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Aromatic azoxybenzene compound and preparation method thereof

A technology for oxidizing azobenzene and compounds, which is applied in the preparation of nitro compounds, the preparation of organic compounds, and the production of hydrocarbons from oxygen-containing organic compounds, etc., can solve the problems of high reaction temperature feed ratio, complicated catalyst preparation, environmental pollution and the like, To achieve the effect of efficient reaction, low cost and simple components

Active Publication Date: 2017-10-17
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The method of glucose reduction is the most classic method, but it requires high reaction temperature and strict feed ratio, and the yield is relatively low; and the preparation of existing catalysts is complicated, and the introduction of metals will cause environmental pollution

Method used

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  • Aromatic azoxybenzene compound and preparation method thereof
  • Aromatic azoxybenzene compound and preparation method thereof
  • Aromatic azoxybenzene compound and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0067] The synthesis of embodiment one aromatic nitro base

[0068] Synthesis of Compound A:

[0069] Add 80 mL of 1,2-dichloroethane to a 250 mL flask, then add 20 mL of concentrated nitric acid (65%) to make it evenly dispersed, react in an ice-water bath, then slowly add 10 g of fluorene, and react for 20 min. It was poured into 300 mL ice methanol, and a light yellow solid 2 (11 g) was obtained after suction filtration. Grind 7.5 g KOH into powder and add it to 100 mL DMSO, disperse evenly, then slowly add 6.3 g of the above-mentioned light yellow solid, stir for 20 min, then add 15 mL 1-bromooctane dropwise to the above system, react for 30 min, It was extracted with petroleum ether, dried, and spin-dried to obtain a crude product, which was then subjected to column chromatography using petroleum ether as a developing solvent to obtain a yellow viscous liquid, Compound A (9.0 g).

[0070] Synthesis of Compound B:

[0071] Add 150 mL of acetone to a 250 mL flask, grind ...

Embodiment 2

[0086] The preparation of embodiment two aromatic azobenzene compounds

[0087] Add 11.2 mg potassium hydroxide, 0.1 mmol aromatic nitro base (compound A, compound B, compound C, compound D, compound E or compound F), 3 mL toluene and 3 mL isopropanol to a 10 mL ampoule successively, After the addition, argon was blown for 10 minutes to deoxygenate and the tube was sealed, and then reacted for 10 hours under the irradiation of a xenon lamp (power 250-1000 W is optional). After the reaction was completed, it was extracted with dichloromethane and dried over anhydrous sodium sulfate. , spin-dried, and then purified by column chromatography (developing solvent: petroleum ether / dichloromethane) to obtain the corresponding aromatic azobenzene oxide compound.

[0088] attached Figure 7-12 The NMR spectra of aromatic azobenzene oxide compounds prepared by Compound A, Compound B, Compound C, Compound D, Compound E, and Compound F respectively, and the yields of the corresponding produ...

Embodiment 3

[0089] Example Preparation of triaromatic azobenzene compounds (under sunlight)

[0090] Add 11.2 mg of potassium hydroxide, 0.1 mmol of compound A, 3 mL of toluene and 3 mL of isopropanol to a 10 mL ampoule successively. After the addition is complete, deoxygenate and seal the tube with argon gas for 10 min, and then store in sunlight at room temperature Reacted for 20 h; after the reaction, extracted with dichloromethane, dried over anhydrous sodium sulfate, spin-dried, and then purified by column chromatography (developing solvent: petroleum ether / dichloromethane=20 / 1-8 / 1) to obtain The corresponding aromatic azobenzene compound has a yield of 93%.

[0091] The process flow diagram of above-mentioned preparation aromatic nitro base is as follows:

[0092] .

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Abstract

The invention discloses an aromatic azoxybenzene compound and a preparation method thereof. The preparation method comprises the following steps: firstly reducing aromatic nitro-compounds into azoxybenzene through photoinduction in an alkaline condition; firstly synthesizing different aromatic nitro-compounds; secondly, carrying out nitro reduction under the irradiation of a xenon lamp under the conditions of potassium hydroxide, methylbenzene and isopropyl alcohol, and thus synthesizing the aromatic azoxybenzene compound. The preparation method disclosed by the invention has the advantages of simple components, mild reaction conditions, low toxicity, environmental protection, high selectivity and the like; the obtained aromatic azoxybenzene compound has potential application in the aspects of dyes, liquid crystal materials, optical materials and the like.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to an aromatic azobenzene compound and a preparation method thereof. Background technique [0002] Aromatic azobenzene oxide compounds are not only important functional materials, but also have important applications in dyes, drugs, food additives, and liquid crystal materials. They are also important organic synthesis intermediates, which can be further reduced to aromatic azo compounds or oxidized to At the same time, it can also be rearranged into hydroxyazobenzene, which provides a convenient way for the synthesis of hydroxyazobenzene. Owing to the similar structures of aromatic azoxyl compounds and aromatic azo compounds, it has many commonalities with aromatic azo compounds in terms of properties and functions, so the research on the properties and functions of aromatic azoxybenzene compounds will be an important subject. Based on the important application value ...

Claims

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Application Information

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IPC IPC(8): C07C245/10C07D209/88C07C205/06C07C201/08C07C201/12C07C13/62C07C1/24C07C2/86C07F5/02C07C43/225C07C41/30
CPCC07C1/24C07C2/861C07C41/30C07C201/08C07C201/12C07C205/06C07C245/10C07C2531/04C07C2531/12C07D209/88C07F5/02C07C13/62C07C43/225
Inventor 张伟陈扬殷露王来兵周年琛朱秀林
Owner SUZHOU UNIV
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