[3-(2-Norbornyl)-2-Norbornyl]Silane High Yield Synthesis
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Solution Overview
Problem
Current silane compounds with a norbornyl radical are insufficient in refractive index and prone to oxidation, leading to colored coatings and the formation of corrosive by-products, necessitating the development of difunctional silane compounds with a linkage of two norbornyl radicals that are free from aliphatic unsaturated radicals and can be produced in high yields.
Innovation Solution
A method involving the reaction of 2-norbornene with a hydrosilane compound using a catalyst composed of a phosphine-free palladium compound and a phosphite compound to produce [3-(2-norbornyl)-2-norbornyl]organodichlorosilane and organoxysilane compounds, which are difunctional and have high yields, avoiding the limitations of existing catalysts.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Illumination intensity
If a vinyl-containing [3-(2-norbornyl)-2-norbornyl]silane compound is used, then the refractive index is improved, but the coating becomes colored with time due to oxidation of vinyl
Solution Approach 1:
The patent removes the vinyl group (aliphatic unsaturated radical) from the silane compound structure, extracting the problematic element that causes oxidation while retaining the norbornyl radical linkage that provides high refractive index. The invention uses a difunctional silane compound with two norbornyl radicals and no vinyl groups, thereby eliminating oxidation issues while maintaining optical properties.
Solution Approach 2:
The patent changes the chemical structure parameter by replacing vinyl-containing compounds with difunctional silane compounds having a linkage of two norbornyl radicals. This structural parameter change eliminates the vulnerable vinyl groups while preserving the high refractive index property through the norbornyl radical linkage.
2Illumination intensity
If trichlorosilane is added to form silicone oil, then the refractive index is improved, but the product loses oiliness when added in high proportion
Solution Approach 1:
The patent changes the functionality parameter of the silane compound from trifunctional (trichlorosilane) to difunctional ([3-(2-norbornyl)-2-norbornyl]organodichlorosilane). This parameter change allows higher addition proportions without compromising oiliness, as difunctional compounds form linear chains rather than cross-linked networks, maintaining the oily texture while providing high refractive index.
3Productivity
If conventional catalysts are used for hydrosilylation, then the reaction proceeds, but the yield of [3-(2-norbornyl)-2-norbornyl]silane compound is low
Solution Approach 1:
The patent introduces a phosphite compound as an intermediary mediator in the catalytic system. The phosphite compound works in conjunction with the phosphine-free palladium compound to form an active catalyst species that significantly improves the yield of [3-(2-norbornyl)-2-norbornyl]silane compound formation, transforming a low-yield reaction into a high-yield process.
Solution Approach 2:
The patent creates a composite catalytic system combining phosphine-free palladium compound with phosphite compound. This composite catalyst leverages the synergistic effects of both components to achieve high yield in the hydrosilylation reaction, overcoming the limitations of using either catalyst alone.
4Reliability
If [3-(2-norbornyl)-2-norbornyl]trichlorosilane is used as coupling agent, then coupling performance is achieved, but corrosive hydrogen chloride is formed as by-product
Solution Approach 1:
The patent changes the functional groups of the silane compound from chlorosilane (trichlorosilane) to organoxysilane ([3-(2-norbornyl)-2-norbornyl]organoxysilane). This parameter change eliminates the formation of corrosive hydrogen chloride during hydrolysis, as the organoxy groups do not produce HCl like the chlorosilane groups do, while maintaining coupling performance.
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 enables the production of [3-(2-norbornyl)-2-norbornyl]silane compounds in high yields, suitable for forming surface coatings on electronic parts without oxidation issues and corrosive by-products, maintaining oiliness and refractive index properties.
Implementation Method 1
reacting 2-norbornene with a hydrosilane compound in the presence of a catalyst composed of a phosphine-free palladium compound and a phosphite compound
Data Source
AI summary
A [3-(2-norbornyl)-2-norbornyl]silane compound having formula (1) is novel, wherein R1 is a monovalent hydrocarbon radical, X is halogen or an organoxy OR2, R2 is a monovalent hydrocarbon radical, n is 1 or 2 when X is halogen, and n is 0, 1 or 2 when X is organoxy. It is a useful reactant for forming surface coatings on electronic parts.