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Method for producing O-methyl phenyl hydroxylamine

A technology of o-methylphenylhydroxylamine and methylphenylhydroxylamine, applied in the production field of o-methylphenylhydroxylamine, can solve the problems of high preparation cost, low bromination yield, restricting the application of synthetic routes, etc., and achieve reduction The effect of simple and controllable reaction and low cost

Active Publication Date: 2014-11-26
SHANDONG XINGQIANG CHEM IND TECH RES INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] Route 1, bromination of o-nitrotoluene requires N-bromosuccinimide (abbreviated as NBS), and o-nitrobenzyl bromide has high preparation cost, strong odor, strong lachrymatory property, and very low bromination yield , not conducive to large-scale industrial production
[0011] Route 2 has the advantages of readily available raw materials and significantly reduced costs, and is more conducive to intensive industrial-scale production in the future. However, the yield of o-nitrotoluene reduction to o-methylphenylhydroxylamine is low, currently the highest is less than 70%, which restricts application of this synthetic route

Method used

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  • Method for producing O-methyl phenyl hydroxylamine
  • Method for producing O-methyl phenyl hydroxylamine
  • Method for producing O-methyl phenyl hydroxylamine

Examples

Experimental program
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Effect test

Embodiment 1

[0030] In a 500ml four-neck flask equipped with an electric stirrer, a thermometer, a reflux condenser and a dropping funnel, add 40 g of o-nitrotoluene, 10 g of ethanol (technical grade), dichloroethane (technical grade) with a concentration of 98%. ) 120g and Raney nickel catalyst 5g, stirred and cooled to 0°C, under this condition, 35g of hydrazine hydrate with a concentration of 80% was added dropwise. The solid catalyst was left standing to separate the water layer, ethanol and dichloroethane were removed by vacuum rotary evaporation, and an orange-red oil was obtained, which was recrystallized with petroleum ether, and after suction filtration and drying, a pure white crystalline product o-formazan was obtained 33.5 g of phenylhydroxylamine, with a liquid chromatography analysis content of 96.4%, and a yield of 91.8%.

Embodiment 2

[0032] In a 500ml four-necked flask equipped with electric stirrer, thermometer, reflux condenser and dropping funnel, adding concentration is 98% o-nitrotoluene 40g, tetrahydrofuran (technical grade) 100g and Raney nickel catalyst 6g, stir Cool to 5°C, add dropwise 35g of hydrazine hydrate with a concentration of 80% under this condition, after the dropwise addition, keep the reaction at 6°C for 6 hours, remove the solid catalyst by suction filtration after cooling, let stand to separate the water layer, The tetrahydrofuran was removed by vacuum rotary evaporation to obtain an orange-red oily substance, which was recrystallized with petroleum ether. After suction filtration and drying, 32.5 g of a pure white crystalline product o-methylphenylhydroxylamine was obtained, and the content was 96.2% according to liquid chromatography analysis. , and the yield was 88.8%.

Embodiment 3

[0034] In a 500ml four-necked flask equipped with electric stirrer, thermometer, reflux condenser and dropping funnel, adding concentration is 98% o-nitrotoluene 40g, tetrahydrofuran (technical grade) 100g and Raney nickel catalyst 6g, stir Cool to 8°C, add dropwise 35g of hydrazine hydrate with a concentration of 80% under this condition, after the dropwise addition, keep the reaction at 10°C for 4 hours, remove the solid catalyst by suction filtration after cooling, let stand to separate the water layer, The tetrahydrofuran was removed by vacuum rotary evaporation to obtain an orange-red oily substance, which was recrystallized with petroleum ether. After suction filtration and drying, 31.5 g of a pure white crystalline product o-methylphenylhydroxylamine was obtained, and the content was 95.6% by liquid chromatography analysis. , the yield was 85.6%.

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Abstract

The invention discloses a method for producing O-methyl phenyl hydroxylamine. The method comprises the following steps: adding ortho-nitrotoluene, a solvent and a catalyst to a reaction kettle, and stirring the materials, wherein the weight ratio of the ortho-nitrotoluene to the solvent to the catalyst is (35-45) to (80-150) to (5-6); then dropwise adding hydrazine hydrate at 0-8 DEG C, wherein the weight ratio of the hydrazine hydrate to the catalyst is (20-50) to (5-6); carrying out heat preservation reaction at 2-10 DEG C for 4-6 hours after dropwise adding is ended; removing the catalyst by suction filtration after cooling, standing and separating a water layer, and then removing the solvent by vacuum rotary evaporation; and recrystallizing the product by using petroleum ether, carrying out suction filtration and drying, so as to obtain the O-methyl phenyl hydroxylamine. The method disclosed by the invention has the advantages that reduction reaction is simple and easy to control, complicated hydrogenation device is not required, the cost is low, a raney nickel catalyst is adopted, and the reaction yield can be up to over 85%, and is much higher than that of normal process production, which is 70%.

Description

technical field [0001] The invention relates to the technical field of chemical materials, in particular to a production method of o-methylphenylhydroxylamine. Background technique [0002] The common name of pyraclostrobin is pyraclostrobin, the code name is BAS500F, the single-dose product names are Cabrio, Headline, Attitude, etc., the CAS registration number: 175013-18-0, and the chemical name is: N-{2-[1-(4 -Chlorophenyl)-1H-pyrazol-3-yloxymethyl]phenyl}(N-methoxy)amino acid methyl ester. The structural formula is: [0003] [0004] Pyraclostrobin is a broad-spectrum fungicide of the methyl methoxyacrylate category with a pyrazole structure discovered by BASF in 1993. It can prevent and control plant diseases caused by almost all types of fungal pathogens such as Ascomycetes, Basidiomycetes, Deuteromycetes and Oomycetes. At the same time, it is a hormone-type fungicide, which can make crops absorb more nitrogen , to promote the growth of crops. This variety is no...

Claims

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Application Information

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IPC IPC(8): C07C239/10
Inventor 刘方单晓军陈允珊徐梦雨任峰
Owner SHANDONG XINGQIANG CHEM IND TECH RES INST CO LTD
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