A method of converting lignin to isoxazoles and aromatic nitriles

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 prospect, and simple preparation

Active Publication Date: 2022-06-07
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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  • A method of converting lignin to isoxazoles and aromatic nitriles
  • A method of converting lignin to isoxazoles and aromatic nitriles
  • A method of converting lignin to isoxazoles and aromatic nitriles

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, sealed, and the reaction was stirred at 120 ° C for 12 h. After the reaction was completed, centrifugation was performed, 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, sealed, and the reaction was stirred at 120 ° C for 12 h. After the reaction was completed, centrifugation was performed, 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 replacement atmosphere, sealed, and stirred at 120 ° C for 12 h. After the reaction was completed, centrifugation was performed, and the product was detected by chromatography. The conversion rate and yield are shown in Table 1.

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Abstract

The invention relates to a method for obtaining isoxazole and aromatic nitrile from lignin model and preoxidized birch lignin. The method adopts the β-O-4 model compound whose benzyl position is a ketone and hydroxylamine hydrochloride as the reaction substrate, and under the action of additives such as magnesium oxide, the C β ‑O bond preparation of isoxazole compounds, and oximation rearrangement cleavage of C α -C β At the same time, this method can be applied to the conversion of preoxidized lignin to isoxazoles and aromatic nitriles. The preparation process is as follows: mix the β-O-4 model compound or pre-oxidized birch lignin, hydroxylamine hydrochloride and additives in an alcohol solvent, put it in a pressure-resistant container, replace it with nitrogen and seal it, at 120 ° C, stir After 8-12 hours, isoxazole and aromatic nitrile products can be obtained. This method is the first to realize nitrogen-containing compounds such as isoxazole and aromatic nitrile from lignin, and the reaction process is simple, controllable and easy to operate.

Description

technical field [0001] The invention relates to a method for converting lignin to isoxazoles and aromatic nitrile, in particular to the oximation of ketones in a lignin system, intramolecular condensation and Beckmann rearrangement reactions. Background technique [0002] The transformation of lignin has received a lot of attention in recent years. Lignin, as the only biomass containing a large amount of aromatic rings, has great potential to replace petroleum as a raw material to produce aromatic compounds. [0003] Through hydrogenation, transhydrogenation, oxidation, acid- and base-catalyzed hydrolysis, and a combination of strategies, lignin can be depolymerized with high efficiency to obtain oxygenated chemicals such as aromatic hydrocarbons, aromatic ketones, aromatic acids, and aromatic esters. However, so far, there have been no reports of obtaining nitrogen-containing compounds such as isoxazoles and aromatic nitriles from lignin. Obtaining high value-added fine c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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