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Preparation method of 2-chloro-5-chloromethylpyridine

A technology of chloromethylpyridine and chloromethyl, which is applied in the field of preparation of 2-chloro-5-chloromethylpyridine, can solve problems such as large amount of wastewater, abnormal marine ecology, and high cost of solvents, and achieve economic benefits, The effect of high product quality and low production cost

Active Publication Date: 2017-05-24
LANZHOU CHEMSPECWEIER CHEM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] But there are obvious disadvantages in this synthetic process route: first, the chlorination ring closure step needs to use a large amount of solvent DMF, and every ton of 2-chloro-5-chloromethylpyridine needs to consume about 1.2 tons, and the solvent cost is high
Second, the by-products produced in the cyclization reaction process cannot be recycled, and the amount of wastewater produced is very large. Each ton of 2-chloro-5-chloromethylpyridine produces 10 tons of high-concentration wastewater, and the treatment cost is high.
Phosphorus-containing wastewater will cause eutrophication of water bodies, seriously affect the survival of aquatic organisms, and even cause catastrophic marine ecological anomalies

Method used

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  • Preparation method of 2-chloro-5-chloromethylpyridine

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preparation example Construction

[0051] One aspect of the present invention provides a method for preparing 2-chloro-5-chloromethylpyridine, the preparation method of 2-chloro-5-chloromethylpyridine may include: 2-chloro-2-chloromethyl- 4-cyanobutyraldehyde (compound of formula I, referred to as CCC) reacts with cyanuric chloride (compound of formula II, referred to as TCT) to prepare 2-chloro-5-chloromethylpyridine (compound of formula III, CCMP). Said reaction can be ring closure reaction, and reaction equation is as follows:

[0052]

[0053]In the preparation method of 2-chloro-5-chloromethylpyridine provided by the present invention, the reaction can be carried out in the presence of a solvent, and the solvent can be an organic solvent. For example, the organic solvent that can be used includes but is not limited to alkanes One or a combination of solvents, cycloalkane solvents, halogenated alkane solvents, halogenated cycloalkane solvents, aromatic hydrocarbon solvents, halogenated aromatic hydrocarb...

Embodiment 1-1

[0077] Preparation of 2-chloro-5-chloromethylpyridine:

[0078]Get compound CCC 0.1mol, be dissolved in 20 milliliters of ethylene dichloride, oil bath is heated to 80 ℃, add 2g catalyst triethylamine, dropwise add the dichloroethane of 20 milliliters containing 7.37g (0.04mol) cyanuric chloride Solution, keep the temperature between 80-85°C, add dropwise for 2 hours, keep warm at 80°C for 30 minutes, then cool down to 50°C, add 10 ml of water, then add 10.7g of 30% NaOH aqueous solution dropwise at 20-50°C, water Phase pH value is about 8.0-10.0, start to filter, filter cake is rinsed with 10 milliliters of dichloroethanes, the separated filtrate stands for stratification, the lower layer is the dichloroethane phase, desolvation, obtains 17.1g brown solid, GC The standard detection contained CCMP 74.6%, and the yield was 78.7%.

Embodiment 1-2

[0080] Preparation of 2-chloro-5-chloromethylpyridine:

[0081] Take 0.1mol of compound CCC, dissolve it in 20ml of cyclohexane, heat the oil bath to 80°C, add 1g of catalyst N,N-dimethylaniline, dropwise add 20ml of cyanuric chloride containing 11.06g (0.06mol) Cyclohexane solution, keep the temperature between 75-80°C, add dropwise for 2h, keep warm at 80°C for 30 minutes, then cool down to 50°C, add 10ml of water, then add 10.7g of 30% NaOH aqueous solution dropwise at 20-50°C , the pH value of the aqueous phase is about 8.0-10.0, start to filter, rinse the filter cake with 10 milliliters of cyclohexane, and separate the filtrate to stand for stratification. The standard detection contained CCMP 75.6%, and the yield was 81.4%.

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Abstract

The invention relates to the field of chemical synthesis, particularly a preparation method of 2-chloro-5-chloromethylpyridine. The preparation method comprises the following step: carrying out cyclization reaction on 2-chloro-2-chloromethyl-4-cyanobutyraldehyde and cyanuric chloride to obtain the 2-chloro-5-chloromethylpyridine. The preparation method provided by the invention has the advantages of low production cost, high product quality, high yield and the like. Besides, the byproduct sodium cyanurate of the preparation method can be treated to prepare thetrichloroisocyanuric acid superior product, thereby further enhancing the economic benefits.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a preparation method of 2-chloro-5-chloromethylpyridine. Background technique [0002] 2-Chloro-5-chloromethylpyridine (CCMP for short) is an important intermediate of best-selling pesticides such as imidacloprid, acetamiprid, thiacloprid, and nitenpyram. At present, there are three main routes for synthesizing 2-chloro-5-chloromethylpyridine by ring method, which are benzylamine method, cyclopentadiene method and morpholine method. Most domestic manufacturers mainly adopt the cyclopentadiene method, and the reaction equation is as follows: [0003] [0004] However, this synthetic route has obvious disadvantages: first, the chlorination and cyclization step requires the use of a large amount of solvent DMF, about 1.2 tons of 2-chloro-5-chloromethylpyridine is consumed per ton, and the solvent cost is high. Second, the by-products produced in the cyclization reaction proces...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/61C07D251/36
CPCC07D213/61C07D251/36
Inventor 顾竞杜友兴俞佳麟何立
Owner LANZHOU CHEMSPECWEIER CHEM CO LTD
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