Trimethylamine Catalyst for Azoxystrobin Intermediate Synthesis
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Solution Overview
Problem
Current methods for synthesizing azoxystrobin intermediates suffer from low yield and high by-product production, and the use of expensive catalysts like DABCO leads to environmental and economic challenges due to high ammoniacal nitrogen content in wastewater and difficulty in catalyst recycling.
Innovation Solution
The method employs trimethylamine as a catalyst for the ring-opening and etherification reaction of benzofuranone with dichloropyrimidine, allowing for increased reaction rate and yield, easy catalyst recycling, and significant reduction in ammoniacal nitrogen content in wastewater, making it environmentally friendly and cost-effective.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Speed
If DABCO catalyst is used to increase reaction rate, then the reaction rate improves, but the cost increases and wastewater treatment becomes more difficult due to high ammoniacal nitrogen content
Solution Approach 1:
The patent changes the chemical parameter of the catalyst from DABCO (high ammoniacal nitrogen) to trimethylamine (low ammoniacal nitrogen), thereby reducing the harmful factors in wastewater while maintaining catalytic activity. This parameter substitution directly addresses the contradiction between reaction rate improvement and environmental harm.
Solution Approach 2:
The patent employs trimethylamine as a catalyst that can be easily disposed of or recycled through simple distillation, replacing DABCO which requires complex wastewater treatment. The low boiling point of trimethylamine allows for easy separation and reuse, reducing both environmental harm and processing costs.
2Speed
If DABCO catalyst is used to improve reaction rate, then the reaction rate increases, but the catalyst recycling becomes difficult due to high boiling point
Solution Approach 1:
The patent changes the physical parameter of the catalyst by selecting trimethylamine with a low boiling point (3°C) compared to DABCO's high boiling point. This parameter change enables easy recycling through simple distillation or evaporation, making the catalyst readily separable from the reaction mixture and reusable.
3Ease of manufacture
If sodium methoxide is added directly without catalyst to synthesize compounds B and C, then the synthesis can be performed, but the yield remains low at 60-70% with many by-products
Solution Approach 1:
The patent introduces trimethylamine as an intermediary catalyst that facilitates the reaction between compound A and dichloropyrimidine. This catalyst mediator enables the reaction to proceed with higher efficiency and selectivity, increasing the yield to 80-90% while maintaining relative simplicity in the synthesis process.
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 approach achieves a high yield of up to 90% for azoxystrobin intermediates, reduces ammoniacal nitrogen content to 20 ppm or less, and enables efficient recycling and reuse of the trimethylamine catalyst, addressing the limitations of previous methods and providing economic advantages for industrial production.
Implementation Method 1
Trimethylamine is used in the method as a catalyst, which greatly increases the reaction rate and the product yield
Implementation Method 2
reacting compound A and dichloropyrimidine in the presence of a trimethylamine catalyst with the addition of a sodium methoxide solution in methanol or the addition of sodium methoxide and methanol separately
Data Source
AI summary
The present invention provides a method for preparing azoxystrobin intermediates, comprising reacting compound A and dichloropyrimidine in the presence of a trimethylamine catalyst with the addition of a sodium methoxide solution in methanol or the addition of sodium methoxide and methanol separately to produce a mixture of compound B and compound C. Azoxystrobin intermediate compound B and compound C are synthesized from compound A in the present invention, which is catalyzed by using a trimethylamine catalyst, allowing the reaction to have high efficiency and high yield. In addition, the trimethylamine catalyst has a low boiling point and thus can be easily recycled so that the ammoniacal nitrogen content in wastewater can be reduced, and the difficulties and high costs for wastewater processing can be also reduced. The recycled trimethylamine catalyst can be reused in preparing intermediate compound B, which also has a high catalytic effect and can also achieve a high product yield. The method of the present invention has significant synthetical cost advantages and is suitable for industrial production.