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Manganese catalyst and application of manganese catalyst in catalyzing epoxidation of triazole alkene to prepare epoxiconazole

A technology for catalyzing triazoles and manganese catalysts, applied in the field of pesticides, can solve problems such as hidden safety hazards, unfriendly environment, increase post-processing steps, etc., and achieve the effects of reducing environmental pressure, low system cost, and simple recovery

Pending Publication Date: 2020-10-30
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The patent U.S.5245042 uses maleic anhydride and hydrogen peroxide to form monoperoxymaleic acid in situ to epoxidize triazolene. This process uses maleic anhydride 10 times the molar amount of triazolene, which is equivalent to producing 1 ton of fluorocyclic Azole produces 3.52 tons of maleic acid, and the generation of a large amount of felic acid increases the post-treatment steps and also brings huge pressure to the environment; at the same time, the process route uses hydrogen peroxide with a mass concentration of 50%, and the use of high-concentration hydrogen peroxide exists in production. Huge potential safety hazard; and this process route uses environmentally unfriendly dichloroethane as a solvent

Method used

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  • Manganese catalyst and application of manganese catalyst in catalyzing epoxidation of triazole alkene to prepare epoxiconazole
  • Manganese catalyst and application of manganese catalyst in catalyzing epoxidation of triazole alkene to prepare epoxiconazole
  • Manganese catalyst and application of manganese catalyst in catalyzing epoxidation of triazole alkene to prepare epoxiconazole

Examples

Experimental program
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Effect test

Embodiment 1

[0029] Add 7.4mg (0.03mmol) of manganese acetate tetrahydrate into a 100mL one-necked flask at room temperature, add 5mL of acetonitrile, and 22.2mg (0.18mmol) of picolinic acid, and start stirring. Under stirring, add 3.14g (10.0mmol, content 99.68%) of recrystallized triazolene, 0.43g (5.0mmol) of distilled 2,3-butanedione, 24.6mg of sodium acetate dispersed in 15mL of acetonitrile solution, and continue stirring . Cool the flask in an ice bath and add 30% hydrogen peroxide dropwise below 2°C, add 3.40g hydrogen peroxide within 5.0hrs, during which the dropping rate should be controlled so that the temperature of the reaction solution is not higher than 5°C. After the hydrogen peroxide was added, the mixture was stirred for 1.0 hr in a cold bath. Remove the ice / water bath, and stir at room temperature for 2.0 hrs, concentrate under reduced pressure to obtain the target epoxiconazole, the material conversion rate is 99%, and the epoxiconazole yield is 65% (HPLC detection)

Embodiment 2

[0031] Add 7.4mg (0.03mmol) of manganese acetate tetrahydrate into a 100mL one-necked flask at room temperature, add 20mL of acetonitrile, and 22.2mg (0.18mmol) of picolinic acid, and start stirring. Under stirring, add 3.14g (10.0mmol, content 99.68%) of recrystallized triazolene, and 0.43g (5.0mmol) of distilled 2,3-butanedione, and stir at room temperature for 15min, then add 24.6mg of sodium acetate , continue stirring. Cool the flask in an ice bath and add 30% hydrogen peroxide dropwise at a temperature below 2°C. Add 3.40g of hydrogen peroxide within 5.0hrs, during which the rate of addition should be controlled so that the temperature of the reaction solution is not higher than 5°C. After the hydrogen peroxide was added, the mixture was stirred for 1.0 hr in a cold bath. Remove the ice / water bath and stir at room temperature for 2.0 hrs. The material conversion rate is 99%, and the yield of epoxiconazole is 66% (HPLC detection).

Embodiment 3

[0032] Example 3: Add 6.9 mg (0.028 mmol) of manganese acetate tetrahydrate into a 100 mL one-necked flask at room temperature, add 20 mL of acetonitrile, and 20.9 mg (0.17 mmol) of picolinic acid, and start stirring. Under stirring, add 3.14g (10.0mmol, content 99.68%) of recrystallized triazolene, 0.43g (5.0mmol) of distilled 2,3-butanedione, and stir at room temperature for 15min, then add 23.0mg of sodium acetate, Continue to stir. Cool the flask in an ice bath and add 30% hydrogen peroxide dropwise below 2°C, add 3.40g hydrogen peroxide within 5.0hrs, during which the dropping rate should be controlled so that the temperature of the reaction solution is not higher than 5°C. After the hydrogen peroxide was added, the mixture was stirred for 1.0 hr in a cold bath. Remove the ice / water bath, stir at room temperature for 2.0 hrs, and concentrate under reduced pressure to obtain the target epoxiconazole. The material conversion rate was 98%, and the epoxiconazole yield was 6...

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Abstract

The invention relates to the field of pesticides, in particular to a manganese catalyst and application of the manganese catalyst in catalyzing epoxidation of triazole alkene to prepare epoxiconazole.According to the manganese catalyst, a pyridine-2-formic acid derivative shown as a general formula (I) is used as a ligand and reacts with manganese salt in a reaction solvent to generate a catalystsystem; the catalyst system can be applied to catalyzing triazole alkene to synthesize epoxiconazole, namely epoxidation reaction of triazole alkene and a hydrogen peroxide aqueous solution with theconcentration of 10-30% in a solvent in the presence of a catalyst. The catalyst is prepared on site, is easy to operate and low in cost, and has the advantages of high substrate conversion rate, lowrequired hydrogen peroxide concentration, high yield, good stability and mild reaction conditions when being applied to catalyzing triazole alkene to synthesize epoxiconazole.

Description

technical field [0001] The invention relates to the field of pesticides, in particular to a manganese catalyst and its application for preparing epoxiconazole by catalyzing the epoxidation of triazolene. Background technique [0002] Epoxiconazole is a broad-spectrum triazole fungicide with high efficiency, low toxicity and low residue, which was developed by BASF in 1983. It has been reported in the literature that there are six synthetic routes for the original drug of epoxiconazole, and triazolene is used to synthesize epoxiconazole in industrial production. Patent U.S.5245042 uses maleic anhydride and hydrogen peroxide to form monoperoxymaleic acid in situ to epoxidize triazolene. This process uses maleic anhydride 10 times the molar amount of triazolene, which is equivalent to producing 1 ton of fluorine rings Azole produces 3.52 tons of maleic acid, and the generation of a large amount of felic acid increases the post-treatment steps and also brings huge pressure to t...

Claims

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Application Information

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IPC IPC(8): C07D213/79B01J31/18C07D405/06
CPCC07D213/79B01J31/1815C07D405/06B01J2531/72B01J2531/0241B01J2231/72
Inventor 姜鹏王嫱于海波杨浩
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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