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Synthesis method of high-purity 1,4-butane sultone

A butane sultone and synthesis method technology, applied in the direction of organic chemistry, etc., can solve the problems of low yield, difficult separation of sodium chloride and sodium acetate, etc., to improve yield, shorten sulfonation reaction time, protect environmental effects

Active Publication Date: 2019-02-01
JINGCHU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Using tetrahydrofuran and acetyl chloride to synthesize 4-chlorobutanol acetate under the catalysis of Lewis acid is a safe and applicable method, but the disadvantage is that 1,4-dichlorobutane and 1,4-butanediol di Acetate and other by-products, so the yield is <80%
The sulfonation of 4-chlorobutanol acetate and sodium sulfite will produce sodium chloride and sodium acetate, and the separation of sodium chloride and sodium acetate is difficult, resulting in environmental problems
[0005] Another method sees sulfonation of 4-chlorobutanol and sodium sulfite to synthesize sodium 4-hydroxybutanesulfonate and then acidifies it into 4-hydroxybutanesulfonic acid. This route has no patent report, but it is in An.chan.Soc. 76 5357-60 19 reported that 4-chlorobutanol was reacted with sodium sulfite solution for 7 days to obtain sodium 4-hydroxybutanesulfonate, but the yield was extremely low, only 58%

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] 1. In a 1000ml reaction flask, add 1mol sodium sulfite and water to prepare a 15wt% sodium sulfite solution, then add 1mol 4-chlorobutanol, 120ml ethanol and 0.1g potassium iodide, heat up to reflux under vigorous stirring, reflux for 6 hours, and sample the gas phase Chromatographic analysis and detection showed that the remaining 4-chlorobutanol content was 0.58%. After the reflux was completed, the mixed solution A was obtained. The mixed solution A was added to the concentration tank, concentrated at normal pressure to recover ethanol, and when the temperature of the kettle reached 110°C, the temperature of the kettle was lowered to 50°C ℃, add 86ml of 36wt% industrial hydrochloric acid, then heat and concentrate under reduced pressure until the material becomes viscous, then add 500ml of ethanol dropwise, stir and reflux for 2 hours, then cool down to 40°C, precipitate sodium chloride crystals, filter, and wash with 100ml of ethanol For filter cake, add the filtrate...

Embodiment 2

[0029] Compared with Step 1 in Example 1, the ethanol in Step 1 of Example 1 was replaced with methanol, and the rest of the operations remained unchanged. Finally, 125.8g of 1,4-butane sultone was obtained as a colorless transparent liquid, and the yield was The yield is 92.5%, the purity is 99.76%, and the moisture content is 0.15wt%.

[0030] Compared with Step 3 in Example 1, the ether in Step 2 of Example 1 was replaced with dichloromethane, and other operations remained unchanged. The purity of the obtained 1,4-butane sultone was 99.92%, and the water content was 70PPM.

Embodiment 3

[0032] Compared with Step 1 in Example 1, the ethanol in Step 1 of Example 1 was replaced with isopropanol, and the rest of the operations remained unchanged, and finally 127.5g of 1,4-butane sultone was obtained as a colorless transparent liquid , the yield is 93.75%, the purity is 99.81%, and the moisture content is 0.18wt%.

[0033] Compared with Step 3 in Example 1, the diethyl ether in Step 2 of Example 1 was replaced with isopropyl ether, and the other operations remained unchanged. The purity of the obtained 1,4-butane sultone was 99.81%, and the water content was 50PPM.

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Abstract

The invention discloses a synthesis method of high-purity 1,4-butane sultone. The synthesis method comprises the steps: 1, adding 4-chlorobutanol and a sodium sulfite solution into an alcohol solvent,raising the temperature until carrying out reflowing for 6 h, ending the reflowing to obtain a mixed solution A, concentrating the mixed solution A to recover the alcohol solvent, then, adding hydrochloric acid for acidification, carrying out concentration until a material becomes viscous, then, adding the alcohol solvent, separating out a sodium chloride crystal, carrying out filtration, and concentrating filtrate to recover the alcohol solvent so as to obtain 4-hydroxybutane sulfonic acid; 2, carrying out continuous flash evaporation dehydration on 4-hydroxybutane sulfonic acid at the vacuum degree of 1-8 mmHg and the temperature of 130-165 DEG C to obtain industrial-grade 1,4-butane sultone; and 3, adding an azeotrope into industrial-grade 1,4-butane sultone, carrying out normal-pressure fractional distillation to recover the azeotrope, then, carrying out reduced-pressure fractional distillation at the vacuum degree of 2-4 mmHg, and collecting fractions with the temperature of 120-121 DEG C to obtain high-purity 1,4-butane sultone. The method is simple and environment-friendly, the sulfonation yield is greatly increased, and the purity and yield of 1,4-butane sultone are greatly increased.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing high-purity 1,4-butane sultone. Background technique [0002] 1,4-Butane sultone is a sulfonating agent, mainly used to synthesize biological buffers and sulfonic acid resins. In recent years, 1,4-butane sultone has gained attention because it can be used as a lithium battery additive. [0003] The report on the synthesis of 1,4-butane sultone was first seen in the 1950s. It was synthesized by dehydrochlorination and cyclization of 4-chlorosulfonyl chloride and copper oxide at 150-160 °C, see DE860637. Later, 1,4-butane sultone was synthesized by dehydration of 4-hydroxybutanesulfonic acid, see DE887341. This method is simple and convenient, and has become the main method for synthesizing 1,4-butane sultone, so the preparation of 4- Hydroxybutanesulfonic acid becomes the key to the synthesis of 1,4-butane sultone. There are also many methods...

Claims

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Application Information

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IPC IPC(8): C07D327/06
CPCC07D327/06
Inventor 胡莉萍胡冠丰
Owner JINGCHU UNIV OF TECH
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