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Method for preparing aromatic azoxycompound based on aromatic amine oxidation

A technology of azo oxide and aromatic amines, which is applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, chemical/physical processes, etc., and can solve the problems of reaction equipment corrosion, alkaline wastewater easily polluting the environment, Does not meet the issues of green and sustainable development

Inactive Publication Date: 2022-04-01
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Due to the strong alkali environment of this preparation method, it has a strong corrosive effect on the reaction equipment, and alkaline wastewater is easy to pollute the environment, so this method does not conform to the concept of green and sustainable development.

Method used

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  • Method for preparing aromatic azoxycompound based on aromatic amine oxidation
  • Method for preparing aromatic azoxycompound based on aromatic amine oxidation
  • Method for preparing aromatic azoxycompound based on aromatic amine oxidation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-9

[0028] Example 1-9: Preparation of Zr-MOFs by hydrothermal method

[0029] Taking UiO-66 as an example, 100mg (0.6mmol) terephthalic acid (H 2 BDC) and 140mg (0.6mmol) ZrCl 4Dissolve in 25mL DMF and add 1.03mL acetic acid with stirring. Sonicate the solution with an ultrasonic cleaner until clear. Subsequently, the solution was transferred to a 50 mL autoclave and heated at 120 °C for 24 h. After the autoclave was naturally cooled to room temperature, the product was centrifuged and washed at least three times with DMF and methanol, respectively. The white solid powder was collected after vacuum drying at 60°C. Other Zr-MOFs S The synthesis method is similar to that of UiO-66, as shown in Examples 1-9 in Table 1.

[0030] See Table 1 below for details.

[0031] Table 1. Zr-MOFs prepared by hydrothermal synthesis

[0032]

Embodiment 10-24

[0033] Embodiment 10-24: Reaction condition screening

[0034] Add 10mg of UiO-66 (Zr=2.67mmol%), 2mmol of aniline, 5mL of deionized water and 511μL of 30% hydrogen peroxide solution into the reaction tube, heat the oil bath to 60°C under magnetic stirring, and finish the reaction for 6h. The reaction product was analyzed by GC-MS, and the yield of azobenzene oxide was >99% (Example 16).

[0035] Except that reaction temperature, reaction time, catalyst consumption, hydrogen peroxide consumption are different, catalyst activity evaluation is identical with embodiment 1. The reaction conditions and catalytic reaction results are shown in Table 2. As can be seen from Table 2, reaction temperature, reaction time, catalyst consumption, hydrogen peroxide consumption have influence on catalytic effect. With reaction temperature (embodiment 10,13,16 and 17), reaction time, (embodiment 10,11 and 12 or 13,14 and 15), catalyst consumption (embodiment 18,19 and 20) and hydrogen peroxid...

Embodiment 25-33

[0039] Examples 25-33: Substrate Expansion

[0040] The evaluation of the catalyst activity was the same as in Example 10 except that the substrate was different. The results of the catalytic reactions are shown in Table 3. Aniline compounds with different substituents have yields of 40-99% aromatic azo compounds.

[0041] See Table 3 below for details.

[0042] Table 3 Different substrate expansion

[0043]

[0044]

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PUM

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Abstract

The invention discloses a method for preparing an aromatic azoic oxide compound based on aromatic amine oxidation, which is characterized in that water is used as a green solvent, hydrogen peroxide is used as an oxidant, a zirconium-based metal organic framework is used as a catalyst, and aromatic amine is selectively catalytically oxidized into the corresponding aromatic azoic oxide compound. The method is simple in reaction, easy and convenient to operate, good in selectivity and high in yield, is a green synthesis method of the azobenzene oxide compound, provides a new synthesis route for preparation of the compound, and has good scientific research value and industrialization potential.

Description

technical field [0001] The invention relates to a synthesis method of azo oxide compounds, in particular to a method for preparing aromatic azo oxide compounds based on the oxidation of aromatic amines. Background technique [0002] As a class of organic chemical raw materials and intermediates, azobenzene oxide compounds have important applications in dyes, indicators and liquid crystal materials. There are two main methods for the preparation of azobenzene compounds: one is through the reduction of aromatic nitro compounds, and the other is through the oxidation of aromatic amino compounds. The azobenzene oxide obtained by these two methods can be listed as follows: [0003] CN103265450A discloses a method for photocatalytically synthesizing azobenzene oxide and azobenzene compounds. After mixing nitrobenzene compounds, alkali and alcohol according to the molar ratio of 1:0.1-20:40-1000 to form a solution, press The mass ratio of nitrobenzene compound to catalyst is 1:0....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C291/08B01J31/22C08G83/00
Inventor 刘爱丽王舜郑健宏余小春陈凯金辉乐尹晓晓仇亦霄
Owner WENZHOU UNIVERSITY
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