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Organic porous polymer palladium-supported catalyst and preparation and application methods thereof

A technology of porous polymer and palladium catalyst is applied in the preparation of organic compounds, organic compound/hydride/coordination complex catalysts, physical/chemical process catalysts, etc. Industrial applications, catalysts are not easy to separate, etc., to achieve good application prospects and economic value, good recycling performance, and small loss of palladium.

Inactive Publication Date: 2019-05-14
LIUPANSHUI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are problems in the homogeneous palladium catalytic system that the catalyst is not easy to separate, the palladium is easy to remain in the product, and the catalyst is not easy to be reused, which largely limits the large-scale industrial application of this type of reaction.

Method used

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  • Organic porous polymer palladium-supported catalyst and preparation and application methods thereof
  • Organic porous polymer palladium-supported catalyst and preparation and application methods thereof
  • Organic porous polymer palladium-supported catalyst and preparation and application methods thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Embodiment 1: Preparation of organic porous polymer supported palladium catalyst (Pd@POP-1)

[0051] 4,5-bisdiphenylphosphine-9,9-dimethylxanthene palladium dichloride (0.005mol), triphenylbenzene (0.005mol), dimethylformal (0.04mol) and 20ml The 1,2-dichloroethane solution was mixed evenly, and then the anhydrous FeCl 3 (0.04mol) was added to the above solution and stirred evenly to obtain a reaction solution. in N 2 Under protection, the reaction solution was heated up to 45°C, stirred at 45°C for 3 hours for pre-polymerization, then heated to 80°C, stirred for 24 hours at 80°C for polymerization. After the reaction, the obtained mixture was filtered, and the obtained precipitate was washed 6 times with anhydrous methanol, and then vacuum-dried at 60° C. for 12 hours to obtain 5.91 g of organic porous polymer-supported palladium catalyst, which was named Pd@POP-1.

[0052] Pd@POP-1 was analyzed by X-ray photoelectron spectrometer, and the spectrum is as follows fi...

Embodiment 2

[0057] Embodiment 2: Preparation of organic porous polymer supported palladium catalyst (Pd@POP-2)

[0058] This example is operated according to the preparation method of Example 1, the only difference is that the raw material 4,5-bisdiphenylphosphine-9,9-dimethylxanthene palladium dichloride is 0.003mol, triphenyl The base benzene is 0.007mol, and the other operations are exactly the same as in Example 1, and finally 5.05g of Pd@POP-2 is obtained.

[0059] As in Example 1, the prepared Pd@POP-2 was subjected to the following characterization analysis:

[0060] The Pd@POP-2 was analyzed by X-ray photoelectron spectroscopy, and the results showed that the prepared C, P, Pd, O, Cl existed, and palladium had divalent palladium (Pd 2+ ) and zero price (Pd 0 ) 2 valence states.

[0061] Using cross-polarized magic-angle spinning solid-state NMR- 13 C Spectrum ( 13 C-CP / MAS) performed characterization analysis on Pd@POP-2, the characteristic peak of substituted benzene ring ca...

Embodiment 3

[0065] Embodiment 3: Preparation of organic porous polymer supported palladium catalyst (Pd@POP-3)

[0066] This example is operated according to the preparation method of Example 1, the only difference is that the solvent used is chloroform (20ml), other operations are exactly the same as Example 1, and finally 5.86g of Pd@POP-3 is obtained.

[0067] As in Example 1, the prepared Pd@POP-3 was subjected to the following characterization analysis:

[0068] The Pd@POP-3 was analyzed by X-ray photoelectron spectroscopy, and the results showed that the prepared C, P, Pd, O, Cl existed, and palladium had divalent palladium (Pd 2+ ) and zero price (Pd 0 ) 2 valence states.

[0069] Using cross-polarized magic-angle spinning solid-state NMR- 13 C Spectrum ( 13 C-CP / MAS) performed characterization analysis on Pd@POP-3, the characteristic peak of substituted benzene ring carbon appeared at 136ppm, the characteristic peak of unsubstituted benzene ring carbon appeared at 128ppm, and ...

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Abstract

The invention relates to the technical field of preparation of catalysts, particularly to an organic porous polymer palladium-supported catalyst and preparation and application methods thereof. The organic porous polymer palladium-supported catalyst containing dichloro[9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene]palladium functional units is prepared by taking dichloro[9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene]palladium and 1, 3, 5-triphenylbenzene as copolymerizing monomers and through a one-step outer crosslinking method. The organic porous polymer palladium-supported catalyst canachieve efficient catalytic carbonylation of brominated aromatic hydrocarbons to synthesize aromatic carbonyl compounds, and meanwhile, is large in specific surface area, wide in pore size distribution range, mild in reaction conditions, high in yield and good in recycling performance, thereby achieving high application potential.

Description

technical field [0001] The invention relates to the technical field of catalyst preparation, in particular to an organic porous polymer supported palladium catalyst and its preparation method and application. Background technique [0002] The carbonylation reaction of halogenated aromatic hydrocarbons is an important class of reactions for the preparation of aromatic carboxylic acid derivatives such as aromatic esters, aromatic amides, aromatic ketones, and aromatic aldehydes. Due to the characteristics of easy availability of raw materials, mild reaction conditions, and wide adaptability to various functional groups, this type of reaction is widely used in the synthesis of medicines, pesticides, food additives, and organic intermediates. [0003] The substrates for the carbonylation reaction of halogenated arenes mainly include iodoarenes, brominated arenes and chlorinated arenes. Usually, iodoarenes have the highest activity and chlorinated arenes have the lowest activity....

Claims

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Application Information

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IPC IPC(8): B01J31/24B01J31/16C07C67/36C07C69/78C07C201/12C07C205/57C07C231/10C07C233/65C07C235/46C07B43/06C07B41/12
Inventor 雷以柱万亚荔李志陈定梅王毅红王仁舒冯静
Owner LIUPANSHUI NORMAL UNIV
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