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2,2'-bipyridine, catalytic coupling synthesis method and applications thereof

A technology for bipyridine and pyridine, which is applied in the field of preparation of 2,2'-bipyridine, can solve the problems of difficulty in the source of raw material 2-halopyridine, high recovery cost of metal catalyst, complicated technological process, etc. The effect of reduced production pollution and simple process flow

Inactive Publication Date: 2015-12-09
ANHUI COSTAR BIOCHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the yield of 2,2'-bipyridine is improved, the source of raw material 2-halopyridine used in this process is difficult, the process is complicated, the recovery cost of metal catalyst is high, and there is also some pollution to the environment.

Method used

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  • 2,2'-bipyridine, catalytic coupling synthesis method and applications thereof
  • 2,2'-bipyridine, catalytic coupling synthesis method and applications thereof
  • 2,2'-bipyridine, catalytic coupling synthesis method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-3

[0016] Weigh 522.8g DMAC, 59.3g Raney nickel, 102.1g sodium ethoxide (58.5g sodium amide or 102.1g aluminum isopropoxide) respectively at room temperature, and add 237.3g raw material pyridine into the autoclave successively. Nitrogen gas was introduced at a certain speed for a period of time to replace the air in the reactor. After the replacement, the temperature of the reactor was raised to 220°C, and the pressure inside the reactor was controlled to be 0.8-1.0 MPa. After 12 hours, the temperature was lowered and the samples were analyzed by gas chromatography. The data are shown in the table below:

[0017]

Embodiment 4-9

[0019] Weigh 522.8g DMAC, 59.3g Raney nickel, 58.5g sodium amide, and 237.3g raw material pyridine into the autoclave respectively at room temperature, and feed nitrogen into the autoclave at a rate of 100ml / min for a period of time to replace the air in the reactor . After the replacement, the temperature of the reactor was raised to 160°C, 180°C, 200°C, 220°C, 240°C, and 260°C respectively, and the pressure inside the reactor was controlled to be 0.8-1.0MPa. After 12 hours, the temperature was lowered and the samples were analyzed by gas chromatography. The data are shown below surface:

[0020]

Embodiment 10-18

[0022] Take by weighing 522.8g DMAC, 59.3g Raney nickel, a certain amount of sodium ethylate (sodium amide or aluminum isopropoxide) respectively at room temperature, and add 237.3g of raw material pyridine into the autoclave successively, and pass through the autoclave at a speed of 100ml / min. Nitrogen was introduced for a period of time to replace the air in the reactor. After the replacement, the temperature of the reactor was raised to 220°C, and the pressure inside the reactor was controlled to 1.0 MPa. After 12 hours, the temperature was lowered and the samples were analyzed by gas chromatography. The data are shown in the table below:

[0023]

[0024]

[0025] From the data in the above three tables, it can be concluded that the conversion rate of pyridine raw material is increased by about 10%, and the yield of 2,2'-bipyridine is increased to more than 30%, which is completely suitable for the scale of the factory. chemical production.

[0026] The 2,2'-bipyrid...

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Abstract

The present invention discloses 2,2'-bipyridine, a catalytic coupling synthesis method and applications thereof. According to the method, Raney nickel is adopted as a catalyst and a reaction aid is added to an autoclave to catalyze pyridine to be subjected to dehydrogenation so as to directly couple to synthesize 2,2'-bipyridine, wherein the chemical formula of the reaction aid is represented by R-X, R represents alkyl or alkoxy or amino, and X represents an alkali metal or third main group element. According to the present invention, the pyridine is adopted as the raw material and the dehydrogenation coupling is performed to obtain the 2,2'-bipyridine, such that the raw material is easy to obtain, the pyridine chlorination process is eliminated, the process is simple, the production cost is substantially reduced, the use of halogenated pyridine is avoided, the production pollution is reduced, and the environmental protection is provided; the used catalyst has the cheap price and effectively replaces the expensive precious metal so as to reduce the catalyst cost; and the reaction aid is added during the reaction process so as to effectively improve the pyridine raw material conversion rate and improve the 2,2'-bipyridine yield, and the method is suitable for factory scale production.

Description

technical field [0001] The invention belongs to the technical fields of fine chemical production and pesticides, and in particular relates to a preparation method of 2,2'-bipyridine. Background technique [0002] 2,2'-Bipyridine is an important intermediate in fine chemical and pharmaceutical synthesis. At the same time, it is also a unique chelating agent, used as an indicator for detecting metal ions, a photosensitizer, a ligand for metal organic catalysts, etc. . Therefore, this product has very important social significance and industrial application prospects for the development of pyridine downstream products. [0003] At present, the main industrial production methods of 2,2'-bipyridine at home and abroad include pyridine coupling method and Ullmann method. As a pioneer of diquat, Syngenta uses the pyridine coupling method to synthesize 2,2'-bipyridine. Pyridine is used as a raw material, and pyridine is directly dehydrogenated and coupled under the action of a meta...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/22C07D213/127C07D471/14
CPCC07D213/22C07D213/127C07D471/14
Inventor 刘善和黄永升杨红兵顾起财杨志红张财华汪中伟周浩吴德清王晓亭
Owner ANHUI COSTAR BIOCHEM CO LTD
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