Method for selectively oxidizing cumene compounds

A technology of compound and cumene, which is applied in the field of organic chemical industry and fine organic synthesis, can solve the problems of reduced environmental compatibility and biocompatibility, product transition metal pollution, and reduced safety, so as to achieve novel reaction methods and avoid toxicity and harm The use of organic solvents, the effect of easy operation

Active Publication Date: 2019-11-08
ZHEJIANG UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this oxidation process, since the intermediate product 2-phenyl-2-propyl hydroperoxide and its derivatives have good stability and are difficult to transform, the selectivity of the target product 2-phenyl-2-propanol and its derivatives not tall
At the same time, due to the presence of a higher concentration of peroxide in the reaction system, the safety of the oxidation system is also reduced.
In addition, the current oxidation process of some cumene and its derivatives also uses a large number of organic solvents and transition metal catalysts that are toxic and harmful to the environment and organisms, which not only reduces the environmental compatibility and biocompatibility of the reaction process, but also causes certain Degree of transition metal contamination of products (Inorganica Chimica Acta 2019,486:425-434; Applied Surface Science2017,419:98-106; Advanced Synthesis&Catalysis 2011,353:147-154)

Method used

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  • Method for selectively oxidizing cumene compounds
  • Method for selectively oxidizing cumene compounds
  • Method for selectively oxidizing cumene compounds

Examples

Experimental program
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Effect test

Embodiment 1

[0030] In a 100mL agate ball mill jar, 1.20g (10mmol) cumene, 0.0004g (0.0005mmol) 5,10,15,20-tetrakis(4-chlorophenyl) porphyrin iron (II), 2.57g (20mmol ) 70% t-butyl hydroperoxide aqueous solution and 3.60 g of anhydrous sodium sulfate were mixed evenly, and the ball milling tank was sealed. At room temperature, the ball milling reaction was carried out at 600 rpm for 12.0 h, and the ball milling was stopped every 1.0 h to release the gas in the ball milling tank. After the reaction was completed, the resulting reaction mixture was dissolved in 30 mL of absolute ethanol, and stirred at room temperature for 30.0 min. Filter, wash the obtained filter cake with 2×10 mL of absolute ethanol, combine the ethanol solution, and dilute the obtained ethanol solution to 100 mL. Pipette 10 mL of the resulting solution, add internal standard 2-naphthoic acid, and perform liquid chromatography analysis. Cumene conversion rate 33%, 2-phenyl-2-propanol selectivity 89%, acetophenone select...

Embodiment 2

[0032] In a 100mL agate ball mill jar, 1.20g (10mmol) cumene, 0.0020g (0.0025mmol) 5,10,15,20-tetrakis(4-chlorophenyl) porphyrin iron (II), 2.57g (20mmol ) 70% t-butyl hydroperoxide aqueous solution and 3.60 g of anhydrous sodium sulfate were mixed evenly, and the ball milling tank was sealed. At room temperature, the ball milling reaction was carried out at 600 rpm for 12.0 h, and the ball milling was stopped every 1.0 h to release the gas in the ball milling tank. After the reaction was completed, the resulting reaction mixture was dissolved in 30 mL of absolute ethanol, and stirred at room temperature for 30.0 min. Filter, wash the obtained filter cake with 2×10 mL of absolute ethanol, combine the ethanol solution, and dilute the obtained ethanol solution to 100 mL. Pipette 10 mL of the resulting solution, add internal standard 2-naphthoic acid, and perform liquid chromatography analysis. Cumene conversion rate 41%, 2-phenyl-2-propanol selectivity 90%, acetophenone select...

Embodiment 3

[0034] In a 100mL agate ball mill jar, 1.20g (10mmol) cumene, 0.0008g (0.0010mmol) 5,10,15,20-tetrakis(4-chlorophenyl) porphyrin iron (II), 2.57g (20mmol ) 70% t-butyl hydroperoxide aqueous solution and 3.60 g of anhydrous sodium sulfate were mixed evenly, and the ball milling tank was sealed. At room temperature, the ball milling reaction was carried out at 600 rpm for 12.0 h, and the ball milling was stopped every 1.0 h to release the gas in the ball milling tank. After the reaction was completed, the resulting reaction mixture was dissolved in 30 mL of absolute ethanol, and stirred at room temperature for 30.0 min. Filter, wash the obtained filter cake with 2×10 mL of absolute ethanol, combine the ethanol solution, and dilute the obtained ethanol solution to 100 mL. Pipette 10 mL of the resulting solution, add internal standard 2-naphthoic acid, and perform liquid chromatography analysis. Cumene conversion rate 38%, 2-phenyl-2-propanol selectivity 91%, acetophenone select...

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Abstract

The invention relates to a method for selectively oxidizing cumene compounds, and the method comprises the following steps: placing cumene compounds shown in a formula (I), an iron porphyrin catalyst,an oxidant and a dispersant into a ball milling tank, sealing the ball milling tank, performing ball milling for 3 to 24 hours at a rotating speed of 100 to 800 rpm at room temperature, stopping ballmilling once every 1 to 3 hours in the ball milling process, discharging gases in the ball milling tank, finishing the reaction, and performing post-treatment on a reaction mixture to obtain product2-phenyl-2-propanol compound shown in a formula (II); according to the invention, the oxidation conversion of the cumene and derivatives thereof is realized through solid-phase ball milling, the reaction mode is novel, the operation is convenient, and the energy consumption is low; the method needs no organic solvent, thus effectively avoiding the use of toxic and harmful organic solvents and being green and environment-friendly; has low peroxide content and high safety factor, and high 2-phenyl-2-propanol and derivative selectivity and meets the social requirements of the current green chemical process, environmental compatibility chemical process and biological compatibility chemical process.

Description

technical field [0001] The invention relates to a new method for preparing 2-phenyl-2-propanol compounds through selective oxidation of cumene compounds, which belongs to the field of organic chemical industry and fine organic synthesis. Background technique [0002] 2-Phenyl-2-propanol and its derivatives are an important class of fine chemical intermediates, widely used in the synthesis of fine chemical products such as medicines, pesticides, dyes, spices (WO 2017068412; WO 2015135094; Chemical Engineering Science 2018, 177: 391-398; ChemCatChem 2014, 6:555-560). At present, the synthesis of 2-phenyl-2-propanol and its derivatives is mainly based on cumene and its derivatives as raw materials, and oxygen is used as an oxidant, and it is prepared by oxidation reaction (ACS Sustainable Chemistry & Engineering 2019, 7:7708- 7715; ChemCatChem 2018, 10:198-205). In this oxidation process, since the intermediate product 2-phenyl-2-propyl hydroperoxide and its derivatives have ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C29/48C07C33/20C07C41/26C07C43/23C07C201/12C07C205/19C07C51/367C07C65/01C07C213/00C07C215/68C07C33/46C07C37/00C07C39/11
CPCC07C29/48C07C41/26C07C201/12C07C51/367C07C213/00C07C37/002C07C33/20C07C43/23C07C205/19C07C65/01C07C215/68C07C33/46C07C39/11
Inventor 佘远斌胡梦云沈海民
Owner ZHEJIANG UNIV OF TECH
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