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Preparation method of isothiazolinone biocide mildewcide

The technology of isothiazolinone, bactericidal and antifungal agent is applied in the field of preparation of isothiazolinone type bactericidal antifungal agent, and can solve the problems of high volatility, high equipment corrosion, and high safety hazard.

Inactive Publication Date: 2010-09-08
HUANGSHAN RUNKE POWDER MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, the preparation method of the traditional antifungal agent 4,5-dichloro-2-n-octyl-4-isothiazolinone-3 is to use methyl acrylate as the starting material, and first react with NaHS and S to form di Methyl thiodipropionate is reacted with n-octylamine to generate dioctyl dithiodipropionamide, and then closed and chlorinated with chlorine to obtain the product. Due to the hydrogen sulfide and hydrogen chloride produced by this process The volatility of n-octylamine and chlorine in the raw materials is large, the equipment is corrosive, and the safety hazard is large, and the purity of the obtained bactericidal antifungal agent is low

Method used

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  • Preparation method of isothiazolinone biocide mildewcide
  • Preparation method of isothiazolinone biocide mildewcide
  • Preparation method of isothiazolinone biocide mildewcide

Examples

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Effect test

Embodiment 1

[0017] a. N, N'-di-n-octyl-3,3'-dithiobisacrylamide: disulfide dichloride: potassium bromate: chlorobenzene: triethylamine in a molar ratio of 1:2:0.1:2 : 1.5 mixed and put into an enamel kettle with a reflux condenser, heat preservation reaction at 100°C for 13 hours, wherein N,N'-di-n-octyl-3,3'-dithiobisacrylamide is based on chlorobenzene Solvent, under the condition that triethylamine exists, react with disulfur dichloride to generate N, N'-di-n-octyl-3,3'-dithio-2,3-dichloro-dipropionamide, and then The N,N'-di-n-octyl-3,3'-dithio-2,3-dichloro-dipropionamide is subjected to a ring-closing reaction with disulfide dichloride in the presence of potassium bromate;

[0018] b. Put the above reaction product into a stainless steel kettle, purify with ethanol at a temperature of 34°C, and recrystallize in an ice-salt water bath at -12°C to obtain 4,5-dichloro-2-n-octyl Base-4-isothiazolinone-3.

Embodiment 2

[0020] a. N, N'-di-n-octyl-3,3'-dithiobisacrylamide: disulfide dichloride: potassium bromate: chlorobenzene: triethylamine in a molar ratio of 1:3:0.3:2.5 : 2.5 mixed and put into an enamel kettle with a reflux condenser, heat preservation reaction at 125°C for 15 hours, wherein N,N'-di-n-octyl-3,3'-dithiobisacrylamide is based on chlorobenzene Solvent, under the condition that triethylamine exists, react with disulfur dichloride to generate N, N'-di-n-octyl-3,3'-dithio-2,3-dichloro-dipropionamide, and then The N,N'-di-n-octyl-3,3'-dithio-2,3-dichloro-dipropionamide is subjected to a ring-closing reaction with disulfide dichloride in the presence of potassium bromate;

[0021] b. Put the above reaction product into a stainless steel kettle, purify with ethanol at a temperature of 40°C, and recrystallize in an ice-salt bath at -10°C to obtain 4,5-dichloro-2-n-octyl Base-4-isothiazolinone-3.

Embodiment 3

[0023] a. N, N'-di-n-octyl-3,3'-dithiobisacrylamide: disulfide dichloride: potassium bromate: chlorobenzene: triethylamine in a molar ratio of 1: 2.5: 0.2: 2.2 : 2 mixed and put into an enamel kettle with a reflux condenser, heat preservation reaction for 18.5 hours at 120°C, wherein N, N'-di-n-octyl-3,3'-dithiobisacrylamide is based on chlorobenzene Solvent, under the condition that triethylamine exists, react with disulfur dichloride to generate N, N'-di-n-octyl-3,3'-dithio-2,3-dichloro-dipropionamide, and then The N,N'-di-n-octyl-3,3'-dithio-2,3-dichloro-dipropionamide is subjected to a ring-closing reaction with disulfide dichloride in the presence of potassium bromate;

[0024] b. Put the above reaction product into a stainless steel kettle, purify it with ethyl acetate at a temperature of 45°C, and recrystallize it in an ice-salt water bath at -15°C to obtain 4,5-dichloro-2- n-Octyl-4-isothiazolinone-3.

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Abstract

The invention belongs to the technical field of a biocide mildewcide, and particularly relates to a preparation method of an isothiazolinone biocide mildewcide. The preparation method comprises the specific steps that: N, N'-di-n-octyl-3, 3'-dithio-diacrylamide, disulphur dichloride, potassium bromate and chlorobenzene are mixed for reaction according to the mole ratio of 1:2-3:0.1-0.3:2-2.5, wherein the N, N'-di-n-octyl-3, 3'-dithio-diacrylamide takes the chlorobenzene as a solvent to react with the disulphur dichloride so as to generate N, N'-di-n-octyl-3, 3'-dithio-2, 3-dichloro-dipropionamide; the N, N'-di-n-octyl-3, 3'-dithio-2, 3-dichloro-dipropionamide reacts with the disulphur dichloride under the existence of potassium bromate in a closed-loop manner; and then the generated substances obtained by the reaction are purified to obtain the isothiazolinone biocide mildewcide. The preparation method carries out following closed-loop chlorination by S2Cl2, has little corrosion to equipment, and is safe and reliable, and simultaneously, the addition of KBrO3 can improve the purity of the prepared biocide mildewcide, namely 4, 5-dichloro-2-di-n-octyl-4-isothiazolinone-3.

Description

technical field [0001] The invention belongs to the technical field of bactericidal and antifungal agents, and in particular relates to a preparation method of an isothiazolinone type bactericidal and antifungal agent. Background technique [0002] 4,5-dichloro-2-n-octyl-4-isothiazolinone-3, referred to as DCOIT, its molecular formula is C 11 h 17 Cl 2 NOS, molecular weight 282.2274, CAS registration number: 64359-81-5, appearance is white or slightly yellow powder, melting point is 43-45°C, and its structural formula is: [0003] [0004] 4,5-dichloro-2-n-octyl-4-isothiazolinone-3 is a variety of isothiazolinone fungicides and antifungal agents. It has low toxicity to human body and is easy to decompose. It has good compatibility with other related products and is an environment-friendly product. 4,5-dichloro-2-n-octyl-4-isothiazolinone-3, as a fungicide and antifungal agent, can be widely used in plastics, powder coatings, latex paints, paints, cutting fluids, paper...

Claims

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Application Information

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IPC IPC(8): C07D275/03
Inventor 夏振华章金利谢大章程成斌方星
Owner HUANGSHAN RUNKE POWDER MATERIALS
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