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Solid carried ion liquid-nanometer metal particle catalyst, and its preparing method, and application in synthesis of arylamine

A technology of nano-metal particles and ionic liquids, applied in the preparation of amino compounds, organic compounds, physical/chemical process catalysts, etc.

Inactive Publication Date: 2007-10-03
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the application of solid-supported ionic liquids and ionic liquids to the catalytic hydrogenation of aromatic nitro compounds has not been reported in the literature so far.

Method used

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  • Solid carried ion liquid-nanometer metal particle catalyst, and its preparing method, and application in synthesis of arylamine
  • Solid carried ion liquid-nanometer metal particle catalyst, and its preparing method, and application in synthesis of arylamine
  • Solid carried ion liquid-nanometer metal particle catalyst, and its preparing method, and application in synthesis of arylamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] The synthesis of palladium nano-catalysts supported by two layers of ionic liquids (terminal is octyl, palladium mass percentage is 2.0%):

[0062] 1g octanized immobilized bis-imidazole (formula 2, carrier=silicon dioxide; m=1, n=0; Q=(CH 2 ) 3 , Q 1 =(CH 2 ) 4 ;L=OCH 2 CH 3 ;R=C 8 h 17 , R 1 -R 6 = H), suspended in 0.033g of palladium chloride (0.19mmol) in 10mL of acetonitrile solution, refluxed for 48h under nitrogen protection, filtered, washed with deionized water and absolute ethanol in turn, dried in vacuum at 60°C, recorded as Immobilization Catalyst Precursor A 0 .

[0063] Will be dissolved with 0.021g NaBH 4 (0.57mmol) of 3mL absolute ethanol solution was slowly added dropwise to the suspended 1.0g A 0 10mL of absolute ethanol, the color of the mixture gradually darkened and finally turned black, after the reaction was complete. Filter, wash with deionized water and absolute ethanol successively, dry under vacuum at 60°C, and suspend the obtain...

Embodiment 2-7

[0067] According to the method of embodiment 1, change terminal substituent group octyl to be other alkanes, change material type or ratio to obtain a series of catalysts as follows:

[0068] 2) 1g of octanized immobilized bis-imidazole (formula 2, carrier=silicon dioxide; m=1, n=0; Q=(CH 2 ) 3 , Q 1 =(CH 2 ) 4 ;L=OCH 2 CH 3 ;R=C 8 h 17 , R 1 -R 6 =H), 0.025g palladium chloride (0.14mmol), 0.015g NaBH 4 (0.42 mmol); Catalyst B (Pdwt% = 1.5) was obtained.

[0069] 3) 1g of octanized immobilized bis-imidazole (formula 2, carrier=silicon dioxide; m=1, n=0; Q=(CH 2 ) 3 , Q 1 =(CH 2 ) 4 ;L=OCH 2 CH 3 ;R=C 8 h 17 , R 1 -R 6 =H), 0.017g palladium chloride (0.09mmol), 0.011g NaBH 4 (0.27 mmol); Catalyst C (Pd wt% = 1.0) was obtained.

[0070] 4) 1g butylated imididazole immobilized (formula 2, carrier=silicon dioxide; m=1, n=0; Q=(CH 2 ) 3 , Q 1 =(CH 2 ) 4 ;L=OCH 2 CH 3 ;R=C 4 h 9 , R 1 -R 6 =H), 0.017g palladium chloride (0.09mmol), 0.011g NaBH 4 (0...

Embodiment 8

[0074] Embodiment 8 (comparative example)

[0075] Synthesis of silica gel directly supported palladium catalyst:

[0076] Suspend 1 g of silica gel activated according to a conventional method directly in 10 mL of deionized aqueous solution of 0.017 g of palladium chloride (0.09 mmol), stir at room temperature for 24 h, and carry out the rest of the synthesis process according to Example 1, and finally obtain a palladium with a weight loading of 1.0%. Catalyst H.

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Abstract

A catalyst carrying ionic liquid and metallic nanoparticles for preparing high-quality arylamine by hydrocatalyzing aromatic nitro compound is prepared through preparing immobilized ionic liquid by bonding the ionic liquid onto carrier, binding it with the active component containing transition metal or precursor, and reductive exchange. Its advantages are low reaction temp, long service life and no waste generation.

Description

Technical field: [0001] The invention relates to an immobilized ionic liquid-nano metal particle catalyst and its preparation method and its application in the hydrogenation of aromatic nitro compounds to synthesize aromatic amines under mild conditions, more specifically, a A liquid stable nanometer metal catalyst, a preparation method thereof, and a method for preparing high-quality aromatic amines by using the catalyst to catalyze the hydrogenation of aromatic nitro compounds. Background technique: [0002] Aromatic amines are an important class of organic raw materials and intermediates, widely used in chemical, pharmaceutical, dye, pesticide and other fields, and can be used to prepare agricultural chemicals, dyes, medicine and polyurethane polymer materials. Catalytic hydrogenation is a simple, clean and economical method for the reduction of nitro compounds to the corresponding aromatic amines, and is currently the main method in industrial production. Among the worl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/02C07C209/36C07C211/43
Inventor 魏俊发毕元元王彦明石先莹
Owner SHAANXI NORMAL UNIV
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