Method for preparing aromatic hydrocarbon alpha ketone carbonyl compound through continuous visible light catalytic molecular oxygen oxidation in micro-channel reactor

A technology of microchannel reactor and visible light, which is applied in the preparation of carbon-based compounds, organic compounds, chemical instruments and methods, etc., can solve the problems of not conforming to the principle of economical green, not suitable for obtaining, and high cost, so as to reduce energy and labor , low cost, and the effect of reducing emissions

Inactive Publication Date: 2020-09-08
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] 3. Alcohol oxidation method, the raw material of this method is 2-methyl-1-phenyl-1-propanol, which is not suitable for obtaining, and most of the catalysts are noble metal ligands, and the required cost is relatively high
[0008] Generally speaking, the current preparation methods of isobutyrophenone not only consume a lot of energy, but also do not conform to the principle of economical green

Method used

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  • Method for preparing aromatic hydrocarbon alpha ketone carbonyl compound through continuous visible light catalytic molecular oxygen oxidation in micro-channel reactor
  • Method for preparing aromatic hydrocarbon alpha ketone carbonyl compound through continuous visible light catalytic molecular oxygen oxidation in micro-channel reactor
  • Method for preparing aromatic hydrocarbon alpha ketone carbonyl compound through continuous visible light catalytic molecular oxygen oxidation in micro-channel reactor

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Experimental program
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Embodiment 1

[0027] Add 0.67g of isobutylbenzene, 0.51g of tert-butyl nitrite, and 0.41g of N-hydroxyphthalimide into the test tube, and add 15ml of acetonitrile into the test tube, mix well in a constant temperature stirrer at 60°C and dissolve completely. The mixed solution is pumped into the microchannel reactor through the feed pump, and oxygen is introduced at the same time. The molar ratio of isobutylbenzene: N-hydroxyphthalimide: tert-butyl nitrite is 2:1: 2. The reaction pressure was controlled to be 5 bar, the light intensity was 475 nm, the temperature was 50° C., and the reaction time of the reactants in the microchannel reactor was 6.45 min to obtain isobutyrophenone with a comprehensive yield of 71.6%. The acetonitrile is refined and reused, and the residue is refined to recover the catalyst.

Embodiment 2

[0029] Add 0.67g of isobutylbenzene, 0.51g of tert-butyl nitrite, and 0.41g of N-hydroxyphthalimide into the test tube, and add 15ml of acetonitrile into the test tube, mix well in a constant temperature stirrer at 60°C and dissolve completely. The mixed solution is pumped into the microchannel reactor through the feed pump, and oxygen is introduced at the same time. The molar ratio of isobutylbenzene: N-hydroxyphthalimide: tert-butyl nitrite is 2:1: 2. The reaction pressure was controlled to be 5 bar, the light intensity was 475 nm, the temperature was 70° C., and the reaction time of the reactants in the microchannel reactor was 2.25 min to obtain isobutyrophenone with a comprehensive yield of 86.3%. The acetonitrile is refined and reused, and the residue is refined to recover the catalyst.

Embodiment 3

[0031] Add 0.67g of isobutylbenzene, 0.51g of tert-butyl nitrite, 0.41g of N-hydroxyphthalimide into the test tube, and add 20ml of acetonitrile into the test tube, mix well in a constant temperature stirrer at 60°C and dissolve completely. The mixed solution is pumped into the microchannel reactor through the feed pump, and oxygen is introduced at the same time. The molar ratio of isobutylbenzene: N-hydroxyphthalimide: tert-butyl nitrite is 2:1: 2. The reaction pressure was controlled to be 5 bar, the light intensity was 475 nm, the temperature was 80° C., and the reaction time of the reactants in the microchannel reactor was 1.17 min to obtain isobutyrophenone with a comprehensive yield of 63.5%. The acetonitrile is refined and reused, and the residue is refined to recover the catalyst.

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Abstract

The invention provides a method for preparing aromatic hydrocarbon alpha ketone carbonyl compounds through continuous visible light catalytic molecular oxygen oxidation in a micro-channel reactor, andbelongs to the technical field of continuous flow photocatalytic synthesis. According to the method, molecular oxygen is used as an oxidizing agent, N-hydroxyphthalimide and tert-butyl nitrite are used as catalysts, and isobutylbenzene is used for preparing isobutyryl benzene under the condition of visible light. The product isobutyryl benzene has photosensitive activity, the catalytic reaction is carried out under visible light, and the highest yield of the obtained isobutyryl benzene can reach 86.3%. The reaction conditions are mild, the isobutyryl benzene can be efficiently prepared without additional metal, alkali and the like, and the operation is simple. With application of the micro-channel reactor, the reaction time is greatly shortened, the mass and heat transfer efficiency is obviously improved, the energy consumption is reduced, and three-waste emission is reduced.

Description

technical field [0001] The invention relates to the technical field of photocatalytic synthesis application, in particular to a method for preparing aryl alpha ketone carbonyl compounds by continuous visible light catalytic molecular oxygen oxidation in a microchannel reactor. [0002] technical background [0003] As an important chemical synthesis intermediate, isobutylbenzene is mainly used as a photosensitizer intermediate, which can further synthesize isobutyrophenone. Oxygen is used in the oxidation of isobutylbenzene as a clean and green source of a wide range of oxidants. As early as 1999, Shende et al. reported a method of preparing isobutylbenzene in a bubble column reactor using sodium carbonate as a catalyst and oxygen as an oxygen source. Butyrophenone method. (Indian, 183049, 1999) In the past five years, researchers have reported a large number of methods for preparing isobutyrophenone by oxidizing isobutylbenzene with molecular oxygen. Kai-Jian et al reporte...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/36C07C49/76B01J19/00
CPCB01J19/0093C07C45/36C07C49/76
Inventor 孟庆伟恽磊李文欣
Owner DALIAN UNIV OF TECH
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