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Process for synthesizing 4,5-dichloro-2-methylisothiazolinone by one-pot method

A technology of methyl isothiazolinone and dimethyl, which is applied in the field of compound preparation, can solve the problems of low product purity, complicated operation, large amount of three wastes, etc., and achieves simplified process, small equipment investment, and reduced generation amount. Effect

Active Publication Date: 2015-10-07
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] In a 1L four-necked flask equipped with a thermometer and agitator, add 129 g (1.5 moles) of methyl acrylate, 5.2 g of a 40% methylamine aqueous solution, 90 g of sulfur, and feed 30.1 g of hydrogen sulfide gas at a temperature of 15-25°C to obtain a light yellow reaction mixture;

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

[0040] 100 g of methanol was added to the above reaction mixture, and 55 g (1.77 moles) of methylamine gas was introduced into the reaction mixture under stirring at a temperature of 5-15 ° C. After the addition, the temperature was maintained and stirred for 24 h to obtain N,N'-dimethyl-3,3'-dithiocyanate. Methanolic suspension of dipropionamide. Atmospheric distillation to remove methanol, steam to stagnant liquid and then vacuum distillation, until the still temperature reaches 70 ℃, and the pressure reaches -0.09Mpa stagnant liquid; add 150g of ethyl acetate in the s...

Embodiment 2

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

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

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

[0047] 100 g of methanol was added to the above reaction mixture, and 52 g (1.68 moles) of methylamine gas was introduced into the reaction mixture under stirring at a temperature of 5-15 °C. Methanolic suspension of dipropionamide. Atmospheric distillation to remove methanol, steam to stagnant liquid and then vacuum distillation, until the still temperature reaches 70 ℃, and the pressure reaches -0.09Mpa stagnant liquid; add 150g of ethyl acetate in the still, continue to distill until the still temperature reaches 80 ℃, the pressure reaches -0.09Mpa until no liquid fl...

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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 one of the 3-isothiazolinone compounds, 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'-dithiodipropionamide as raw material, and react with chlorine gas in a solvent. [0005] Among them, N,N'-dimethyl-3,3'-dithiodipropionamide is syn...

Claims

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Application Information

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Patent Type & Authority Applications(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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