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Method for synthesizing cyclohexenone through catalytic oxidation of cyclohexene

A technology of cyclohexenone and catalytic oxidation is applied in the field of synthesis of cyclohexenone by catalytic oxidation of cyclohexene, and the synthesis field of cyclohexenone achieves the effects of reducing energy consumption, low reaction temperature and improving reaction efficiency

Active Publication Date: 2014-05-14
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But so far, there has been no public report on the process of preparing cyclohexenone by selectively catalyzing the allylic oxidation of cyclohexene using carbon nanotubes as a heterogeneous catalyst and oxygen or air as an oxidant.

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  • Method for synthesizing cyclohexenone through catalytic oxidation of cyclohexene

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Experimental program
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Effect test

Embodiment 1

[0024] Add 8.1g of cyclohexene, acetonitrile, solid catalyst nitrogen-doped carbon nanotubes, and o-dichlorobenzene (internal standard) into a closed reaction kettle and mix to form a mixed suspension, which is then ultrasonically treated to form a suspension (frequency 40KHz, power 200W and time 15min). Among them, the volume ratio of acetonitrile to cyclohexene is 2:1, and the weight ratio of nitrogen-doped carbon nanotubes (3.96% nitrogen content, atomic content) as a catalyst to cyclohexene is 0.00617:1. The mixed suspension was heated to 80° C. with stirring, and oxygen was introduced. Oxygen is continuously replenished and kept at a constant pressure of 1.0 MPa through a pressure stabilizing device and a flow meter connected to an oxygen source during the reaction process because the oxygen is continuously consumed in a stoichiometric ratio. After reacting for 4 hours, discharge the liquid-solid phase mixture from the bottom of the reactor, and filter it to obtain a sol...

Embodiment 2～5

[0026] Add 8.1g of cyclohexene, acetonitrile, solid catalyst nitrogen-doped carbon nanometer, and o-dichlorobenzene (internal standard) into a closed reaction kettle and mix to form a mixed suspension, which is then ultrasonically treated to form a suspension (frequency of 40KHz, power 200W and time 15min). Wherein, the volume ratio of acetonitrile to cyclohexene is 2:1, and the weight ratio of nitrogen-doped carbon nanotubes as catalyst to cyclohexene is 0.00617:1. The mixed suspension was heated to the temperature shown in Table 1 respectively under stirring, and oxygen gas was introduced. Oxygen is continuously replenished and kept at a constant pressure of 1.0 MPa through a pressure stabilizing device and a flow meter connected to an oxygen source during the reaction process because the oxygen is continuously consumed in a stoichiometric ratio. After reacting for 4h, the liquid mixture was analyzed to measure the conversion rate of cyclohexene and the selectivity of cyclo...

Embodiment 6～9

[0030]Add 8.1g of cyclohexene, acetonitrile, solid catalyst nitrogen-doped carbon nanotubes, and o-dichlorobenzene (internal standard) into a closed reaction kettle and mix to form a mixed suspension, which is then ultrasonically treated to form a suspension (frequency 40KHz, power 200W and time 15min). Wherein, the volume ratio of acetonitrile to cyclohexene is 2:1, and the weight ratio of nitrogen-doped carbon nanotubes as catalyst to cyclohexene is 0.00617:1. The mixed suspension was heated to 80° C. under stirring, and oxygen gas was introduced. Because the reaction process constantly consumes oxygen in a stoichiometric ratio, oxygen is constantly replenished and kept constant at 1.0 MPa by a pressure stabilizing device and a flow meter connected to an oxygen source during the reaction, and the reaction is performed at the time shown in Table 2. The results of the conversion of cyclohexene and the selectivity of cyclohexenone are shown in Table 2. Analysis of the data in...

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Abstract

The invention discloses a method for synthesizing cyclohexenone through the catalytic oxidation of cyclohexene. The method comprises the following steps: adding reactants including cyclohexene, a solvent and a solid catalyst into a reactor to mix, and carrying out ultrasonic processing on the obtained mixture so as to form suspension liquid, wherein the solid catalyst is a carbon material, the carbon material is a carbon nanotube, a nitrogen-doped carbon nanotube, diamond, graphite or activated carbon, and the solvent is an organic solvent mutually soluble in cyclohexene and oxidation products thereof; heating the suspension liquid to 40-150 DEG C, feeding oxygen or air as an oxidant, and reacting 0.1-20 h at a pressure of 0.1-5 MPa; separating the obtained reaction mixture so as to obtain the solid catalyst and a liquid mixture containing a reaction product, unreacted reactants and the solvent; carrying out separation and purification to obtain a product cyclohexenone, mixing residual mother liquor with reaction raw materials and then returning the mixture to the reactor. According to the invention, the used nonmetal catalyst is non-corrosive, environment-friendly, cheap, reusable, high in reaction selectivity, and good in activity.

Description

technical field [0001] The invention relates to a method for synthesizing cyclohexenone, in particular to a method for synthesizing cyclohexenone by catalytic oxidation of cyclohexene, belonging to the technical field of organic synthesis applications. Background technique [0002] It is one of the important chemical synthesis processes to oxidize organic compounds containing double bonds at the allylic position to obtain α, β‐unsaturated carbonyl compounds or allyl alcohol compounds. The generated hydroxyl or carbonyl products can be widely used as organic compounds in organic synthesis. It is an important intermediate in the production of pharmaceuticals, spices, food additives, agricultural chemical products, etc. The research on the catalytic performance of the catalyst used in the allylic oxidation and the selection of the reaction conditions are the key to this kind of reaction. The allylic oxidation product of cyclohexene, cyclohexenone, is an important chemical inte...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/603C07C45/34
CPCC07C45/34C07C2601/16C07C49/603
Inventor 余皓彭峰曹永海王红娟
Owner SOUTH CHINA UNIV OF TECH
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