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Synthesis method of asymmetric azoxybenzene compound

A technology of azobenzene oxide and synthesis method, which is applied in the direction of organic chemistry, can solve the problems of harsh reaction conditions, restrictions on extensive research and application, and complex preparation of raw materials, and achieve good product yield, good research value and application potential.

Active Publication Date: 2018-10-23
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented technology allows for efficient production of certain chemicals that have specific functions or uses within them (such as an antioxidant). By combining different reagents together with special techniques like controlled temperature cycles during manufacturing processes, this process results in improved yields compared to traditional methods such as organic solvent extraction from crude oil residue.

Problems solved by technology

This patented technical problem addressed in this patent relates to finding new chemicals that could efficiently produce specific types of molecules called chloroazobenzoic acid without generating unwanted side products like formaldehydes during production processes.

Method used

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  • Synthesis method of asymmetric azoxybenzene compound
  • Synthesis method of asymmetric azoxybenzene compound
  • Synthesis method of asymmetric azoxybenzene compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1 1-phenyl-2-(4-chlorophenyl)azo oxide

[0030]

[0031] 4-Chloroaniline (127.5mg, 1.0mmol), nitrosobenzene (117.8mg, 1.1mmol), Ag 2 O (254.5 mg, 1.1 mmol), DMSO (2 mL). Then, seal the tube. Put the reaction mixture in an oil bath at 65°C and stir for 24 hours, then take it out and cool it to room temperature, transfer the reaction stock solution, add an appropriate amount of ethyl acetate to wash, mix the stock solution with the washing solution, concentrate under reduced pressure and adsorb on silica gel powder, Directly carry out silica gel column chromatography separation, using the mixture of petroleum ether and ethyl acetate with a volume ratio of 100:1 as the eluent, and obtain 1-phenyl-2-(4-chlorophenyl) oxidation after column chromatography separation Azo, yield 85%.

[0032] The structural data confirmed by NMR are: 1 H NMR (500MHz, CDCl 3 , TMS): δ8.29(d, J=8.0Hz, 2H), 8.16(d, J=9.0Hz, 2H), 7.56(t, J=8.0Hz, 1H), 7.51(t, J=8.0Hz ,2H),7.44(d,J=...

Embodiment 2

[0033] Example 2 1-phenyl-2-(4-methyl carboxylate phenyl)azo oxide

[0034]

[0035] Add 4-methylaniline formate (151.2mg, 1.0mmol), nitrosobenzene (117.8mg, 1.1mmol), Ag 2 O (254.5 mg, 1.1 mmol), DMSO (2 ml). Then, seal the tube. Put the reaction mixture into an oil bath at 80°C and stir for 24 hours, then take it out and cool to room temperature, transfer the reaction stock solution, add an appropriate amount of ethyl acetate to wash, mix the stock solution with the washing solution, concentrate under reduced pressure and adsorb on silica gel powder, Directly carry out silica gel column chromatography separation, use the mixture of petroleum ether and ethyl acetate with a volume ratio of 50:1 as eluent, obtain 1-phenyl-2-(4-methyl phenyl carboxylate after separation by column chromatography ) azo oxide, yield 71%.

[0036] The structural data confirmed by NMR are: 1 H NMR (500MHz, CDCl3 , TMS): δ8.31(d, J=8.0Hz, 2H), 8.14(s, 4H), 7.58(t, J=7.5Hz, 1H), 7.52(t, J=7.5Hz,...

Embodiment 3

[0037] Example 3 1-phenyl-2-(4-iodophenyl)azo oxide

[0038] Add 4-iodoaniline (221.3mg, 1.0mmol), nitrosobenzene (117.8mg, 1.1mmol), Ag 2 O (254.5 mg, 1.1 mmol), DMSO (2 ml). Then, seal the tube. Put the reaction mixture in an oil bath at 65°C and stir for 24 hours, then take it out and cool it to room temperature, transfer the reaction stock solution, add an appropriate amount of ethyl acetate to wash, mix the stock solution and washing solution, concentrate under reduced pressure and adsorb on silica gel powder, Directly carry out silica gel column chromatography separation, using the mixture of petroleum ether and ethyl acetate with a volume ratio of 100:1 as the eluent, and obtain 1-phenyl-2-(4-iodophenyl) oxidation after column chromatography separation Azo, yield 90%.

[0039] The structural data confirmed by NMR are: 1 H NMR (500MHz, CDCl 3 , TMS): δ8.29(d, J=8.0Hz, 2H), 7.92(d, J=8.5Hz, 2H), 7.81(d, J=8.5Hz, 2H), 7.57(t, J=8.0Hz ,1H),7.51(t,J=8.0Hz,2H). 13 C ...

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Abstract

The invention relates to a synthesis method of an asymmetric azoxybenzene compound. According to the synthesis method, in an organic solvent, silver oxide is taken as the only promoter to carry out dehydrogenation condensation reactions. According to the synthesis method, aromatic amines and nitrosobenzene are taken as raw materials, and high efficient and selective synthesis is carried out undermild conditions to obtain the asymmetric azoxybenzene compound, which has a wide application range. The used promoter is commercial silver oxide, the synthesis raw materials are cheap and easily available; after reactions, silver oxide is converted into silver, which can be recovered and reused; the synthesis method is environment friendly, and compared with the prior art, the synthesis method ismore practical, is worthy to popularize, and is sustainable.

Description

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Claims

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Application Information

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Owner WENZHOU UNIVERSITY
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