Cyclic Sulfonic Acid Ester Synthesis for Higher Yield and Purity
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Solution Overview
Problem
Existing methods for preparing cyclic sulfonic acid ester derivative compounds face issues such as low yield, product instability, and the generation of corrosive gases, making them unsuitable for non-aqueous electrolyte additives in lithium secondary batteries.
Innovation Solution
A method involving a thiol-ene reaction between a compound represented by Formula 1 and thioacetic acid, followed by an oxidative cyclization reaction under specific acid catalysts and solvents, using oxidizing agents like H2O2, HOCl, NCS, or KHSO5·0.5KHSO4·0.5K2SO4, to produce a compound represented by Formula 3.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Ease of manufacture
If a hydrosulfonation reaction is used to prepare cyclic sulfonic acid ester derivative compounds, then the reaction can proceed, but it is difficult to purify the sulfonate product from inorganic salt by-products, resulting in low yield and black tar form product
Solution Approach 1:
The patent introduces an organic sulfonic acid as an intermediary substance to replace inorganic salts in the hydrosulfonation reaction. This organic sulfonic acid intermediate can be easily purified from the reaction mixture and subsequently converted to the desired cyclic sulfonic acid ester derivative, thereby eliminating the purification difficulties and low yields associated with inorganic salt by-products.
Solution Approach 2:
The patent changes the chemical nature of the reaction parameters by using organic sulfonic acid instead of inorganic salts, and by conducting the reaction in organic solvents rather than aqueous media. These parameter changes enable easier purification and higher yields while maintaining the effectiveness of the hydrosulfonation reaction.
2Ease of manufacture
If SOCl2 is used in the dehydration reaction to prepare cyclic sulfonic acid ester derivative compounds, then the reaction can proceed, but corrosive gas is generated
Solution Approach 1:
The patent replaces the harmful SOCl2 reagent with alternative dehydrating agents that do not generate corrosive gases. The alternative reagents achieve the same dehydration function without the harmful side effects, converting a harmful process into a benign one while maintaining reaction effectiveness.
Solution Approach 2:
The patent uses organic sulfonic acid as an intermediary that facilitates the dehydration reaction without requiring corrosive reagents like SOCl2. This intermediary approach allows the reaction to proceed effectively while avoiding the generation of harmful corrosive gases.
3Productivity
If conventional methods are used to prepare cyclic sulfonic acid ester derivative compounds, then the reaction can proceed, but the overall yield is low due to purification issues and reactivity problems
Solution Approach 1:
The patent divides the synthesis process into distinct sequential steps: first performing hydrosulfonation with organic sulfonic acid to form an intermediate, then dehydrating this intermediate to form the final cyclic sulfonic acid ester derivative. This segmentation allows each step to be optimized independently, improving overall yield while making the process more manageable and less complex.
Solution Approach 2:
The patent performs the hydrosulfonation reaction first to create a purified organic sulfonic acid intermediate before proceeding to the dehydration step. This preliminary action of creating a clean, purifiable intermediate enables higher overall yields by eliminating purification difficulties that would otherwise affect the final product yield.
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 method improves the yield and product properties, resulting in higher purity and stability of the cyclic sulfonic acid ester derivative compounds, suitable for use in lithium secondary batteries.
Implementation Method 1
reacting a compound represented by Formula 1 below and a thioacetic acid to prepare a compound represented by Formula 2 below
Implementation Method 2
subjecting the compound represented by Formula 2 above to an oxidative cyclization reaction to prepare a compound represented by Formula 3 below
Data Source
Figure 1~2
Figure 3(a)~3(b)
AI summary
The present invention is an invention for providing a manufacturing method capable of improving the yield and properties of a cyclic sulfonic acid ester derivative compound, wherein in the method includes (A) reacting a compound represented by Formula 1 described herein and thioacetic acid to prepare a compound represented by Formula 2 described herein, and (B) subjecting the compound represented by Formula 2 above to an oxidative cyclization reaction to prepare a compound represented by Formula 3 described herein.