Method for preparing nitrogen-containing heterocyclic ring compound by use of chitin biomass

A technology of nitrogen heterocyclic compounds and chitin, which is applied in the field of preparation of high value-added nitrogen-containing heterocyclic compounds deoxyfructosazine, can solve the problems of poor selectivity of target products, complicated reaction steps, long reaction time, etc., and improve catalytic conversion efficiency , abundant reserves, and the effect of reducing the cost of separation

Active Publication Date: 2014-07-30
SHANXI INST OF COAL CHEM CHINESE ACAD OF SCI
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  • Abstract
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Problems solved by technology

The reaction steps are complicated, the reaction time is too long, and the yield is not high (Chem. Pharm. Bull., 1991,39,792-794. Chemical Drug Letters, 1991,39,792-794)
Kwasi and others studied the reaction of glucose and a series of ammonium salts to prepare deoxyfructosazine, and the Maillard reaction occurred. This reaction requires an external nitrogen source and the selectivity of the target product is poor (Carbohydr. Res., 2002, 337, 2273-2277. Carbohydrate Compound Research, 2002, 337, 2273-2277)

Method used

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  • Method for preparing nitrogen-containing heterocyclic ring compound by use of chitin biomass

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Experimental program
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Embodiment 1

[0022] (1) Prepare 30 g of an ethanol solution with a mass concentration of 12% 1-butyl-3-methylimidazolium hydroxide ionic liquid, add 10 g of D-glucosamine hydrochloride with a molecular weight of 215.5, add D-glucosamine Hydrochloride equimolar boric acid, after mixing evenly, react at 20°C for 8 hours.

[0023] (2) After the reaction, at room temperature, take 10 ml of the reaction product solution, add 50 ml of acetic anhydride and 30 ml of pyridine for acylation for 12 hours, then take 10 ml of the acylation reaction solution, extract three times, add 3×15 ml Ethyl acetate was used as the extractant to extract the acylated deoxyfructosine. The acylated product is obtained by rotary evaporation and concentration, the extractant is recovered, and the imidazole ionic liquid is recovered and reused;

[0024] (3) Add 1 g of the obtained acylated product to 5 ml of alkaline solution of 2 mol / L sodium hydroxide for deacetylation treatment. Under the condition of water bath, th...

Embodiment 2

[0026] (1) Prepare 45 g of an ethanol solution with a mass concentration of 50% 1-butyl-3-methylimidazolium hydroxide ionic liquid, add 35 g of D-glucosamine hydrochloride with a molecular weight of 215.5, and add D-glucosamine Hydrochloride and sodium hydroxide with an equal molar number were uniformly mixed and reacted at 80°C for 10 minutes.

[0027](2) After the reaction, at room temperature, take 2 ml of the reaction product solution, add 10 ml of acetic anhydride and 6 ml of pyridine for acylation for 15 hours, then take 10 ml of the acylation reaction solution, extract five times, add 5 ×20 ml tetrahydrofuran was used as the extractant to extract the acylated deoxyfructosazine.

[0028] (3) Concentrate the obtained ethyl acetate phase in which the product was dissolved, evaporate to dryness and concentrate, add 1 g of the obtained acylated product to 10 ml of sodium hydroxide alkaline solution with a concentration of 5 mol / L, and perform deacetylation treatment , under...

Embodiment 3

[0030] (1) Prepare 40 g of 1-butyl-3-methylimidazolium acetate ionic liquid with a mass concentration of 100%, add 35 g of chitin with a molecular weight of 250,000, and add glacial acetic acid whose molar mass is twice that of chitin , mixed evenly, and reacted at 150°C for 6 hours.

[0031] (2) After the reaction, at room temperature, take 3ml of the reaction product solution, add 15ml of acetic anhydride and 9ml of pyridine for acylation for 24 hours, then take 20ml of the acylation reaction solution, extract twice, add 2× 25 ml methyl isobutyl ketone was used as extractant to extract acylated deoxyfructosine.

[0032] (3) Concentrate the obtained methyl isobutyl ketone phase in which the product has been dissolved, evaporate to dryness and concentrate, add 1 g of the obtained acylated product to 15 ml of sodium hydroxide alkaline solution with a concentration of 10 mol / L, and carry out desorption Acetylation treatment, under water bath conditions, the reaction time is 30 ...

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Abstract

The invention discloses a method for preparing a nitrogen-containing heterocyclic ring compound by use of chitin biomass. The method comprises the following steps: uniformly mixing a chitin biomass raw material, an imidazole type ionic liquid solution and an additive for reaction, sequentially adding acetic oxide and pyridine into a reaction product for acylation, quenching the acylation-finished reaction liquid, adding an extracting agent into the acylation-finished reaction liquid for extraction, rotationally evaporating and concentrating to obtain an acylation product, adding an NaOH solution into the acylation product which is obtained through the extraction, stirring under a water-bath condition, adding hydrochloric acid which has the same molar weight as alkali, adding methanol, filtering to remove inorganic salt, rotationally evaporating and concentrating the filtrate to obtain a deacylation product, and crystallizing the deacylation product. The method disclosed by the invention has the advantages of simple process, high product purity, high yield and short reaction time.

Description

technical field [0001] The invention relates to a method for preparing high value-added nitrogen-containing heterocyclic compound deoxyfructosazine by using chitin biomass. technical background [0002] As the global petrochemical energy supply is becoming increasingly scarce and environmental pollution is becoming increasingly serious, people's demand for renewable energy and chemicals derived from biomass resources has increased significantly. At present, the research on replacing petrochemical resources with renewable biomass resources mainly focuses on two directions, one is to directly convert biomass resources into energy substances, and the other is to convert biomass resources into high value-added fine chemicals. Chitin and its partially or fully deacetylated derivative chitosan is an important marine biomass resource in nature, mainly found in the bones and shells of aquatic crustaceans (such as shrimp, crab, etc.), and in fungi, algae, etc. It is also found in th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/12
CPCC07D241/12
Inventor 王英雄贾玲玉侯相林齐永琴乔岩
Owner SHANXI INST OF COAL CHEM CHINESE ACAD OF SCI
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