Method for synthesizing cyclohexanone by accelerated hydrogenation of aromatic compounds using carbon dioxide

A technology of aromatic compounds and carbon dioxide, which is applied in the synthesis field of aromatic compounds to synthesize cyclohexanone, can solve problems such as low conversion rate, complex products, harsh reaction conditions, etc., and achieve the effect of alleviating environmental problems

Active Publication Date: 2021-07-16
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the relatively mature industrial processes for producing cyclohexanone mainly include the oxidation of cyclohexane and the hydrogenation of phenol, but these two production processes have great problems, such as the conversion rate of the reaction is too low, the product Complicated and extremely harsh reaction conditions and other issues

Method used

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  • Method for synthesizing cyclohexanone by accelerated hydrogenation of aromatic compounds using carbon dioxide
  • Method for synthesizing cyclohexanone by accelerated hydrogenation of aromatic compounds using carbon dioxide
  • Method for synthesizing cyclohexanone by accelerated hydrogenation of aromatic compounds using carbon dioxide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] The catalyst used in this example is commercial 10% Pd / C.

[0041] Reaction steps: Accurately weigh 10 mg of 10% Pd / C catalyst and 0.25 mmol of nitrobenzene into a reaction flask, and then add 5 mL of water as a solvent. and filled with CO through the air bag 2 and H 2(molar ratio is 1:3), add CO 2 and H 2 The post-reaction pressure is 0.1 MPa, the reaction temperature is 35°C, and after 6 hours of reaction, the yield of the final product cyclohexanone can reach 90%.

[0042] figure 1 for the ligand CO in the gas phase 2 With the help of palladium nanoparticles catalyzed hydrogenation of nitrobenzene to produce cyclohexanone, the gas phase ligand CO 2 With the help of nitrobenzene and under the action of Pd / C catalyst, the nitro group in nitrobenzene is reduced to amine group to generate aniline, and then the benzene ring in aniline undergoes hydrogenation reaction and hydrolyzes to remove ammonia with the help of water , which is further reduced to cyclohexanone...

Embodiment 2

[0047] The catalyst used in this example is commercial 10% Pd / C.

[0048] Accurately weigh 10 mg of 10% Pd / C catalyst and 0.25 mmol of aniline into the reaction flask, and then add 5 mL of water as a solvent. and filled with CO through the air bag 2 and H 2 (molar ratio is 1:3), add CO 2 and H 2 The post-reaction pressure is 0.1 MPa, the reaction temperature is 35° C., and after 6 hours of reaction, the yield of the final product cyclohexanone can reach 28%.

Embodiment 3

[0050] The catalyst used in this example is commercial 10% Pd / C.

[0051] Accurately weigh 10 mg of 10% Pd / C catalyst and 0.25 mmol of N-methylaniline into the reaction flask, and then add 5 mL of water as a solvent. and filled with CO through the air bag 2 and H 2 (molar ratio is 1:3), add CO 2 and H 2 The final reaction pressure is 0.1 MPa, the reaction temperature is 35°C, and the yield of the final product can reach 99% after 6 hours of reaction.

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Abstract

The present invention relates to the method for using carbon dioxide to accelerate the hydrogenation of aromatic compounds to synthesize cyclohexanone, the method is by CO 2 Soluble in water to form H 2 CO 3 Molecules, and then by forming hydrogen bonds with aromatic nitro compounds (such as nitrobenzene), it accelerates the adsorption to the surface of metal nanoparticles, and then the metal nanoparticles activate hydrogen to reduce it to the corresponding cyclohexanone. The method efficiently utilizes the greenhouse gas CO 2 , turning waste into treasure, the method involved in the invention not only has the characteristics of simple process operation, green safety and low cost, but also can realize large-scale continuous production, and has obvious economic and environmental benefits.

Description

technical field [0001] The invention relates to a method for synthesizing cyclohexanone from an aromatic compound, in particular to a method for accelerating the hydrogenation of an aromatic compound to synthesize cyclohexanone by using carbon dioxide with the help of metal nanoparticles. Background technique [0002] For more than a hundred years, the environmental pollution caused by the extensive use of non-renewable fossil energy such as coal and oil has greatly affected the survival and development of people. Among them, the CO emitted by the combustion of fossil fuels 2 It will lead to serious global environmental problems, such as global average temperature rise, sea level rise, and irreversible increase in ocean acidity. Although carbon capture and storage technologies have been proposed for large-scale power plants, there are still many problems to be solved. Therefore, to explore and develop CO 2 The rational reuse of the material has aroused widespread concern a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/00C07C49/403
CPCC07C45/00C07C2601/14C07C49/403
Inventor 李新昊赵天健陈接胜张军军刘永兴王梦影
Owner SHANGHAI JIAO TONG UNIV
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