Method for preparing 1, 2-benzisothiazolin-3-one through catalytic oxidation

A benzisothiazoline, catalytic oxidation technology, applied in chemical instruments and methods, catalytic reactions, physical/chemical process catalysts, etc. The effect of less product, less waste, simple and cheap catalyst

Active Publication Date: 2021-08-03
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Chlorine gas, liquid bromine, SOCl2, SO2Cl2 used in the above patent Chemicals such as sub> are highly corrosive and have great potential safety hazards. The use of a large amount of salty wastewater is not conducive to their application

Method used

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  • Method for preparing 1, 2-benzisothiazolin-3-one through catalytic oxidation
  • Method for preparing 1, 2-benzisothiazolin-3-one through catalytic oxidation
  • Method for preparing 1, 2-benzisothiazolin-3-one through catalytic oxidation

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Experimental program
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Effect test

Embodiment 1

[0028] In a 250 mL reactor, put 15.28 g of a mixture of 2-mercaptobenzamide and 2,2’-dithiodibenzamide (molar ratio 3:1), 0.42 g of Mn(OH) 3 , 0.60 g of triethanolamine and 160 mL of ethanol; heated to 120°C with stirring, fed oxygen to keep the pressure in the reactor at 0.2 MPa, stopped the reaction after 10 hours of reaction, removed ethanol by rotary evaporation, added 100 mL of water and stirred for 20 min , filtered, and the filter cake was dried to obtain 12.23 g of white solid BIT with a yield of 90%, a melting point of 154-156°C, and a purity of 98% according to liquid chromatography analysis.

Embodiment 2

[0030] In a 250 mL reactor, put 30.6 g of 2-mercaptobenzamide, 0.11 g of manganese carbonate monohydrate, 0.28 g of 2-dimethylaminoethylamine, 100 mL of water and 50 mL of methanol; heat to 40 ℃, press air, keep the pressure in the reactor at 1.0 MPa, stop the reaction after 40 hours of reaction, remove methanol by rotary evaporation, cool, filter, wash with water, and dry to obtain 29.6 g of BIT with a yield of 98%. Chromatography analysis product purity is 99%.

Embodiment 3

[0032] In a 250 mL reactor, put 45.95 g 2,2'-dithiodibenzamide, 0.02 g 2,2'-bipyridyl manganese (II) complex and 130 mL DMF; heat to 80 ℃, feed oxygen, keep the pressure in the reactor at 0.4 MPa, stop the reaction after 7 hours of reaction, distill off most of the DMF under reduced pressure, add 100 mL of water and stir for 40 min, filter, and dry the filter cake to obtain 44.85 g of white solid BIT , the yield was 99%, the melting point was 154-156°C, and the purity of the product by liquid chromatography analysis was 98%.

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Abstract

The invention provides a method for preparing 1, 2-benzisothiazoline-3-one through catalytic oxidation, which comprises the following steps of: by taking a metal manganese salt or a manganese complex as a catalyst, carrying out oxidative cyclization reaction on an amine compound in an oxygen or air environment to generate the 1, 2-benzisothiazoline-3-one. In the reaction, oxygen or air is used as an oxidant; the catalyst is simple, cheap, high in catalytic activity and high in reaction efficiency; the preparation process is simple, the product selectivity is high, and byproducts are few; and less waste is produced, and the method is environment-friendly, and has a relatively good industrial application prospect.

Description

technical field [0001] The invention relates to the field of preparation of benzo[d]isothiazolin-3(2H)-one, in particular to a method for preparing 1,2-benzisothiazolin-3-one by catalytic oxidation. Background technique [0002] 1,2-Benzisothiazolin-3-one (abbreviated as BIT) is an important and commonly used fungicide and preservative. It has excellent properties such as strong bactericidal ability, small application dosage, good compatibility, strong temperature resistance, acid and alkali resistance, and environmental safety. Widely used in daily chemical products, polymer products, adhesives, textiles, coatings, papermaking, building materials, leather, light industry, oil products, inks, industrial circulating cooling water, agriculture, forestry and environmental protection and other fields. [0003] There are many synthetic methods of 1,2-benzisothiazolin-3-one, and the cyclization reaction of 2-mercaptobenzamide or 2,2'-dithiodibenzamide is the mainstream industrial...

Claims

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Application Information

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IPC IPC(8): C07D275/04B01J23/34B01J27/232B01J31/22B01J27/187B01J27/10B01J27/08B01J27/053B01J27/25B01J27/02
CPCC07D275/04B01J23/34B01J27/232B01J31/183B01J31/2213B01J31/2239B01J27/187B01J27/10B01J27/08B01J27/053B01J27/25B01J27/02B01J2531/72B01J2231/70
Inventor 杨贯羽何攀
Owner ZHENGZHOU UNIV
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