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Method for preparing 3-acetamido-5-acetylfuran by catalyzing chitin monomer N-acetylglucosamine with amino acid ionic liquid

A technology of acetylfuran and acetamido, applied in the field of biomass conversion, can solve the problems of poor economic benefit, low conversion rate and high energy consumption

Inactive Publication Date: 2020-04-28
TIANJIN POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The traditional synthesis method of nitrogen-containing compounds generally needs to pass through the ammonia synthesis method, which has high energy consumption, low conversion rate, and poor economic benefits

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1 Take 100mg of N-acetylglucosamine and 200mg of glycine chloride salt ionic liquid in a round bottom flask, add 10mL of N-methylpyrrolidone, heat and stir in a constant temperature oil bath at 180°C for 60min under normal pressure reflux conditions. After the reaction was completed and cooled to room temperature, it was filtered. Take 0.5 mL of the filtrate, add 15 mL of methanol to dilute, and detect the content of 3-acetylamino-5-acetylfuran by high performance liquid chromatography, and the yield of 3-acetylamino-5-acetylfuran is 24.47%. After the filtrate was distilled under reduced pressure to remove the solvent, the residue was dissolved in 20 mL of distilled water, extracted several times with 20 mL of ethyl acetate, and the extract was concentrated under reduced pressure to obtain a solid crude product containing 3-acetylamino-5-acetylfuran.

Embodiment 2

[0021] Example 2 Take 100mg of N-acetylglucosamine and 200mg of valine chloride salt ionic liquid in a round bottom flask, add 10mL of N-methylpyrrolidone, and heat, stir and reflux in a constant temperature oil bath at 180°C for 60min under normal pressure reflux conditions . After the reaction was completed and cooled to room temperature, it was filtered. Take 0.5 mL of the filtrate, add 15 mL of methanol to dilute, and detect the content of 3-acetylamino-5-acetylfuran by high performance liquid chromatography, and the yield of 3-acetylamino-5-acetylfuran is 17.64%. After the filtrate was distilled under reduced pressure to remove the solvent, the residue was dissolved in 20 mL of distilled water, extracted several times with 20 mL of ethyl acetate, and the extract was concentrated under reduced pressure to obtain a solid crude product containing 3-acetylamino-5-acetylfuran.

Embodiment 3

[0022] Example 3 Take 100 mg of N-acetylglucosamine and 200 mg of glycine bisulfate ionic liquid in a round-bottomed flask, add 10 mL of N-methylpyrrolidone, and heat, stir and reflux in a constant temperature oil bath at 180°C for 60 min under normal pressure reflux conditions. After the reaction was completed and cooled to room temperature, it was filtered. Take 0.5 mL of the filtrate, add 15 mL of methanol to dilute, and detect the content of 3-acetylamino-5-acetylfuran by high performance liquid chromatography, and the yield of 3-acetylamino-5-acetylfuran is 2.29%. After the filtrate was distilled under reduced pressure to remove the solvent, the residue was dissolved in 20 mL of distilled water, extracted several times with 20 mL of ethyl acetate, and the extract was concentrated under reduced pressure to obtain a solid crude product containing 3-acetylamino-5-acetylfuran.

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Abstract

3-acetamido-5-acetylfuran as a biomass-based nitrogen-containing platform compound can be used for synthesizing a plurality of important nitrogen-containing fine chemicals. The invention discloses a method for preparing the 3-acetamido-5-acetylfuran by taking chitin monomer N-acetylglucosamine as a raw material. The method is accomplished by the following means: the N-acetylglucosamine is taken asthe raw material, glycine ionic liquid is taken as a catalyst, calcium chloride is taken as a cocatalyst, N, N-dimethylacetamide is taken as a solvent, reaction is carried out for a certain period oftime at a certain temperature, the yield of the obtained product is as high as 52.61%, and in addition, the ionic liquid still shows good catalytic activity after being repeatedly used for eight times. The chitin monomer used in the method is cheap, easy to obtain and renewable, and the application field of chitin biomass is broadened. The ionic liquid used in the reaction is simple in preparation method, cheap and easily available in raw materials, recyclable, green and environment-friendly, and has a good industrial application prospect.

Description

technical field [0001] The invention belongs to the field of biomass conversion, and uses natural renewable chitin biomass resource N-acetylglucosamine as raw material, and highly catalytic and reusable amino acid ionic liquid as catalyst to prepare high value-added nitrogen-containing compound 3- Acetylamino-5-acetylfuran. Background technique [0002] Naturally renewable biomass resources have attracted widespread attention as an alternative to fossil fuels. Most of the current studies are devoted to the most widely distributed and abundant cellulose biomass in nature, however, the second largest biomass in annual production after cellulose, chitin biomass, has received less attention. In 2015, Professor Yan Ning proposed the concept of chitin biomass refining, which has attracted widespread attention in the research community for the value of chitin biomass. [0003] Chitin biomass contains valuable nitrogen atoms, which can be directly used to produce nitrogen-containi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/66
CPCC07D307/66
Inventor 臧洪俊王娇焦硕磊尚帧杜延楠丁宏颖常誉泷
Owner TIANJIN POLYTECHNIC UNIV
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