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Three-phase catalyst Pd@COF-QA as well as preparation method and application thereof

A technology of catalysts and synthesis methods, applied in catalytic reactions, organic chemistry methods, chemical instruments and methods, etc., can solve the problem of unclear connection position and degree of connection between catalytic functional groups and carriers, uncertain polymer carrier structure, difficult Accurately analyze catalysts and other issues to achieve the effects of easy recovery, reduced energy consumption, and improved utilization

Active Publication Date: 2019-07-09
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Nevertheless, the inventors found that the current three-phase phase transfer catalyst still has the following problems: (1) the catalytic site is a functional group with catalytic performance, and the polymer carrier almost only plays a supporting role, resulting in waste of materials; (2) The structure of the polymer carrier is often uncertain, making the position and degree of connection between the catalytic functional group and the carrier unclear, making it difficult to accurately analyze the composition of the catalyst; (3) Whether it is a polymer carrier or an inorganic carrier, the modifiability Relatively low, making it less likely that the three-phase phase transfer catalyst will combine other functions

Method used

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  • Three-phase catalyst Pd@COF-QA as well as preparation method and application thereof
  • Three-phase catalyst Pd@COF-QA as well as preparation method and application thereof
  • Three-phase catalyst Pd@COF-QA as well as preparation method and application thereof

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preparation example Construction

[0040] In yet another specific embodiment of the present invention, a synthesis method of the organic ligand L is provided, comprising the following steps:

[0041] (1) With 2,5-dibromotoluene and 4-methoxycarbonylphenylboronic acid as raw materials, cesium fluoride as base, tetrakis(triphenylphosphine palladium) as catalyst, in 1,4-dioxane solution, heated to 85-95° C. (preferably 90° C.) for reaction, silica gel column chromatography to separate the product, and decompression to remove the solvent to obtain intermediate product A. The structure of intermediate A is as follows:

[0042]

[0043] (2) intermediate A is reacted with N-bromosuccinimide (NBS) and azobisisobutyronitrile (AIBN), carbon tetrachloride is used as a solvent, and the product is separated by silica gel column chromatography to obtain intermediate B; The structural formula of the intermediate B is as follows:

[0044]

[0045] (3) Intermediate B is reacted with N,N-dimethyldodecylamine, acetonitrile...

Embodiment 1

[0070] Embodiment 1: the preparation of organic ligand L

[0071] Concrete preparation steps are as follows:

[0072] (1) Under nitrogen protection, 4.33g (24mmol) 4-methoxycarbonylphenylboronic acid, 6g (40mmol) cesium fluoride were placed in a 250ml three-necked flask, and 150ml 1,4-dioxane and 2.754ml (10mmol) were added ) mixed solution of 2,5-dibromotoluene, and then add 1.6g of tetrakis(triphenylphosphine)palladium catalyst, and reflux at 90°C for 48h. After the reaction, an orange solution with black precipitate was obtained. The system was evaporated to dryness under reduced pressure, and after drying in the air, silica gel column chromatography (petroleum ether and dichloromethane) gave 3.0 g of a white product with a yield of 82%.

[0073]

[0074] (2) Under the protection of nitrogen, 2.5g (6.937mmol) of intermediate A, 0.114g (0.693mmol) of azobisisobutyronitrile, and 1.48g (8.324mmol) of N-bromosuccinimide were placed in a 100ml three-necked flask , Add 45ml...

Embodiment 2

[0081] Example 2: Synthesis of Pd@COF-QA

[0082]

[0083] (1) 29.40mg (0.045mmoL) of ligand L and 4.86mg (0.03mmoL) of trimesin tricarbaldehyde are placed in a pressure-resistant tube, add mesitylene: dioxane: acetic acid (6M) = 16:4 : 3 (volume ratio) mixed solvent 2mL in total, degassed under liquid nitrogen bath, then warmed up to room temperature, kept at 120 ℃ for 3 days (72h). Cool to room temperature, centrifuge, take out the precipitate, and vacuum-dry to obtain 0.039g. Yield: 47.3%.

[0084] (2) In a 25ml round-bottomed flask, first add palladium acetate (6mg), dissolve it in 5mL of dichloromethane, then add 20mg of COF-QA and stir at room temperature for 24 hours, after the reaction is completed, centrifuge, wash 3 times with dichloromethane, and then Washed with acetone three times, dried at 80°C for 3 h to obtain Pd@COF-QA.

[0085] The polymer was characterized by IR and PXRD, the results are shown in Image 6 , 7 .

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Abstract

The invention provides a three-phase catalyst Pd@covalent organic framework (COF)-QA as well as a preparation method thereof and an application of the catalyst in catalysis of a Suzuki-Miyaura reaction, and belongs to the technical field of catalyst preparation. The three-phase catalyst Pd@COF-QA provided by the invention is obtained by reacting covalent organic framework (COF)-QA with palladium acetate at room temperature, the preparation method is simple and convenient, through experimental verification, the three-phase catalyst has a high utilization rate, the reaction conditions are mild,the catalytic costs can be effectively reduced, high temperature and an organic solvent are not needed, the usage amount of the catalyst is less, and heterogeneous catalysis can be realized without other additives; and at the same time, the catalyst can be reused and easy to recover, the utilization rate of the catalyst is improved, the costs are reduced, and industrialized promotion application is facilitated.

Description

technical field [0001] The invention belongs to the technical field of catalyst preparation, in particular to a three-phase catalyst Pd@COF-QA and its preparation method and application. Background technique [0002] The information disclosed in this background section is only intended to increase the understanding of the general background of the present invention, and is not necessarily taken as an acknowledgment or any form of suggestion that the information constitutes the prior art already known to those skilled in the art. [0003] Covalent Organic Framework (COF) is a research hotspot in recent years. Compared with traditional porous materials, COFs materials not only have uniformly distributed pores of a specific size inside, but also have a strong resistance to acid and alkali environments. The stability is much higher than other porous materials. Therefore, COFs have great advantages as crystalline porous materials for catalytic applications. [0004] After 50 ye...

Claims

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Application Information

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IPC IPC(8): C07C243/38C07C241/04B01J31/22C07B37/00C07C1/32C07C15/14C07C201/12C07C205/06C07C209/68C07C211/45C07C253/30C07C255/50
CPCC07C243/38B01J31/1691B01J31/1815C07B37/00C07C1/321C07C201/12C07C209/68C07C253/30B01J2231/4227B01J2531/824C07C15/14C07C205/06C07C211/45C07C255/50
Inventor 董育斌王建成刘从学
Owner SHANDONG NORMAL UNIV
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