulfur-containing organosilicon compounds, then the production can be carried out with existing methods, but undesirable co-products are formed by side reactions resulting in low yields and inefficiency

Engineering Contradiction:
ImproveyieldVSAvoidundesirable co-products
Core Design Contradiction:
ProductivityVSObject-generated harmful factors

Solution Approach 1:

The patent changes the pH parameter of the reaction medium to maintain it at or below 10, which suppresses side reactions that produce undesirable co-products. This parameter control resolves the contradiction by creating conditions that favor the main reaction while minimizing harmful by-products, thereby improving yield without sacrificing production feasibility

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces a phase transfer catalyst as an intermediary substance that facilitates the reaction between sulfide and haloalkyl silane. This catalyst mediates the reaction to proceed more efficiently with fewer side reactions, resolving the contradiction between maintaining production capability and reducing harmful by-products

Inventive Principle:
Principle #24Intermediary (Mediator)

2Productivity

If conventional synthetic processes are used for producing mercaptoalkylalkoxysilanes, then existing production methods can be maintained, but the processes are deficient in efficiency and environmental acceptability

Engineering Contradiction:
ImproveefficiencyVSAvoidenvironmental impact
Core Design Contradiction:
ProductivityVSObject-affected harmful factors

Solution Approach 1:

The patent maintains the reaction pH at or below 10, which improves reaction efficiency while reducing environmental impact. This parameter control prevents the formation of harmful by-products and makes the process more environmentally acceptable without sacrificing productivity

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent extracts or removes the problematic aspect of conventional processes by eliminating the conditions that lead to harmful by-products. By controlling pH and using a phase transfer catalyst, the process extracts only the desired mercaptoalkylalkoxysilane product while leaving behind minimal unwanted co-products, thereby improving both efficiency and environmental acceptability

Inventive Principle:
Principle #2Taking out (Extraction)

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 process results in increased yield, higher purity, and improved efficiency of mercaptoalkylalkoxysilane production, reducing the formation of undesirable products and environmental impact.

Implementation Method 1

in the additional presence of phase transfer agent, thereby providing a reaction mixture containing mercaptoalkylalkoxysilanes and water soluble co-products

Methodology Applied
Scientific EffectPhase transfer catalysis: Catalysis

Implementation Method 2

using an acidic gas to maintain the pH of the reaction medium at or below about 10

Methodology Applied
Scientific EffectpH control:

Data Source

PatentEP1960408B1Process for the production of mercaptoalkylalkoxysilanes
Publication Date: 2011.07.20 MOMENTIVE PERFORMANCE MATERIALS INC
  • EP1960408B1 patent drawing
  • EP1960408B1 patent drawing
  • EP1960408B1 patent drawing

AI summary

Mercaptoalkylalkoxysilane is obtained by reacting at least one sulfide of the general formula MHS wherein M is an alkali metal or ammonium with a haloalkyl silane in an aqueous reaction medium in the presence of an acidic gas to maintain the pH of the reaction medium at or below about (10), and in the additional presence of alkylguanidinium salt phase transfer catalyst to provide mercaptoalkylalkoxysilane, the alkylguanidinium salt phase transfer catalyst being represented by the general formula: wherein each of R1-5 is a primary alkyl radical and R6 is a primary alkyl or bis(primary alkylene) radical, or at least one of the R1-R2, R3-R4 and R5-R6 combinations with the respective connecting nitrogen atom forms a heterocyclic radical; X is an anion; and n is l or 2.