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Process for producing 2-alkyl-4-isothiazoline-3-one

A technology of isothiazoline and alkyl, which is applied in the field of preparation of 2-alkyl-4-isothiazolin-3-one, can solve the problems of complex, difficult and loss in the preparation process, and achieve economical preparation method and yield loss small effect

Inactive Publication Date: 2005-11-16
CHEMICREA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, it is still difficult to completely remove 5-chloro-2-alkyl-4-isothiazolin-3-ones through the refining process, and some loss of 2-alkyl-4-isothiazolin-3-ones is inevitable. -ketone
In addition, due to the increased refining process, the preparation process is more complicated

Method used

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  • Process for producing 2-alkyl-4-isothiazoline-3-one
  • Process for producing 2-alkyl-4-isothiazoline-3-one
  • Process for producing 2-alkyl-4-isothiazoline-3-one

Examples

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Effect test

Embodiment 1

[0056] Put 120g (0.508mol) of N,N'-dimethyl-3,3'-dithiopropionamide and 480ml of dichloromethane into a device equipped with a stirrer, a chlorine inlet tube, a thermometer and a calcium chloride condenser A 2-liter four-necked flask with a condenser. 108 g (1.523 mol) of chlorine gas were introduced into the solution at a temperature of 39-41° C. during 3 hours 15 minutes, and then stirred overnight at room temperature. The precipitated crystals were filtered off under reduced pressure and washed with dichloromethane. The crystals were dispersed in 400 ml of water and neutralized to pH7 with sodium carbonate. The solution was extracted with dichloromethane and the solvent was removed to afford 90.12 g (77% yield) of 2-methyl-4-isothiazolin-3-one as a light brown solid.

Embodiment 2

[0058] React under the same conditions as in Example 1, but use cyclohexane (0.015 in molar fraction, 1 atm, 298, 15k) as a solvent, as shown in Table 1, to obtain 2-methyl-4-isothiazoline-3- Ketone, 70% yield.

Embodiment 3

[0060] The reaction was carried out under the same conditions as in Example 1, but using chloroform as the reaction solvent and for washing the hydrochloride to obtain 2-methyl-4-isothiazolin-3-one in a yield of 75%.

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Abstract

Chloridizing reagent and one of two specified compounds are made to react in solvent, in which hydrogen chloride is insoluble or less insoluble, to prepare 2-alkyl-4-isothiazoline-3-ketone.

Description

Technical field: [0001] The invention relates to a preparation method of 2-alkyl-4-isothiazolin-3-one as an industrial disinfectant. Background technique: [0002] Isothiazolin-3-ones, which have been used as industrial disinfectants, are mixtures of 2-alkyl-4-isothiazolin-3-ones and 5-chloro-2-alkyl-4-isothiazolin-3-ones. However, with the recent mutagenicity issues associated with 5-chloro-2-alkyl-4-isothiazolin-3-ones, there is a need for 5-chloro-2-alkyl-4-isothiazolin-3-ones 2-Alkyl-4-isothiazolin-3-ones with low or no 3-ketone content. [0003] A number of methods have been discovered for the preparation of 2-alkyl-4-isothiazolin-3-ones. For example, as proposed in USP 3,849,430 and EP 95907, chlorination of N-alkyl-3-mercaptopropionamides in ethyl caproate solvent gives 2-alkyl-4-isothiazoline-3 -A mixture of ketones and 5-chloro-2-alkyl-4-isothiazolin-3-ones. However, the preparation method proposed there does not provide any means of reducing the content of 5-ch...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D275/03
Inventor 森田真之刘国斌米田纪子
Owner CHEMICREA