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Nitrogen-containing porous organic polymer composite material as well as preparation method and application thereof

A composite material and polymer technology, applied in the field of catalytic chemistry, to achieve a wide range of applications, large specific surface area, green and mild reaction conditions

Active Publication Date: 2022-04-08
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the existing technology still needs to be improved in terms of reducing metal pollution and catalyst recovery performance.

Method used

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  • Nitrogen-containing porous organic polymer composite material as well as preparation method and application thereof
  • Nitrogen-containing porous organic polymer composite material as well as preparation method and application thereof
  • Nitrogen-containing porous organic polymer composite material as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Under a nitrogen atmosphere, 2,6-bis(benzimidazole)pyridine (1 mmol), biphenyl (0.154 g, 1 mmol) and aluminum chloride (10 mmol, 1.33 g) were added to anhydrous chloroform 20 mL, and then stirred and reacted at 58°C for 24 hours. 2 O, v / v = 1 : 1), water, methanol, and ether, and then vacuum-dried to obtain a nitrogen-containing porous organic polymer.

Embodiment 2

[0031] RuCl 3 (17 mg) and pyrazole polymer (200 mg) were added to a three-neck round bottom flask containing 25 mL of absolute ethanol, liquid nitrogen freezing-pumping-nitrogen-filling-thawing was repeated three times, and then refluxed and stirred for 12 hours, and the reaction After the end, the solid was separated by centrifugation, washed with water, ethanol and ether in turn, and then vacuum-dried to obtain the corresponding nitrogen-containing polymer-loaded metal ruthenium composite material (the loading of ruthenium was 3.11 wt%), which was used as the catalyst in the following examples .

[0032] The above reaction is shown as follows:

[0033]

[0034] figure 1 It is a scanning electron microscope image of the above-mentioned nitrogen-containing porous organic polymer material; figure 2 It is the solid NMR carbon spectrogram of the above-mentioned nitrogen-containing porous organic polymer material; image 3 is the nitrogen adsorption / desorption isotherm of...

Embodiment 3

[0036]

[0037] Add secondary alcohol (1 mmol), primary alcohol (1.2 mmol), nitrogen-containing polymer-supported metal ruthenium composite material (20 mg), potassium hydroxide (0.5 mmol) into a 15 mL reaction tube equipped with a magnetic stirrer, Add 2 mL of toluene, repeat three times of liquid nitrogen freezing-pumping-nitrogen-filling-thawing, and react in an oil bath at 130 °C for 12 hours; Extract with ethyl acetate, combine the organic phases, dry the organic phases over anhydrous sodium sulfate, and concentrate under reduced pressure, and the crude product is purified by silica gel column, using petroleum ether and ethyl acetate as eluents to obtain the corresponding secondary Alcohol, HPLC yield 93%, separation yield 88%.

[0038] The NMR data of the resulting product are as follows:

[0039] 1 H NMR (400 MHz, CDCl 3 , ppm): δ 7.34 – 7.26 (m, 4H), 7.26 – 7.20 (m,3H), 7.15 (t, J = 6.2 Hz, 3H), 4.59 (dd, J = 7.4, 5.7 Hz, 1H), 2.65 (m, 2H),2.23 (s, 1H), 2.14 – 1...

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Abstract

The invention discloses a nitrogen-containing porous organic polymer composite material as well as a preparation method and application thereof. Specifically, aluminum trichloride serves as a catalyst, 2, 6-bis (benzimidazole) pyridine and biphenyl are copolymerized to obtain a porous organic polymer, the porous organic polymer serves as a carrier, ruthenium trichloride is loaded on the polymer through coordination, and the composite material is obtained. The material can efficiently catalyze the cross-coupling reaction of secondary alcohol and primary alcohol to synthesize beta-alkylated secondary alcohol compounds. The catalytic system has wide functional group tolerance, and after the catalyst is continuously and cyclically used for multiple times, the catalyst still keeps high catalytic activity, and the metal ruthenium is not leached out.

Description

technical field [0001] The invention belongs to the technical field of catalytic chemistry, and relates to the preparation of a nitrogen-containing porous organic polymer composite material and its catalyzed cross-coupling reaction of secondary alcohols and primary alcohols to synthesize β-alkylated secondary alcohol compounds. Background technique [0002] Alcohols are very important in organic synthesis and chemical industry. Traditional routes to obtain β-alkylated alcohols from secondary alcohols usually require a multistep process involving oxidation of secondary alcohols, metallation of alkyl halides, and reduction of β-alkylated ketones. Reacting an alcohol as an alkylating agent with another alcohol has been considered as a green and direct approach to obtain β-alkylated alcohols, in a transition-metal-catalyzed reaction, H 2 and / or H 2 O is produced as a by-product with high atom utilization efficiency and is environmentally friendly. Among them, the metal-cataly...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12B01J31/22B01J35/10C07C29/34C07C33/46C07C33/24C07C41/30C07C43/23
CPCY02P20/584
Inventor 李红喜崔耀李海燕徐泽
Owner SUZHOU UNIV
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