Method for preparing benzofuroxan under catalysis of surfactant micelle

A technology of benzofuroxan and surfactant, which is applied in the field of micellar catalytic oxidation in organic synthesis methods, can solve the problems of difficult crystallization of products, low product purity, incomplete reaction and the like, and achieves easy products, little environmental pollution, reaction to full effect

Inactive Publication Date: 2015-09-30
中国兵器工业第二一三研究所
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the poor solubility of o-nitroaniline in water, the reaction is not complete and the product purity is low
At the same time, the product prepared by this method is difficult to crystallize, which puts forward higher requirements for the separation and purification of the product

Method used

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  • Method for preparing benzofuroxan under catalysis of surfactant micelle
  • Method for preparing benzofuroxan under catalysis of surfactant micelle
  • Method for preparing benzofuroxan under catalysis of surfactant micelle

Examples

Experimental program
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Effect test

preparation example Construction

[0023] Concrete synthetic method comprises the following steps in turn:

[0024] (1) Add 0.1-1g surfactant, 1-2g KOH, 20-25ml water into a dry reactor, stir and mix evenly, then add 6-8g o-nitroaniline;

[0025] (2) Add 70-90ml sodium hypochlorite solution dropwise at 30-35°C, stir while adding dropwise, and continue to react for 2-4 hours after dropping;

[0026] (3) The reaction solution was filtered, and the solid was vacuum-dried at 30° C. to obtain a yellow solid, which was the crude product BFO;

[0027] (4) Wash the solid three times with water, and then recrystallize it with absolute ethanol. The amount of solvent used in the crystallization is 5 to 7 times the mass of the product. After heating and dissolving, place the solution in an environment of -10 to -25°C to cool and crystallize , to obtain yellow flaky crystals.

[0028] Surfactant micelles can catalyze the reaction of o-nitroaniline to prepare benzofurazan, but the catalytic effect varies with the types of ...

Embodiment 1

[0031] Example 1: Preparation of hydroxyl-containing cationic gemini surfactants for catalytic oxidation of BFO

[0032] Add 0.1g hydroxyl-containing cationic gemini surfactant, 1gKOH, and 20ml water into a dry reactor, stir and mix evenly, then add 6g o-nitroaniline, add 80ml sodium hypochlorite solution dropwise at 30~35°C, and add While stirring, the reaction continued for 2 hours after the drop was completed. After the reaction was completed, the reaction solution was filtered, and the solid was vacuum-dried at 30°C to obtain a yellow solid, which was the crude product BFO. The solid was washed with water, and then washed with absolute ethanol Recrystallized to obtain pure BFO yellow crystals. The yield was 97% and the purity was 96%.

Embodiment 2

[0033] Example 2: Preparation of BFO Catalyzed Oxidation by Anionic Gemini Surfactant

[0034] Add 0.5g of anionic gemini surfactant, 1gKOH, and 20ml of water into a dry reactor, stir and mix evenly, then add 6g of o-nitroaniline, add 80ml of sodium hypochlorite solution dropwise at 30-35°C, and stir while adding After the drop, the reaction was continued for 2 hours. After the reaction, the reaction solution was filtered, and the solid was dried in vacuum at 30°C to obtain a yellow solid, which was the crude product BFO. The solid was washed with water, and then recrystallized with absolute ethanol , to obtain pure BFO yellow crystals. The yield was 92% and the purity was 91%.

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Abstract

The invention provides a method for preparing benzofuroxan under catalysis of surfactant micelle. According to the method, water is used as a solvent; oxidization of ortho-nitroaniline and derivatives of ortho-nitroaniline with NaClO to prepare benzofuroxan is catalyzed by micelle made of a surfactant. The method comprises the following steps: adding a certain quantity of water, a certain quantity of alkali, a small quantity of the surfactant and a small quantity of ortho-nitroaniline into a reactor; dripping a sodium hypochlorite solution at room temperature; carrying out reaction for two hours after dripping is finished; carrying out filtration to obtain the benzofuroxan product. The method has the advantages that the conditions are mild; the process is simple; the purity of the obtained product is relatively high; purification and crystallization are easy; the quantity of organic contents in the effluent after reaction is low; environmental pollution is low; the environment is protected; suitability for industrial large-scale production is high.

Description

technical field [0001] The invention relates to a synthesis method of benzofurazan, which belongs to the field of micellar catalytic oxidation in organic synthesis methods. Background technique [0002] Benzofuroxan-N-oxide (Benzofuroxans), also known as benzofuroxan, or BFO for short, is an important oxygen-containing furoxan compound with the molecular formula: [0003] [0004] It has important application and research value in various fields such as chemistry, medicine, agriculture and military, such as dye synthesis, rubber additives, pharmaceutical intermediates and energetic materials. So far, the BFO synthetic route reported in the literature has azide method (P.A Grieco, J.P.Mason.J.Chem.Eng.Data, (1967) 12,623-624), o-phthaloxime method (Pedersen, Christian..Acta. Chem.Scand Ser. (1976) 30,675-679), iodobenzene acetate method (L.K.Dyall, J.J.Harvey.Aust.J.Chem., (1992) 45,371-384), sodium hypochlorite oxidation method (Fan Leigang, Yang Xiaohui. Industrial cata...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D271/12
CPCC07D271/12
Inventor 解战峰李晓东巨涛吴向东刘永涛盛涤伦雷晓蓉
Owner 中国兵器工业第二一三研究所
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