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Preparation method of N-butyl-1,2-benzo isothiazolin-3-ketone

A technology of benzisothiazoline and n-butyl, applied in the field of preparation of N-n-butyl-1,2-benzisothiazolin-3-one, can solve the problem of difficult to meet environmental protection requirements and incomplete halogen absorption , serious equipment corrosion and other problems, to achieve the effect of low production cost, high product yield, and reduce the pressure of environmental protection

Inactive Publication Date: 2013-04-03
SHAANXI RES DESIGN INST OF PETROLEUM CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The above preparation methods all need to use highly toxic and highly corrosive halogens (such as bromine or chlorine gas), which brings great difficulty and danger to the production process. It is difficult to meet the current environmental protection requirements, and the excessive halogen absorption is not complete. Very easy to cause secondary pollution
In addition, from the perspective of cost, the above synthesis method is quite corrosive to equipment, and it is necessary to purchase anti-corrosion equipment, which will inevitably increase production costs

Method used

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  • Preparation method of N-butyl-1,2-benzo isothiazolin-3-ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] (1) Synthesis of N-n-butyl-2,2'-dibenzamide disulfide

[0025] Add 34.3g of 2,2-dibenzoyl chloride disulfide and 100mL of toluene into the flask, add 14.6g of n-butylamine dropwise within 30°C, keep warm for 1 hour after the dropwise addition, and stop the reaction. Suction filtration, the product was washed several times with water and ethanol, and dried to obtain milky white N-n-butyl-2,2'-dibenzamide powder.

[0026] (2) Synthesis of N-n-butyl-1,2-benzisothiazolin-3-one

[0027] Add 41.7g of N-n-butyl-2,2'-dibenzamide disulfide, 100mL of toluene, aqueous sodium hydroxide solution (8.0g of sodium hydroxide, 200mL of water) and 20.2g of triethylamine into the reaction flask, and heat up to Slowly add 40.8g of 10% hydrogen peroxide solution dropwise to the reaction system within 8 hours at 55°C. After the dropwise addition, distill off triethylamine and toluene, pour the remaining liquid into a 500mL beaker, separate the lower organic phase, and dry to obtain yellow N ...

Embodiment 2

[0029] (1) Synthesis of N-n-butyl-2,2'-dibenzamide disulfide

[0030] The synthesis process is the same as step (1) of Example 1.

[0031] (2) Synthesis of N-n-butyl-1,2-benzisothiazolin-3-one

[0032] Add 41.7g of N-n-butyl-2,2'-dibenzamide disulfide, 100mL of toluene, aqueous sodium hydroxide solution (8.0g of sodium hydroxide, 200mL of water) and 30.4g of triethylamine into the reaction flask, and heat up to 60°C, slowly add 10% hydrogen peroxide solution dropwise to the reaction system within 6 hours, after the drop is completed, lower the temperature to 50°C and continue the reaction for 1 hour to end the reaction. Evaporate triethylamine and toluene, separate the lower organic phase, and dry to obtain yellow N-n-butyl-1,2-benzisothiazolin-3-one liquid with a yield of 32.4%.

Embodiment 3

[0034] (1) Synthesis of N-n-butyl-2,2'-dibenzamide disulfide

[0035] The synthesis process is the same as step (1) of Example 1.

[0036] (2) Synthesis of N-n-butyl-1,2-benzisothiazolin-3-one

[0037] Add 41.7g of N-n-butyl-2,2'-dibenzamide disulfide, 50mL of toluene, aqueous sodium hydroxide solution (16.0g of sodium hydroxide, 200mL of water) and 40.5g of triethylamine into the reaction flask, and raise the temperature to At 55°C, slowly add 51.0 g of 10% hydrogen peroxide solution dropwise into the reaction system within 6 hours, keep the temperature for 1 hour after the drop, and finish the reaction. Evaporate triethylamine and toluene, pour the remaining liquid into a 500mL beaker, separate the lower organic phase, and dry to obtain a yellow N-n-butyl-1,2-benzisothiazolin-3-one liquid with a yield of 28.1 %.

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Abstract

The invention relates to a preparation method of N-butyl-1,2-benzo isothiazolin-3-ketone. The preparation method comprises the steps that 2,2'-disulfide diphenyl formyl chloride serves as a raw material and is transformed into N-butyl-2,2'-disulfide diphenyl formyl amine by amidation; and an oxidant is added to disproportionately synthesize N-butyl-1,2-benzo isothiazolin-3-ketone in an alkaline environment and with the existence of a catalyst. The preparation method has the following characteristics that (1), the oxidant (or an oxygen releasing agent) is adopted to replace halogen (chlorine or liquid bromine), the defect of using highly toxic chemicals is avoided, the operation is easier, the cost is lowered, and the pressure of environmental protection is reduced greatly; (2), the process during a reaction course is simple and high temperature and high pressure are not needed; and (3), the preparation method is simple in process, low in manufacturing cost, high in product yield, and suitable for commercial production, and the process is clean and does not pollute an environment.

Description

technical field [0001] The invention relates to a method for synthesizing organic compounds with an oxidant in an alkaline system in the presence of a catalyst, in particular to a method for preparing N-n-butyl-1,2-benzisothiazolin-3-one. Background technique [0002] Isothiazolinone compounds have excellent properties such as strong antibacterial ability, small application dose, good compatibility, long duration of drug effect, environmental safety and broad antibacterial spectrum, and have been highly concerned by the industry. It is widely used in medicine and other industries. Among many isothiazolinone compounds, benzisothiazolinone compounds have received more and more attention in the field of antiseptic and sterilization due to their excellent temperature resistance and alkali resistance, and have been difficult to exert their effects in many conventional antiseptic products. It has shown unique advantages in the special industrial field. [0003] N-n-butyl-1,2-ben...

Claims

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Application Information

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IPC IPC(8): C07D275/04
Inventor 张可青杨俊伟李程碑杨杰徐亚霞
Owner SHAANXI RES DESIGN INST OF PETROLEUM CHEM IND
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