Preparation method of o-methyl phenyl hydroxylamine

The technology of o-methylphenylhydroxylamine and methylphenylhydroxylamine is applied in the field of preparation of o-methylphenylhydroxylamine, and can solve the problems of low product content and yield, poor product purity, complicated hydrogenation reduction reaction process, and the like, To achieve the effect of simple process operation and low cost

Inactive Publication Date: 2016-06-08
ANHUI COSTAR BIOCHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

ASHUTOSHH etc. (Processforthepreparationofahydroxylamine [p]. US: 5166435) use precious metals such as Pt as catalysts, and the o-methylphenylhydroxylamine obtained by catalytic hydrogenation of o-nitrotoluene has the following problems: 1) the catalyst used in the present invention is expensive , easily deactivated and difficult to regenerate and recycle; 2) the hydrogenation reduction reaction process of nitrobenzene compounds is very complicated, and the product has many by-products except o-methylphenyl hydroxylamine, resulting in low product content and yield, and the product Purity is poor; 3) the waste water waste residue that the inventive method produces is serious, has increased the three wastes treatment cost of enterprise greatly

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] A preparation method of o-methylphenylhydroxylamine, the specific preparation steps are:

[0018] (1) Ion exchange: take 3g of FeCl respectively 3 and 34.5g ZSM-5 molecular sieve, then add water, raise the temperature to 60°C, stir for 4h to get 3% Fe 3+ ZSM-5, named A;

[0019] (2) Impregnation method: metal Ni is loaded on the A molecular sieve after the above-mentioned treatment by the impregnation method, and then dried at 120 ° C to obtain a compound containing 3% (wt%) Ni 2+ The ZSM-5, named Ni / A, spare;

[0020] (3) Add 100g of o-nitrotoluene, 300g of dichloroethane and 7.5g of catalyst into a 1000ml four-neck flask, then raise the temperature to 35°C, start to add 100g of hydrazine hydrate dropwise, and the dropping time is controlled at 1.5h. The dropping temperature is at 40°C. After the dropping is finished, stir and react at 40°C for 2 hours, take a sample and control it. After the control is qualified, the reaction is over; filter while it is hot, wash t...

Embodiment 2

[0022] A preparation method of o-methylphenylhydroxylamine, the specific preparation steps are:

[0023] (1) Ion exchange: Take 5g FeCl respectively 3 And 34.5gZSM-5 molecular sieve, then add water, be warming up to 60 ℃, stir 4h, get 5% (wt%) Fe 3+ ZSM-5, named A;

[0024] (2) Impregnation method: metal Ni is loaded on the A molecular sieve after the above treatment by the impregnation method, and then dried at 120 ° C to obtain a compound containing 2% (wt%) Ni 2+ The ZSM-5, named Ni / A, spare.

[0025] (3) Add 100g of o-nitrotoluene, 300g of dichloroethane and 7g of catalyst into a 1000ml four-neck flask, then raise the temperature to 30°C, start to add 100g of hydrazine hydrate dropwise, and control the dropping time within 1h, and control the dropping The temperature is 35°C. After the dropwise addition, stir and react at 35°C for 2 hours, take a sample and control it. After the control is qualified, the reaction ends; filter while it is hot, wash the filter cake with a...

Embodiment 3

[0027] A preparation method of o-methylphenylhydroxylamine, the specific preparation steps are:

[0028] (1) Ion exchange: take 5g FeCl respectively 3 And 34.5gZSM-5 molecular sieve, then add water, be warming up to 60 ℃, stir 4h, get 5% (wt%) Fe 3+ ZSM-5, named A;

[0029] (2) Impregnation method: metal Ni is loaded on the A molecular sieve after the above-mentioned treatment by the impregnation method, and then dried at 120 ° C to obtain a compound containing 2.5% (wt%) Ni 2+ The ZSM-5, named Ni / A, spare;

[0030] (3) Add 100g of o-nitrotoluene, 300g of dichloroethane and 7g of catalyst into a 1000ml four-neck flask, then raise the temperature to 35°C, start to add 60g of hydrazine hydrate dropwise, and control the dropping time at 1.5h. The adding temperature is 40°C. After the dropwise addition, stir and react at 40°C for 2 hours, take a sample and control it. After the control is qualified, the reaction ends. Filtrate while hot, wash the filter cake with absolute etha...

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PUM

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Abstract

The invention discloses a preparation method of o-methyl phenyl hydroxylamine. The preparation method includes: using ortho nitrotoluene as a raw material, hydrazine hydrate as reductant, a ZSM-5 molecular sieve loaded with metal Ni as a catalyst to synthesize o-methyl phenyl hydroxylamine. Reaction yield can reach 95.0%, and byproducts are lower than 0.1%. The ZSM-5 molecular sieve treated with Fe3+ is adopted, Ni is loaded, the catalyst is an environment-friendly catalyst which is short in reaction period, high in product quality and high in yield, discharge of three wastes is reduced, requirements of environment-friendly chemical process is met, and the preparation method has good industrial application value.

Description

technical field [0001] The invention belongs to the technical field of compound synthesis, and in particular relates to a preparation method of o-methylphenylhydroxylamine. Background technique [0002] Pyraclostrobin, also known as pyraclostrobin, is a broad-spectrum methyl methoxyacrylate fungicide with a pyrazole structure discovered by BASF in 1993. The synthetic route of pyraclostrobin reported in the current literature is to use o-nitrotoluene as a raw material through reduction to o-methylphenylhydroxylamine, and then react with methyl chloroformate and dimethyl sulfate. The raw materials are easy to get. It is easy for industrial production, so the preparation of o-methylphenylhydroxylamine becomes the key. ASHUTOSHH etc. (Processforthepreparationofahydroxylamine [p]. US: 5166435) use precious metals such as Pt as catalysts, and the o-methylphenylhydroxylamine obtained by catalytic hydrogenation of o-nitrotoluene has the following problems: 1) the catalyst used in t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C239/10
CPCC07C239/10
Inventor 王红伟刘敏杨红兵戴顺坤黄会真杨继华
Owner ANHUI COSTAR BIOCHEM CO LTD
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