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Method for preparing azobenzene derivatives

A technology of azobenzene derivatives and nitrobenzene derivatives, which is applied in the field of synthesis of azo compounds, can solve problems such as difficult control of reactions, and achieve low cost, simple process, and environmental friendliness

Active Publication Date: 2010-12-15
产学研共同体(山东)科技成果转化有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Other existing supported metal nanocatalysts (Au, Pd, Pt nanoparticles, etc.) are used in the reduction process of nitrobenzene, which often require harsh reaction conditions such as high temperature and high pressure, and the reaction is difficult to control in one step of azobenzene, resulting in The azobenzene usually continues to be hydrogenated to generate hydroazobenzene, and the hydrogenated azobenzene will also continue to react to eventually generate aniline

Method used

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  • Method for preparing azobenzene derivatives
  • Method for preparing azobenzene derivatives
  • Method for preparing azobenzene derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Example 1: Synthesis of platinum nanowires

[0020] The synthesis method is: reducing platinum acetylacetonate in oleylamine at 160°C and thermally decomposing iron pentacarbonyl to obtain FePt nanowires with a diameter of 2-3nm, and then heating and stirring under acidic conditions to corrode the Fe wrapped around the Pt nanowires. Platinum nanowires were obtained, and the obtained nanowires were scanned by an electron microscope, and the results were as follows figure 1 ,From figure 1 It can be seen that the diameter of the platinum nanowire is 2 to 3 nm.

Embodiment 2

[0021] Embodiment two: if figure 2 As shown, the catalyst catalyzes the preparation of azobenzene derivatives.

[0022] The platinum nanowire obtained in Example 1 was used as the catalyst, and 0.1 mL of the catalyst (platinum nanowire, about 1 mg), 1 mmol of nitrobenzene, 1 mmol of potassium hydroxide, and 2 mL of p-xylene were added to the reaction tube. The system was connected with a hydrogen bag, then cooled-vacuumized-released hydrogen, cycled 3 to 4 times, put in hydrogen, and returned to room temperature; the system was heated in an oil bath at 20-120°C for 3-9 hours to obtain the product ( Concrete reaction time, reaction temperature are shown in Table 1).

[0023] The product was taken for gas-mass chromatography (GC-MS) and gas chromatography (GC) analysis, and the product was subjected to column separation, and the obtained azo product was characterized by NMR.

[0024] The influence of table 1 different reaction temperature, reaction time on reaction

[0025] ...

Embodiment 3

[0027] Embodiment three: as figure 2 As shown, the catalyst catalyzes the preparation of azobenzene derivatives.

[0028] Using the platinum nanowires obtained in Example 1 as a catalyst, add 0.1 mL of catalyst (platinum nanowires, about 1 mg), 1 mmol of nitrobenzene, 0-2 mmol of potassium hydroxide (see Table 2 for specific dosage), and 2 mL of toluene. The system was connected with a hydrogen bag, then cooled-vacuumized-released hydrogen, cycled 3 to 4 times, put in hydrogen, and returned to room temperature; the system was heated in an oil bath at 80°C for 3.5 hours to obtain the product. The product was analyzed by gas-mass spectrometry (GC-MS) and gas chromatography (GC).

[0029] Table 2 Effect of different potassium hydroxide dosages on the reaction

[0030]

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Abstract

The invention belongs to the field of organic synthesis, in particular relates to a method for synthesizing azobenzene compounds and discloses a method for preparing azobenzene derivatives. In the method, one of nitrobenzene derivatives is used as a reactant; one or a mixture of two of platinum nanowires or palladium nanowires is used as a catalyst; and potassium hydroxide, sodium hydroxide, (CH3)3CONa or (CH3)3COK is used as alkali. The method comprises the following steps of: adding the reactant, the catalyst and the alkali into a solvent; and performing a reaction for 2 to 24 hours at the temperature of between 20 and 140 DEG C under normal pressure in the hydrogen atmosphere to obtain azobenzene. The platinum nanowires or the palladium nanowires are taken as the catalyst and the suitable alkali and solvent are adopted, so that the reaction conditions of preparing the azobenzene derivatives are mild and the reaction can be carried out under the conditions of normal pressure and room temperature. Moreover, the conversion rate and selectivity are higher and is about 90 percent, a reactor is environment-friendly, the catalyst is easy to separate and can be recycled, and reagents which cause serious pollution to the environment, such as nitrite and the like, are not used.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a synthesis method of azo compounds, in particular to a method for preparing azobenzene and derivatives thereof by catalytic reduction of aromatic compounds with nitro groups. Background technique [0002] Azo compounds are important organic synthesis intermediates in the chemical industry, and can be used to synthesize antioxidants, dyes, active components, polymer modifiers, adhesives, photoresists, photosensitive materials, food additives and drugs, etc. . [0003] In the prior art, the method for synthesizing azobenzene compounds is usually: (1) reduction of nitroaromatic compounds, (2) oxidation of aromatic amines, and (3) by diazotization of aniline and in liquid phase Electron-rich aromatic compound reaction diazotization method. The first two methods usually use some metals that are more polluting to the environment, such as lead, tellurium, etc. (referring ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C245/08C07D295/135B01J23/44B01J23/42B01J35/06
Inventor 顾宏伟路建美胡磊洪海燕李敏
Owner 产学研共同体(山东)科技成果转化有限公司
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