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Synthetic method for o-nitrobenzyl chloride

A technology of ortho-nitrobenzyl chloride and a synthesis method, which is applied in the field of organic compound synthesis, can solve the problems of many side reactions, low equipment capacity, low yield and the like, and achieves the advantages of reducing production cost, reducing environmental protection pressure and simple synthesis steps. Effect

Active Publication Date: 2016-10-12
SICHUAN FOURSTAR BIOTECH RANDD CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The thermal chlorination method has slow speed, many side reactions, and low yield. The general yield is less than 5%, and it is basically eliminated; while the photochlorination method is more mature, but due to the limitation of light, there are low equipment capacity and side effects in dark places. There are many products, and the mass transfer is difficult to strengthen. In addition, there are many researches on catalytic chlorination. Although the yield is limited, the industrialization is relatively mature and the development prospect is good.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] A synthetic method of o-nitrobenzyl chloride includes the following processes:

[0038] Add catalyst (50 mesh activated carbon) to o-nitrotoluene, control the mass ratio of o-nitrotoluene to catalyst at 1:0.01, stir at 200r / min and heat to 100°C, slowly pass in chlorine gas, and use gas chromatography to track The reaction by-product o-nitrobenzylidene dichloride reaches 4% and the conversion rate of o-nitrotoluene is 39.7%. Stop the reaction; after the reaction is over, distill under reduced pressure at a vacuum of -0.097Mpa and a temperature of 110°C to recover the o-nitro group Toluene continues to be recycled for chlorination and utilization; the residue after the recovery of o-nitrotoluene is purified by recrystallization with petroleum ether to obtain white crystal-like solid powder of o-nitrobenzyl chloride.

[0039] This embodiment can achieve the production effect of 99.3% purity of o-nitrobenzyl chloride and 83.7% yield (based on the actual consumption of o-nitroto...

Embodiment 2

[0041] A synthetic method of o-nitrobenzyl chloride includes the following processes:

[0042] Add catalyst (a mixture of activated carbon and DMF with a mass ratio of 2:1200 mesh) to o-nitrotoluene, control the mass ratio of o-nitrotoluene to catalyst at 1:0.2, stir at 400r / min and heat to 180℃ , Slowly introduce chlorine gas, use gas chromatography to track the reaction by-product o-nitrobenzylidene dichloride to 6%, and the conversion rate of o-nitrotoluene is 41%. Stop the reaction; after the reaction is over, the vacuum is -0.098Mpa and the temperature is 100 Distill under reduced pressure at ℃ to recover the o-nitrotoluene and continue to chlorinate it for recycling; the residue after the recovery of the o-nitrotoluene is purified by recrystallization with petroleum ether to obtain white crystalline solid powder of o-nitrobenzyl chloride.

[0043] This embodiment can achieve the production effect of 99.6% purity of o-nitrobenzyl chloride and 80.0% yield (calculated based on t...

Embodiment 3

[0045] A synthetic method of o-nitrobenzyl chloride includes the following processes:

[0046] Add catalyst to o-nitrotoluene (a mixture of bromine, azobisisobutyronitrile and azobisisoheptonitrile with a mass ratio of 1:1:2), and control the mass ratio of o-nitrotoluene to catalyst at 1 : 0.15, stirring at 300r / min and heating to 130°C, slowly introducing chlorine gas, using gas chromatography to track the reaction by-product o-nitrobenzylidene dichloride to 5%, o-nitrotoluene conversion rate 40.2%, stop the reaction; After the reaction is over, distill under reduced pressure at a vacuum of -0.097Mpa and a temperature of 115°C to recover the o-nitrotoluene and continue to be recycled for chlorination; the residue after the recovery of the o-nitrotoluene is purified by recrystallization with petroleum ether to obtain white Crystal-like solid o-nitrobenzyl chloride powder.

[0047] This embodiment can achieve the production effect of 99.0% purity of o-nitrobenzyl chloride and 82.9%...

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PUM

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Abstract

The invention discloses a synthetic method for o-nitrobenzyl chloride. The synthetic method comprises the following steps: adding a catalyst into o-nitrotoluene, carrying out heating and stirring, slowly introducing chlorine and recovering o-nitrotoluene after completion of reaction so as to obtain o-nitrobenzyl chloride. The synthetic method provided by the invention overcomes defects like low yield and a great number of by-products of conventional thermal chlorination methods and luminescence methods for synthesis of o-nitrobenzyl chloride; the catalyst is added into o-nitrotoluene, chlorine is introduced after heating and stirring, and o-nitrotoluene is recovered after completion of the reaction, so o-nitrobenzyl chloride is obtained; and with the synthetic method provided by the invention, o-nitrobenzyl chloride (in terms of actual consumption of o-nitrotoluene) with a purity of no less than 99% and a yield of no less than 80% can be obtained, higher than the purity and yield of o-nitrobenzyl chloride produced by using the thermal chlorination methods and luminescence methods.

Description

Technical field [0001] The invention is a method for synthesizing o-nitrobenzyl chloride, specifically relates to a synthesis process of o-nitrobenzyl chloride in the pyraclostrobin production process, and belongs to the field of organic compound synthesis. Background technique [0002] Pyraclostrobin has received widespread attention and applications since it was launched by BASF in 2002. As an effective broad-spectrum fungicide, Pyraclostrobin has a good control effect on diseases caused by all kinds of true pathogens. For example: potato and tomato early blight, late blight, leaf bitter, powdery mildew, rust, etc., have the effect of preventing and curing. [0003] Ortho-nitrobenzyl bromide is an important synthetic intermediate of the new broad-spectrum fungicide pyraclostrobin. As an important synthetic intermediate, there are many production processes for o-nitrobenzyl bromide, but the existing synthetic methods have several important The most important of the shortcomings ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C201/12C07C205/11
CPCC07C201/12C07C205/11
Inventor 马青伟王文刘虎陈熙李舟张华王蕾
Owner SICHUAN FOURSTAR BIOTECH RANDD CORP