Azoxystrobin Synthesis Using DBU or DBN Catalysts
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Solution Overview
Problem
Existing methods for preparing azoxystrobin and its intermediates result in low yield and low purity, necessitating the development of a more efficient, scalable, and cost-effective process.
Innovation Solution
The use of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) as catalysts to facilitate the preparation of azoxystrobin and intermediates, achieving high yield and high purity by reducing impurity formation.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Manufacturing precision
If prior art processes are used for preparation of azoxystrobin, then the process can be carried out with conventional catalysts, but the yield and purity of azoxystrobin are low
Solution Approach 1:
The patent applies parameter changes by switching from conventional catalysts (DABCO, crown ethers, PEG) to diazabicyclo compounds (DBU, DBN) with different chemical structures and basicities. This catalyst substitution fundamentally changes the reaction parameters, leading to improved yield (90-95%) and purity (>98%) of azoxystrobin while reducing impurity formation.
2Manufacturing precision
If prior art processes are used for preparation of azoxystrobin, then conventional catalysts can be employed, but impurity formation is high
Solution Approach 1:
The patent converts the potential harm of catalyst selection into a benefit by choosing diazabicyclo compounds that specifically promote the desired reaction pathway while suppressing side reactions. This catalyst choice transforms what could be harmful impurity formation into a beneficial selective reaction process, achieving >98% purity by minimizing unwanted byproducts.
3Ease of manufacture
If prior art processes are used, then the synthesis method is established, but the process is not cost-effective and scalable
Solution Approach 1:
The patent employs cheap and readily available diazabicyclo compounds (DBU, DBN) as catalysts that can be used in small catalytic amounts (0.1-5 mol%). These catalysts are inexpensive, stable, and require minimal purification steps, making the process cost-effective and easily scalable for industrial production while maintaining high yield and purity.
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 process significantly improves the yield and purity of azoxystrobin, producing compounds substantially free from impurities, with the catalysts enabling complete conversion of reactants and minimizing undesired product formation.
Implementation Method 1
reacting a compound of formula (II) with compound of formula (III) in the presence of a catalyst selected from 1,8-Diazabicyclo[5.4.0]undec-7-ene or 1,5-Diazabicyclo [4.3.0]non-5-ene or salts and derivatives thereof
Data Source
AI summary
The present invention relates to a process for preparation of strobilurin compound, azoxystrobin and its intermediates using a catalyst selected from 1,8-Diazabicyclo[5.4.0]undec-7-ene or 1,5-Diazabicyclo[4.3.0]non-5-ene, salts thereof, or derivatives thereof.