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Method for synthesizing 5-[(phenylamino) methyl]-2-furfuryl alcohol through bimetallic catalysis

A bimetallic catalyst and phenylamino technology, which is applied in metal/metal oxide/metal hydroxide catalysts, chemical instruments and methods, physical/chemical process catalysts, etc., can solve the problems of cumbersome separation process and difficult separation, Achieve the effects of simple process, simplified production process and reduced production cost

Active Publication Date: 2020-09-08
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The divalent ruthenium complex used in this system is a homogeneous catalyst, which is not easy to separate during the experimental operation, and the separation process is cumbersome.

Method used

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  • Method for synthesizing 5-[(phenylamino) methyl]-2-furfuryl alcohol through bimetallic catalysis
  • Method for synthesizing 5-[(phenylamino) methyl]-2-furfuryl alcohol through bimetallic catalysis
  • Method for synthesizing 5-[(phenylamino) methyl]-2-furfuryl alcohol through bimetallic catalysis

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Experimental program
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preparation example Construction

[0037] The preparation method of supported bimetallic catalyst of the present invention, take 5wt%Ni-Pd / C catalyst (the ratio of the amount of substance of Ni, Pd is 9:1) as example: take 200 order activated carbon 1g and place in crucible, 400 ℃ roasting for 5 hours, weighed 0.2169g Ni(NO 3 ) 2 ·6H 2 O was placed in another crucible, 2.1g of deionized water was added, completely dissolved, and 0.0147g of PdCl was weighed 2 Add to nickel nitrate solution, mix nickel nitrate and palladium chloride fully, ultrasonically dissolve it fully, add activated carbon, stir, impregnate at room temperature for 24 hours, dry at 100°C for 10 hours, and reduce under hydrogen atmosphere at 500°C for 3 hours , to obtain a Ni-Pd / C catalyst with a total metal loading of 5 wt%.

[0038] According to the same method as above, by changing the two metal types, the molar ratio of the two metals or the carrier type, bimetallic catalysts with different metal types, different metal molar ratios or di...

Embodiment 1

[0040] Take 0.5g (3.965mmol) of 5-hydroxymethylfurfural and 0.4881g (3.965mmol) of nitrobenzene in a beaker, add 5mL of 1,4-dioxane and 5mL of water to dissolve, add the solution to 25mL of high pressure reaction In the still, add 0.05g loading capacity and be the Ni-Pd / C catalyst of 5wt% (ratio of the amount of substance of Ni, Pd is 9:1), pass into nitrogen and purge five times, reaction temperature is 90 ℃, hydrogen pressure is 1.0 MPa, reacted for 4 hours to obtain 5-[(phenylamino)methyl]-2-furanmethanol with a yield of 90.7%.

Embodiment 2

[0042] Take 0.5g of 5-hydroxymethylfurfural and 0.4881g of nitrobenzene in a beaker, add 5mL of 1,4-dioxane and 5mL of water to dissolve, add the solution to a 25mL autoclave, and add 0.05g of load 5wt% Ni-Pd / C catalyst (ratio of Ni, Pd substance amount is 7:1), pass into nitrogen and purge five times, reaction temperature 90 ℃, hydrogen pressure is 1.0MPa, react for 4 hours, prepare 5-[(phenylamino)methyl]-2-furanmethanol was obtained in a yield of 79.7%.

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Abstract

The invention discloses a method for synthesizing 5-[(phenylamino) methyl]-2-furfuryl alcohol through bimetallic catalysis. Biomass derivatives 5-hydroxymethylfurfural and nitrobenzene are used as initial raw materials, a supported bimetallic catalyst is used as a catalyst, H2 is used as a hydrogen source, and in a 1, 4-dioxane + H2O mixed solvent, 5-[(phenylamino) methyl]-2-furfuryl alcohol is synthesized by adopting a'one-pot method 'through reductive amination. Supported metal of the supported bimetallic catalyst is bimetal composed of two precious metals, bimetal composed of one precious metal and one non-precious metal A or non-precious metal B, or bimetal composed of one non-precious metal A and one non-precious metal B. According to the method, the yield of the 5-[(phenylamino) methyl]-2-furfuryl alcohol can reach 90% or above. The method has the advantages of environment-friendly process, simple operation, recyclable catalyst, high reaction selectivity, high product yield, andobvious industrial production advantages.

Description

technical field [0001] The present invention relates to a kind of synthesis method of 5-[(phenylamino)methyl]-2-furanmethanol, especially catalytic reductive amination of 5-hydroxymethylfurfural and nitrobenzene under the action of supported bimetallic catalyst Process for the preparation of 5-[(phenylamino)methyl]-2-furanmethanol. Background technique [0002] With the continuous depletion of fossil energy and the increasingly serious problem of environmental pollution, the development and utilization of green renewable energy is imminent. Among them, biomass resources have the characteristics of renewable, large storage capacity, and extensive sources, and have received more and more attention. Lignocellulose is an abundant organic substance derived from natural biomass renewable resources, which can be converted into an important platform compound, 5-hydroxymethylfurfural. The molecule of 5-hydroxymethylfurfural contains a furan ring, an aldehyde group and a hydroxymeth...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/52B01J23/89
CPCC07D307/52B01J23/892Y02P20/584
Inventor 刘迎新郭良玉陈梦婷魏作君
Owner ZHEJIANG UNIV OF TECH