Method for preparing alpha-tetralin ketone by catalyzed oxidation tetrahydronaphthalene

A technology of tetralin and tetralone, which is applied in the preparation of carbon-based compounds, chemical instruments and methods, preparation of organic compounds, etc., can solve problems such as low efficiency, and achieve good selectivity, mild reaction conditions, and reaction conversion. high rate effect

Inactive Publication Date: 2008-05-14
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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Problems solved by technology

However, most of the catalysts used in this method are metal

Method used

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  • Method for preparing alpha-tetralin ketone by catalyzed oxidation tetrahydronaphthalene

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Experimental program
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Effect test

Embodiment 1

[0023] Embodiment 1: tetralin air oxidation

[0024] In a 250 ml three-necked flask, put 100 ml of tetralin, 1.6 g of N-hydroxyphthalimide and 15.7 g of 1-fluoro-9,10-anthraquinone; heat up to 80°C while stirring, and use Insert the air guide tube in the reaction solution, feed air continuously, the air flow rate is 50 ml / min, and the excess air is discharged from the serpentine condenser tube, react for 15 hours, and analyze the product composition with a gas chromatograph. As a result, the conversion of tetralone was 90%, and the selectivity of α-tetralone was 93%.

Embodiment 2

[0025] Embodiment 2: tetralin oxygen oxidation

[0026] In a 250 ml autoclave, put 50 ml of tetralin, 2.0 gram of N-hydroxyphthalimide and 1.0 gram of 2-ethyl-9,10-anthraquinone; seal the autoclave and heat up to When the temperature in the kettle was 80°C, feed oxygen until the oxygen pressure in the kettle reached 0.5 MPa, react for 5 hours, and analyze the composition of the product with a gas chromatograph. As a result, the conversion rate of α-tetralin was 93%, and the selectivity of α-tetralone was 96%.

Embodiment 3

[0027] Embodiment 3: tetralin oxygen oxidation

[0028] Tetralin was catalyzed and oxidized in the same manner as in Example 2, except for the quinone compound used. The reaction results are shown in Table 1.

[0029] Table 1: Reaction results of various quinones or diphenols for tetralin oxidation

[0030]

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Abstract

The invention relates to a method of preparing Alpha-tetralone by catalysis and oxidation of tetralin, comprising following steps: quinonyl compounds and N-hydroxyphthalimade are combined to be double-component non-metallic catalysis system; air or oxygen is used as oxygen source to prepare Alpha-tetralone through catalysis and oxidation of tetralin with high efficiency under a certain condition; the applied quinonyl compounds comprise organic compounds, such as benzoquinones, naphthoquinones and anthraquinones and substituted derivatives of the organic compounds. The invention has the advantages of mild preparation conditions for the method of preparing the Alpha-tetralone, high efficiency and environmental friendliness.

Description

technical field [0001] The invention relates to a method for preparing α-tetralone by catalyzing the oxidation of tetralin, that is, a non-metallic composite catalytic system composed of two kinds of organic substances, specifically, it is composed of quinones or can generate α-tetralone under oxygen conditions. Diphenolic organic compounds of quinone compounds act as catalysts in cooperation with N-hydroxyphthalimide, using air or oxygen as the oxygen source, under certain conditions, efficiently catalyze the oxidation of tetralin to prepare α-tetrahydro naphthalene. Background technique [0002] α-tetralone is an important intermediate in the production of pharmaceuticals and agricultural chemicals, especially for the insecticide carbaryl, the contraceptive drug 18-methyl norethindrone and the antidepressant sertraline synthesis. As an important pharmaceutical and agricultural chemical intermediate, the market demand for α-tetralone exceeds 5 billion RMB per year. Howev...

Claims

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Application Information

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IPC IPC(8): C07C45/36C07C49/447B01J31/02
Inventor 徐杰张巧红马红
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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