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A kind of synthetic method of 2,2'-bipyridine-4,4'-diformyl chloride

A technology for the synthesis of diformyl chloride, which is applied in chemical instruments and methods, physical/chemical process catalysts, organic chemistry, etc., can solve the problems of large environmental pollution, strong corrosion, unsafe operation, etc., and achieve simple post-processing, Simple operation and cheap effect

Active Publication Date: 2019-05-14
HENAN BUSINESS SCI RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, 2,2'-bipyridine-4,4'-dicarboxylic acid needs to be synthesized with 4,4'-dimethyl-2,2'-bipyridine with strong oxidants such as dichromic acid, such as Chemical Communications (Cambridge, United Kingdom), 2016, 52(46), 7398-7401, these oxidants are highly corrosive, unsafe to operate, and cause serious environmental pollution

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] A kind of synthetic method of 2,2'-bipyridine-4,4'-diformyl chloride, comprising the following steps:

[0022] 1) Mix selenium oxide, catalyst, and solvent S1 and heat to 85°C to obtain liquid A; mix 2,2'-bipyridine with solvent S2 to obtain liquid B; mix dichloromethane with solvent S3 to obtain liquid C, and solvents S1 and S2 And S3 is DMF; Wherein the molar ratio of 2,2'-bipyridine, oxidizing agent, halogenated hydrocarbon is 1:2.1:2.05;

[0023] Described catalyst adopts following method to make:

[0024] Dissolve ruthenium chloride dihydrate in water, add γ-alumina, stir at 40°C for 2 days, vacuumize to remove moisture, dry at 100°C, grind and activate at 150°C for 10 hours; γ-alumina The mass ratio of ruthenium chloride dihydrate and water is 1:0.12:8;

[0025] 2) First take 10% of liquid C and add it to liquid A, maintain the system at 85°C, stir for 10 minutes, then add 30% of liquid B to the system, after stirring for 20 minutes, first add the remaining liqu...

Embodiment 2

[0029] A kind of synthetic method of 2,2'-bipyridine-4,4'-diformyl chloride, comprising the following steps:

[0030] 1) Mix selenium oxide, catalyst, and solvent S1 and heat to 100°C to obtain liquid A; mix 2,2'-bipyridine with solvent S2 to obtain liquid B; mix phosphorus pentachloride, chloroform and solvent S3 to obtain liquid C, Solvents S1, S2 and S3 are DMSO; wherein the molar ratio of 2,2'-bipyridyl, oxidizing agent and halogenated hydrocarbon is 1: 2.3: 2.1;

[0031] Described catalyst adopts following method to make:

[0032] Dissolve ruthenium chloride dihydrate in water, add γ-alumina, stir at 46°C for 3 days, vacuumize to remove moisture, dry at 100°C, grind and activate at 170°C for 13 hours to obtain the product; the γ- The mass ratio of aluminum oxide, ruthenium chloride dihydrate and water is 1:0.14:9;

[0033] 2) First take 20% of liquid C and add it to liquid A, maintain the system temperature at 100°C, stir for 20 minutes, then add 40% of liquid B to the ...

Embodiment 3

[0037] A kind of synthetic method of 2,2'-bipyridine-4,4'-diformyl chloride, comprising the following steps:

[0038] 1) Mix selenium oxide, catalyst, and solvent S1 and heat to 90°C to obtain liquid A; mix 2,2'-bipyridine with solvent S2 to obtain liquid B; mix phosphorus pentachloride, chloroform and solvent S3 to obtain liquid C, Solvents S1, S2 and S3 are DMSO; wherein the molar ratio of 2,2'-bipyridyl, oxidizing agent and halogenated hydrocarbon is 1:2.2:2.08;

[0039] Described catalyst adopts following method to make:

[0040] Dissolve ruthenium chloride dihydrate in water, add γ-alumina, stir at 50°C for 3 days, vacuumize to remove moisture, dry at 100°C, grind and activate at 180°C for 15 hours to obtain the product; the γ- The mass ratio of aluminum oxide, ruthenium chloride dihydrate and water is 1: 0.16: 10;

[0041] 2) Take 15% of liquid C and add it to liquid A, maintain the system temperature at 90°C, stir for 15 minutes, then add 35% of liquid B to the system...

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Abstract

The invention relates to a synthesis method of 2,2'-dipyridyl-4,4'-dicarbonyl chloride. The method comprises the following steps: (1) mixing an oxidizing agent, a catalyst and a solvent S1, and heating the mixture up to 85-100 DEG C to obtain liquid A; mixing 2,2'-dipyridyl with a solvent S2 to obtain liquid B; mixing halogenated hydrocarbon with a solvent S3 to obtain liquid C; (2) firstly, taking 10-20% of the liquid C, adding the taken liquid C into the liquid A, maintaining the temperature of a system to be 85-100 DEG C, stirring for 10-20min, then adding 30-40% of the liquid B into the system, and stirring for 20-25min; then, firstly adding the rest liquid C, then adding 30-40% of the liquid B, continuously stirring for 15-20min, and then adding the rest liquid B; (3) maintaining the temperature of the system to be 90-100 DEG C, carrying out a reaction for 2-3h, then heating the system up to 140-150 DEG C, and continuously reacting for 8-13h; (4) carrying out aftertreatment to obtain the product. The synthesis method is low in price of raw materials and easy in raw material obtaining, thus being low in production cost; the synthesis method is short in steps, simple to operate, high in yield and less in pollution.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of 2,2'-bipyridine-4,4'-diformyl chloride. Background technique [0002] 2,2'-bipyridine-4,4'-diformyl chloride is an important raw material for dyes, medicines and pesticides, and also an important intermediate, especially as a dye sensitizer in dye-sensitized solar cells use. Because its molecules have strong electron-donating coordination ability, they can be used as ligands of metal-organic compounds to form metal complexes with a series of transition metal ions. These complexes have special optical, electrical and catalytic properties. [0003] In the prior art, the synthesis of 2,2'-bipyridyl-4,4'-dicarboxylic acid chloride is mainly synthesized by chlorination of 2,2'-bipyridine-4,4'-dicarboxylic acid. Such as Molecular Crystals and Liquid Crystals, 607(1), 250-263; 2015, Inorganic Chemistry, 47(15), 6974-6983; 2008 and Advanced S...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/78B01J27/13
CPCB01J27/13C07D213/78
Inventor 王永张立攀王法云刘红伟周莉张亚勋智军丽任钊郭青照
Owner HENAN BUSINESS SCI RES INST