Covalent organic framework material, preparation method therefor and application of covalent organic framework material in synthesis of hindered amines

A covalent organic framework and organic solvent technology, applied in the field of synthesis and preparation of covalent organic framework materials, can solve problems such as low yield, decreased yield, and heavy metal pollution

Active Publication Date: 2019-01-29
天罡新材料(廊坊)股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In prior art CN103508938A, CN104974075A and WO2017/024608, N,N'-bis(2,2,6,6-tetramethyl-4-piperidinyl)-1,3- Phthalamide, but because the acid chloride is easily hydrolyzed, an acid-binding agent needs to be used, resulting in extremely cumbersome treatment processes such as subsequent purification and a large amount of waste water; in the prior art CN106905225A, although the isophthalic acid diester is used as a raw material to synthesize N, N'-bis(2,2,6,6-tetramethyl-4-piper

Method used

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  • Covalent organic framework material, preparation method therefor and application of covalent organic framework material in synthesis of hindered amines
  • Covalent organic framework material, preparation method therefor and application of covalent organic framework material in synthesis of hindered amines
  • Covalent organic framework material, preparation method therefor and application of covalent organic framework material in synthesis of hindered amines

Examples

Experimental program
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preparation example 1

[0043] Preparation Example 1: Preparation of Catalyst C1

[0044] P1: Mix 2,5-pyridinedimethanol and selenium dioxide in the 1,4-dioxane solution at a molar ratio of 1.2:1, and react vigorously under reflux at 100°C. The reaction time is 7 hours. After completion, it was filtered and concentrated to obtain a solid, and the obtained solid was separated by column chromatography (developing solvent: dichloromethane: ethyl acetate = 2:1) to obtain a light pink solid, namely 2,5-diformylpyridine.

[0045] P2: The mass ratio of p-aminobenzonitrile and trifluoromethanesulfonic acid is 0.15:1, fully stirred and reacted at room temperature under nitrogen protection for 24 hours, then add appropriate amount of distilled water and adjust it to pH = 7 with 2M sodium hydroxide solution , filtered, washed several times with distilled water and dried to obtain a light yellow solid that is 2,4,6-tris(4-aminophenyl)-1,3,5-triazine.

[0046] P3: Mix the synthesized 2,5-diformylpyridine and 2,4...

preparation example 2

[0048] Preparation Example 2: Preparation of Catalyst C2

[0049] P1: Mix 2,5-pyridinedimethanol and selenium dioxide in a 1,4-dioxane solution at a molar ratio of 0.8:1, and react vigorously under reflux at 100°C. The reaction time is 4 hours. After completion, it was filtered and concentrated to obtain a solid, and the obtained solid was separated by column chromatography (developing solvent: dichloromethane: ethyl acetate = 2:1) to obtain a light pink solid, namely 2,5-diformylpyridine.

[0050] P2: The mass ratio of p-aminobenzonitrile and trifluoromethanesulfonic acid is 0.15:1, fully stirred and reacted at room temperature under nitrogen protection for 24 hours, then add appropriate amount of distilled water and adjust it to pH = 7 with 2M sodium hydroxide solution , filtered, washed several times with distilled water and dried to obtain a light yellow solid that is 2,4,6-tris(4-aminophenyl)-1,3,5-triazine.

[0051] P3: The synthesized 2,5-diformylpyridine and 2,4,6-tri...

preparation example 3

[0053] Preparation Example 3: Preparation of Catalyst C3

[0054] P1: Mix 2,5-pyridinedimethanol and selenium dioxide in a 1,4-dioxane solution at a molar ratio of 1:1, and react vigorously under reflux at 100°C. The reaction time is 6 hours. After completion, it was filtered and concentrated to obtain a solid, and the obtained solid was separated by column chromatography (developing solvent: dichloromethane: ethyl acetate = 2:1) to obtain a light pink solid, namely 2,5-diformylpyridine.

[0055] P2: The mass ratio of p-aminobenzonitrile and trifluoromethanesulfonic acid is 0.15:1, fully stirred and reacted at room temperature under nitrogen protection for 24 hours, then add appropriate amount of distilled water and adjust it to pH = 7 with 2M sodium hydroxide solution , filtered, washed several times with distilled water and dried to obtain a light yellow solid that is 2,4,6-tris(4-aminophenyl)-1,3,5-triazine.

[0056] P3: Mix the synthesized 2,5-diformylpyridine and 2,4,6-t...

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Abstract

The invention relates to a covalent organic framework material, a preparation method therefor and a method for synthesizing N,N'-di(2,2,6,6-tetramethyl-4-piperidyl)-1,3-benzenediformamide by using thecovalent organic framework (COFs) catalyst. The method comprises the specific steps: subjecting dimethyl isophthalate and 2,2,6,6-tetramethyl-4-aminopiperidine to a heterogeneous catalytic reaction with stirring in an organic solvent by taking the covalent organic framework material (COFs) as a catalyst, and carrying out aftertreatment after the reaction ends up, thereby obtaining the product. The catalyst has sufficient alkaline loci and can be used for effectively catalyzing the reaction and remarkably increasing yield; and after the catalyst is used, treatment steps are simpler, the emission of salt-bearing wastewater is reduced, heavy-metal pollution is avoided, and the catalyst is environmentally friendly.

Description

technical field [0001] The present invention relates to the synthesis and preparation of a covalent organic framework material (COFs), and the catalytic synthesis of N,N'-bis(2,2,6,6-tetramethyl-4-piperidinyl)- A method for hindered amine light stabilizers such as 1,3-phthalamide belongs to the technical field of organic synthesis. Background technique [0002] With the development of the world's plastics industry, especially the increase in the application range and output of outdoor plastic products, light stabilizers have become one of the fastest growing categories of plastic additives. Among them, N,N'-bis(2,2,6,6-tetramethyl-4-piperidinyl)-1,3-benzenedicarboxamide is a new type of high-efficiency hindered amine light stabilizer, because It can capture free radicals, quench excited oxygen, and decompose hydroperoxides, thereby effectively inhibiting or slowing down the breakage of polymer chemical bonds, showing strong photostability; the effective group can be recycle...

Claims

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Application Information

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IPC IPC(8): C08G83/00C07D211/58B01J31/06
CPCB01J31/06C07D211/58C08G83/008
Inventor 李靖李玉庆
Owner 天罡新材料(廊坊)股份有限公司
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