A kind of preparation method of aryl triazolone

A technology for aryl triazolinone and aryl triazolidinone is applied in the field of preparing aryl triazolinone, which can solve problems such as pollution and wastewater treatment difficulties, achieve high purity and yield, and achieve obvious economic and environmental benefits. , the effect of high product content and yield

Active Publication Date: 2017-06-27
SHANDONG WEIFANG RAINBOW CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to provide a preparation method of aryl triazolinone, to overcome the existing wastewater treatment difficulties caused by using hypohalous acid, hypohalous acid salt as oxidant or oxygen as oxidant and metal-containing compound as catalyst , the serious problem of pollution

Method used

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  • A kind of preparation method of aryl triazolone
  • A kind of preparation method of aryl triazolone
  • A kind of preparation method of aryl triazolone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] In a 500ml four-necked flask, add a mixed solution of 250g tert-butanol and water (the mass ratio of tert-butanol and water is 85:15), 50g99.0% of 5-methyl-2-phenyl-1,2,4-tri Oxazolidin-3-one, 1g activated carbon (specific surface area 2000-3000m 2 / g, micropore diameter 0.5~3.0nm), heated to 70 ℃ after fully stirring, slowly added dropwise the hydrogen peroxide 69.2g of 27.5wt%, stirred 60 minutes after dropping, filtered while hot, obtained wet filter cake 2g, will The filtrate was heated to 100°C to remove the solvent, then cooled to 15°C, filtered after crystallization for 1 hour, the filter cake was washed with 5 g of deionized water, and the filter cake was dried to obtain 48.8 g of solid A1, which was 99.0% by gas phase detection. Based on 5-methyl-2-phenyl-1,2,4-triazolidin-3-one, the yield is 98.7%.

Embodiment 2

[0035] In the 500ml four-necked flask, add the mixed solution of 250g tert-butanol and water (the mass ratio of tert-butanol and water is 9:1), 50g99.0% 2-(2-fluorophenyl)-5-methyl-1, 2,4-Triazolidin-3-one, 2.5g activated carbon (specific surface area 2000-3000m 2 / g), fully stirred and heated to 50°C, slowly fed 8.1g of pure oxygen, the reaction pressure was 0.3MPa, and the pressure was maintained for 100 minutes after the oxygen was passed through, and then filtered while it was hot to obtain 5g of wet filter cake, and the filtrate was heated to 100 ℃ to remove the solvent, then lower the temperature to 15 ℃, filter after crystallization for 1h, wash the filter cake with 5g deionized water, dry the filter cake to obtain a total of 48.6g of solid G1, the gas phase detection content is 98.8%, and the 2-( Based on 2-fluorophenyl)-5-methyl-1,2,4-triazolidin-3-one, the yield is 98.0%.

Embodiment 3

[0037] In the 500ml four-necked flask, add the mixed solution of 250g tert-butanol and water (the mass ratio of tert-butanol and water is 85:15), 50g99.0% N-(2,4-dichloro-5-(4-(di Fluoromethyl)-3-methyl-5-oxo-1,2,4-triazolidin-1-yl)phenyl)methanesulfonamide, 1.5g activated carbon (specific surface area 1500-2500m 2 / g), fully stirred and then heated to 40°C, slowly fed 5g of gas containing 50% by volume of oxygen, the reaction pressure was 1.0MPa, kept pressure and reacted for 100 minutes after passing through oxygen, then cooled to 60°C and filtered to obtain 3g of wet filter cake , the filtrate was heated to 100°C to remove the solvent, then cooled to 15°C, crystallized for 1 hour and filtered, the filter cake was washed with 5g of deionized water, and the filter cake was dried to obtain a total of 49.7g of solid F2, the content of which was 98.0 by gas phase detection. %, as N-(2,4-dichloro-5-(4-(difluoromethyl)-3-methyl-5-oxo-1,2,4-triazolidin-1-yl)phenyl ) methanesulfona...

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Abstract

The invention discloses a method for preparing aryl triazolinone. The method comprises the following steps: by taking aryl triazolinone as a raw material, taking an oxygen-containing gas or hydrogen peroxide water solution as an oxidant, and taking active carbon as a catalyst, performing oxidation reaction to obtain aryl triazolinone. By adopting the method, a new concept for the synthesis of the aryl triazolinone compound is provided, the hydrogen peroxide solution or the oxygen-containing gas is taken as the oxidant, the active carbon is taken as the catalyst, and the traditional processing modes of hypohalous acid and salt thereof, halogen oxidant or metal compound catalyst are substituted; the halogen and the metal compound are not contained in the wastewater, so that the environment is not polluted; when the optimized active carbon is adopted, the purity and the yield of the product are high. The environment pollution caused by the halogen-containing oxidant and the metal compound is avoided, the production process is clean, the reaction process is environmentally friendly, the product content and the yield are high and the economic and environmental protection benefits are obvious, so that the method is a scientific and environment-friendly novel method for producing the aryl triazolinone compound.

Description

technical field [0001] The invention relates to a method for preparing aryl triazolone, in particular to a method for obtaining aryl triazolone by oxidative dehydrogenation under a catalyst by using oxygen-containing gas or hydrogen peroxide solution. Background technique [0002] Aryl triazolinone (aryl-1,2,4-triazolin-5-one, aryl triazolinone) is an important synthetic intermediate, which can be used in the synthesis of pesticides and human medicines, For example, it can be used as an intermediate of the herbicide sulfentrazone, and its structural formula is as follows: [0003] [0004] There are many preparation methods of aryl triazolinones disclosed in the prior art. The more commonly used method is to use aryl triazolidinone as a raw material and oxidize it with hypochlorite to obtain aryl triazolinone. For example, patent CN1079963A discloses a method for forming triazolinone in tert-butanol, using aryl triazolidinone as raw material, reacting with hypohalous aci...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D249/12
CPCC07D249/12
Inventor 孙国庆侯永生赵广理朱宝仁徐延磊张少鹏
Owner SHANDONG WEIFANG RAINBOW CHEM
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