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Process for one-pot synthesis of 4,5-dichloro-2-methylisothiazolinone

A technology of methylisothiazolinone and dimethyl, which is applied in the field of compound preparation, can solve the problems of low product purity, complicated operation, and large amount of three wastes, and achieve simplified process, small equipment investment, and reduced operating cost Effect

Active Publication Date: 2017-05-24
DALIAN BIO CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] In order to overcome the above-mentioned defects existing in the prior art field, the object of the present invention is to provide a kind of simple and convenient operation, safe and environment-friendly, one-pot synthetic high-purity DCMIT process, solve the complex operation in the prior art, the intermediate product needs to be separated and Purification, large amount of three wastes, low product purity, etc.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] 1) Synthesis of methyl 3,3'-dithiodipropionate

[0038] Add 129g (1.5 moles) of methyl acrylate, 5.2g of 40% methylamine aqueous solution, and 90g of sulfur into a 1L four-necked bottle equipped with a thermometer and a stirrer, and feed 30.1g of hydrogen sulfide gas into a temperature controlled 15-25°C to obtain light yellow reaction mixture;

[0039] 2) Synthesis of N,N'-dimethyl-3,3'-dithiodipropionamide

[0040] Add 100g of methanol to the above reaction mixture, add 55g (1.77 moles) of methylamine gas under stirring at a temperature of 5-15°C, and keep stirring for 24 hours after adding, to obtain N,N'-dimethyl-3,3'-dithio Methanol suspension of dipropionamide. Atmospheric distillation to remove methanol, steam to no liquid, then distill under reduced pressure until the temperature of the kettle reaches 70°C, and the pressure reaches -0.09Mpa and no liquid flows; add 150g of ethyl acetate to the kettle, and continue distilling until the temperature of the kettle...

Embodiment 2

[0044] 1) Synthesis of methyl 3,3'-dithiodipropionate

[0045] Add 129g (1.5 moles) of methyl acrylate, 5.2g of 40% methylamine aqueous solution, and 90g of sulfur into a 1L four-necked bottle equipped with a thermometer and a stirrer, and feed 30.1g of hydrogen sulfide gas into a temperature controlled 15-25°C to obtain light yellow reaction mixture;

[0046] 2) Synthesis of N,N'-dimethyl-3,3'-dithiodipropionamide

[0047] Add 100g of methanol to the above reaction mixture, add 52g (1.68 moles) of methylamine gas under stirring at a temperature of 5-15°C, and keep stirring for 24 hours after adding, to obtain N,N'-dimethyl-3,3'-dithio Methanol suspension of dipropionamide. Atmospheric distillation to remove methanol, steam to no liquid, then distill under reduced pressure until the temperature of the kettle reaches 70°C, and the pressure reaches -0.09Mpa and no liquid flows; add 150g of ethyl acetate to the kettle, and continue distilling until the temperature of the kettle...

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Abstract

The invention discloses a process for synthesizing 4,5-dichloro-2-methylisothiazolinone by a one-pot method. The process comprises the following steps: mixing methyl acrylate, a methylamine aqueous solution and sulfur to obtain a mixture, introducing hydrogen sulfide gas into the mixture to generate a dimethyl 3,3'-dithiobispropionate crude product; and then, on the basis of the dimethyl 3,3'-dithiobispropionate crude product, introducing methylamine gas to synthesize N, N'-dimethyl-3,3`- dithiodipropionamide, thereby obtaining the product 4,5-dichloro-2-methylisothiazolinone by reacting chlorine gas with the N, N'-dimethyl-3,3- dithiodipropionamide. According to the method provided by the invention, the technical process is simplified, the operation cost is reduced, and wastewater generation amount is greatly reduced; and three steps of carrying out Michael addition reaction, amidation and chlorination can be carried out in the same reaction kettle, so that separating and purifying processes of an intermediate product are reduced, and therefore, the equipment investment is low, and the obtained product is high in purity.

Description

technical field [0001] The invention relates to a preparation method of a compound, in particular to a preparation method of high-purity 4,5-dichloro-2-methylisothiazolinone with bactericidal effect. Background technique [0002] 3-isothiazolinone compounds are a new type of broad-spectrum fungicides, which have the advantages of high efficiency, broad-spectrum, low toxicity, and natural degradation in the environment, and have a wide range of applications. [0003] 4,5-dichloro-2-methylisothiazolinone (hereinafter referred to as DCMIT) is a kind of 3-isothiazolinone compound, which is mainly used in coatings, crop disease prevention, industrial water treatment and other fields. [0004] Among the DCMIT synthesis methods reported in the literature, the most suitable synthesis route for industrial production is to use N,N'-dimethyl-3,3'-dithiobispropionamide as raw material and react with chlorine gas in a solvent. [0005] Among them, N,N'-dimethyl-3,3'-dithiodipropionamide...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D275/03
CPCC07D275/03
Inventor 王勇顾振鹏刘海龙张晓娜杨兆辉
Owner DALIAN BIO CHEM
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