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Preparation method of azoxybenzene compound

A technology for oxidizing azobenzene and compounds, applied in the direction of organic chemistry, etc., can solve the problems of complicated operation, high cost, corrosion of concentrated alkali equipment, etc., and achieve the effects of reducing environmental pollution, reducing reaction cost and short reaction period

Inactive Publication Date: 2010-10-06
SHANXI UNIV
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Problems solved by technology

Its preparation is mainly realized by reducing the corresponding nitrobenzene compounds. There are many related reports at present, such as: 1. The hydrogenation method is used to reduce the nitrobenzene compounds. This method is environmentally friendly and the post-treatment is simple, but often It is necessary to use precious metals as catalysts, which requires strict equipment and hydrogen sources, which increases the cost of the experiment and complicates the process; 2. The reduction of nitrobenzene compounds with glucose in a concentrated alkali medium has easy-to-obtain raw materials and relatively high yields. 3. Using formaldehyde to reduce nitrobenzene compounds in concentrated alkali medium is economical and efficient, but the operation is more complicated, and the use of toxic formaldehyde makes it harmful to human body Larger, serious environmental pollution; 4. Reduction of nitrobenzene compounds with metals or metal compounds in organic solvents. This type of method has better selectivity and higher yields, but generally has higher costs, cumbersome operations, and three wastes. Difficult governance, serious environmental pollution and other issues

Method used

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  • Preparation method of azoxybenzene compound
  • Preparation method of azoxybenzene compound

Examples

Experimental program
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Effect test

Embodiment 1

[0017] Embodiment 1: the preparation of azobenzene oxide

[0018] 1. At room temperature, add 0.25g (2mmol) nitrobenzene, 0.4g (10mmol) solid NaOH and 4mL PEG-400 into a reaction flask equipped with an electromagnetic stirrer, a reflux condenser and a thermometer, then stir and heat up to 90°C Left and right reactions, traced by thin layer chromatography until the disappearance of raw materials, took 1h;

[0019] 2. Stop the reaction, dilute with water, place, filter with suction, and dry at room temperature to obtain a crude product;

[0020] 3. Recrystallized with absolute ethanol to obtain azobenzene oxide as a yellow solid with a yield of 85%, m.p.35-36°C, 1 HNMR (CDCl 3 , 300MHz) δ: 7.40-7.54 (m, 6H), 8.05-8.19 (t, 2H), 8.30-8.32 (d, 2H).

Embodiment 2

[0021] Embodiment 2: the preparation of 3,3'-azobenzene dichloride

[0022] 1. At room temperature, add 0.32g (2mmol) 3-chloronitrobenzene, 0.2g (5mmol) solid NaOH and 4mL PEG-400 into a reaction flask equipped with an electromagnetic stirrer, a reflux condenser and a thermometer, and then stir to raise the temperature Reaction at about 90°C, followed by thin-layer chromatography until the disappearance of the raw materials, took 1h;

[0023] 2. Stop the reaction, dilute with water, place, filter with suction, and dry under normal pressure to obtain a crude product;

[0024] 3. Recrystallized with absolute ethanol to obtain 3,3'-dichloroazobenzene oxybenzene as a light yellow solid with a yield of 90%, m.p.96-97°C, 1 HNMR (CDCl 3 , 300MHz) δ: 7.40-7.57 (m, 4H), 7.99-8.21 (m, 2H), 8.26-8.32 (m, 2H).

Embodiment 3

[0025] Embodiment 3: the preparation of 3,3'-azobenzene dichloride

[0026] 1. At room temperature, add 0.32g (2mmol) 3-chloronitrobenzene, 0.4g (10mmol) solid NaOH and 4mL PEG-400 into a reaction flask equipped with an electromagnetic stirrer, a reflux condenser and a thermometer, then stir to raise the temperature Reaction at about 90°C, followed by thin-layer chromatography until the disappearance of raw materials, took 0.5h;

[0027] 2. Stop the reaction, dilute with water, place, filter with suction, and dry under normal pressure to obtain a crude product;

[0028] 3. Recrystallized with absolute ethanol to obtain 3,3'-dichloroazobenzene oxybenzene as a light yellow solid with a yield of 90%, m.p.96-97°C, 1 HNMR (CDCl 3 , 300MHz) δ: 7.40-7.57 (m, 4H), 7.99-8.21 (m, 2H), 8.26-8.32 (m, 2H).

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Abstract

The invention provides a preparation method of an azoxybenzene compound, which comprises the steps of: adding a nitrobenzene compound, solid NaOH and PEG-400 into a reaction bottle at the room temperature; stirring and raising the temperature to 70-110 DEG C for reaction, and using thin-layer chromatography for tracking until the raw materials disappear; stopping reaction, adding water for dilution, standing still, leaching, and obtaining a crude product; and finally, carrying out recrystallization on the crude product by absolute ethyl alcohol, and obtaining the azoxybenzene compound. The method is environment-friendly, low in cost, simple in operation, short in reaction period and high in product yield.

Description

technical field [0001] The invention relates to an azobenzene compound, in particular to a preparation method of an azobenzene compound. Background technique [0002] Azobenzene compounds are an important class of fine organic chemical raw materials and synthetic intermediates, and are widely used in the construction of natural compounds and functional materials. Its preparation is mainly realized by reducing the corresponding nitrobenzene compounds. There are many related reports at present, such as: 1. The hydrogenation method is used to reduce the nitrobenzene compounds. This method is environmentally friendly and the post-treatment is simple, but often It is necessary to use precious metals as catalysts, which requires strict equipment and hydrogen sources, which increases the cost of the experiment and complicates the process; 2. The reduction of nitrobenzene compounds with glucose in a concentrated alkali medium has easy-to-obtain raw materials and relatively high yiel...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C245/08
Inventor 刘宇芳刘博董振明
Owner SHANXI UNIV
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