Preparation method of 2-fluoro-1, 3-propanesulfonic acid lactone

A propane sultone and strong acid technology, applied in the direction of organic chemistry, can solve the problems of difficult separation and purification of intermediates or products, poor thermal stability of propane sultone, poor reaction site selectivity, etc. Side effects, simple operation effect

Active Publication Date: 2019-06-28
SHANGHAI ROLECHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The above preparation method, when preparing the substituted propane sultone intermediate, the reaction site selectivity is poor, it is easy to generate other position substituted propane sultone, and the substituted propane sultone thermal stability is poor, and it is easy to eliminate Propylene sultone
In the whole preparation process, due to obvious side reactions, it is difficult to separate and purify intermediates or products, and the yield is low

Method used

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  • Preparation method of 2-fluoro-1, 3-propanesulfonic acid lactone
  • Preparation method of 2-fluoro-1, 3-propanesulfonic acid lactone
  • Preparation method of 2-fluoro-1, 3-propanesulfonic acid lactone

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preparation example Construction

[0032] In order to solve the above problems, the first aspect of the present invention provides a method for preparing 2-fluoro-1,3-propane sultone, the steps comprising:

[0033] (1) Sulfonation reaction: carry out a substitution reaction with a sulfite aqueous solution and the reactant (I) in the presence of a phase catalyst to obtain compound (II), or further acidify with a strong acid to obtain compound (III);

[0034] (2) Cyclization reaction: react the compound (II) or compound (III) obtained in step (1) with a dehydrating agent, remove the dehydrating agent after the reaction, wash and extract the reaction solution, remove the solvent, and then Purification by distillation under reduced pressure and recrystallization to obtain the product (IV), namely 2-fluoro-1,3-propane sultone;

[0035] The reactant (I) is a halogenated fluoropropanol, and the general structural formula is: X means Cl, Br, I;

[0036] The compound (II) is 2-fluoro-3-hydroxypropanesulfonate, and it...

Embodiment 1

[0080] Example 1 provides a method for preparing 2-fluoro-1,3-propane sultone, the synthesis reaction formula is as follows:

[0081]

[0082] Preparation steps include:

[0083] (1) Synthesis of sodium 2-fluoro-3-hydroxypropanesulfonate

[0084] Add 62.15 grams of sodium sulfite to 310.75 grams of water, stir to dissolve, then add 1.24 grams of tetrabutylammonium bromide, raise the temperature to 50°C-55°C, add 94.09 grams of 2-bromo-3-fluoropropanol dropwise under stirring, and add dropwise The time is 40-60 minutes. After the dropwise addition is completed, the temperature is kept at 50°C-55°C overnight, and the reaction is lowered to room temperature. Add 35 grams of methyl tert-butyl ether for extraction, and the obtained aqueous phase is dehydrated under reduced pressure and dried at 80°C to obtain a solid crude product 157 grams (semi-dry product), this solid does not need to be refined, and is directly subjected to the next reaction.

[0085] Spectrum characteriza...

Embodiment 2

[0100] Example 2 provides a method for preparing 2-fluoro-1,3-propane sultone, the synthesis reaction formula is as follows:

[0101]

[0102] Preparation steps include:

[0103] (1) Synthesis of sodium 2-fluoro-3-hydroxypropanesulfonate

[0104] Add 62.15 grams of sodium sulfite to 310.75 grams of water, stir to dissolve, then add 1.24 grams of tetrabutylammonium chloride, add 66.61 grams of 2-chloro-3-fluoropropanol dropwise under stirring, dropwise for 40-60 minutes, add dropwise After completion, the temperature was raised to reflux for overnight reaction. The reaction liquid was lowered to room temperature, and 35 g of methyl tert-butyl ether was added for extraction. The obtained aqueous phase was dehydrated under reduced pressure and dried at 80° C. to obtain 88.95 g of a crude solid product, which was directly subjected to the next reaction without purification.

[0105] (2) Synthesis of 2-fluoro-1,3-propane sultone

[0106] Weigh 577 grams of phosphorus oxychlor...

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Abstract

The invention relates to the technical field of synthesis methods of organic compounds, in particular to a preparation method of 2-fluoro-1, 3-propanesulfonic acid lactone, which comprises the following steps of: sulphonation reaction: carrying out substitution reaction on a sulfite water solution and a reactant (I) under a phase catalyst to obtain a compound (II), or acidifying with strong acid to obtain a compound (III), (1) cyclization reaction: reacting the compound (II) or compound (III) obtained in step (1) with a dehydrating agent, removing the dehydrating agent after the reaction is finished, washing, extracting, removing the solvent, vacuum-distilling and recrystallizing to obtain a product (IV), namely the 2-fluoro-1, 3-propanesulfonic acid lactone. The preparation method has theadvantages of cheap and easily obtained raw materials, simple operation, mild reaction conditions, good intermediate stability, difficult side reaction, and simple product separation and purification.

Description

technical field [0001] The invention belongs to the technical field of synthesis methods of organic compounds, and more specifically, the invention relates to a preparation method of 2-fluoro-1,3-propane sultone. Background technique [0002] Sultones can be used as additives for non-aqueous electrolytic solutions in lithium-ion secondary batteries, and various battery characteristics can be improved. Compared with sultone and vinylene carbonate, fluorosultone exhibits better battery cycle characteristics in a wider temperature range (25 ° C ~ 60 ° C), and fluoro sultone has a good Good anode stability, cathode activity and thermal stability (J.Mater.Chem.A., 2013, 1(38):11975-11981). Therefore, fluorosultone has a good application prospect in lithium-ion batteries. [0003] The usual preparation method for fluorosultone is to firstly prepare halogenated or hydroxy-substituted propane sultone, and then carry out fluorination reaction to generate the corresponding fluorosul...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D327/04
Inventor 石柳刘继成
Owner SHANGHAI ROLECHEM CO LTD
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