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Porphyrin-based porous organic polymer, preparation method thereof, and preparation method and application of supported palladium catalyst of porphyrin-based porous organic polymer

A palladium catalyst and polymer technology, applied in the field of porphyrin-based porous organic polymers, can solve problems such as the need for additional reducing agents, harsh reaction conditions, and complicated preparation processes, and achieve high catalytic activity and selectivity, and mild reaction conditions , the effect of simple preparation method

Active Publication Date: 2022-04-19
SINO PLATINUM METALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The homogeneous palladium catalyst system has the advantages of good dispersibility, high catalytic activity, and good chemoselectivity, but it also has the disadvantages of expensive catalysts, harsh reaction conditions, and complex separation operations due to the reaction between the homogeneous catalyst and the reaction system in the same phase. The catalyst is difficult to recycle and reuse, and the residual palladium will cause certain pollution to the product, and the catalyst has disadvantages such as poor stability at high temperature, which restricts its large-scale use
Although heterogeneous catalysts avoid some disadvantages of homogeneous catalysts and have the advantages of easy separation, high temperature resistance, and long life, heterogeneous catalysts based on porous materials (microporous zeolite, mesoporous carbon, activated carbon, etc.) There are also problems such as metal nanoparticles are easy to agglomerate or fall off, the preparation process is complicated, or additional reducing agents are required.

Method used

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  • Porphyrin-based porous organic polymer, preparation method thereof, and preparation method and application of supported palladium catalyst of porphyrin-based porous organic polymer
  • Porphyrin-based porous organic polymer, preparation method thereof, and preparation method and application of supported palladium catalyst of porphyrin-based porous organic polymer
  • Porphyrin-based porous organic polymer, preparation method thereof, and preparation method and application of supported palladium catalyst of porphyrin-based porous organic polymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Pd-PMPOP(H 2 PdCl 4 ) (using chloropalladium acid as the palladium source, the theoretical loading of palladium is 10wt%): take by weighing the porphyrin-based porous polymer PMPOP (48mg), add 20ml of deionized water, and ultrasonically disperse for 1h; then slowly drip 5mM chloropalladium Acid solution; filter after continuous stirring for 72 hours, and wash three times with deionized water and ethanol, and obtain the catalyst after drying. After testing, the actual content of palladium in the catalyst was 9.414 wt %.

[0061] Pd-PMPOP(PdCl 2 ) (using palladium dichloride as palladium source, the theoretical loading of palladium is 10wt%): Weigh PMPOP (54mg) and palladium dichloride (10mg) and add ethanol 10mL, namely m (carrier): m (palladium)= 9:1, ultrasonic for 3 hours, then centrifuged, alternately washed three times with deionized water and 50% ethanol, and dried to obtain the catalyst. After testing, the actual content of palladium in the catalyst is 9.365wt...

Embodiment 2

[0064] Pd-PUPOP(H 2 PdCl 4 ) (with chloropalladium acid as palladium source, the theoretical loading of palladium is 10wt%): take by weighing porous polymer PUPOP (48mg), add 20ml of deionized water, ultrasonically disperse 1h; then slowly drip the chloropalladium acid solution of 5mM; After continuous stirring for 72 hours, the mixture was filtered, washed three times with deionized water and ethanol, and dried to obtain the catalyst. After testing, the actual content of palladium in the catalyst was 9.342 wt %.

[0065] Pd-PUPOP(PdCl 2 ) (using palladium dichloride as palladium source, the theoretical loading of palladium is 10wt%): Weigh PUPOP (54mg) and palladium dichloride (10mg) and add ethanol 10mL, namely m (carrier): m (palladium)= 9:1, ultrasonic for 3 hours, then centrifuged, alternately washed three times with deionized water and 50% ethanol, and dried to obtain the catalyst. After testing, the actual content of palladium in the catalyst was 9.935wt%.

[0066]...

Embodiment 3

[0068] Pd-PAPOP(H 2 PdCl 4 ) (with chloropalladium acid as palladium source, the theoretical loading of palladium is 10wt%): take porous polymer PAPOP (48mg), add 20ml of deionized water, ultrasonically disperse for 1h; then slowly drip the 5mM chloropalladium acid solution; After continuous stirring for 72 hours, the mixture was filtered, washed three times with deionized water and ethanol, and dried to obtain the catalyst. After testing, the actual content of palladium in the catalyst was 7.995wt%.

[0069] Pd-PAPOP(PdCl 2 ) (using palladium dichloride as the palladium source, the theoretical loading of palladium is 10wt%): Weigh PAPOP (54mg) and palladium dichloride (10mg) and add 10mL of ethanol, namely m (carrier): m (palladium)= 9:1, ultrasonic for 3 hours, then centrifuged, alternately washed three times with deionized water and 50% ethanol, and dried to obtain the catalyst. After testing, the actual content of palladium in the catalyst was 9.666 wt %.

[0070] Amo...

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Abstract

The invention discloses a porphyrin-based porous organic polymer, a preparation method of the porphyrin-based porous organic polymer and a preparation method and application of a palladium-loaded catalyst of the porphyrin-based porous organic polymer. The polymer contains rich micropores or mesopores, has a large specific surface area and also has high physical and chemical stability. The invention also provides a catalyst prepared by taking the porphyrin-based porous organic polymer as a carrier to load palladium ions or palladium nanoparticles. The invention also provides application of the catalyst. The catalyst is used for catalyzing cross coupling of boric acid derivatives and aromatic halides to generate coupling products and catalyzing nitro reduction of aromatic nitro compounds. The catalyst has the advantages of high catalytic activity, easiness in recovery, reusability and the like. The porphyrin-based porous organic polymer provided by the invention has a repetitive structural unit shown as a formula 1 or a formula 2,

Description

technical field [0001] The invention relates to a series of porphyrin-based porous organic polymers, a preparation method and a preparation method of a supported palladium catalyst, and the use of the catalyst in Suzuki-Miyaura cross-coupling reaction and p-nitrophenol hydrogenation reduction reaction. Background technique [0002] Porous organic polymers (POPs) have abundant micropores (<2nm) or mesopores (between 2nm and 50nm) in their structure, with large specific surface area and high physical, Chemical stability; in addition, it also has the characteristics of structural designability and functional modification, making it suitable for a variety of application scenarios. Among them, due to the open pores on the structure, the large specific surface area and the introduction of heteroatoms during the synthesis process, they can anchor metal ions and disperse nanoparticles, so they are often used as carrier synthesis catalysts. However, most POPs materials themselves...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/06B01J31/30B01J35/10C07C1/00C07C15/14C07C213/02C07C215/76
CPCC08G73/0611C08G73/0638C08G73/065C08G73/0633B01J31/30B01J35/1019B01J35/1023B01J35/1061C07C1/00C07C213/02C07C2531/30B01J2231/4211B01J2231/641C07C15/14C07C215/76Y02P20/584
Inventor 何建云蒋云波李鸿鹏
Owner SINO PLATINUM METALS CO LTD
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