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Method for converting lignin into isoxazole and aromatic nitrile

A technology of lignin and isoxazole, which is applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., to achieve the effects of simple conversion method, expanded application prospects, and easy operation

Active Publication Date: 2019-06-04
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, so far, there has been no report on obtaining nitrogen-containing compounds such as isoxazole and aromatic nitrile from lignin.

Method used

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  • Method for converting lignin into isoxazole and aromatic nitrile
  • Method for converting lignin into isoxazole and aromatic nitrile
  • Method for converting lignin into isoxazole and aromatic nitrile

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] In a 15mL pressure bottle, add 1mL methanol, 0.1mmol 3-hydroxy-2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)propyl-1-one and 0.3mmol hydrochloric acid Hydroxylamine was filled with nitrogen to replace the atmosphere, airtight, stirred and reacted at 120°C for 12 hours, after the reaction, centrifuged, and the product was detected by chromatography. The conversion rate and yield are shown in Table 1.

Embodiment 2

[0038] In a 15mL pressure bottle, add 1mL methanol, 0.1mmol 3-hydroxy-2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)propyl-1-one, 0.3mmol hydrochloric acid Hydroxylamine and 0.2 mmol MgO were filled with nitrogen to replace the atmosphere, airtight, and stirred at 120°C for 12 hours. After the reaction, centrifuged, and the product was detected by chromatography. The conversion rate and yield are shown in Table 1.

Embodiment 3

[0040] In a 15mL pressure bottle, add 1mL methanol, 0.1mmol 3-hydroxy-2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)propyl-1-one, 0.3mmol hydrochloric acid Hydroxylamine and 0.2 mmol ZnO were filled with nitrogen to replace the atmosphere, airtight, and stirred at 120°C for 12 hours. After the reaction, centrifuged and chromatographically detected the product. The conversion rate and yield are shown in Table 1.

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Abstract

The present invention relates to a method for obtaining isoxazole and aromatic nitrile from a lignin model and pre-oxidized birch lignin. The method is characterized in that hydroxylamine hydrochloride and a beta-O-4 model compound containing ketone in the benzyl position, which are used as reaction substrates, undergo oximation condensation Cbeta-O bond fracture under the action of magnesium andother additives to prepare the isoxazole compound, and undergo oximation rearrangement Calpha-Cbeta bond fracture the action of magnesium and other additives to prepare the fragrant nitrile compound.The method can be applied to the conversion of pre-oxidized lignin into the isoxazole and aromatic nitrile. The preparation method comprises the following steps: mixing the beta-O-4 model compound orpre-oxidized birch lignin, hydroxylamine hydrochloride and the additives in an alcohol solvent, adding the obtained mixture into a pressure-resistant container, replacing air in the container with nitrogen, sealing the container, and stirring the mixture at 120 DEG C for 8-12 h to obtain the products isoxazole and aromatic nitrile. The method realizes the obtaining of nitrogen-containing compoundssuch as isoxazole and aromatic nitrile from lignin for the first time, and the reaction process is simple and controllable, and is easy to operate.

Description

technical field [0001] The invention relates to a method for transforming lignin into isoxazole and aromatic nitrile, in particular to oximation, intramolecular condensation and Beckmann rearrangement reactions of ketones in a lignin system. Background technique [0002] Lignin conversion has received a lot of attention in recent years. As the only biomass containing a large number of aromatic rings, lignin has great potential to replace petroleum as a raw material for the production of aromatic compounds. [0003] Through hydrogenation, hydrogenation, oxidation, acid, base catalyzed hydrolysis, and a combination of strategies, lignin can be depolymerized efficiently to obtain oxygenated chemicals such as aromatic hydrocarbons, aromatic ketones, aromatic acids, and aromatic esters. However, so far, there is no report on obtaining nitrogen-containing compounds such as isoxazole and aromatic nitrile from lignin. Obtaining high value-added fine chemicals from lignin provides ...

Claims

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Application Information

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IPC IPC(8): C07D261/08C07C255/54C07C253/00C07C43/23C07C41/26C07C69/92C07C67/317
CPCY02P20/52
Inventor 王峰李宏基张超峰刘慧芳罗能超张晓辰
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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