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Synthesis method of 2,2'-bipyridine-4,4'-dicarboxaldehyde

一种合成方法、联吡啶的技术，应用在有机化学等方向，能够解决限制研究和应用、反应周期长、价格昂贵等问题，达到收率高、成本低、反应步骤短的效果

Inactive Publication Date: 2013-04-10
HENAN BUSINESS SCI RES INST
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

2,2'-bipyridyl-4,4'-dicarbaldehyde is currently completely dependent on imports, and the price is very expensive, which seriously limits its research and application
Leopoldo Della Ciana et al. (Journal of Heterocyclic Chemistry, 1990, 27(2), 163-5) disclosed a synthesis method of 2,2'-bipyridyl-4,4'-dicarbaldehyde, which is 4,4' -Dimethyl-2,2'-bipyridine is used as a raw material, and the target product is obtained through oxidation, esterification, reduction and reoxidation. This method requires four steps of reaction to obtain, the reaction cycle is long, the energy consumption is large, and the cost is high

Method used

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  • Synthesis method of 2,2'-bipyridine-4,4'-dicarboxaldehyde

Examples

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Embodiment 1

[0022] A kind of synthetic method of 2,2'-bipyridine-4,4'-dicarbaldehyde, 2 g (10.86 mmol) 4,4'-dimethyl-2,2'-bipyridine and 80g mass concentration 70% Sulfuric acid was added to a 250 mL round-bottomed flask (slightly heated to facilitate the full dissolution of the two, such as heating to a temperature not higher than 80°C), then slowly added 3.2g (36.80mmol) manganese dioxide in batches, and the addition was completed , heated to 115 ° C for 8 hours. Cool naturally to room temperature after the reaction, then slowly pour the reaction product into a beaker filled with 250g of crushed ice and stir evenly to obtain a solid-liquid mixture a, (it is advisable that the ice cubes completely melt), and then cool in an ice-water bath in order First use 30% sodium hydroxide aqueous solution and then use 35% sodium carbonate aqueous solution to adjust a to neutral. Filtrate, extract the filtrate and filter cake with dichloromethane respectively, combine the extracts and evaporate and...

Embodiment 2

[0024] The amount of sulfuric acid with a mass concentration of 98% is 120g, the mass of manganese dioxide is 8.2g, and the temperature is raised to 135°C for 10h. Others refer to Example 1, and finally light yellow 2,2'-bipyridine-4,4' is obtained -Diformaldehyde powder 0.71g, yield 30.8%.

Embodiment 3

[0026] A kind of synthetic method of 2,2'-bipyridine-4,4'-dicarbaldehyde, 2 g (10.86 mmol) 4,4'-dimethyl-2,2'-bipyridine and 100g mass concentration 70% Sulfuric acid was added to a 250 mL round-bottomed flask (slightly heated to facilitate the full dissolution of the two, such as heating to a temperature not higher than 100°C), then slowly added 7.2g of manganese trioxide in batches, after the addition was complete, the temperature was raised to Reaction at 130°C for 10h. After the reaction, cool naturally to room temperature, then slowly pour the reaction product into a beaker filled with 320g of crushed ice and stir to obtain a solid-liquid mixture a, (it is advisable to completely melt the ice cubes), and then cool in an ice-water bath in order First use 40% sodium hydroxide aqueous solution and then use 35% sodium carbonate aqueous solution to adjust a to neutral. After filtration, the filtrate and filter cake were extracted with chloroform respectively, and the combined...

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Abstract

The invention relates to a synthesis method of 2,2'-bipyridine-4,4'-dicarboxaldehyde. The synthesis method comprises the following steps that 2,2'-bipyridine-4,4'-dicarboxaldehyde is dissolved in a sulfuric acid solution with mass concentration of 70 to 80%; a manganese oxide is added into the mixed solution obtained by the previous to undergo a reaction at a temperature of 100 to 145 DEG C for 7to 20 hours; after the reaction finishes, the reaction products are cooled to room temperature; the cooled reaction products are mixed with an ice-water mixture or ice cubes to form a solid-liquid mixture a; the solid-liquid mixture a is adjusted to a pH value of 7; and the adjusted solid-liquid mixture is subjected orderly to extraction and evaporation concentration to form a product of 2,2'-bipyridine-4,4'-dicarboxaldehyde, wherein a mass ratio of 2,2'-bipyridine-4,4'-dicarboxaldehyde to the manganese oxide to sulfuric acid is 1: (1.4 to 4.4): (30 to 70). The synthesis method has the advantages of simple reaction step, simple operation, high yield, low cost and low pollution. Therefore, the synthesis method has a good prospect of industrialized application.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a synthesis method of 2,2'-bipyridine-4,4'-dicarbaldehyde. Background technique [0002] 2,2'-bipyridyl-4,4'-dicarbaldehyde is an important chemical and pharmaceutical synthesis intermediate and ligand, molecular formula C 12 h 8 N 2 o 2 , with a molecular weight of 212, can form metallic complexes with conjugated electronic systems with various metals such as platinum, osmium, europium, terbium and ruthenium. These complexes can exhibit optical, electrical, thermal, magnetic functions and catalytic properties, so In particular, it shows important application value in photoelectric conversion. The ruthenium complexes of 2,2'-bipyridyl-4,4'-dicarbaldehyde are used in dye-sensitized solar cells and are an important class of photosensitizers. 2,2'-bipyridyl-4,4'-dicarbaldehyde is currently completely dependent on imports, and the price is very expensive, which seri...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/48
Inventor 王永张立攀郭良起翟凤英伍季王法云郭彦春
Owner HENAN BUSINESS SCI RES INST
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