Tartaric Acid Enantiomer Separation for Triazine Salts
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Solution Overview
Problem
Existing methods for separating enantiomers of dihydro-1,3,5-triazine derivatives are inefficient, requiring expensive chiral reagents and involving costly processes, especially when using the free base form of triazine derivatives, which necessitates re-formation of hydrochloride salts and is not universally applicable.
Innovation Solution
A process involving the formation of diastereoisomeric salts using tartaric acid as a chiral reagent, allowing for the direct separation of enantiomers from triazine derivatives in their salt form, which enhances yield, reduces impurities, and lowers costs by avoiding the need for expensive reagents and re-formation steps.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Manufacturing precision
If expensive chiral reagents like di-O,O'-p-toluyl-L-tartaric acid are used for separation, then separation efficiency is improved, but manufacturing cost increases
Solution Approach 1:
The patent replaces expensive chiral reagents (di-O,O'-p-toluyl-L-tartaric acid) with a cheaper alternative (tartaric acid) that can be used effectively for the separation process. This substitution maintains adequate separation efficiency while dramatically reducing the cost of chiral reagents, directly addressing the contradiction between separation efficiency and manufacturing cost.
Solution Approach 2:
The patent changes the chemical parameters of the chiral reagent system by switching from complex derivatives (di-O,O'-p-toluyl-L-tartaric acid) to the simpler tartaric acid. This parameter change in reagent structure and complexity achieves cost reduction while maintaining the essential separation functionality through optimized reaction conditions.
2Device complexity
If the free base form of triazine derivatives is used for separation, then separation process is simplified, but additional re-formation steps are required
Solution Approach 1:
The patent performs a preliminary action by converting the triazine derivative to its salt form before the separation process. This preliminary salt formation eliminates the need for subsequent re-formation steps, streamlining the overall process. The salt form is maintained through the separation and into the final product, avoiding unnecessary cyclic steps.
Solution Approach 2:
Instead of using the conventional free base form and then re-forming the salt, the patent inverts the approach by starting with and maintaining the salt form throughout the process. This inversion eliminates the need for re-formation steps and simplifies the overall process architecture.
3Manufacturing precision
If conventional separation methods are used, then enantiomers can be separated, but yield is reduced and impurities increase
Solution Approach 1:
The patent uses tartaric acid as an intermediary substance that forms diastereomeric salts with the enantiomers of the triazine derivative. This intermediary approach enables selective crystallization and separation of enantiomers with high efficiency, achieving both high separation precision and high yield while minimizing impurities.
Solution Approach 2:
The patent exploits phase transitions (crystallization) of diastereomeric salts to achieve separation. By controlling the crystallization conditions, the desired enantiomer can be selectively recovered in high purity and high yield, effectively resolving the contradiction between separation precision and productivity.
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 effectively separates enantiomers with higher yields and lower impurities, reducing expenses and allowing for the direct use of triazine derivatives in their salt form, overcoming the limitations of previous methods.
Implementation Method 1
formation of diastereoisomeric salts using tartaric acid as a chiral reagent
Implementation Method 2
the desired dihydro-1,3,5-triazine salt crystallize
Data Source
Figure 1
AI summary
The present invention relates to a new process of separation of triazine derivatives enantiomers involving tartaric acid.