Alpha, beta-unsaturated aldehyde in-situ selective hydrogenation reaction process taking water as cheap hydrogen donor

A technology for hydrogenation reaction and aldehyde selectivity, which is applied in chemical instruments and methods, reduction preparation of oxygen-containing functional groups, and metal/metal oxide/metal hydroxide catalysts, etc., can solve problems such as high cost and achieve a simple preparation process. and controllable and excellent catalytic hydrogenation performance

Inactive Publication Date: 2022-06-03
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above-mentioned hydrogen sources have disadvantages such as high cost, and water, as a hydrogen donor with a large amount of natural storage and low price, has a wide range of application potentials

Method used

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  • Alpha, beta-unsaturated aldehyde in-situ selective hydrogenation reaction process taking water as cheap hydrogen donor

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Weigh 25mg 1Au@MoC x Catalyst is loaded in 100mL autoclave, adds 0.5mmol α, β-unsaturated aldehyde, adds 15mL 1,4-dioxane aqueous solution (V H2O :V 1,4-Dioxane =1:3), and then the reaction system was replaced with carbon monoxide gas, accumulatively five times. Then charge 3MPa carbon monoxide. After that, the reaction device was placed in the heating mantle, and the heating was started at 800 rpm, and the reaction was carried out for 5 h to carry out the in-situ hydrogenation of α,β-unsaturated aldehyde to prepare unsaturated alcohol and its by-products. The reaction products were filtered through organic microporous membranes and analyzed qualitatively and quantitatively by nuclear magnetic resonance and gas chromatography-mass spectrometry. The specific reaction properties are listed in Table 1.

Embodiment 2

[0022] Weigh 25mg 1.5Au@MoC x Catalyst is loaded in 100mL autoclave, adds 0.5mmol α, β-unsaturated aldehyde, adds 15mL 1,4-dioxane aqueous solution (V H2O :V 1,4-Dioxane =1:3), and then the reaction system was replaced with carbon monoxide gas, accumulatively five times. Then charge 3MPa carbon monoxide. After that, the reaction device was placed in the heating mantle, and the heating was started at 800 rpm, and the reaction was carried out for 5 h to carry out the in-situ hydrogenation of α,β-unsaturated aldehyde to prepare unsaturated alcohol and its by-products. The reaction products were filtered through organic microporous membranes and analyzed qualitatively and quantitatively by nuclear magnetic resonance and gas chromatography-mass spectrometry. The specific reaction properties are listed in Table 1.

Embodiment 3

[0024] Weigh 25mg 3Au@MoC x Catalyst is loaded in 100mL autoclave, adds 0.5mmol α, β-unsaturated aldehyde, adds 15mL 1,4-dioxane aqueous solution (V H2O :V 1,4-Dioxane =1:3), and then the reaction system was replaced with carbon monoxide gas, accumulatively five times. Then charge 3MPa carbon monoxide. After that, the reaction device was placed in the heating mantle, and the heating was started at 800 rpm, and the reaction was carried out for 5 h to carry out the in-situ hydrogenation of α,β-unsaturated aldehyde to prepare unsaturated alcohol and its by-products. The reaction products were filtered through organic microporous membranes and analyzed qualitatively and quantitatively by nuclear magnetic resonance and gas chromatography-mass spectrometry. The specific reaction properties are listed in Table 1.

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Abstract

The invention discloses an alpha, beta-unsaturated aldehyde in-situ selective hydrogenation reaction process taking water as a cheap hydrogen donor. According to the method, gas containing carbon monoxide is used as an oxygen acceptor, alpha, beta-unsaturated aldehyde is subjected to a selective hydrogenation reaction in water through a catalytic material, and the unsaturated alcohol is prepared through selective hydrogenation of the alpha, beta-unsaturated aldehyde. According to the method, the C = O double bond of the alpha, beta-unsaturated aldehyde can be activated and hydrogenated by using a catalytic material and taking water as a hydrogen donor, the excellent catalytic activity is shown, the selectivity can reach 80% or above, and the method has the advantages that the low-cost water is used as a hydrogen source, and the alpha, beta-unsaturated aldehyde is obtained through in-situ hydrogen production. The invention relates to one-step conversion from beta-unsaturated aldehyde to unsaturated alcohol through catalytic hydrogenation.

Description

technical field [0001] The invention relates to the selective activation and hydrogenation of α,β-unsaturated aldehydes, in particular to a process for in-situ hydrogenation of α,β-unsaturated aldehydes by using water as an inexpensive hydrogen donor. Background technique [0002] The selective hydrogenation of α,β-unsaturated aldehydes is widely used in biomedicine, food processing, organic synthesis and other fields. As a typical α,β-unsaturated aldehyde compound, cinnamaldehyde is the product of selective hydrogenation. Cinnamyl alcohol is an important chemical raw material and pharmaceutical intermediate. It can be used to prepare edible flavors such as apricot, peach, raspberry, and plum, as well as cosmetic flavors such as perfume and soap [Gallezot, P.; Richard , D. Rev.: Sci. Eng. 1998, 40, 81-126.]. Competitive adsorption exists between the C=C bond and C=O bond of α,β-unsaturated aldehydes. From the perspective of thermodynamics and kinetics, the bond energy of C=...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C29/14C07C33/03B01J27/22B01J23/52
CPCC07C29/14B01J27/22B01J23/52C07C33/03
Inventor 邓徳会陈俏黄瑞
Owner DALIAN UNIV OF TECH
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