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Green synthesis method of 4-pyridine sulfonic acid

A technology for green synthesis and pyridine sulfonic acid, applied in the field of green synthesis of 4-pyridine sulfonic acid, can solve the problems of difficult preparation, low conversion rate and yield of raw materials, pungent taste and the like, and achieves easy availability of raw materials and simple raw materials. , the effect of reducing the difficulty of reaction

Active Publication Date: 2022-08-05
NANJING REDSUN BIOCHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The raw material conversion rate and yield of this method are all low, and 4-mercaptopyridine is not easy to obtain, and the pungent taste is bigger;
[0005] (2), using bispyridinethione as a raw material, in a hydrogen peroxide and acetic acid system, react to obtain 4-pyridine sulfonate, with a yield of 49%, but bispyridinethione is not easy to obtain and difficult to prepare;

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Step (1), in the four-necked flask, add 100g 4-chloropyridine, 100g hydrogen peroxide (mass fraction is 27.5%), 100g purified water, 3g TS-1 titanium silicon molecular sieve (Dalian Multiphase Catalyst Co., Ltd.), mechanical Stir, condense and reflux, then heat to 80 ° C, use liquid chromatography to monitor the reaction process, react for 2 hours, after the reaction is completed, filter out the TS-1 titanium silicon molecular sieve, and use liquid alkali (mass fraction is 20%) to adjust the filtrate. The pH was to neutral, the conversion of 4-chloropyridine was 100%, and the yield of 4-chloropyridine nitrogen oxide was 98%.

[0030] Step (2), adding the pH-neutral filtrate obtained in step (1) into a 1-liter autoclave, adding 260 g of sodium sulfite heptahydrate, stirring and dissolving, warming up to 120 ° C, and the reaction pressure is 0.5 MPa, using liquid chromatography. The reaction progress was monitored, and the reaction was carried out for 14 hours. At this ti...

Embodiment 2

[0033] Step (1), in the four-necked flask, add 100g 4-chloropyridine, 100g hydrogen peroxide (mass fraction is 27.5%), 100g purified water, 3g TS-1 titanium silicon molecular sieve (Dalian Multiphase Catalyst Co., Ltd.), mechanical Stir, condense and reflux, then heat to 80 ° C, use liquid chromatography to monitor the reaction process, react for 2 hours, after the reaction is completed, filter out the TS-1 titanium silicon molecular sieve, and use liquid alkali (mass fraction is 20%) to adjust the filtrate. pH to neutral, the conversion of 4-chloropyridine was 100%, and the yield of 4-chloropyridine nitrogen oxide was 98%.

[0034] Step (2), adding the pH-neutral filtrate obtained in step (1) into a 1-liter autoclave, adding 260 g of sodium sulfite heptahydrate, stirring and dissolving, warming up to 120° C., the reaction pressure being 0.5 MPa, and monitoring by liquid chromatography. The reaction progressed for 14 hours. At this time, the conversion rate of 4-chloropyridine...

Embodiment 3

[0037] Step (1), in the four-necked flask, add 100g 4-chloropyridine, 100g hydrogen peroxide (mass fraction is 27.5%), 100g purified water, 3g TS-1 titanium silicon molecular sieve (Dalian Multiphase Catalyst Co., Ltd.), mechanical Stir, condense and reflux, then heat to 80 ° C, use liquid chromatography to monitor the reaction process, react for 2 hours, after the reaction is completed, filter out the TS-1 titanium silicon molecular sieve, and use liquid alkali (mass fraction is 20%) to adjust the filtrate. pH to neutral, the conversion of 4-chloropyridine was 100%, and the yield of 4-chloropyridine nitrogen oxide was 98%.

[0038] Step (2), adding the pH neutral filtrate into a 1-liter autoclave, adding 275g of sodium sulfite heptahydrate simultaneously, stirring and dissolving, warming up to 125 ° C, the reaction pressure is 0.5MPa, using liquid chromatography to monitor the reaction progress, reaction 12 Within hours, the conversion of 4-chloropyridine nitroxide was 100%, ...

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PUM

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Abstract

The invention discloses a green synthesis method of 4-pyridine sulfonic acid, which comprises the following steps: by taking 4-chloropyridine as a raw material, hydrogen peroxide as an oxidant and water as a reaction solvent, carrying out oxidation reaction under the catalytic action of a titanium silicalite molecular sieve to generate 4-chloropyridine nitrogen oxide; the method comprises the following steps: by taking water as a reaction solvent, reacting 4-chloropyridine nitrogen oxide with sulfinate to obtain 4-sulfonate pyridine nitrogen oxide; under the catalytic action of a metal catalyst, the 4-pyridine sulfonate oxynitride and hydrogen are subjected to a reduction reaction to obtain 4-pyridine sulfonate, after the reaction is finished, the pH of a reaction solution is adjusted to be neutral, filtering and drying are conducted, and 4-pyridine sulfonate is obtained. 4-chloropyridine is taken as a starting raw material, the raw material is simple and easy to obtain, a product of each step of reaction does not need to be separated and is directly used as a raw material of the next step of reaction, use of a large amount of strong acid and strong alkali is avoided, a large amount of waste water and waste residues cannot be generated, pollution is basically avoided, and the development requirement of green chemistry is met.

Description

technical field [0001] The invention belongs to the fields of chemical industry and medicine, and relates to a green synthesis method of 4-pyridinesulfonic acid. Background technique [0002] 4-Pyridinesulfonic acid is widely used and can be used as organic synthesis intermediates and raw materials, such as intermediates for sulfonamide and other drugs, and 4-hydroxypyridine can also be prepared; 4-pyridinesulfonic acid is also used as water-soluble Reactive dyes; 4-pyridine sulfonic acid can also be applied to the field of electrochemistry, which has the effect of improving the precipitation performance of the electrodeposition bath during the electroplating process. 4-Pyridinesulfonic acid is an irritant substance that is irritating to the eyes, respiratory system and skin. [0003] The synthesis of 4-pyridinesulfonic acid mainly includes the following methods: [0004] (1) Using 4-mercaptopyridine as a raw material, in a hydrogen peroxide and acetic acid system, the rea...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/71
CPCC07D213/71Y02P20/584
Inventor 丁永山陈洪龙岳瑞宽罗超然王文魁
Owner NANJING REDSUN BIOCHEM CO LTD
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