Norbornene Alkyl Silyl Ethers With Borane Catalysis and Vacuum Distillation
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Solution Overview
Problem
Existing industrial processes for preparing norbornene alkyl silyl ethers generate significant waste due to the use of stoichiometric amounts of base, making them costly and environmentally unfriendly.
Innovation Solution
A catalytic amount of tris(pentafluorophenyl) borane is used to facilitate the reaction of norbornene alkanols with silane, allowing for the preparation of high purity norbornene alkyl silyl ethers through a controlled addition process and subsequent treatment with a base to remove residual catalyst, followed by vacuum distillation.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If stoichiometric amounts of base are used to prepare norbornene alkyl silyl ethers, then the reaction proceeds effectively, but large amounts of waste are generated
Solution Approach 1:
The patent changes the stoichiometric parameter from 1:1 base to substrate ratio to catalytic amount ratio, fundamentally altering the material consumption profile while maintaining reaction effectiveness through the discovery of catalytic activity of specific bases
Solution Approach 2:
The patent employs inexpensive, easily removable base catalysts such as cesium carbonate and potassium carbonate that can be used in catalytic amounts and removed through simple filtration or washing, replacing the need for stoichiometric base consumption
2Reliability
If stoichiometric amounts of base are used in the preparation process, then the reaction is effective, but operational costs increase due to waste management
Solution Approach 1:
The patent fundamentally changes the base consumption parameter from stoichiometric to catalytic amounts, reducing material costs and waste management expenses while maintaining reaction effectiveness through optimized catalytic cycles
Solution Approach 2:
The catalytic base system enables the reaction to be self-sustaining with minimal base consumption, where the base catalyst is regenerated at the end of the reaction cycle and can be recovered or easily removed, eliminating the need for continuous base addition
3Ease of manufacture
If conventional methods are used to prepare norbornene silyl ethers, then the process is established, but the process is not environmentally friendly
Solution Approach 1:
The patent modifies the environmental impact parameters by reducing base consumption from stoichiometric to catalytic amounts, minimizing waste stream generation and enabling greener chemistry practices while maintaining process reliability
Solution Approach 2:
The patent implements base recovery strategies where the catalytic base is removed through simple filtration or washing and can be recovered or disposed of in minimal amounts, significantly reducing environmental impact compared to stoichiometric base consumption
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 achieves high purity norbornene alkyl silyl ethers with minimal waste generation, suitable for high-quality polymer production, and reduces operational costs.
Implementation Method 1
catalytic amounts of tris(pentafluorophenyl) borane facilitates the reaction of norbornene alkanols of formula (II) with a silane of formula (III)
Implementation Method 2
followed by vacuum distillation
Data Source
AI summary
A process for the preparation of high purity norbornene alkyl silyl ether is disclosed and claimed. Specifically, a process for the preparation of industrial scale high purity norbornene methyl silyl ether is disclosed and claimed. The high purity monomers prepared in accordance with the process of this invention are useful in a variety of applications including but not limited to the preparation of high quality and high purity polynorbornenes having utility in a variety of electronic applications, among various other applications.