Method of synthesizing imine and amine compounds by means of borrowing-hydrogen reduction coupling

A technology of amine compounds and compounds, which is applied in the preparation of amino compounds, organic compounds, and imino compounds through condensation/addition reactions. It can solve the problems of expensive precious metals, limited earth reserves, and limited applications. Inexpensive, easy to operate, mild effect

Active Publication Date: 2018-10-23
QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Precious metals are expensive and the earth's reserves are limited, which severely limits their wide application in actual production, especially large-scale industrial production

Method used

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  • Method of synthesizing imine and amine compounds by means of borrowing-hydrogen reduction coupling
  • Method of synthesizing imine and amine compounds by means of borrowing-hydrogen reduction coupling
  • Method of synthesizing imine and amine compounds by means of borrowing-hydrogen reduction coupling

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Example 1: Preparation of nitrogen-doped porous carbon material-supported Co catalyst

[0041] Cut 1kg of cleaned bamboo shoots into pieces, heat them in an oven at 70°C until dry, grind the dried solid into powder, and put it into powder for later use; add 2g of the powder into 15mL of water, stir and mix evenly, and then transfer it to a hydrothermal reaction kettle. React at 180°C for 8 hours, filter after the reaction, wash the filtered product with water, and dry to obtain a brown solid, vacuum-dry the obtained solid for 24 hours, and grind until the particles are uniform to obtain hydrothermal carbon. After that, 0.5 g of brown solid hydrothermal carbon obtained above was dispersed in 0.0495 g of CoCl 2 ·6H 2 O in 15mL of water, stirred at 60°C for 2h, dried the reaction solution at 100°C for 12h, then put the obtained dry solid in a tube furnace for calcination in a nitrogen gas atmosphere, and kept it at 800°C for 2 hours , after the tube furnace dropped to ro...

Embodiment 2

[0044] The invention discloses a method for preparing imine compounds by hydrogen-reductive coupling of nitroaromatic compounds and differently substituted benzyl alcohol compounds using nitrogen-doped carbon material supported cobalt catalysts. The steps are:

[0045] Add 0.2mmol of nitroaromatic compounds, 0.6mmol of different substituted benzyl alcohol compounds, 20mg of the supported catalyst, 5mL of toluene, 67.5mg (0.6mmol) of potassium tert-butoxide into the reaction tube. Carry out the reaction, after reacting for 15 hours, cool to room temperature, filter the reaction solution, and perform silica gel column chromatography to obtain imine compounds;

[0046] Same operation and steps as in Example 2, changing the types of nitro compounds and differently substituted benzyl alcohol compounds (i.e. substrates), the obtained imine compounds (products), conversions > 99%, and yields of 60-90% The % varies, as shown in Table 1:

[0047] Table 1

[0048]

[0049]

Embodiment 22

[0051] The invention discloses a method for preparing amine compounds through hydrogen reductive coupling of nitroaromatic compounds and differently substituted benzyl alcohol compounds by using nitrogen-doped carbon material supported cobalt catalyst to catalyze. The steps are:

[0052] Add 0.2mmol of nitroaromatic compounds, 0.8mmol of differently substituted benzyl alcohol compounds, 20mg of the supported catalyst, 5mL of toluene, 89.6mg (0.8mmol) of potassium tert-butoxide into the reaction tube, and seal it at 120°C Carry out the reaction, after reacting for 15 hours, cool to room temperature, filter the reaction solution, and obtain the imine compound by silica gel column chromatography; the same operation and steps as in Example 23, change the nitro compound and differently substituted benzyl alcohol compounds (i.e. The kind of substrate), the amine compound (product) that obtains, transformation rate all>99%, productive rate 60~90% differ, specifically as shown in tabl...

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Abstract

The invention belongs to energy and chemical industry and particularly relates to a method of synthesizing imine and amine compounds by means of borrowing-hydrogen reduction coupling by using a nitrogen-doped hierarchical-porous biomass-based carbon material supported catalyst. The method includes the steps of: under a seal reaction condition, adding a nitro-aromatic hydrocarbon compound, benzyl alcohol compounds with different substituent groups, the supported catalyst, methylbenzene and potassium tert-butoxide; performing a reaction at 50-150 DEG C for 4-24 h, cooling the product to room temperature and filtering a reaction liquid to obtain the imine compound represented in the formula (1) or the amine compound represented in the formula (2). The raw materials of the catalyst are regenerable resources, are widely distributed, are green and environment-friendly, are easy to prepare and abundant in sources, and are low in cost; the catalyst can be recycled without deactivation and is stable to air, water and heat. By means of the supported metal catalyst, the conversion rate of the borrowing-hydrogen reduction coupling reaction on the nitro-compound and alcohol to prepare the iminecompounds is higher than 99%, and yield can reach 90-60%; the conversion rate of same to prepare the amine compounds is higher than 99%, and yield can reach 90-60%.

Description

technical field [0001] The invention belongs to energy and chemical industry, and in particular relates to a method for synthesizing imines and amine compounds by using nitrogen-doped hierarchical porous biomass-based carbon material as a supported catalyst by hydrogen reduction coupling. Background technique [0002] As a common synthetic building block, amine compounds have been widely used in the fields of fine chemical industry, medicinal chemistry and material science. According to the University of Arizona Jón According to the "Top 200 Drugs Sales in the US Market in 2015" by the professor's team, about 170 drug molecules contain nitrogen-containing groups such as amino groups. As an important chemical raw material, amines can be used in synthetic resins and plastics, textiles, surfactants, disinfection and cleaning products, etc. Traditional amine synthesis methods include Gabriel synthesis, Buchwald-Hartwig coupling reaction, Hofmann degradation method, nitro redu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B43/00C07B43/04C07C249/02C07C251/24C07C253/30C07C255/61C07D213/74C07D217/02C07D307/79C07C209/60C07C211/48C07C211/52C07C211/29C07C213/02C07C217/84C07C217/58B01J27/24
CPCB01J27/24C07B43/00C07B43/04C07C209/60C07C213/02C07C249/02C07C253/30C07D213/74C07D217/02C07D307/79C07C251/24C07C255/61C07C211/48C07C211/52C07C211/29C07C217/84C07C217/58Y02P20/584
Inventor 杨勇宋涛段亚南任鹏
Owner QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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