Dimethyl Muconate Cycloaddition via Solid-Phase Transfer
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Solution Overview
Problem
Conventional cycloaddition processes for dimethyl muconate to produce dimethylcyclohex-2-ene-1,4-dicarboxylate face challenges with low yield and high side reactions at high concentrations, requiring long reaction times and being inefficient economically.
Innovation Solution
A process involving a reactor filled with ethylene gas, where trans,trans-dimethyl muconate is introduced in a solid phase for cycloaddition, allowing for efficient reaction under high-concentration conditions without side reactions, followed by aromatization to obtain dimethyl terephthalate.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If the concentration of reactants is increased to solve the problem of low reaction efficiency, then the reaction rate improves, but too many side reactions take place reducing the yield
Solution Approach 1:
The reactor is filled with ethylene gas in advance before introducing the solid-phase dimethyl muconate. This preliminary preparation of the reaction environment allows the cycloaddition reaction to proceed efficiently at high concentration without excessive side reactions, as the ethylene gas is already in position to react with the muconate upon contact.
2Loss of substance
If the reaction temperature is lowered to reduce side reactions, then the selectivity improves, but the cycloaddition reaction is not carried out well
Solution Approach 1:
The invention changes the physical state parameter of the dimethyl muconate from dissolved (liquid phase) to solid phase, and changes the concentration parameter to high concentration. This parameter change allows the reaction to proceed efficiently at temperatures that minimize side reactions while maintaining good cycloaddition reaction efficiency, as the solid-phase material provides high local concentration without requiring elevated temperatures.
3Loss of substance
If a long reaction time is used to achieve high yield at low concentration, then the yield improves, but the efficiency is reduced
Solution Approach 1:
The invention changes the concentration parameter to high concentration and the physical state to solid phase, which dramatically increases the reaction rate. This allows high yield to be achieved in short reaction time, eliminating the trade-off between yield and time that exists in conventional low-concentration processes.
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 process achieves high yield and purity of dimethylcyclohex-2-ene-1,4-dicarboxylate with reduced reaction time and lower costs, enhancing the economic viability for mass synthesis of dimethyl terephthalate.
Implementation Method 1
preparing a reactor filled with ethylene gas
Implementation Method 2
carrying out a cycloaddition reaction to obtain dimethylcyclohex-2-ene-1,4-dicarboxylate
Implementation Method 3
introducing a compound of the following Formula 1 in a solid phase to the reactor
Data Source
AI summary
A method for cycloaddition of dimethyl muconate is disclosed. According to the method, a direct transferring of a solid phase trans,trans-dimehtyl muconate into a reactor pre-filled with ethylene gas increases the efficiency of the reaction and suppress side reactions resulting an improvements in yield and purity. Furthermore, the method is capable of obtaining a high yield of dimethylcyclohex-2-en-1,4-dicarboxylate at a lower cost, and therefore is also useful for the mass synthesis of dimethyl terephthalate.