Esteramide Synthesis via Co-Addition of Amine and Base
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Solution Overview
Problem
Existing methods for producing esteramide compounds from diesters are not esteramide-selective, require cumbersome purification steps, and have low productivity due to slow reaction kinetics, often resulting in colored crude products that necessitate additional purification.
Innovation Solution
A process involving a reaction between a diester and an amine in the presence of a basic compound, conducted at a temperature of 30° C or higher, with simultaneous co-addition of the amine and basic compound to the diester, which enhances esteramide selectivity and reaction kinetics, simplifying the process and reducing the need for extensive purification.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Manufacturing precision
If the reaction is conducted at low temperatures (lower than ambient temperature) to improve esteramide selectivity, then the selectivity is improved, but the reaction kinetics are significantly reduced and productivity decreases
Solution Approach 1:
The patent changes the temperature parameter from low (below ambient) to elevated (30°C or higher), which reverses the conventional approach. This parameter change enables both high esteramide selectivity (>90%) and fast reaction kinetics to be achieved simultaneously, resolving the contradiction between selectivity and productivity
Solution Approach 2:
The patent introduces a basic compound as an intermediary substance that mediates the reaction between diester and amine. This intermediary enables the reaction to proceed with high esteramide selectivity at elevated temperatures, overcoming the limitation that normally requires low temperatures for selectivity
2Manufacturing precision
If conventional purification methods (distillation) are used to separate esteramide from diamide, then separation is achieved, but the process becomes complex and costly
Solution Approach 1:
The patent extracts or removes the need for complex purification steps by achieving high esteramide selectivity (>90%) directly in the reaction step. The simple filtration step replaces cumbersome distillation processes, dramatically simplifying the overall manufacturing process while maintaining high product purity
Solution Approach 2:
The reaction system itself provides the purification function through high selectivity. The process is self-service in that the reaction conditions automatically favor esteramide formation, eliminating the need for separate, complex purification operations
3Quantity of substance
If conventional methods are used to prepare esteramides from diesters, then the reaction can proceed, but the esteramide is considered a by-product and diamide is the majority product
Solution Approach 1:
The patent inverts the conventional outcome where diamide was the major product and esteramide was the by-product. By using elevated temperatures (30°C or higher) and a basic compound, the patent makes esteramide the major product with >90% selectivity, completely reversing the product distribution
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 achieves high esteramide selectivity (>90%) with rapid reaction times and eliminates the need for complex purification, resulting in high-purity esteramide compounds suitable for direct use in applications like plant health solvents.
Implementation Method 1
a reaction step between: a diester compound of following formula (II): R1OOC-A-COOR1 (II) and an amine of following formula (III): HNR2R3 (III) in the presence of a basic compound
Data Source
AI summary
The present invention concerns a process for preparing esteramide compounds. More particularly, the invention relates to a process for preparing esteramide compounds by reaction between a diester and an amine, in the presence of a basic compound, wherein the basic compound and the amine in gaseous form are co-added to the diester, the reaction being conducted at a temperature of 30° C. or higher.