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A method for heterogeneous catalytic hydrogenation reduction of unsaturated compounds

A heterogeneous catalysis and unsaturated technology, applied in chemical instruments and methods, preparation of organic compounds, carbon compound catalysts, etc., can solve the problems of less research and slow reaction, so as to increase hydrogen concentration, reduce requirements and risks, The effect of increasing the hydrogenation reaction rate

Active Publication Date: 2019-06-18
INST OF CHEM CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the adsorption of hydrogen on the catalyst surface also plays a very important role in the catalytic reaction rate, but there are very few related studies.
The concentration of hydrogen on the surface of the catalyst is very low under normal pressure, resulting in a slow heterogeneous hydrogenation catalytic reaction under normal pressure

Method used

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  • A method for heterogeneous catalytic hydrogenation reduction of unsaturated compounds
  • A method for heterogeneous catalytic hydrogenation reduction of unsaturated compounds
  • A method for heterogeneous catalytic hydrogenation reduction of unsaturated compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1, Hydrophobic and aerophilic catalyst Pd / GA and a series of comparative catalysts Pd / NGA-2, Pd / NGA-4, commercial Pd / C adsorption behavior of hydrogen in liquid

[0035] 1. Preparation of aerophilic catalyst palladium / graphene airgel Pd / GA

[0036] (1) Preparation of carrier GA: Mix 5 mL of graphene oxide aqueous solution (1 mg / mL) with 5 mL of water, add 0.5 g of KI and 0.5 mL of concentrated hydrochloric acid, and react in an oven at 80 ° C for 8 hours to obtain a hydrogel. The obtained hydrogel was soaked in water for 3 days, during which the water was changed every 12 h, and the graphene airgel GA was obtained by freeze-drying. Under Ar atmosphere, burn GA at 140°C for one hour to remove I 2 , and then raised to 800 ° C for 2 hours to remove other impurities.

[0037] (2) Loaded palladium: Measure the sodium chloropalladate solution according to the theoretical load of 3.8wt%, add 2mL of absolute ethanol to the sodium chloropalladate solution (0.0564mol / L)...

Embodiment 2

[0046] Embodiment 2, heterogeneous catalytic hydrogenation reduction styrene

[0047] According to the following steps for the heterogeneous catalytic hydrogenation reduction of styrene:

[0048]Add Pd / GA (1 mg), styrene (12 μL, 0.1 mmol) and mesitylene (internal standard, 15 μL, 0.1 mmol) into 4 mL of solvent (water or ethanol), bubble hydrogen, and react at 35 ° C for 40 min. After the reaction, it was extracted with ethyl acetate, and the organic phase was analyzed by GC. Comparative catalyst addition: Pd / NGA-2 (0.7mg), Pd / NGA-4 (0.5mg), Pd / C (0.1mg).

[0049] Experimental results such as image 3 As shown, when the solvent is water, when Pd / GA is used as a catalyst to catalyze the hydrogenation of styrene, the conversion rate is close to 100%.

Embodiment 3

[0050] Embodiment 3, heterogeneous catalytic hydrogenation reduction nitro compound

[0051] According to the following steps heterogeneous catalytic hydrogenation reduction nitro compound:

[0052] Pd / GA (2 mg), substrate (0.1 mmol) and n-tridecane (internal standard, 12 μL, 0.05 mmol) were added to 4 mL of water, hydrogen was bubbled, and reacted at a certain temperature for a certain period of time. After the reaction, it was extracted with ethyl acetate, and the organic phase was analyzed by GC. Comparative catalyst addition amount: Pd / NGA-4 (1 mg), Pd / C (0.18 mg). The reaction conditions and conversion rates of different substrates (nitro compounds) are shown in Table 1.

[0053] Table 1. Performance comparison of catalysts for nitro hydrogenation

[0054]

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Abstract

The invention discloses a multi-phase catalytic hydrogenation reduction method of an unsaturated compound. The method comprises a step of carrying out multi-phase catalytic hydrogenation reaction to reduce the unsaturated compound; the multi-phase catalytic hydrogenation reaction takes water as a solvent and a hydrophobic and atmophile material as a catalyst. According to the multi-phase catalytichydrogenation reduction method, hydrophobic and atmophile properties of the catalyst are utilized, so that hydrogen gas can be rapidly adsorbed and spread on the surface of the catalyst, the surfacehydrogen concentration of the catalyst is improved, and the hydrogenation reaction speed is improved; a conventional pressurizing method is changed, so that requirements on equipment and dangerousnessare reduced. The atmophile catalyst Pd / GA can be used for hydrogenation of double bonds, nitryl and an aldehyde group under normal pressure, and is applicable to wide types. The method provided by the invention has a wide application potential in other fields needing gas to react.

Description

technical field [0001] The invention belongs to the field of catalysts, in particular to a method for heterogeneous catalytic hydrogenation reduction of unsaturated compounds. Background technique [0002] Liquid-phase hydrogenation reaction plays a huge role in fine chemical and pharmaceutical fields. Compared with other hydrogen sources, hydrogen is a hydrogen source with high atom economy and environmental friendliness. However, the low reactivity of hydrogen has always been the focus and difficulty of research. In order to improve the reaction rate of heterogeneous catalytic hydrogenation, researchers generally control the morphology and structure of the synthetic catalyst, adjust the surface interface and electronic structure of the catalyst, so as to achieve efficient activation of the reaction substrate; or by adjusting the hydrophilicity and hydrophobicity of the catalyst surface, Thus, the enrichment and conversion of reaction substrate molecules on the surface of...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C209/36C07C211/46C07C211/45C07C211/52C07C29/141C07C33/46C07C33/22C07C33/20C07C5/03C07C15/073B01J23/44
CPCB01J23/44C07C5/03C07C29/141C07C209/36C07C2523/44C07C211/46C07C211/45C07C211/52C07C33/46C07C33/22C07C33/20C07C15/073
Inventor 宋卫国李肇华曹昌燕江雷
Owner INST OF CHEM CHINESE ACAD OF SCI
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