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Preparation method and application of Pd-Ru catalyst with mesoporous structure

A mesoporous structure and catalyst technology, applied in the field of medicine, can solve the problems of lack of interaction, easy loss of catalytic active species, easy reduction of catalytic activity and reusable performance, and achieve the effect of mild reaction conditions and high catalytic yield

Active Publication Date: 2017-11-21
SHAOXING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the lack of interaction between Pd / Ru and the support activated carbon, these catalysts tend to lose catalytically active species during the catalytic hydrogenation process, thereby easily reducing their catalytic activity and reusability.

Method used

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  • Preparation method and application of Pd-Ru catalyst with mesoporous structure
  • Preparation method and application of Pd-Ru catalyst with mesoporous structure
  • Preparation method and application of Pd-Ru catalyst with mesoporous structure

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] In a 500mL round bottom flask, add magneton, hydroquinone (20mmol, 1eq), potassium carbonate (60mmol, 6eq), CH 3 CN (100 mL), and allyl bromide (48 mmol, 2.4 eq). The reaction mixture was reacted at room temperature for 48 h, and the reaction was complete as detected by TLC. Transfer the reaction solution to a separatory funnel, add 300mL ethyl acetate and 100mL water for extraction, wash the organic phase once with saturated brine, wash over anhydrous Na 2 SO 4 Drying, concentration under reduced pressure, and column chromatography yielded p-diallyloxybenzene. through 1 H-NMR detection, determine the product structure, 1 H-NMR spectrum and data such as figure 1 Shown: 1 H-NMR (CDCl 3 , 400MHz) δppm 6.87 (s, 3H), 6.12-6.02 (m, 3H), 5.45-5.39 (m, 3H), 5.31-5.28 (m, 3H), 4.51-4.50 (m, 6H).

Embodiment 2

[0046] Azobisisobutyronitrile (0.5g), p-diallyloxybenzene (1.5g), divinylbenzene (0.5g), 4-vinylbenzoic acid (1.5g), ferric chloride (0.1 g), ammonium persulfate (0.02 g) and water (3 mL) were sequentially added to tetrahydrofuran (30 mL). The reaction mixture was stirred at room temperature for 3 hours, then transferred to a hydrothermal reactor, and heated at 100° C. for 24 hours to obtain a crude paste-like mesoporous organic polymer BisAllB-DVB-VBA. The crude product was filtered with a sand core funnel, washed with water, ethanol and ether in sequence, and dried in vacuum at 80°C to obtain the organic polymer BisAllB-DVB-VBA with open channels and mesoporous structure characteristics.

[0047] Weigh BisAllB-DVB-VBA (2g), Pd(OAc) 2 (0.1g) and RuCl 3 .H 2 O (0.1g) in 40mL THF, after stirring at room temperature for 3 hours, added KBH 4 (0.5g). After the reactant was stirred at room temperature for 10 hours, the catalyst was filtered, washed with tetrahydrofuran, and drie...

Embodiment 3

[0050] Embodiment 3: Catalyst reuses for the first time:

[0051] Catalytic hydrogenation of 6-benzyl-5,7-dioxo-pyrrolo[3,4,b]pyridine: In a 500mL round bottom flask, add magnetons, 6-benzyl-5,7-dioxo- Pyrrolo[3,4,b]pyridine (20g), isopropanol (100mL), catalyst BisAllB-DVB-VBA@Pd-Ru (1g), round-bottomed flask with condenser and hydrogen balloon (1bar) , stirred at room temperature for 12 hours, recovered the BisAllB-DVB-VBA@Pd-Ru catalyst by filtration, removed the solvent from the filtrate, and obtained 18.5 g of a light yellow solid by column chromatography. 1 H-NMR detection identified as racemic cis-8-benzyl-7,9-dioxo-2,8-diazabicyclo[4,3,0]nonane, 1 The H-NMR data are as follows:

[0052]

[0053] 1 H-NMR (CDCl 3 ,400MHz)δppm 7.32–7.24(m,5H),4.64(s,2H),3.84(d,1H,J=6.8Hz),2.89-2.2.83(m,1H),2.82-2.76(m,1H ), 2.70-2.64(m,1H), 2.08(br s,1H), 2.03-1.93(m,1H), 1.68–1.61(m,1H), 1.54-1.50(m,1H).

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Abstract

The invention discloses a preparation method and application of a Pd-Ru catalyst with a mesoporous structure. The preparation method is characterized by including the steps of firstly, allowing hydroquinone to have reaction with allyl halohydrocarbon to obtain p-triallyloxy benzene; secondly, allowing the p-triallyloxy benzene, divinyl benzene and 4-vinyl benzoic acid to polymerize in a mixed solvent of ethers and water to obtain TriAllB-DVB-VBA; in an ether solvent, mixing the TriAllB-DVB-VBA with Pd(OAc)2 and RuCl3.6H2O, stirring at room temperature, and adding KBH4 for reduction to obtain the catalyst TriAllB-DVB-VBA@Pd-Ru. The catalyst prepared by the preparation method has good catalytic activity and reusability in a preparation method using the catalytic hydrogenation of 6-benzyl-5, 7-dioxo-pyrrolo [3, 4, b] pyridine to prepare 8-benzyl-7, 9-dioxo-2, 8-diazabicyclo [4, 3, 0]-1-alkenyl nonane.

Description

Technical field: [0001] The invention belongs to the technical field of medicine, and in particular relates to a preparation method of a Pd-Ru composite catalyst with a mesoporous structure and its application in the synthesis of moxifloxacin side chains. Background technique: [0002] The synthesis process of moxifloxacin side chain requires catalytic hydrogenation of 6-benzyl-5,7-dioxo-pyrrolo[3,4,b]pyridine (1) to obtain 8-benzyl-7,9-dioxo Geno-2,8-diazabicyclo[4,3,0]-1-enenonane (2). Currently, this conversion uses Pd-C and Ru-C as catalysts. Due to the lack of interaction between Pd / Ru and the carrier activated carbon, these catalysts tend to lose catalytically active species during the catalytic hydrogenation process, thereby easily reducing their catalytic activity and reusability. Research and development of porous supports that can interact with catalytically active substances is of great significance to improve the catalytic activity and reusability of catalysts....

Claims

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Application Information

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IPC IPC(8): B01J31/06B01J35/10C07D471/04
CPCC07D471/04B01J31/06B01J2231/646B01J35/617Y02P20/584
Inventor 冯高峰何静耀白其凡张永林
Owner SHAOXING UNIVERSITY
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