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A kind of preparation method of 2,2'-bipyridine

A technology of bipyridine and chloropyridine, which is applied in the field of preparation of 2,2'-bipyridine, can solve the problems of high production cost and high price of 2,2'-bipyridine, and achieve low price and low production cost , the effect of not being poisoned

Active Publication Date: 2017-07-07
GUANGAN LIER CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to: in the existing 2,2'-bipyridine preparation method, a large amount of heavy metal zinc and a relatively expensive catalyst need to be used, or expensive 2-bromopyridine needs to be used, resulting in 2,2 The problem of high production cost of '-bipyridine provides a preparation method of 2,2'-bipyridine

Method used

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  • A kind of preparation method of 2,2'-bipyridine
  • A kind of preparation method of 2,2'-bipyridine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Get 30ml of anhydrous tetrahydrofuran (THF) solution of 2-chloropyridine Grignard reagent (which contains 10mmol of 2-chloropyridine Grignard reagent), add 0.3mmol of MnCl 2 And 9.5mmol of 2-chloropyridine, reacted at room temperature for 1h. The reaction mixture was quenched with water, then extracted with dichloromethane, filtered, and dichloromethane washed the filter cake, and the liquid part obtained by washing was left to stand for phase separation, and the organic phase was collected. The organic phase was distilled off the solvent under reduced pressure to obtain a crude product, which was then distilled under reduced pressure to obtain 1.17 g of a white solid.

[0029] It was determined that the melting point of the white solid was 69.4-69.8°C, MS: m / z=156.1, and it was determined to be 2,2'-bipyridine.

Embodiment 2

[0031] Add 0.6g (0.025mol) of magnesium chips into a 100mL three-necked flask, and replace with nitrogen three times. Take 4.54g (0.04mol) 2-chloropyridine and 45.4g THF to form the first solution. A small amount of the first solution was added to the three-necked flask replaced by nitrogen, and then 0.2 g (10 mol%) of bromoethane was added at room temperature to initiate the Grignard reaction, and the remaining first solution was continued to be added dropwise after initiation. After the dropwise addition, add 0.16g (3mol%) of anhydrous MnCl 2 , Continue to stir the reaction for 1h and then stop the reaction. Then add 5g of water to the there-necked flask to quench, add 10ml of dichloromethane for extraction, filter, dichloromethane rinses the filter cake, the liquid part is left to stand for phase separation, collects the organic phase, and evaporates the solvent under reduced pressure to obtain the crude product. Pressure distillation afforded 2.18 g of white solid.

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Embodiment 3

[0034] Add 0.024mol magnesium chips into a 100mL three-necked flask, and replace with nitrogen three times. Take 4.54g (0.04mol) 2-chloropyridine and 45.4g THF to form the first solution. A small amount of the first solution was added to the three-necked flask replaced by nitrogen, and then 0.2 g (10 mol%) of bromoethane was added at room temperature to initiate the Grignard reaction, and the remaining first solution was continued to be added dropwise after initiation. After the dropwise addition is completed, add 0.16g (3mol%) of anhydrous CoCl 2 , After continuing to stir the reaction for 1h, stop the reaction. Then add 5g of water to the there-necked flask to quench, add 10ml of dichloromethane for extraction, filter, dichloromethane rinses the filter cake, the liquid part is left to stand for phase separation, collects the organic phase, and evaporates the solvent under reduced pressure to obtain the crude product. Pressure distillation afforded 2.1 g of white solid.

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Abstract

The invention discloses a preparation method of 2, 2'-bipyridyl. In the preparation method, with a manganese salt or a cobalt salt as a catalyst, 2-chloropyridine Grignard reagent reacts with 2-chloropyridine to produce the 2, 2'-bipyridyl. The invention further discloses a method for performing Grignard reaction and coupling reaction with the 2-chloropyridine as a raw material by one-pot method to produce the final 2, 2'-bipyridyl. The preparation method of the 2, 2'-bipyridyl has the advantages of easily available raw materials, inexpensive and stable catalyst, environmental protection, and being low in cost, and simple and convenient to operate; by the preparation method, needs of large-scale industrial production can be met; the preparation method has a wide market prospect.

Description

technical field [0001] The invention relates to the field of chemical engineering, especially the field of synthesis, and specifically relates to a preparation method of 2,2'-bipyridine. Background technique [0002] 2,2'-Bipyridyl is an important chemical intermediate, which is widely used in the synthesis of pesticides, medicines, spices and dyes. At the same time, it is also a metal chelating agent, which can be used as a metal developer. [0003] Synthesis of 2,2′‐Bipyridines: Versatile Building Blocks for SexyArchitectures and Functional Nanomaterials (G R Newkome et al., Eur.J.Org.Chem, 2004, 235-254) introduced the use of 2-halopyridine self-coupling to prepare One of the commonly used methods for 2,2'-bipyridine. Chinese patents CN103172559 and CN103030594 disclose a method for producing 2,2'-bipyridine using cheap 2-chloropyridine as a raw material. However, these methods usually require the use of a large amount of heavy metal zinc and relatively expensive catal...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/22C07D213/127
CPCC07D213/127C07D213/22
Inventor 吴锋程柯李世洪
Owner GUANGAN LIER CHEM CO LTD
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