Sulfolane Solvent for Triazine Synthesis Yield
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Solution Overview
Problem
The production of 2,4,6-tris(hydroxyphenyl)-1,3,5-triazine is hindered by rapid solidification and the generation of by-products, leading to low yields and the need for large amounts of catalyst, resulting in increased waste and environmental concerns.
Innovation Solution
A method involving a solvent with sulfolane as the main component is used in the reaction between cyanuric halide and hydroxyphenyl compounds, with a Lewis acid at 0.3 to 0.7 equivalents, to suppress by-product formation and reduce catalyst usage, allowing for easier production and higher yields.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If conventional methods using large amounts of catalyst are used, then the reaction proceeds efficiently, but the amount of waste materials increases and environmental issues arise
Solution Approach 1:
The patent changes the physical-chemical parameters of the reaction system by introducing sulfolane as a specific solvent and controlling the catalyst amount at 0.3 to 0.7 equivalents. This parameter optimization allows the reaction to proceed efficiently with reduced catalyst usage, thereby improving productivity while reducing waste materials and environmental impact.
2Ease of manufacture
If conventional solvents are used, then the reaction can proceed, but rapid solidification occurs and by-products are generated, leading to low yields
Solution Approach 1:
Sulfolane acts as an intermediary solvent that mediates between the reactants and prevents direct contact that would cause rapid solidification. It provides a suitable reaction medium that maintains reactant solubility while preventing premature product precipitation, thereby suppressing by-product formation and improving yield without compromising reaction feasibility.
Solution Approach 2:
The patent changes the solvent parameter from conventional solvents to sulfolane, which has specific physical-chemical properties (high boiling point, good solubility, and ability to prevent solidification). This parameter change resolves the contradiction by enabling the reaction to proceed smoothly without rapid solidification and by-product generation, thereby improving both ease of manufacture and productivity.
3Speed
If the reaction is carried out with sufficient catalyst, then the reaction rate is maintained, but purification becomes difficult due to by-product formation
Solution Approach 1:
The patent optimizes the catalyst parameter to 0.3 to 0.7 equivalents and changes the solvent parameter to sulfolane. This combined parameter change maintains adequate reaction rate by using sufficient (but not excessive) catalyst while the sulfolane solvent prevents by-product formation through suppression of side reactions, thereby making purification easier without sacrificing reaction speed.
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 method enables the production of 2,4,6-tris(hydroxyphenyl)-1,3,5-triazine with improved yield and purity, reducing waste and environmental impact by minimizing by-product generation and catalyst requirements.
Implementation Method 1
by using a solvent containing sulfolane as the main component as the reaction solvent
Implementation Method 2
in the reaction between cyanuric halide compound and hydroxyphenyl compound, the compound is easily produced
Data Source
AI summary
The present invention provides a method of producing 2,4,6-tris(hydroxyphenyl)-1,3,5-triazine compound in which no rapid solidification or the like occurs and generation of by-products is suppressed, thereby enabling to reduce decrease in the yield. Particularly, the present invention is a method of producing 2,4,6-tris(hydroxyphenyl)-1,3,5-triazine compound represented by the following Formula (1): wherein the reaction between cyanuric halide compound represented by the following Formula (2): and hydroxyphenyl compound represented by the following Formula (3) : is carried out by using, as the reaction solvent, a solvent containing sulfolane as the main component in the presence of a Lewis acid at an amount of 0.3 to 0.7 equivalent with respect to 1 equivalent of halogen atom of the cyanuric halide compound represented by the Formula (2), or by using a mixed solvent of inert solvent and cycloalkyl alkyl ether represented by the following Formula (4): Z1-0-Z2 (4)