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Method for preparing cyclohexyl crown ether by catalytic hydrogenation of carbon supported ruthenium catalyst

A ruthenium catalyst, catalytic hydrogenation technology, applied in chemical instruments and methods, physical/chemical process catalysts, metal/metal oxide/metal hydroxide catalysts, etc., can solve the problem of easy combustion of metal catalysts, large amount of precious metal ruthenium Catalysts are difficult to separate and other problems, to achieve the effect of strong operability of the synthesis process, simple preparation method, and reduced process cost

Inactive Publication Date: 2012-06-27
TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The purpose of this invention is to provide a kind of method that utilizes carbon-loaded ruthenium catalyst catalytic hydrogenation to prepare cyclohexyl crown ether, take benzocrown as raw material, carry out catalytic hydrogenation reaction under the effect of carbon-loaded ruthenium catalyst, thereby overcome In the prior art, the precious metal ruthenium is used in a large amount and is difficult to recycle, the catalyst is difficult to separate from the product, and the metal catalyst is easy to burn and has the disadvantages of poor safety.

Method used

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  • Method for preparing cyclohexyl crown ether by catalytic hydrogenation of carbon supported ruthenium catalyst
  • Method for preparing cyclohexyl crown ether by catalytic hydrogenation of carbon supported ruthenium catalyst
  • Method for preparing cyclohexyl crown ether by catalytic hydrogenation of carbon supported ruthenium catalyst

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[0020] The invention provides a method for preparing cyclohexyl crown ether by catalytic hydrogenation of a carbon-supported ruthenium catalyst. The preparation method uses benzocrown ether as a raw material, and carries out a catalytic hydrogenation reaction under the action of a carbon-supported ruthenium catalyst to generate the corresponding The cyclohexyl crown ether, its concrete steps are as follows:

[0021] 1) With benzo-12 crown 4, benzo-15 crown 5, benzo-18 crown 6, benzo-21 crown 7, dibenzo-12 crown 4, dibenzo-15 crown 5, dibenzo -18 crown 6, dibenzo-21 crown 7, and one of the methyl, ethyl, isopropyl or tert-butyl substituents of the above-mentioned benzo crown ethers are used as raw materials, with n-butanol, n-octyl At least one of alcohol, ethylene glycol, dichloromethane, chloroform, ethylene dichloride, ethylene glycol monomethyl ether, ethylene glycol dimethyl ether and toluene is used as a reaction solvent, and benzo crown ether is added to dissolved in an...

Embodiment 1

[0026] 1) Preparation of cyclohexyl-12 crown 4

[0027] The reaction equation is as follows:

[0028]

[0029] Using benzo-12 crown 4 as a raw material, n-butanol as a reaction solvent, under the action of a ruthenium catalyst supported by a carbon molecular sieve, the catalytic hydrogenation reaction is carried out under stirring conditions; the loading capacity of the ruthenium catalyst supported by a carbon molecular sieve is 25% , the mass ratio of benzo-12 crown 4 to the catalyst is 1:0.01, the reaction temperature is controlled at 70°C, and the hydrogen pressure is 2MPa. After 24 hours of reaction, the mixture of the reaction product and the catalyst is filtered to remove the catalyst. After the filtrate is concentrated, The obtained product was detected by gas chromatography, wherein the conversion rate of benzo-12 crown 4 reached 94%, and the yield of cyclohexyl-12 crown 4 was 84%.

[0030] 2) The ruthenium catalyst supported by the above-mentioned carbon molecular...

Embodiment 2

[0033] 1) Preparation of dicyclohexyl-15 crown 5

[0034]The reaction equation is as follows:

[0035]

[0036] Using dibenzo-15 crown 5 as a raw material, n-octanol as a reaction solvent, under the action of a carbon nanotube-supported ruthenium catalyst, the catalytic hydrogenation reaction is carried out under stirring conditions; the loading capacity of the carbon nanotube-supported ruthenium catalyst 10%, the mass ratio of dibenzo-15 crown 5 and catalyst is 1:1, the reaction temperature is controlled at 100° C., and the hydrogen pressure is 10 MPa. After reacting for 2 hours, the reaction product and the catalyst mixture are filtered to remove the catalyst. After the filtrate was concentrated, the obtained product was detected by gas chromatography, wherein the conversion rate of dibenzo-15 crown 5 reached 100%, and the yield of dicyclohexyl-15 crown 5 was 92%.

[0037] 2) The ruthenium catalyst supported by the above-mentioned carbon nanotubes is prepared by the foll...

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Abstract

The invention discloses a method for preparing cyclohexyl crown ether by catalytic hydrogenation of a carbon supported ruthenium catalyst. According to the method for preparing the cyclohexyl crown ether, a cyclohexyl substituted crown ether product is prepared by performing catalytic hydrogenation on benzo-crown ether which is used as raw materials under the action of the carbon supported ruthenium catalyst; and the mass ratio of the benzo-crown ether to the carbon supported ruthenium catalyst is 1:(0.01-1), the temperature in a reaction process is controlled to be 70 to 200 DEG C, and hydrogen pressure is 2 to 10 Mpa. The method for preparing the cyclohexyl crown ether has the advantages of high operability, and high safety; the catalyst is easy to recover; a carbon material with a large specific area is used as a catalyst carrier, so the dispersion degree of ruthenium is improved, and the using amount of ruthenium is reduced; and therefore, the method is low in cost.

Description

technical field [0001] The invention relates to a method for preparing cyclohexyl crown ether through catalytic hydrogenation of a carbon-loaded ruthenium catalyst, which belongs to the technical field of organic compound preparation. Background technique [0002] Since Pedersen (C.J.Pedersen, Journal of the American Chemical Society, 89(26), 7017-7036, 1967) discovered and reported the synthesis method of crown ethers in 1967, the research on crown ether compounds has achieved rapid development. New crown ether compounds are constantly being synthesized, and new properties are constantly being discovered. Because these compounds have special complexing ability to alkali metal and alkaline earth metal cations, they are widely used in coordination chemistry, ion pair extraction, phase transfer catalytic reaction and other fields. [0003] Benzo crown ethers can generate cycloaliphatic crown ethers after catalytic hydrogenation under the action of catalysts. Compared with be...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D323/00B01J23/46
CPCY02P20/584
Inventor 高杰陈崧哲陈靖
Owner TSINGHUA UNIV
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