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Synthesis and application of novel catalyst used in preparation of arone by carrying out catalytic oxidation on ethylbenzene and derivative of ethylbenzene

A catalytic oxidation and catalyst technology, applied in the direction of organic compound/hydride/coordination complex catalyst, carbon-based compound preparation, organic compound preparation, etc., can solve environmental pollution and other problems, achieve reduced production costs and high conversion rate , cost reduction effect

Inactive Publication Date: 2014-12-10
UNIV OF JINAN
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Molecular oxygen, as a green oxygen source, is not only cheap and easy to obtain, but also solves serious environmental pollution problems to a greater extent

Method used

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  • Synthesis and application of novel catalyst used in preparation of arone by carrying out catalytic oxidation on ethylbenzene and derivative of ethylbenzene
  • Synthesis and application of novel catalyst used in preparation of arone by carrying out catalytic oxidation on ethylbenzene and derivative of ethylbenzene
  • Synthesis and application of novel catalyst used in preparation of arone by carrying out catalytic oxidation on ethylbenzene and derivative of ethylbenzene

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Experimental program
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Effect test

preparation example Construction

[0036] Preparation and characterization of the above catalysts

[0037] The preparation method of the above-mentioned catalyst I is as follows: 3,3',4,4'-benzophenone tetracarboxylic dianhydride is used as raw material, and it is mixed with hydroxylamine hydrochloride at 115°C, DMF is used as a solvent, and pyridine is used as an acid-binding agent. The reaction was carried out for three hours, and then the pyridine hydrochloride formed by the reaction was filtered, recrystallized from acetonitrile, and then the target product was separated by plate chromatography. Pale yellow solid with a purity of 97% and a yield of 75%. The NMR characterization of the prepared catalyst is as follows: 1 HNMR (d-DMSO, ppm): 12.255 (1H, C=N-OH), 10.901~10.920 (2H, N-OH), 7.450~8.042 (6H, Ph).

[0038] The preparation method of the above-mentioned catalyst II is similar to that of I, that is, using ortho-xylene as the starting material, dimethylphenone is obtained through the Friedel-Crafts a...

Embodiment 1

[0041]Put 2 mL (16 mmol) of ethylbenzene, 10 mL of acetonitrile, and 10 mol% of catalyst I into a 70 mL stainless steel polytetrafluoroethylene sealed autoclave, replace the air in the autoclave with oxygen three times, and seal it. Turn on the stirring, and the oil bath heating starts to heat up. After reaching the set temperature of 80°C, inject oxygen to 0.3 MPa, and start timing. During the reaction process, if the pressure drops, supplement oxygen at any time to keep the oxygen pressure at 0.3MPa. After reacting for 10 h, it was left to cool to room temperature, and the reactor was depressurized, and the oxidation product was analyzed by GC. In this example, the separation of the liquid phase mixture and the purification of acetophenone adopt conventional vacuum distillation method, and acetophenone with a purity of 99.0% can be obtained. The conversion rate of ethylbenzene was 80.5%, the selectivity of acetophenone was 92.3%, and the yield was 74.3%.

Embodiment 2

[0043] The operation method is the same as in Example 1, except that acetonitrile is changed to acetone, the conversion rate of ethylbenzene is 42.3%, the selectivity of product acetophenone is 90.1%, and the yield is 38.1%.

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Abstract

The invention relates to synthesis and application of a novel catalyst used in preparation of arone by carrying out catalytic oxidation on ethylbenzene and a derivative of ethylbenzene. According to the synthesis, on the basis of a substrate being 16mmol of ethylbenzene or a derivative of ethylbenzene, 1-15mol% of novel catalyst with a double structure of N-hydroxyphthalimide (NHPI) and ketoxime is used as a catalyst; reaction is carried out in the presence of the novel catalyst without any catalyst promoter to obtain a main product acetophenone or other arones, wherein the oxygen pressure is 0.1-0.5 MPa, the reaction temperature is 20-100 DEG C, the reaction time is 1-12h, the ethylbenzene conversion rate is up to 80.5%,the selectivity of the product acetophenone is up to 92.3% and the yield can be up to 74.3%. The catalytic system used in the invention uses molecular oxygen as an oxidant, no catalyst promoter is added and the reaction conditions are mild, so that the cost is reduced, the yield is improved, the application range is wide and a good method is provided to the preparation of acetophenone or other arones.

Description

technical field [0001] The present invention relates to a preparation method of aromatic ketones, in particular to the preparation of aromatic ketones by synthesizing a novel catalyst having a double structure of N-hydroxyphthalimide (NHPI) and ketoxime. A new approach to keto. Background technique [0002] Acetophenone is an important intermediate in organic synthesis, widely used in the synthesis of medicines, pesticides, dyes, spices, etc. It is also a good solvent for cellulose ethers, cellulose esters and resins, and a plasticizer for plastics. application prospects. In the traditional production process of acetophenone, it is mainly produced by Friedel-Crafts alkylation homogeneous reaction, which is produced by the reaction of benzene with acetyl chloride, acetic anhydride or acetic acid under the catalysis of stoichiometric anhydrous aluminum trichloride. This method will generate a large amount of by-product HCl, which will easily cause serious corrosion to produc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/48B01J31/02C07C45/36C07C49/78C07C49/786C07C49/633
CPCB01J31/0247B01J2231/70C07C45/36C07D209/48C07C49/78C07C49/786C07C49/633
Inventor 王秋芬郑庚修许燕杨倩姜守相赵晶晶
Owner UNIV OF JINAN
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