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Synthesis method for converting lignin 4-O-5 model compound diaryl ether into nitrogen-containing compound

A 4-O-5, model compound technology, used in the preparation of amino compounds by condensation/addition reactions, organic chemistry, etc., can solve problems such as low industrial value

Active Publication Date: 2019-04-02
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Throughout the above research results, it can be seen that their work mainly degrades diphenyl ether into the simplest small molecular organic compounds (benzene, phenol, cyclohexane, cyclohexanol, cyclohexanone, dicyclohexyl ether etc.), its industrial value is relatively low

Method used

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  • Synthesis method for converting lignin 4-O-5 model compound diaryl ether into nitrogen-containing compound
  • Synthesis method for converting lignin 4-O-5 model compound diaryl ether into nitrogen-containing compound
  • Synthesis method for converting lignin 4-O-5 model compound diaryl ether into nitrogen-containing compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025]

[0026] Put a moderate stirring bar in a dry reaction tube (20 ml), add palladium hydroxide / carbon (30mol%), NaBH 4 (1.5 times the equivalent), then the reaction tube was evacuated, filled with argon, and replaced three times. Under the argon atmosphere, the solution of diphenyl ether (0.2 mmol) and hexahydropyridine (0.7 mmol) dissolved in the solvent was injected with a syringe Slowly add to the reaction tube, add 10 uL of water into the reaction tube with a micro-injector, then add 1 mL of air into the reaction tube with a syringe, heat the reaction tube in an oil bath at 160 degrees Celsius and stir the reaction. The reaction was stopped after 24 hours, the reaction tube was taken out from the oil bath, naturally cooled to room temperature, diluted with ethyl acetate, and then the reaction solution was filtered with diatomaceous earth, and the yield of benzene in the filtrate was 85% by gas phase detection. After the filtrate was concentrated, the final product...

Embodiment 2

[0028]

[0029] Put a moderate stirring bar in a dry reaction tube (20 ml), add palladium hydroxide / carbon (30mol%), NaBH 4 (1.5 times equivalent), then the reaction tube was evacuated, filled with argon, and replaced three times, and diphenyl ether (0.2mmol) and 2-methylpiperidine (0.7mmol) dissolved in the solvent were dissolved in the argon atmosphere. The solution was slowly added to the reaction tube with a syringe, 10 uL of water was added to the reaction tube with a micro injector, and 1 mL of air was added to the reaction tube with a syringe, and the reaction tube was heated in an oil bath at 160 degrees Celsius and stirred for reaction. The reaction was stopped after 24 hours, the reaction tube was taken out from the oil bath, naturally cooled to room temperature, diluted with ethyl acetate, and then the reaction solution was filtered with diatomaceous earth. The yield of benzene in the filtrate was 84% ​​by gas phase detection. After the filtrate was concentrated...

Embodiment 3

[0031]

[0032] Put a moderate stirring bar in a dry reaction tube (20 ml), add palladium hydroxide / carbon (30mol%), NaBH 4 (1.5 times the equivalent), then the reaction tube was evacuated, filled with argon, and replaced three times, and the diphenyl ether (0.2mmol) and 3-methylpiperidine (0.7mmol) dissolved in the solvent were dissolved in the argon atmosphere. The solution was slowly added to the reaction tube with a syringe, 10 uL of water was added to the reaction tube with a micro injector, and 1 mL of air was added to the reaction tube with a syringe, and the reaction tube was heated in an oil bath at 160 degrees Celsius and stirred for reaction. After 24 hours, the reaction was stopped. The reaction tube was taken out from the oil bath, cooled to room temperature naturally, diluted with ethyl acetate, and then filtered with diatomaceous earth. The yield of benzene in the filtrate was 87% by gas phase detection. After the filtrate was concentrated, the final product...

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Abstract

The invention discloses a synthesis method for converting lignin 4-O-5 model compound diaryl ether into a nitrogen-containing compound. According to the synthesis method, a diaryl ether compound andan amine compound are subjected to a heating reaction in a certain amount of a solvent (containing a certain amount of water) in an argon atmosphere (containing a certain amount of air) under the actions of a metal catalyst and sodium borohydride, such that the drug with the important physiological activity or the compound with the natural product skeleton containing nitrogen is formed by directlycoupling the C-O bond cut and the amine compound cross while the corresponding aromatic hydrocarbon is obtained. According to the present invention, the synthesis method has characteristics of simpleand easily-available raw materials, high conversion rate, important product and good yield, and has broad application prospects in the degradation and deep development and utilization of lignin.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a synthesis method for converting lignin 4-O-5 model compound diaryl ether into nitrogen-containing compounds. Background technique [0002] Wood is one of the most widely distributed renewable resources in nature. Lignin mainly exists between wood cellulose fibers, and the lignin content in woody plants is as high as 25%. It is the second most abundant organic matter in the world (cellulose is the first), and is a very important biochemical recycled resources. Lignin structural fragments such as figure 1 shown. It is a biopolymer with a three-dimensional network structure formed by the structural units of oxyphenylpropanol connected to each other through ether bonds and carbon-carbon bonds. The most important chain connection is β-O-4, α-O-4, 4-O-5 three ether bonds ( figure 1 shown) and part of the carbon-carbon bonds. Cracking these aryl ether bonds can conver...

Claims

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Application Information

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IPC IPC(8): C07D295/033C07D211/14C07C209/60C07C211/35C07C211/45C07C211/51C07D207/323C07D207/327C07D295/155
CPCC07C209/60C07D207/323C07D207/327C07D211/14C07D295/033C07D295/155C07C2601/14C07C2601/08C07C211/35C07C211/45C07C211/51
Inventor 曾会应曹大伟李朝军
Owner LANZHOU UNIVERSITY
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