Method for producing cyclic sulfonic acid ester and intermediate thereof

A technology of acid anhydrides and compounds, applied in the field of manufacture of cyclic sulfonic acid esters (sultones), can solve problems such as low yields

Inactive Publication Date: 2014-06-04
FUJIFILM WAKO PURE CHEM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, above-mentioned all methods all have low yield, must have a large amount of more expensive reagents, be difficult to stably obtain the problem points such as target product cyclic sulfonate (sultone) under industrial scale, therefore, not necessarily is an advantageous method

Method used

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  • Method for producing cyclic sulfonic acid ester and intermediate thereof
  • Method for producing cyclic sulfonic acid ester and intermediate thereof
  • Method for producing cyclic sulfonic acid ester and intermediate thereof

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 12

[0090] Synthesis example 12, Synthesis of 3-dihydroxypropanesulfonate sodium (reaction formula [I])

[0091] To a solution obtained by dissolving 120 g of sodium sulfite (924 mmol, content: 97.0%; manufactured by Wako Pure Chemical Industries, Ltd.) in 400 ml of water, 107.2 g of 3-chloro-1,2-propanediol (970 mmol; manufactured by Wako Pure Chemical Industries, Ltd. fabrication), heated to reflux for 1 h. After the reaction is terminated, concentrate the reaction solution, then add 750 ml of methanol to the concentrated residue, filter the resulting crystals, and dry the obtained crystals to obtain white crystals that are 2,3-dihydroxy Sodium propanesulfonate 202.6g (content: 67.2%, yield: 82.7%). Furthermore, the content of 2,3-dihydroxypropanesulfonate sodium, by adopting 1 Calculated by the internal standard method of H-NMR. In addition, it was confirmed that sodium chloride crystals were mixed as by-products in the above-mentioned white crystals. Shown below 1 Measure...

Embodiment 11

[0094] Example 11, Synthesis of 3,2-dioxotetrahydrothiophene-2-oxo-4-yl-methanesulfonyl chloride (the first step; reaction formula [II])

[0095] Make 80.0g (301mmol, content: 67.2%) in the total amount of 2,3-dihydroxypropanesulfonate obtained in Synthesis Example 1 in N, N-dimethylformamide (DMF) 110.3g (1509mmol; Wako Pure Pharmaceutical Co., Ltd.), and cooled to -20°C to 10°C. 107.7 g (905 mmol; manufactured by Wako Pure Chemical Industries, Ltd.) of thionyl chloride was added dropwise to the cooled suspension, followed by stirring at room temperature for 3 hours to allow a reaction. After the reaction was terminated, the reaction solution was added to 400 ml of water cooled to -20°C to 10°C, then 200 ml of toluene was added to the mixed solution, stirred, and the organic layer was separated. After the separated organic layer was washed with water, the organic layer was concentrated to obtain 1,3,2-dioxotetrahydrothiophene-2-oxyethylene-4-yl-methanol of the above-mentione...

Embodiment 22

[0101] Example 2 Synthesis of 2-hydroxy-1,3-propanesultone (second step; reaction formula [III])

[0102]To 4.21 g (19.1 mmol) of the total amount of 1,3,2-dioxotetrahydrothiophene-2-oxo-4-yl-methanesulfonyl chloride obtained in Example 1, under ice cooling, add 12N hydrochloric acid 1.75g ​​(hydrogen chloride; 21.0mmol, water; 62.2mmol; manufactured by Wako Pure Chemical Industries, Ltd.), stirred at room temperature for 30 minutes, and allowed to react. After the reaction was terminated, 50 ml of ethyl acetate was added to the reaction liquid, followed by stirring, and then, the organic layer was separated. After the separated organic layer was washed with water, the organic layer was concentrated, then, toluene was added to the concentrated residue, and the resulting crystal was collected by filtration, and the obtained crystal was dried to obtain a white crystal, which is the 2- Hydroxy-1,3-propane sultone 2.51 g (yield: 95%). Shown below 1 Measurement results of H-NMR....

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Abstract

The invention relates to a method for producing unsaturated sultone having a specified structure and a cyclic sulfite having a specified structure. The present invention is directed to provide an efficient production method which is capable of not only obtaining a cyclic sulfonic acid ester (sultone) at low cost and in high yield, but also the sulfonic acid ester (sultone) stably even in a commercial scale. The present invention relates to a method for producing hydroxysultone comprising a first step where a diol having a specified structure and a thionyl halide are reacted to obtain a cyclic sulfite having a specified structure, a second step where the cyclic sulfite is reacted with water or / and alcohol, and a third step where a hydroxylsultone having a specified structure is reacted with an acid halide or an acid anhydride to obtain an intermediate, subsequently the intermediate is treated with a base.

Description

[0001] This application is a divisional application, the application number of its parent case is 201080032606.3 (the international application number is PCT / JP2010 / 063062, the international application date is August 3, 2010), and the date of entering the Chinese national phase is January 18, 2012 , the applicant is: Wako Pure Chemical Industry Co., Ltd., and the name of the invention is: the manufacturing method of cyclic sulfonic acid ester and its intermediate. technical field [0002] The present invention relates to, for example, a method for producing a cyclic sulfonate (sultone) useful as a non-aqueous electrolyte additive in a lithium-ion secondary battery, and more specifically relates to a high-efficiency The manufacture method of the cyclic sulfonate (sultone). Background technique [0003] Cyclic sulfonic acid esters (sultones), for example, are known as compounds useful as non-aqueous electrolytic solution additives that can improve various battery characterist...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D327/04
CPCC07D327/10C07D327/04Y02E60/10H01M10/0567H01M10/0569
Inventor 藏本绚子冈本训明绵引勉角野元重
Owner FUJIFILM WAKO PURE CHEM CORP
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