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Method for reducing carbonyl into methylene at normal temperature and normal pressure

A methylene, normal pressure technology, used in chemical instruments and methods, preparation of organic compounds, preparation of amino compounds from amines, etc., can solve the problems of uneconomical environmental protection, easy generation of by-products, and high PMHS prices, and achieves a reduction in Cost, mild conditions, no pollution cost effect

Inactive Publication Date: 2017-03-29
SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As an important catalytic hydrogenation reduction catalyst, palladium catalyst has also been reported for its catalytic performance of carbonyl reduction into methylene, such as Hans Adolfsson recently reported using Pd / C as catalyst, adding polymethylhydrogensiloxane (PMHS) As a hydrogen source, the carbonyl is catalytically reduced to methylene (Angew.Chem.Int.Ed., 2015, 54, 5122-5126). This method requires the addition of PMHS, which is expensive and easily generates by-products during the reaction. Not economical and environmentally friendly

Method used

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  • Method for reducing carbonyl into methylene at normal temperature and normal pressure
  • Method for reducing carbonyl into methylene at normal temperature and normal pressure
  • Method for reducing carbonyl into methylene at normal temperature and normal pressure

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] In the flask, add 1mmol vanillin, 15mL water and 0.02g Pd / CN catalyst, remove the air in the reaction flask, and stir the reaction for 3h under a hydrogen balloon at normal temperature (25°C) and normal pressure to obtain vanillyl alcohol and 4-methylhexanol Genocinol. After the reaction, the catalyst was separated by centrifugation, and the reactants and hydrogenation products were qualitatively and quantitatively analyzed by gas chromatography (GC), and the conversion rate of vanillin and the selectivity of vanillyl alcohol and 4-methylguaiacol were calculated.

[0033] The schematic diagram of the hydrogenation reduction of vanillin is as follows: figure 1 as shown, figure 1 Among them, A is vanillin, B is vanillyl alcohol, and C is 4-methylguaiacol, from figure 1 It can be seen from the figure that the products of hydrogenation reduction of vanillin include both vanillyl alcohol and 4-methylguaiacol. In order to obtain 4-methylguaiacol with a higher yield, the 4-m...

Embodiment 2-5

[0036] Embodiment 2-5 and embodiment 1 step and operation are identical, only change the solvent that adds, obtain vanillyl alcohol and 4-methylguaiacol, the conversion rate of vanillyl alcohol and vanillyl alcohol and 4-methylguaiacol The selectivity is shown in Table 1:

[0037] Table 1. The results of using different solvents to catalyze the reduction of vanillin

[0038] Example solvent time (h) A conversion rate (%) B selectivity (%) C selectivity (%) 1 water 3 98.3 15.2 78.2 2 ethanol 3 98.7 0 93.9 3 Isopropanol 3 99.7 0 95.0 4 Tetrahydrofuran 3 100 0 >99 5 ethyl acetate 3 100 8.3 89.2

[0039] Experiment 1: Pd / CN catalyst reuse experiment

[0040] The Pd / CN catalyst among the embodiment 4 is separated and used continuously more than ten times by the method in the embodiment 4, and the conversion rate and the selectivity of each test reaction are respectively, and the results are shown in Table 2:...

Embodiment 6-27

[0045] The operations of Examples 6-27 are the same as those of Example 4, but the type and amount of carbonyl compound (substrate), the amount of Pd / CN catalyst, and the reaction time are changed.

[0046] Qualitative and quantitative analysis of the substrate and hydrogenation products were carried out by gas chromatography (GC), and the conversion rate of the substrate and the selectivity of the product were calculated.

[0047] Table 3 The results of hydrogenation reduction of different substrates

[0048]

[0049]

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PUM

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Abstract

The invention discloses a method for reducing carbonyl into methylene at normal temperature and normal pressure. The method includes the following steps that a carbonyl compound, a nitrogen doped carbon material loaded palladium catalyst and a solvent are added into a reaction container, the ratio of the carbonyl compound to the nitrogen doped carbon material loaded palladium catalyst is (1-5) mol:(10-40) g, hydrogen is introduced, reacting is carried out for 0.5-20 h at normal temperature and normal pressure, and carbonyl can be reduced into methylene through catalytic hydrogenation. The reaction formula of the reaction is shown in the specification. The method is simple, easy to operate, mild in condition, high in conversion rate, good in selectivity, low in cost and free of pollution to the environment.

Description

technical field [0001] The invention relates to a method for reducing carbonyl to methylene at normal temperature and pressure, in particular to a method for reducing carbonyl compounds to methylene by using a nitrogen-doped carbon material loaded with palladium as a catalyst. Background technique [0002] The reduction of carbonyl groups in aldehydes and ketones to the corresponding methylene groups is a very important class of functional group conversion reactions, and has a wide range of applications in the fields of synthesis, pharmaceuticals, and pesticides. The traditional method mainly adopts Clemmensen reduction method and WolffL-Kishner-Huang Minglong reduction method, but these two methods have high cost and serious pollution. In recent years, it has also been reported to use catalysts containing Cu-Cr, Fe or Ni to catalyze the hydrogenation reduction of carbonyl compounds to methylene, but these catalysts have low activity and require high reaction temperature (20...

Claims

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Application Information

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IPC IPC(8): C07C41/18C07C43/23C07C43/205C07C1/22C07C15/06C07C15/073C07C15/08C07C15/24C07C15/44C07C15/16C07C13/18C07C9/12C07C9/15C07C11/107C07C17/354C07C25/02C07C25/13C07C37/00C07C39/07C07C209/68C07C211/48C07D307/36C07D307/79
CPCY02P20/52C07C41/18C07C1/22C07C17/354C07C37/002C07C209/68C07D307/36C07D307/79C07C43/23C07C43/205C07C15/06C07C15/073C07C15/08C07C15/24C07C15/44C07C15/16C07C13/18C07C9/12C07C9/15C07C11/107C07C25/02C07C25/13C07C39/07C07C211/48
Inventor 张泽会汪帆王树国
Owner SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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