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Preparation method of 2-chloro-5-tirfluoromethylpyridine

A technology of trifluoromethylpyridine and trichloromethylpyridine, applied in the field of preparation of 2-chloro-5-trifluoromethylpyridine, which can solve the problems of dangerous operation, many reaction by-products, and poor atom economy

Active Publication Date: 2013-09-11
LIAONING TIANYU CHEM +3
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The technical problem to be solved by the present invention is to overcome the high raw material price and high cost of the existing 2-chloro-5-trifluoromethylpyridine preparation method, high toxicity of reaction raw materials, dangerous operation, many reaction by-products, poor atom economy, Difficult post-processing, serious environmental pollution and other defects, and a preparation method of 2-chloro-5-trifluoromethylpyridine is provided

Method used

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  • Preparation method of 2-chloro-5-tirfluoromethylpyridine
  • Preparation method of 2-chloro-5-tirfluoromethylpyridine

Examples

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Embodiment 1

[0127] (1) Step 1: N 2 After testing the airtightness of the autoclave, in a 500mL autoclave, add 39.2g of benzyl chloride and 80.6g of 32% NaOH aqueous solution in succession (mass percentage means that the quality of sodium hydroxide accounts for the total amount of the aqueous solution of sodium hydroxide mass percentage), lower the temperature to 5°C to 15°C, add 42.2g of ammonia water with a mass percentage of 25% (mass percentage refers to the percentage of the mass of ammonia gas in the total mass of the ammonia solution), and control the temperature at 5°C to 15°C, after the dropwise addition, the temperature was raised to 60°C (at this time, the pressure in the kettle was about 0.25MPa), and after keeping at this temperature for 7 hours, samples were taken, and the content of benzyl chloride was detected by HPLC to be less than 0.3%. ×2 toluene extraction, combined organic phase, using 30% hydrochloric acid by mass percentage (mass percentage refers to the mass percen...

Embodiment 2

[0133] (1) Step 1: N 2 After testing the tightness of the autoclave, in a 500mL autoclave, successively add 49.8g of o-chlorobenzyl chloride, 70.6g of toluene and 90.3g of KOH solution with a mass percentage of 40% (mass percentage refers to the mass of potassium hydroxide percentage of the total mass of potassium hydroxide aqueous solution), lower the temperature to 5°C to 15°C, and add 42.2g of ammonia water with a mass percentage of 25% (mass percentage refers to the percentage of the mass of ammonia gas in the total mass of ammonia solution), when adding Control the temperature at 5°C to 15°C, raise the temperature to 45°C after the dropwise addition (at this time, the pressure in the kettle is about 0.15MPa), keep the temperature at this temperature for 10 hours, take a sample, and determine that the content of o-chlorobenzyl chloride is less than 0.3% by HPLC. After the reaction is over, the reaction solution is extracted with 40g×2 toluene, the organic phases are combin...

Embodiment 3

[0139] (1) N 2 After testing the airtightness of the autoclave, in a 500mL autoclave, add 43.5g of m-methylbenzyl chloride and 80.6g of NaOH solution with a mass percentage of 32% (mass percentage means that the mass percentage of sodium hydroxide accounts for the percentage of sodium hydroxide percentage of the total mass of the aqueous solution), lower the temperature to 5°C to 15°C, add 42.2g of ammonia water with a mass percentage of 25% (mass percentage refers to the percentage of the mass of ammonia gas in the total mass of the ammonia solution), and control the temperature at 5 ℃~15℃, after the dropwise addition, the temperature is raised to 60℃ (at this time, the pressure in the kettle is about 0.25MPa), after keeping at this temperature for 9h, take a sample, and the HPLC detection of m-methylbenzyl chloride content is less than 0.3%, confirming that the reaction is over. The reaction solution was extracted with 60g×2 toluene, the organic phases were combined, and the...

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Abstract

The invention discloses a preparation method of 2-chloro-5-tirfluoromethylpyridine. The invention provides a preparation method of 2-chloro-5-tirfluoromethylpyridine, and the preparation method comprises the following steps of: reacting 2-chloro-5-trichloromethylpyridine with hydrogen fluoride in a closed system in the presence of a catalyst to obtain the 2-chloro-5-tirfluoromethylpyridine, wherein the catalyst is antimony trioxide and / or antimony pentoxide. The invention further provides a preparation method of a compound 2, and the preparation method comprises the following steps of: reacting a compound 3 with ammonia in the presence of alkali to obtain the compound 2. The preparation method provided by the invention is cheap and liable to obtain raw materials, low in cost, few in reaction by-products, simple in post treatment, safe to operate, environment-friendly and suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to a preparation method of 2-chloro-5-trifluoromethylpyridine. Background technique [0002] 2-Chloro-5-trifluoromethylpyridine is a very valuable fluorine-containing, heterocyclic organic intermediate, used for the production of herbicides fluazifop-p-p and valoxop-p-p, and fungicide picoxystrobin and other varieties of key intermediates. At the same time, it can also be used to develop important fine chemical intermediates such as 2,3-dichloro-5-trifluoromethylpyridine, 2-hydroxy-5-trifluoromethylpyridine, 2-hydroxy-3-chloro-5-tri Fluoromethylpyridine and 2-amino-5-trifluoromethylpyridine, etc. [0003] At present, the synthetic method of reported 2-chloro-5-trifluoromethylpyridine mainly contains following three kinds: [0004] 1. Using 3-picoline as raw material, 2-chloro-5-trifluoromethylpyridine was obtained through chlorination (CN1772380, CN102452977 and US2005240024) and fluorination (GB1599123, US4567273 and US4680406...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/61C07C209/08C07C211/27C07C211/29C07C231/02C07C233/05C07C233/13
Inventor 樊小彬银亮熊亮吕鑫江杨阳范晶
Owner LIAONING TIANYU CHEM
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