Industrial production method for preparing 2-chloro-5-picoline

A picoline and production method technology, which is applied in the production field of pesticide intermediates, can solve the problems of low cost and achieve the effects of good product quality, less tar, and simple post-processing

Inactive Publication Date: 2012-10-31
JIANGSU YANGNONG CHEM GROUP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Imidacloprid has special effects on aphids, planthoppers, whiteflies, leafhoppers and other Lepidoptera and Coleoptera pests and is low in cost. At this stage, there is no product that can completely replace it
And morpholine-propionaldehyde method except phosphorus oxychloride synthesis CMP technology and equipment requirement are higher, and other pr

Method used

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  • Industrial production method for preparing 2-chloro-5-picoline
  • Industrial production method for preparing 2-chloro-5-picoline
  • Industrial production method for preparing 2-chloro-5-picoline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Weigh 27.75g of 5-methyl-3,4-dihydro-2(1H)pyridone, and prepare 5-methyl-3,4-dihydro-2( 1H) A solution of pyridone in dichloroethane.

[0022] Weigh 61.9 g of solid phosgene and dissolve it in dichloroethane to prepare a phosgene dichloroethane solution with a mass fraction of 34.8%.

[0023] Put the prepared 5-methyl-3,4-dihydro-2(1H)pyridone in dichloroethane solution in the reaction vessel, heat it, when the temperature of the solution in the reaction vessel rises to 20-30°C, pass it into Chlorine 17.8 g, stop when the solution in the container is observed to be bright yellow.

[0024] Add catalyst—N,N-dimethylformamide (DMF) 3.3 g to the above reaction solution, stir and heat up to reflux, then add phosgene dichloroethane solution dropwise, dropwise time is 2 hours, after dropwise addition, in Keep warm under reflux for 6 hours, reflux to drive off excess chlorinating agent for 0.5 hour, lower the reaction system to room temperature, then add dilute alkali dropwis...

example 2-5

[0027] In order to investigate the effect of the amount of phosgene on the synthesis of 2-chloro-5-picoline (CMP), experiments were carried out in which different amounts of phosgene participated in the reaction, and the rest of the conditions were the same as in Example 1. The data is as follows:

[0028]

[0029] It can be seen from the above table that under the same reaction conditions, when the molar ratio of phosgene to adduct is 2.3, the yield of monochlorine is the highest, which is 92.2%. Too much or too little amount of phosgene will lead to a decrease in the yield of monochlorine.

example 6-8

[0031] In above-mentioned example 1, replace the phosgene dichloroethane solution with triphotodichloroethane liquid, all the other remain unchanged. The following are the experimental results under different Sanguang dosages.

[0032]

[0033] It can be seen from the above table that under the same reaction conditions, when the molar ratio of Sanguang to the adduct is 0.833, the yield of monochlorine is the highest, which is 94.2%. However, the dosage of Sanguang is too high or the high and low yields are all reduced.

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PUM

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Abstract

The invention provides an industrial production method for preparing 2-chloro-5-picoline, and relates to the technical field of production of pesticide intermediates. According to the method, 2-chloro-5-picoline is synthesized by taking 5-methyl-3, 4-dihydro-2 (1H) pyridine as a raw material and triphosgene or phosgene as a chlorinating agent in the presence of a basic catalyst. The method has the characteristics of high reaction yield and good product quality; and the reaction yield is 94%; and the content detected by liquid chromatography is more than 94%.

Description

technical field [0001] The invention relates to the technical field of production of pesticide intermediates, in particular to a production method of imidacloprid intermediate 2-chloro-5-picoline. Background technique [0002] 2-Chloro-5-chloromethylpyridine (CCMP) is an important intermediate of the nicotinic insecticide imidacloprid, and its source has two routes: one is direct synthesis, and the other is through 2-chloro-5- Preparation of 2-chloro-5-chloromethylpyridine by chlorination of methylpyridine (CMP). The synthesis process route introduced by the data includes: 3-picoline nitrogen oxidation chlorination method (see JACS76: 1286 (1954); and CA: 100: 51464; Hung: 25878; DE3800179A1)); picoline direct chlorination method (JP7 -149726); nicotinic acid method (see DE0373463); cyclopentadiene method, ring method (propionaldehyde-morpholine and propionaldehyde-benzylamine method), etc. Due to the cost, source of raw materials and waste problems, there are two main syn...

Claims

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Application Information

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IPC IPC(8): C07D213/61
Inventor 曹晶晶王秋萍冯为林吴翔王奇黄文嵘王周洲陈鑫
Owner JIANGSU YANGNONG CHEM GROUP
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