Azoxystrobin Synthesis Catalyst Reduction
Find Innovative SolutionsGenerate Solutions
Solution Overview
Problem
Current methods for producing azoxystrobin require high amounts of the expensive catalyst 1,4-diazabicyclo[2.2.2]octane (DABCO), leading to increased costs and environmental concerns due to catalyst discharge in aqueous process effluent.
Innovation Solution
A process using between 0.1 and 2 mol% of DABCO to react 2-cyanophenol with methyl (E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxyacrylate or its derivatives, significantly reducing catalyst usage while maintaining high yields.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If high amounts of DABCO catalyst are used in the reaction, then the reaction yield is improved, but the manufacturing cost increases and environmental harm worsens due to catalyst discharge
Solution Approach 1:
The patent applies parameter changes by optimizing the catalyst concentration from the conventional high amount (40 mol% as per WO 01/727191) to a significantly reduced range of 0.1-2 mol%. This parameter modification maintains high reaction yields while dramatically reducing the amount of DABCO catalyst discharged into aqueous effluent, thereby resolving the contradiction between productivity and environmental harm.
2Productivity
If high amounts of DABCO catalyst are used, then the reaction proceeds efficiently, but the manufacturing cost increases due to the expensive catalyst
Solution Approach 1:
The patent resolves this contradiction by changing the catalyst concentration parameter from high (40 mol%) to low (0.1-2 mol%). This parameter optimization maintains sufficient reaction efficiency while dramatically reducing the quantity of expensive DABCO catalyst required, thereby lowering manufacturing costs without sacrificing productivity.
3Productivity
If conventional catalyst amounts (40 mol% DABCO) are used, then the reaction yield is high, but the quantity of catalyst discharged in aqueous process effluent increases
Solution Approach 1:
The patent addresses this contradiction by modifying the catalyst concentration parameter from 40 mol% to 0.1-2 mol%. This change maintains high reaction yields while minimizing the absolute quantity of DABCO catalyst that ends up in aqueous process effluent, thereby reducing substance loss and environmental contamination.
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 significantly reduces the cost of azoxystrobin production and minimizes environmental impact by using less DABCO, achieving yields comparable to or exceeding those with higher catalyst concentrations.
Implementation Method 1
reacting 2-cyanophenol with methyl (E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxyacrylate in the presence of between 0.1 and 2 mol % of 1,4-diazabicyclo[2.2.2]octane
Data Source
AI summary
The present invention relates to a process for preparing a compound of formula (IV) where W is the methyl (E)-2-(3-methoxy)acrylate group, which comprises the steps of: (i) reacting the compound of formula (IV) where W is the methyl 2-(3,3-dimethoxy)propanoate group with a reagent that will protect the hydroxyl group of that compound from reaction during subsequent demethanolysis; (ii) eliminating methanol from the hydroxyl-protected compound formed in step (i); and (iii) removing the hydroxyl-protecting group formed in step (i) to form a compound of formula (IV) where W is the methyl (E)-2-(3-methoxy)acrylate group.