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A kind of method for preparing carboxylate by electrochemical dechlorination of trichloromethylpyridine derivatives

A technology of trichloromethylpyridine and derivatives, which is applied in electrolytic components, electrolytic processes, electrolytic organic production, etc., can solve problems such as unsafe preparation conditions, and achieve the effect of avoiding high COD acidic waste liquid

Active Publication Date: 2020-08-14
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the above reaction has the use of highly toxic sulfur oxychloride toxic substances, and it is easy to produce a large amount of acid waste liquid, and the preparation conditions are not safe.

Method used

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  • A kind of method for preparing carboxylate by electrochemical dechlorination of trichloromethylpyridine derivatives
  • A kind of method for preparing carboxylate by electrochemical dechlorination of trichloromethylpyridine derivatives
  • A kind of method for preparing carboxylate by electrochemical dechlorination of trichloromethylpyridine derivatives

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Preparation of methyl 6-chloronicotinate by electrolysis of 2-chloro-5-trichloromethylpyridine (TCP)

[0028] The beaker is the reactor, the silver mesh is the cathode, and the zinc sheet is the anode. 200 mL of methanol solution of 0.5 mol / L TCP + 1.0 mol / L lithium acetate is the electrolyte. During the electrolysis process, oxygen is introduced into the electrolyte, the temperature is controlled at 20-25°C, and the current density is controlled at 1A / dm 2 . Stop the electrolysis after feeding 6 F / mol TCP electricity. After diluting the catholyte with methanol, it was analyzed by HPLC: the conversion rate of TCP was 98%, and the yield of methyl 6-chloronicotinate was 92%.

Embodiment 2

[0030] Preparation of methyl 6-chloronicotinate by electrolysis of 2-chloro-5-trichloromethylpyridine (TCP)

[0031] The beaker is the reactor, the silver mesh is the cathode, and the zinc sheet is the anode. 200 mL of methanol solution of 0.5 mol / L TCP + 1.0 mol / L lithium acetate is the electrolyte. During the electrolysis process, oxygen is introduced into the electrolyte, the temperature is controlled at 60-70°C, and the current density is controlled at 15 A / dm 2 . Stop the electrolysis after feeding 6 F / mol TCP electricity. After diluting the catholyte with methanol, it was analyzed by HPLC: the conversion rate of TCP was 96%, and the yield of methyl 6-chloronicotinate was 94%.

Embodiment 3

[0033] Preparation of methyl 6-chloronicotinate by electrolysis of 2-chloro-5-trichloromethylpyridine (TCP)

[0034] The beaker is the reactor, the silver mesh is the cathode, and the zinc sheet is the anode. 200 mL of methanol solution of 0.5 mol / L TCP + 1.0 mol / L lithium acetate is the electrolyte. During the electrolysis process, oxygen is introduced into the electrolyte, the temperature is controlled at 60-70°C, and the current density is controlled at 10 A / dm 2 . Stop the electrolysis after feeding 6 F / mol TCP electricity. After diluting the catholyte with methanol, it was analyzed by high performance liquid phase: the conversion rate of TCP was 95%, and the yield of methyl 6-chloronicotinate was 98%.

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Abstract

The present invention discloses a method for preparing carboxylate by electrochemical dechlorination of trichloromethylpyridine derivatives, which is characterized in that the method comprises the following steps: (1) dissolving polychlorinated pyridine derivatives in alcohol containing electrolytes or phenol solution to obtain an electrolytic reaction solution; (2) using the electrolytic reaction solution as catholyte, carry out electrolytic reduction dechlorination alcoholysis reaction at the cathode to obtain polychloropyridine carboxylate derivatives, and the polychloromethane The base pyridine derivative is shown in formula (I), and the product polychlorinated pyridine carboxylate derivative is shown in formula (II): in formula (I), m is 0, 1, 2, 3 or 4; formula ( II) m and the same formula (I), R is C 1 —C 8 Alkyl, phenyl or phenyl containing functional groups, the beneficial effects of the present invention are mainly reflected in: the reaction can be completed in the next step at normal temperature and pressure; the reaction process does not use concentrated sulfuric acid, thereby avoiding a large amount of difficult-to-handle high COD acidic waste liquid ; Do not use more toxic thionyl chloride and avoid generating sulfur dioxide gas.

Description

technical field [0001] The invention relates to the field of electrochemistry of polychloromethylpyridine derivatives, in particular to a method for preparing carboxylate by electrochemical dechlorination of trichloromethylpyridine derivatives. Background technique [0002] Pyridine carboxylate is an important molecular fragment of a variety of new pesticides (such as halopyridinate and chlorofluoropyridinate). Therefore, the green and efficient preparation methods of such substances have always attracted the attention of entrepreneurs. [0003] In the prior art, the Chinese patent (201710993290.8) discloses that 4-fluoro-6-trifluoromethyl-3-pyridinecarboxylic acid is used as a raw material, which is first acylated with a chlorinated reagent and then esterified with an alcohol to prepare the corresponding pyridine Carboxylate method. Zheng Hui et al. reported the method of using picolinyl cyanide as a raw material, first hydrolyzing sulfuric acid as a catalyst, then carryin...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C25B3/04C25B3/25
CPCC25B3/25
Inventor 徐颖华韩方玉郭利巧李斌石凯
Owner ZHEJIANG UNIV OF TECH
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