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A kind of preparation method of 2,2'-bipyridine-4,4'-dicarboxylic acid

A technology of bipyridine and dicarboxylic acid, applied in directions such as organic chemistry, can solve the problems of difficult separation of the target product, unsuitable for industrial production, high environmental hazards, etc., and achieves the effects of being suitable for large-scale production, easy to operate, and low in preparation cost.

Inactive Publication Date: 2017-09-19
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The current oxidation methods mostly use potassium dichromate or chromium trioxide to react in a sulfuric acid system. Although these reactions react quickly and are simple to operate, they use concentrated sulfuric acid that is corrosive and harmful, and heavy metal chromium ions are more harmful to the environment. Large, the reaction needs to be heated, has a certain degree of danger, and is not suitable for large-scale industrial production
The patent with the publication number CN102321017A is to oxidize 4,4'-dimethyl-2,2'-bipyridine with potassium permanganate in a mixed system of glacial acetic acid and water to avoid the poisoning of potassium dichromate and sulfuric acid. used, but the target product is not easy to separate from the reaction system, and the post-treatment is more complicated

Method used

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  • A kind of preparation method of 2,2'-bipyridine-4,4'-dicarboxylic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Synthesis of 2,2'-bipyridine-4,4'-dicarboxylic acid

[0013] In a four-neck flask equipped with a magnet, a thermometer and a reflux condenser, add 3.7g (0.02mol) of analytically pure 4,4'-dimethyl-2,2'-bipyridine, dissolve it in 40mL of water and 4mL In the mixed system of nitric acid, heat to 80°C under stirring, and add potassium permanganate solid (a total of 6.3g, 0.04mol) five times while maintaining this temperature. Then add the next batch of potassium permanganate, and stop heating after reacting for 6 hours. After cooling to room temperature, the reaction solution was suction-filtered under reduced pressure. After the insoluble matter was filtered off, concentrated hydrochloric acid was added to the filtrate to adjust the pH value to 1. Static crystallization, white crystals precipitated. After the crystallization is complete, suction filtration under reduced pressure is performed, and the obtained white crystals are washed with deionized water. Finally, th...

Embodiment 2

[0015] Synthesis of 2,2'-bipyridine-4,4'-dicarboxylic acid

[0016] Add 3.7g (0.02mol) of analytically pure 4,4'-dimethyl-2,2'-bipyridine to a four-necked flask equipped with a thermometer, a magnet and a reflux condenser, dissolve it in 40mL of water and 4mL In the mixed system of nitric acid, heat to 80°C under stirring, and add potassium permanganate solid (total 12.6g, 0.08mol) five times while maintaining this temperature. Then add the next batch of potassium permanganate, and stop heating after reacting for 6 hours. After cooling to room temperature, the reaction solution was suction-filtered under reduced pressure. After the insoluble matter was filtered off, concentrated hydrochloric acid was added to the filtrate to adjust the pH value to 1. Static crystallization, white crystals precipitated. After the crystallization is complete, suction filtration under reduced pressure is performed, and the obtained white crystals are washed with deionized water. Finally, the p...

Embodiment 3

[0018] Synthesis of 2,2'-bipyridine-4,4'-dicarboxylic acid

[0019] Add 3.7g (0.02mol) of analytically pure 4,4'-dimethyl-2,2'-bipyridine to a four-necked flask equipped with a thermometer, a magnet and a reflux condenser, dissolve it in 40mL of water and 4mL In the mixed system of nitric acid, heat to 80°C under stirring, and add potassium permanganate solid (a total of 25.28g, 0.16mol) five times while maintaining this temperature. Then add the next batch of potassium permanganate, and stop heating after reacting for 6 hours. After cooling to room temperature, the reaction solution was suction-filtered under reduced pressure. After the insoluble matter was filtered off, concentrated hydrochloric acid was added to the filtrate to adjust the pH value to 1. Static crystallization, white crystals precipitated. After the crystallization is complete, suction filtration under reduced pressure is performed, and the obtained white crystals are washed with deionized water. Finally,...

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Abstract

The invention discloses a preparation method of 2'-bipyridine-4,4'-dicarboxylic acid, belonging to the technical field of synthesis of sensitization fuel and medicinal intermediates. The point of the technical scheme adopted in the invention is as follows: 4,4'-dimethyl-2,2'-bipyridine is dissolved in a mixed system of water and nitric acid, and the 2'-bipyridine-4,4'-dicarboxylic acid is prepared through the oxidation of potassium permanganate. The method disclosed by the invention is easy to operate, the reaction conditions are mild, the reaction time is relatively short, and the yield of the obtained product is relatively high; and moreover, the after-treatment of the reaction is simple, the product is easily crystallized and separated from the system and is convenient to separate to obtain the target compound, and the method is suitable for large-scale production.

Description

technical field [0001] The invention belongs to the technical field of synthesis of sensitized fuels and pharmaceutical intermediates, and in particular relates to a preparation method of 2,2'-bipyridine-4,4'-dicarboxylic acid. Background technique [0002] Bipyridyl derivatives are important raw materials for the synthesis of functional materials, and can form complexes with conjugated electron systems with various metals. These complexes have good photoelectric conversion effects. As energy conversion materials-dye sensitizers, they have played an important role in dye-sensitized solar cells. Among them, 2,2'-bipyridine is an important kind of bipyridine compounds. As an important chemical synthesis intermediate, it can form complexes with various metal ions, and can be widely used to detect the existence and content of trace metal ions Wait. It can also form important noble metal complex ligands for the preparation of photoelectron transfer complexes for the preparation...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/807C07D213/79
CPCC07D213/79C07D213/807
Inventor 过治军张玮玮郭利兵李玉江许霞
Owner HENAN NORMAL UNIV