Covalent organic framework material BM-SO3H with acid-base dual functions as well as preparation method and application of covalent organic framework material BM-SO3H

A covalent organic framework, acid-base dual function technology, applied in the preparation of organic compounds, the preparation of carboxylic acid nitrile, organic compounds/hydrides/coordination complex catalysts, etc., to achieve mild catalytic conditions, good thermal stability, low cost effect

Active Publication Date: 2022-04-22
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, most current methods for synthesizing COFs use solvothermal methods, which require high temperature and mixed solvent systems.

Method used

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  • Covalent organic framework material BM-SO3H with acid-base dual functions as well as preparation method and application of covalent organic framework material BM-SO3H
  • Covalent organic framework material BM-SO3H with acid-base dual functions as well as preparation method and application of covalent organic framework material BM-SO3H
  • Covalent organic framework material BM-SO3H with acid-base dual functions as well as preparation method and application of covalent organic framework material BM-SO3H

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] A covalent organic framework material BM-SO with dual functions of acid and base 3 H has a structure as shown in formula (I):

[0034]

[0035] A covalent organic framework material BM-SO with dual functions of acid and base 3 The preparation method of H, concrete steps are as follows:

[0036] (1) Synthesis of 1,3,5-tris(p-formylphenyl)benzene (TFPB)

[0037] Into a 100 mL round bottom flask was added 251 mg of 1,3,5-tribromobenzene, 553 mg of 4-formylphenylboronic acid, 530 mg of potassium carbonate and 10 mg of Pd (pph 3 ) 2 Cl 2 , and then added 40 mL of ethanol, and refluxed at 80° C. for 8 h. After the reaction finishes, remove salt of wormwood and catalyst Pd (pph 3 ) 2 Cl 2 , the filtrate was collected and concentrated, and the trisubstituted product 1,3,5-tri(p-formylphenyl)benzene was obtained as a white solid by column chromatography.

[0038]

[0039] (2) Synthesis of benzimidazole-based covalent organic framework material BM

[0040] Add 100...

Embodiment 2

[0050] The BM-SO that embodiment 1 makes 3 As a heterogeneous catalyst, H participates in the series decarboxylation Knoevenagel condensation reaction, as shown in formula (II), and the specific steps are as follows:

[0051]

[0052] (1) Add respectively benzaldehyde dimethyl acetal (0.152g, 1mmol), malononitrile (0.07g, 1.05mmol), 1mol% BM-SO4 to the reaction flask 3 H (0.005g) and water (5mL) were stirred at 60°C for 5h. After the reaction, separate and reclaim the filter cake by filtration (i.e. catalyst BM-SO 3 H), the filtrate was first extracted with ethyl acetate to obtain an organic layer, and then the product was purified by silica gel column chromatography, the eluent was ethyl acetate and petroleum ether, and the product yield was calculated.

[0053] (2) Catalyst BM-SO recovered in the reaction 3 H was washed with ethanol, centrifuged, vacuum-dried, and then subjected to the next cycle of catalysis under the same conditions. The catalysis reaction was cycled...

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Abstract

The invention discloses a covalent organic framework material BM-SO3H with acid-base dual functions as well as a preparation method and application thereof, the material has a structure as shown in a formula (I), and the preparation method comprises the following steps: firstly, synthesizing a benzimidazolyl covalent organic framework material BM under the catalysis condition of a photocatalyst; then, the BM and 1, 3-propane sultone are subjected to a ring-opening N atom alkylation reaction, and the covalent organic framework material BM-SO3H is obtained. The material has benzimidazole and propane sulfonic acid structures, so that the material has acid-base dual functions. BM-SO3H is used as a heterogeneous catalyst to catalyze a tandem decarboxylaldehyde Knoevenagel condensation reaction, and the yield can reach 95%-99%. The heterogeneous catalyst BM-SO3H shows excellent catalytic performance, thermal stability and recycling performance, and has a good application prospect.

Description

technical field [0001] The invention belongs to the technical field of chemistry and chemical engineering, and in particular relates to a covalent organic framework material BM-SO with dual functions of acid and base 3 H and its preparation method and application. Background technique [0002] Many homogeneous catalysts have been used for cascade reactions that require coordinated catalysis by acid-base functional groups. However, the homogeneous catalytic system is cumbersome in product separation and the catalyst is difficult to reuse, which causes the problem of increased cost. In addition, the activity of bifunctional acid-base catalysts is easily deactivated in a homogeneous reaction medium due to acid-base neutralization. Therefore, for one-pot cascade reactions, solid heterogeneous bifunctional acid-base catalysts, in which acidic and basic functional groups are immobilized at different positions in the solid matrix, have received increasing attention. To date, aci...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G83/00B01J31/06C07C253/30C07C255/34
CPCC08G83/008B01J31/06C07C253/30B01J2231/4205C07C255/34
Inventor 巩凯张慧敏李浩然冯荟如董营刘艳勤
Owner JIANGNAN UNIV
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