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Method for preparing propiophenone by biomimetic catalytic oxidation of n-propylbenzene with oxygen

A technology of oxygen oxidation and biomimetic catalysis, which is applied in the preparation of carbon-based compounds, chemical instruments and methods, and the preparation of organic compounds, can solve the problems of increasing operating costs and production costs, equipment investment and operating costs, and cost increases. Achieve the effects of increasing contact probability and reaction efficiency, reducing energy consumption and operating costs, and reducing energy consumption and costs

Inactive Publication Date: 2013-01-02
BEIJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Not only because of its toxicity and harmfulness, it may cause serious environmental pollution, but also because of the increase of energy consumption due to the recovery of solvents, which greatly increases operating costs and production costs;
[0014] (3) Due to the use of high-pressure reaction conditions, equipment investment and operating costs are doubled, and energy consumption is extremely high, especially making production potentially dangerous and greatly reducing safety;
[0015] (4) The use of loaded or polymerized metalloporphyrins results in high energy consumption, high discharge of three wastes, complex processes, and increased costs due to the complex preparation process
In addition, due to the large amount of catalyst used (480ppm), it must be separated and recovered after use, and the cost of separating and recovering the catalyst is high, energy consumption is large, and three wastes are discharged.
In addition, because the reaction using supported or polymerized metalloporphyrins is a heterogeneous reaction, the high catalytic activity of metalloporphyrins cannot be well reflected.
[0016] (5) The induction time of the reaction is too long (up to 3h), thus prolonging the entire reaction time, resulting in serious waste of energy and increase in operating costs

Method used

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  • Method for preparing propiophenone by biomimetic catalytic oxidation of n-propylbenzene with oxygen
  • Method for preparing propiophenone by biomimetic catalytic oxidation of n-propylbenzene with oxygen
  • Method for preparing propiophenone by biomimetic catalytic oxidation of n-propylbenzene with oxygen

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] In a 100mL three-necked flask, add 12.172g n-propylbenzene, 1ppm (0.07mg) tetraphenyliron porphyrin (i.e. R in formula (I) 11 for H, R 12 for H, R 13 for H, M 1 Fe), 10ppm (0.86mg) four-(p-chlorophenyl) cobalt porphyrin (that is, R in the formula (I) 11 for H, R 12 for H, R 13 for Cl, M 1 For Co), oxygen was introduced at a flow rate of 40 mL / min, the reaction was initiated at 140°C, and the reaction was carried out at 90°C for 6h. The reacted mixture was distilled under reduced pressure to obtain propiophenone, the conversion rate of n-propylbenzene was 79.6%, the yield of propiophenone was 70.4%, and the purity was 99.1%.

Embodiment 2

[0033] In a 100mL three-necked flask, add 12.156g n-propylbenzene, 5ppm (0.38mg) tetra-phenylmanganese porphyrin chloride (i.e. R in formula (II) 21 for H, R 22 for H, R 23 for H, M 2 is Mn, X is Cl), 5ppm (0.44mg) tetrakis-(o-methoxyphenyl) cobalt porphyrin chloride (that is, R in the formula (II) 21 for OCH 3 , R 22 for H, R 23 for H, M 2 is Co, X is Cl), oxygen was introduced at a flow rate of 40 mL / min, the reaction was initiated at 140°C, and the reaction was carried out at 90°C for 7h. The reacted mixture was distilled under reduced pressure to obtain propiophenone, the conversion rate of n-propylbenzene was 81.4%, the yield of propiophenone was 71.6%, and the purity was 99.8%.

Embodiment 3

[0035] In a 100mL three-necked flask, add 12.132g n-propylbenzene, 1ppm (0.15mg) μ-oxygen-binuclear tetra-phenyliron porphyrin (i.e. R in formula (III) 31 for H, R 32 for H, R 33 for H, M 3 , M 4 Fe), 5ppm (0.88mg) μ-oxygen-binuclear four-(p-chlorophenyl) cobalt porphyrin (that is, R in formula (III) 31 for H, R 32 for H, R 33 for Cl, M 3 , M 4 For Co), oxygen was introduced at a flow rate of 50 mL / min, the reaction was initiated at 140°C, and the reaction was carried out at 80°C for 7h. The reacted mixture was distilled under reduced pressure to obtain propiophenone, the conversion rate of n-propylbenzene was 68.3%, the yield of propiophenone was 61.4%, and the purity was 99.6%.

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Abstract

The invention relates to a method for preparing propiophenone by biomimetic catalytic oxidation of n-propylbenzene with oxygen, comprising the following steps: taking n-propylbenzene as the raw material, selecting any one of 1-30ppm of mononuclear metalloporphyrin and mu-oxo-dinuclear metalloporphyrin or the composition of the two substances as the catalyst under normal pressure and in the absence of solvents, introducing oxygen at the flow rate of 10-60mL / min, initiating reaction at 140-160 DEG C and then carrying out reaction at 70-110 DEG C for 4-10h, thus obtaining the propiophenone. In the method, the way of high temperature quick initiation and low temperature reaction is adopted, thus minimizing the reaction initiation time, greatly shortening the reaction time, improving the reaction efficiency, reducing the energy consumption, lowering the operation cost and improving the reaction safety.

Description

technical field [0001] The invention relates to a method for preparing aromatic ketones, in particular to a method for preparing propiophenone by biomimetic catalytic oxygen oxidation of n-propylbenzene. Background technique [0002] Propiophenone is an important intermediate in organic synthesis, widely used in the synthesis of medicines, pesticides, dyes, flavors and fragrances, perfumes, etc. At present, the preparation methods of propiophenone mainly include Friedel-Crafts acylation method, 1-phenylpropanol oxidation method and n-propylbenzene oxidation method, etc., wherein the n-propylbenzene oxidation method is divided into chemical oxidation method and molecular oxygen oxidation method, and oxygen is used as cheap The oxidant which is easy to obtain, clean and pollution-free, and has good atom economy, and the method for preparing propiophenone by direct oxidation of n-propylbenzene with oxygen has significant advantages over other methods. [0003] The biomimetic c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/76C07C45/36B01J31/22
Inventor 佘远斌赵文伯孙志成钟儒刚
Owner BEIJING UNIV OF TECH
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