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Preparation of N-(1- ethyl propyl)-3,4-methyl toluidine

A technology of dimethylaniline and ethylpropyl, which is applied in the field of dinitroaniline pesticides, can solve the problems of easy decomposition, influence and large amount of catalyst of 2-naphthalenesulfonic acid, so as to improve the reuse rate and simplify the operation. Process, the effect of reducing the generation of by-products

Inactive Publication Date: 2012-11-28
QINGDAO HANSEN BIOLOGIC SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The weak point of this prior art is: 1) catalyst consumption is big; 2) 2-naphthalenesulfonic acid is easy to decompose, may influence N-(1-ethylpropyl)-3,4-dimethylaniline in industry purity

Method used

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  • Preparation of N-(1- ethyl propyl)-3,4-methyl toluidine
  • Preparation of N-(1- ethyl propyl)-3,4-methyl toluidine
  • Preparation of N-(1- ethyl propyl)-3,4-methyl toluidine

Examples

Experimental program
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Effect test

Embodiment 1

[0032] (1) Nitration: Put 34.8Kg concentrated sulfuric acid (98%, 348mol) into a 50L mixed acid configuration kettle, stir and slowly put 10.8Kg concentrated nitric acid (98%, 168mol); in a 100L reaction kettle, first add 12.84 Kg o-xylene (99%, 120mol), then add catalyst, slowly add mixed acid at 20-25°C, after the addition of mixed acid is completed, reflux reaction for 4-6 hours, and the end point of the reaction is controlled by HPLC. After passing the test, 13.65Kg of 3,4-dimethylnitrobenzene was obtained through rectification and separation, with a content of 99%.

[0033] (2) Hydrogenation, addition, and hydrogenation: In a 100L pressure reactor, add 12.65Kg 3,4-dimethylnitrobenzene, 13.73Kg 3-pentanone (99%, 158mol), 0.05Kg Pd / C catalyst , control the pressure and feed hydrogen, heat up, start stirring, react until no hydrogen is absorbed, cool down, press out the kettle material, filter out the catalyst, separate the filtrate, distill the organic layer under reduced p...

Embodiment 2

[0036] (1) Nitration: Put 34.8Kg concentrated sulfuric acid (98%, 348mol) into a 50L mixed acid configuration kettle, stir and slowly put 10.8Kg concentrated nitric acid (98%, 168mol); in a 100L reaction kettle, first add 12.84 Kg o-xylene (99%, 120mol), then add catalyst, slowly add mixed acid at 20-25°C, after the addition of mixed acid is completed, reflux reaction for 4-6 hours, and the end point of the reaction is controlled by HPLC. After passing the test, 13.5Kg of 3,4-dimethylnitrobenzene was obtained by rectification and separation, with a content of 99.2%.

[0037] (2) Hydrogenation, addition, and hydrogenation: In a 100L pressure reactor, add 12.65Kg 3,4-dimethylnitrobenzene, 13.73Kg 3-pentanone (99%, 158mol), 0.05Kg Pd / γ- Al2O3 catalyst, control the pressure to feed hydrogen, raise the temperature, start stirring, and react until no hydrogen is absorbed, and the end point is controlled by gas chromatography. After qualified, lower the temperature, press out the ke...

Embodiment 3

[0040] Repeat the same steps as described in Example 1, but add 0.05Kg of improved polystyrene-supported palladium catalyst in step (2) hydrogenation, addition, and hydrogenation reactions, and measure the end point of the reaction by gas chromatography to finally obtain 14.95Kg N-(1-ethylpropyl)-3,4-dimethylaniline, content 99.3%.

[0041] All the other are with embodiment 1.

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Abstract

The invention provides a method for making N-(1-ethyl propyl)-3,4-dimethylaniline, belonging to the dinitroaniline class pesticide technical field. The method has the characteristics that o-xylene is used as a starting material, which is nitrified under a function of a catalyst to obtain 3,4-dimethyl nitrobenzene, and is hydrogenated, added and re-hydrogenated with 3-pentanone under the function of the catalyst, and then the N-(1-ethyl propyl)-3,4-dimethylaniline is obtained. The content of N-(1-ethyl propyl)-3,4-dimethylaniline is more than or equal to 98 percent; the operation procedure is simplified, and the row material is easy to obtain with low cost, thereby easily and industrially realizing.

Description

technical field [0001] The invention belongs to the technical field of dinitroaniline pesticides, in particular to a method for preparing pendimethalin technical intermediate N-(1-ethylpropyl)-3,4-dimethylaniline. Background technique [0002] Pendimethalin (pendimethalin) is also known as pendimethalin, Shitianbu, Chuyatong, Bicaotong, Pendimethalin, Shacaotong, Caicaotong, etc., and its chemical name is N-(1-ethylpropane) base)-2,6-dinitro-3,4-dimethylaniline, which belongs to dinitroaniline herbicides, is a water and upland herbicide with excellent performance, and is a recognized green pesticide with low toxicity and low residue , High safety for humans and animals, most crops, and the environment. And because the soil has strong adsorption to it, it is not easy to leaching, it has little mobility in the soil, and is environmentally friendly. Pendimethalin is a selective broad-spectrum herbicide with high activity and broad herbicidal spectrum. It can not only effectiv...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/48C07C209/36B01J31/06
Inventor 李树柏姜红林刘瑞宾陈军
Owner QINGDAO HANSEN BIOLOGIC SCI
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