Organoxysilane Synthesis Using Bulky Secondary Amine Neutralization
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Solution Overview
Problem
Existing methods for producing nitrogen-containing polyfunctional organoxysilane compounds face challenges such as low yield and high energy consumption due to the use of inorganic bases that hydrolyze the organoxysilyl group or require excessive amounts of organic bases under high pressure and temperature, leading to inefficiencies and increased costs.
Innovation Solution
A substitution reaction using a secondary amine with at least one bulky substituent as a base in equimolar amounts to hydrogen halide generated during the reaction between a primary amine compound and a haloalkylalkoxysilane compound, conducted under mild conditions of normal pressure and 130°C or lower, to produce the nitrogen-containing polyfunctional organoxysilane compound in high yield and purity.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If inorganic base is used to neutralize hydrogen halide, then neutralization is achieved, but water is generated which hydrolyzes the organoxysilyl group
Solution Approach 1:
A secondary amine compound is introduced as an intermediary base to neutralize hydrogen halide during the substitution reaction. The secondary amine accepts the hydrogen halide to form a secondary ammonium halide, preventing water generation that would occur with inorganic bases. This intermediary approach allows effective neutralization while protecting the organoxysilyl group from hydrolysis, thereby maintaining high yield of the desired product.
2Productivity
If large excess amount of base is used under pressure and high temperature, then reaction proceeds efficiently, but energy cost and waste increase
Solution Approach 1:
The reaction conditions are optimized by changing parameters: using a secondary amine base at equimolar amount to hydrogen halide, conducting the reaction at normal pressure (0.09 to 0.11 MPa) and moderate temperature (130°C or lower). This eliminates the need for large excess base, high pressure (3 to 4 atm), and high temperature (175°C) required by conventional methods, thereby significantly reducing energy cost and waste while maintaining high productivity.
3Reliability
If secondary amine compound captures hydrogen halide, then neutralization occurs, but reaction rate is significantly reduced
Solution Approach 1:
By optimizing the reaction temperature to 130°C or lower and using a secondary amine compound with specific structural characteristics, the reaction maintains an appropriate rate while achieving effective neutralization. The moderate temperature prevents excessive slowing of the reaction rate that would occur at lower temperatures, while the secondary amine's basicity ensures complete neutralization of hydrogen halide.
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 achieves high yield and high purity of the nitrogen-containing polyfunctional organoxysilane compound under environmentally friendly and cost-effective conditions, avoiding the need for excessive bases and high temperatures.
Implementation Method 1
a secondary amine compound having at least one bulky substituent such as a secondary or tertiary alkyl group as a base in an equimolar amount to a hydrogen halide to be generated
Implementation Method 2
a substitution reaction between a primary amine compound and a haloalkylalkoxysilane compound
Data Source
AI summary
In the production of a compound having formula (3) or (3'): wherein R10 is a group having formula (4): wherein R4' and R5' each are a hydrocarbon group or the like, and X' is a single bond or the like, by reacting an amine having formula (1) or (1'): wherein R1, R2, and R3 each are a hydrocarbon group, R4 and R5 each are H or the like, X is a single bond or the like, and n is 1-3, with a haloalkoxysilane having formula (2): wherein R7, R8, and R9 each are a hydrocarbon group, Y is Cl or the like, and m is 0-2, a secondary amine having formula (5): wherein R11 is a branched or cyclic saturated hydrocarbon group in which C bonded to N is branched, and R12 is a hydrocarbon group or the like (exclusive of a group of R11), is used.