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Method for synthesizing cumene hydroperoxide through catalytic oxidation of cumene by zinc (II) porphyrin

A porphyrin-catalyzed technology for oxidizing cumene and cumene hydrogen peroxide, which can be used in the preparation of peroxy compounds, chemical instruments and methods, preparation of organic compounds, etc., and can solve the problem that the selectivity of cumene hydrogen peroxide is not high enough , The conversion rate of cumene is not ideal, the safety factor is low, etc., to achieve the effect of improving atomic economy, small environmental impact, and reducing emissions

Pending Publication Date: 2020-11-17
ZHEJIANG UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The main problem of existence is that the conversion rate of cumene is not ideal, the selectivity of cumene hydroperoxide is not high enough, the reaction temperature is high, and the safety factor is low

Method used

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  • Method for synthesizing cumene hydroperoxide through catalytic oxidation of cumene by zinc (II) porphyrin
  • Method for synthesizing cumene hydroperoxide through catalytic oxidation of cumene by zinc (II) porphyrin

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Experimental program
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Effect test

Embodiment 52

[0023] Embodiment 52 is a scale-up experiment.

Embodiment 1

[0025] In a 25mL reaction tube, disperse 0.0009g (0.001mmol) 5,10,15,20-tetrakis(4-carboxyphenyl)porphyrin zinc (II) in 1.2019g (10mmol) cumene, stir and heat up to 80°C, feed oxygen (0.20MPa). At 80°C, the reaction was stirred at 800rpm for 8.0h. After completion of the reaction, cool to room temperature, add 1.3115g (5.00mmol) triphenylphosphine (PPh 3 ), stirred at room temperature for 40min to reduce the generated peroxide. Using acetone as solvent, the resulting reaction mixture was adjusted to 50 mL. Pipette 10 mL of the resulting solution, and use naphthalene as an internal standard for gas chromatographic analysis. The conversion rate of cumene was 16.5%, the selectivity of 2-phenyl-2-propanol was 0.9%, the selectivity of acetophenone was 0%, the selectivity of cumene hydroperoxide was 99.1%, and the formation of benzoic acid was not detected.

Embodiment 2

[0027] In a 25mL reaction tube, disperse 0.0009g (0.001mmol) 5,10,15,20-tetrakis(3-carboxyphenyl)porphyrin zinc (II) in 1.2019g (10mmol) cumene, stir and heat up to 80°C, feed oxygen (0.20MPa). At 80°C, the reaction was stirred at 800rpm for 8.0h. After completion of the reaction, cool to room temperature, add 1.3115g (5.00mmol) triphenylphosphine (PPh 3 ), stirred at room temperature for 40min to reduce the generated peroxide. Using acetone as solvent, the resulting reaction mixture was adjusted to 50 mL. Pipette 10 mL of the resulting solution, and use naphthalene as an internal standard for gas chromatographic analysis. The conversion rate of cumene was 9.1%, the selectivity of 2-phenyl-2-propanol was 0.0%, the selectivity of acetophenone was 0.0%, the selectivity of cumene hydroperoxide was 100%, and the formation of benzoic acid was not detected.

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Abstract

The invention relates to a method for synthesizing cumene hydroperoxide by catalytically oxidizing cumene with zinc (II) porphyrin, which comprises the following steps: dispersing zinc (II) porphyrinin cumene, wherein the amount of substance of zinc (II) porphyrin being 1*10<-4>% to 1% (mol / mol); and sealing the reaction system, introducing an oxidant, heating the reaction system to 40-100 DEG Cwhile stirring, keeping the set temperature and pressure, and stirring the reaction system to react for 3.0-24.0 hours, thereby obtaining the cumene solution of cumene hydroperoxide, which can be directly used in subsequent reactions; carrying out post-treatment on the reaction solution, and calculating the cumene conversion rate and the cumene hydroperoxide selectivity. The method has the advantages of low reaction temperature, high cumene conversion rate, high cumene hydroperoxide selectivity, few byproducts, small environmental influence and the like, and is low in reaction temperature andhigh in safety coefficient. The invention provides the efficient, feasible and safe method for synthesizing cumene hydroperoxide through catalytic oxidation of cumene.

Description

technical field [0001] The invention relates to a method for synthesizing cumene hydroperoxide by catalytically oxidizing cumene with zinc (II) porphyrin, and belongs to the field of organic catalysis and fine organic synthesis. Background technique [0002] The oxidation of cumene to prepare cumene hydroperoxide is an important conversion process in the chemical industry. The oxidized product cumene hydroperoxide is not only the basic raw material for the industrial production of phenol and acetone, but also the industrial production of propylene oxide for the production of epoxy Important oxidizing agent for propane. Globally, 90% of phenol is produced through the decomposition of cumene hydroperoxide, which also shows the importance of cumene hydroperoxide synthesis in the chemical industry (ACS Sustainable Chemistry & Engineering 2019, 7: 7708-7715; Chemical Engineering Science 2018, 177: 391-398). At present, the industrial production of cumene hydroperoxide is mainly...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C407/00C07C409/10B01J31/22
CPCC07C407/00C07C407/003B01J31/183B01J2231/70B01J2531/025B01J2531/26C07C409/10
Inventor 佘远斌叶宏亮胡梦云沈海民
Owner ZHEJIANG UNIV OF TECH
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