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Metal organic framework based on imidazole sulfonic acid as well as preparation method and application

A metal organic framework, imidazole sulfonic acid technology, applied in organic chemistry, chemical instruments and methods, organic compound/hydride/coordination complex catalysts, etc., can solve problems such as poor catalytic effect, and achieve less catalyst dosage , The effect of obvious catalytic effect and mild reaction conditions

Inactive Publication Date: 2017-06-23
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the use of existing metal-organic framework materials as catalysts makes the catalytic effect poor because it only relies on metal sites as the catalytic centers of Lewis acids.

Method used

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  • Metal organic framework based on imidazole sulfonic acid as well as preparation method and application
  • Metal organic framework based on imidazole sulfonic acid as well as preparation method and application
  • Metal organic framework based on imidazole sulfonic acid as well as preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0101] Embodiment 1: the preparation of organic ligand L

[0102] (1) 2-Methyl-terephthalic acid (0.9g, 5mmol) was mixed with methanol (50mL), reacted under the catalysis of concentrated sulfuric acid (5mL), and refluxed for 12 hours. Cooling, suction filtration to obtain the crude product is a white solid, which is intermediate A, and the productive rate is 95.0%. 1 H-NMR spectrum see figure 1 .

[0103](2) In a 100mL round bottom flask, add 2-methyl-terephthalic acid dimethyl ester (1.04g, 5mmol), bromosuccinimide (1.335g, 7.5mmol), AIBN (0.246g, 1.5 mmol), and then added benzene (45 mL), heated to 80° C., and refluxed for 12 hours. After cooling, the solvent was evaporated under reduced pressure to obtain a crude product. Dissolve in dichloromethane, filter to obtain the filtrate, remove the solvent under reduced pressure, and separate by column chromatography (petroleum ether:dichloromethane=1:1) to obtain 1.45 g of light yellow semi-solid, which is intermediate B, wit...

Embodiment 2

[0106] Example 2: Reactivity of Ligands with Sulfonic Acid Compounds

[0107] Intermediate C (0.274g, 1mmol) obtained in Example 1 and propyl group sultone (0.112g, 1mmol) in equimolar amounts were refluxed in 30mL acetone for 5h, and the solvent was removed by rotary evaporation to obtain product D. 1 H-NMR spectrum see Figure 5 .

Embodiment 3

[0108] Example 3: Preparation of metal-organic frameworks based on imidazole ligands

[0109] ZrCl 4 (28.8 mg, 0.12 mmol) and glacial acetic acid (0.342 mL), dissolved in 4.8 mL of DMF by sonication (20 min). Then organic ligand L (29.52 mg, 0.12 mmol) was added into the autoclave, and the solution was sonicated for 10-30 min. Then the mixture was heated to 120°C for 24-48h. Cool to room temperature, then centrifuge to obtain a white crystalline powder, wash with fresh DMF (~10-20ml×3), organic solvent (~10-20ml×3), centrifuge, and then in 40~80℃ Vacuum drying to obtain powder metal organic framework crystalline material, SEM photo see Figure 6 , see the PXRD spectrum Figure 7 , the crystals after digestion 1 H-NMR spectrum see Figure 8 .

[0110] Wherein, "~10-20 ml×3" means about 10-20 ml was washed 3 times.

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Abstract

The invention provides a metal organic framework based on imidazole sulfonic acid as well as a preparation method and application. The metal organic framework based on the imidazole sulfonic acid is obtained by synthesizing and modifying a metal organic framework based on an imidazole ligand through a sulfonic compound; a chemical structural formula of the metal organic framework based on the imidazole ligand is [Zr6O4(OH)4L6]n, wherein n is a natural number more than 0; L is an organic ligand L and a chemical structural formula of the organic ligand L is show in the description; a synthesis method of the organic ligand L comprises the following steps: firstly, enabling 3-methyl-terephthalic acid to react to obtain an intermediate A; secondly, taking the intermediate A and bromosuccinimide as raw materials and reacting to obtain an intermediate B; thirdly, taking the intermediate B and imidazole as raw materials and reacting to obtain an intermediate C; finally, carrying out hydrolysis reaction on the intermediate C to prepare the organic ligand L. The metal organic framework based on the imidazole sulfonic acid has a catalytic effect on benzaldehyde under normal pressure and has the characteristics of moderate reaction conditions, short reaction time, less dosage of a catalyst and capability of being recycled and repeatedly utilized.

Description

technical field [0001] The invention belongs to the technical field of nanomaterial preparation, and in particular relates to a metal-organic framework based on imidazole sulfonic acid, its preparation method and application. Background technique [0002] Metal-organic frameworks (MOFs) materials are hybrid materials with a repeating network structure formed by self-assembly of organic ligands and metal ions, and have developed rapidly in the field of coordination chemistry in recent decades. of new materials. Compared with traditional inorganic porous materials, MOFs materials have larger porosity and specific surface area, especially adjustable pore size and variable functional groups, so MOFs materials are used as porous functional materials in gas separation and storage. application shows great advantages. At present, MOFs materials have been applied in hydrogen storage, drug delivery, catalytic reaction, biosensor, gas adsorption and separation, etc. The research on ...

Claims

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Application Information

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IPC IPC(8): C08G83/00B01J31/22C07D317/12
CPCB01J31/1691C07D317/12C08G83/008
Inventor 姚丙建丁罗刚范琪毕延雪刘慧马坤玉
Owner SHANDONG NORMAL UNIV
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