Application of carbon-supported ruthenium nanomaterials in the catalytic reaction of aromatic amines and aromatic methanol

A technology of nanomaterials and aromatic amines, applied in the field of catalytic chemistry, can solve problems such as environmental pollution, low atom utilization rate, and difficult separation of catalysts, and achieve high conversion efficiency, mild reaction conditions, and wide application range

Active Publication Date: 2021-09-28
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods have their own shortcomings, such as the need for additional oxidants, low utilization of atoms, and easy to cause environmental pollution, etc.
At the same time, the prior art transition metal catalysis has the problem that the catalyst is not easy to separate, and the recycling of the catalyst cannot be realized.

Method used

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  • Application of carbon-supported ruthenium nanomaterials in the catalytic reaction of aromatic amines and aromatic methanol
  • Application of carbon-supported ruthenium nanomaterials in the catalytic reaction of aromatic amines and aromatic methanol
  • Application of carbon-supported ruthenium nanomaterials in the catalytic reaction of aromatic amines and aromatic methanol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1: Preparation of carbon-supported ruthenium nanomaterials

[0032] Ru(phen) 2 Cl 2 (0.0520 g), absolute ethanol (40 ml) were added to a 100 ml round bottom flask containing a magnetic stirrer, stirred at room temperature for 30 minutes, and then carbon material (VULCAN XC72R, 1.0000 g) was added to it, and reacted at 60°C 12 hours; after the reaction, ethanol was distilled off under reduced pressure in vacuum, and the solid was dried in an oven at 60° C. for 12 hours. Then, put it in a magnetic boat, place it in a tube furnace, and pass nitrogen gas at room temperature for 30 minutes, then raise it from room temperature to 800 °C at a rate of 5 °C per minute, keep it for 2 hours, and then cool it down to room temperature naturally. Promptly obtain the corresponding carbon-loaded ruthenium nanomaterial, its characterization sees attached Figure 1-4 . Thermogravimetric analysis showed that the loading amount of ruthenium was 1.08% wt, and the ruthenium na...

Embodiment 2

[0033] Example 2: Acceptor-free dehydrogenation coupling reaction of benzyl alcohol and aniline catalyzed by carbon-supported ruthenium nanomaterials

[0034]

[0035] Carbon-supported ruthenium nanomaterials (20 mg) and sodium hydroxide (20 mg) were added to a 25 ml reaction tube with a branched port equipped with a magnetic stirrer, nitrogen gas was pumped repeatedly three times, and benzyl alcohol (1.3 mmol ), aniline (1mmol), toluene (3 ml) and then sealed and heated at 110°C for 24 h; after the reaction, filter to remove the catalyst, add water and ethyl acetate to extract the filtrate, combine the organic phase, dry, Filtration, concentration under reduced pressure, and purification by silica gel column chromatography gave N-benzylideneaniline (90% yield).

[0036] The NMR data of the resulting product are as follows:

[0037] 1 H NMR (400 MHz, DMSO- d 6 , ppm) δ 8.61 (s, 1H), 7.95 (d, J = 5.0 Hz,2H), 7.53 (s, 3H), 7.42 (t, J = 7.5 Hz, 2H), 7.30–7.22 (m, 3H);1...

Embodiment 3

[0041] Example 3: Acceptor-free dehydrogenation coupling reaction of 4-methylbenzyl alcohol and aniline catalyzed by carbon-supported ruthenium nanomaterials

[0042]

[0043] Add 4-methylbenzyl alcohol (1.3 mmol), carbon-supported ruthenium nanomaterials (20 mg), and sodium hydroxide (20 mg) into a 25 ml branched reaction tube equipped with a magnetic stirrer, and pump nitrogen repeatedly Three times, add aniline (1 mmol) and toluene (3 ml) successively through a syringe, and then seal and heat at 110 °C for 24 h; after the reaction, remove the catalyst by filtration, add water and ethyl acetate to extract the filtrate, and combine organic phase, dried, filtered, concentrated under reduced pressure, and purified by silica gel column chromatography to obtain N-(4-methylbenzylidene)aniline (92% yield).

[0044] The NMR data of the resulting product are as follows:

[0045] 1 H NMR (400 MHz, DMSO- d 6 , ppm) δ 8.56 (s, 1H), 7.83 (d, J = 7.8 Hz,2H), 7.41 (t, J = 7.7 Hz...

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Abstract

The invention discloses the application of a carbon-supported ruthenium nanomaterial in catalyzing the reaction of aromatic amine and aromatic methanol. Specifically, the carbon-supported ruthenium metal nanometers of the present invention can catalyze the acceptor-free dehydrogenation coupling reaction to synthesize imines with aromatic methanol and aromatic amines as raw materials, and have the characteristics of high conversion efficiency, wide application range, mild reaction conditions and the like. After the conversion reaction, the catalyst was centrifuged out of the reaction system, and the next round of reaction was carried out after simple washing and drying. After 5 cycles, the catalyst remained stable and its catalytic activity did not decrease significantly.

Description

technical field [0001] The invention belongs to the technical field of catalytic chemistry, and relates to the use of a carbon-loaded ruthenium nanometer material in catalyzing a receptor-free dehydrogenation coupling reaction and using aromatic methanol and aromatic amine as raw materials to synthesize imines. Background technique [0002] Imine compounds are widely used organic chemical raw materials for the manufacture of medicines, chemical agricultural products, artificial substitutes for natural products, dyes and fragrances. At present, the main methods used to synthesize such compounds include the condensation reaction of primary amines and carbonyl compounds under acidic conditions, the oxidation reaction of secondary amines, and the coupling reaction of primary amines and primary alcohols under oxidative conditions. However, these methods have their own shortcomings, such as the need for additional oxidants, low utilization of atoms, and easy environmental pollutio...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J27/24C07B43/00C07C249/02C07C251/24C07D213/53C07D307/52C07D317/58C07F17/02
CPCB01J27/24B01J35/006B01J35/0073C07B43/00C07C249/02C07D213/53C07D307/52C07D317/58C07F17/02C07C251/24
Inventor 李红喜郭斌郎建平
Owner SUZHOU UNIV
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