Phosphoric Acid Aryl Ester Diamide Synthesis via Selective Catalysis
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Solution Overview
Problem
Current methods for producing aryl phosphoric ester diamides are complex and costly, with issues such as the formation of by-products, need for vacuum distillation, and caking during ammonolysis, which affect yield and product quality.
Innovation Solution
A process using phosphorus oxychloride and phenol in the presence of phosphine or phosphine oxide catalysts, eliminating the need for vacuum distillation and optimizing ammonolysis conditions to produce aryl phosphoric ester diamides with high yield and purity.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Manufacturing precision
If a larger excess of phosphorus oxychloride is used to suppress byproduct formation, then byproduct formation is reduced, but space-time yield decreases
Solution Approach 1:
The patent changes the chemical parameters by introducing phosphine or phosphine oxide as catalysts, which fundamentally alter the reaction pathway and selectivity. This allows the reaction to proceed with high selectivity using only a slight excess of phosphorus oxychloride (1.05-1.2 equivalents), resolving the contradiction between suppressing byproducts and maintaining high productivity.
Solution Approach 2:
Phosphine or phosphine oxide acts as an intermediary catalyst in the reaction between phosphorus oxychloride and phenol. This intermediary substance facilitates the formation of the desired phosphoric acid aryl ester dichloride while preventing side reactions, thereby achieving high selectivity without requiring large excesses of reactants.
2Manufacturing precision
If vacuum distillation is used to separate phosphoric aryl ester dichlorides from byproducts, then separation purity is improved, but device complexity and production costs increase
Solution Approach 1:
The patent extracts or removes the problematic byproduct formation issue at its source by using selective catalysis. Instead of dealing with separation after the reaction, the catalyst ensures that minimal byproducts are formed in the first place, making complex vacuum distillation systems unnecessary.
Solution Approach 2:
The reaction system becomes self-service through high selectivity catalysis. The phosphine or phosphine oxide catalyst automatically directs the reaction toward the desired product with minimal side products, eliminating the need for additional complex separation equipment and operations.
3Productivity
If phosphoric aryl ester dichlorides are atomized with liquid ammonia and ammonia gas, then ammonolysis efficiency is improved, but nozzle clogging occurs due to solid formation
Solution Approach 1:
The patent uses a disposable inert solvent that dissolves the phosphoric aryl ester dichloride and prevents solid formation during ammonolysis. The solvent serves its purpose of preventing clogging and can be easily removed afterward, sacrificing a simple substance to solve the operational problem.
Solution Approach 2:
The inert solvent acts as an intermediary medium between the phosphoric aryl ester dichloride and ammonia. It maintains the reactants in solution, preventing premature solidification and nozzle clogging while allowing efficient ammonolysis to proceed.
4Speed
If conventional catalysts are used to accelerate the reaction between phenols and phosphorus oxychloride, then reaction speed is improved, but selectivity decreases leading to more byproducts
Solution Approach 1:
The patent changes the chemical parameter of catalysis by using phosphine or phosphine oxide instead of conventional catalysts. This fundamental change in catalyst type simultaneously achieves both fast reaction rates and high selectivity, resolving the contradiction between speed and precision.
Solution Approach 2:
The use of phosphine or phosphine oxide represents a composite approach to catalysis, combining the ability to activate the reaction with high selectivity for the desired product. This composite catalytic function achieves both rapid reaction and minimal byproduct formation.
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 simplifies production, reduces by-product formation, and prevents caking, resulting in high-yield, cost-effective aryl phosphoric ester diamides with improved product quality and stability.
Implementation Method 1
phosphorus oxychloride and phenol or a phenol substituted by one or more C1-C4-alkyl, C1-C4-alkoxy, halogen, hydroxy or nitro groups is reacted in the presence of at least one phosphine and/or one phosphine oxide as a catalyst
Implementation Method 2
which is then reacted in a second reaction step, after separation of the excess phosphorus oxychloride by distillation at normal pressure or at slight vacuum of 100 to 500 mbar, without further purification in an inert solvent with ammonia to give the phosphoric acid aryl ester diamide
Implementation Method 3
separation of the excess phosphorus oxychloride by distillation at normal pressure or at slight vacuum of 100 to 500 mbar
Implementation Method 4
distillation at normal pressure or at slight vacuum of 100 to 500 mbar
Data Source
AI summary
The present invention relates to a technically simple process for the production of phosphoric aryl ester diamides starting from phosphorus oxychloride and phenols, wherein the phosphoric aryl ester dichlorides formed as intermediates are reacted with ammonia to give the final product without an additional purification step. The process also relates to various variants of the reaction of phosphoric aryl ester dichlorides with ammonia.