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Method for preparing 5-hydroxymethylfurfural by catalyzing cellulose formate with dimethyl sulfoxide-water cosolvent system

A technology of dimethyl sulfoxide and hydroxymethyl furfural, applied in the direction of organic chemistry, etc., can solve the problems of limited dissolving and dispersing ability, unfavorable results, etc., and achieve the effect of excellent directional selectivity

Pending Publication Date: 2021-01-26
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, cellulose is a high molecular polymer composed of multiple glucose units connected by β-(1,4)-glycosidic bonds. Due to the strong inter-molecular and intra-molecular hydrogen bonding and van der Waals forces, they form directional arrangements. And the highly crystalline supramolecular structure makes its ability to dissolve and disperse in solvents extremely limited
Although some studies have reported the direct conversion of cellulose to 5-hydroxymethylfurfural, the results are not impressive. Therefore, the design of highly reactive substrates and the development of green and efficient catalytic reaction systems are the key to improving the production of cellulose conversion. The Selectivity of 5-Hydroxymethylfurfural and the Key Way to Inhibit Further Degradation of 5-Hydroxymethylfurfural

Method used

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  • Method for preparing 5-hydroxymethylfurfural by catalyzing cellulose formate with dimethyl sulfoxide-water cosolvent system
  • Method for preparing 5-hydroxymethylfurfural by catalyzing cellulose formate with dimethyl sulfoxide-water cosolvent system
  • Method for preparing 5-hydroxymethylfurfural by catalyzing cellulose formate with dimethyl sulfoxide-water cosolvent system

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Experimental program
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Effect test

Embodiment 1

[0028] Step 1, formic acid treatment of α-cellulose

[0029] Add 300mL 99% formic acid solution into the round bottom flask and place it in an oil bath to raise the temperature to 120°C, and carry out magnetic stirring (800r / min); weigh 10g of α-cellulose and slowly add it to the formic acid solution, the reaction time is 3h Afterwards, the suspension was centrifuged at 4000r / min for 10min to remove cellulose residues; the reaction filtrate was transferred to a single-necked flask and rotatively evaporated at 45r / min in a water bath at 50°C, and the solution was concentrated to about 10mL; the concentrated The reaction solution was slowly poured into 150mL ethanol solution, the white fine precipitate was precipitated rapidly by magnetic stirring, and it was centrifuged at 10000r / min for 10min, and the white precipitate was obtained by filtration; the white precipitate was then added to ethanol, magnetically stirred, centrifuged (4°C , 10000r / min, 10min), filter, and repeat 3 t...

Embodiment 2

[0033] Step 1, formic acid treatment of α-cellulose

[0034] Add 300mL 99% formic acid solution into the round bottom flask and place it in an oil bath to raise the temperature to 120°C, and carry out magnetic stirring (800r / min); weigh 10g of α-cellulose and slowly add it to the formic acid solution, the reaction time is 3h Afterwards, the suspension was centrifuged at 4000r / min for 10min to remove cellulose residues; the reaction filtrate was transferred to a single-necked flask and rotatively evaporated at 45r / min in a water bath at 50°C, and the solution was concentrated to about 10mL; the concentrated The reaction solution was slowly poured into 150mL ethanol solution, the white fine precipitate was precipitated rapidly by magnetic stirring, and it was centrifuged at 10000r / min for 10min, and the white precipitate was obtained by filtration; the white precipitate was then added to ethanol, magnetically stirred, centrifuged (4°C , 10000r / min, 10min), filter, and repeat 3 t...

Embodiment 3

[0038] Catalytic Preparation of 5-Hydroxymethylfurfural from α-Cellulose

[0039]The catalytic reaction was carried out in a microwave reactor (CEM Discover System) with α-cellulose as substrate. Add 1.25mmol of the substrate into a 10mL quartz tube, add 0.5mL of hydrochloric acid (0.5M), 0.5mL of aluminum chloride (1.0M) as a combined catalyst, and then add 4mL of dimethyl sulfoxide. The final concentrations of the hydrochloric acid and aluminum chloride combined catalysts were 50 mM and 100 mM, respectively. Seal the microwave reaction tube, heat the target reaction temperature to 160°C, and hold the temperature for 20 minutes. After the reaction is finished, cool to room temperature, and measure the content of 5-hydroxymethylfurfural in the filtrate by high performance liquid chromatography.

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Abstract

The invention discloses a method for preparing 5-hydroxymethylfurfural by catalyzing cellulose formate with a dimethyl sulfoxide-water cosolvent system. The method comprises the following steps: firstly, adding alpha-cellulose into a formic acid solution for oil-bath heating, and carrying out centrifugal filtration to obtain a reaction filtrate; carrying out rotary evaporation and concentration onthe reaction filtrate, pouring the filtrate into an ethanol solution, and carrying out centrifugal filtration to obtain a white precipitate; pouring the white precipitate into an ethanol solution, carrying out centrifuging and filtering, repeating the operation for three times, and implementing freeze-drying to obtain cellulose formate; finally, performing microwave catalytic conversion in a dimethyl sulfoxide water cosolvent system by taking alpha-cellulose or cellulose formate as a substrate, and hydrochloric acid and aluminum chloride as catalysts to obtain the 5-hydroxymethylfurfural. Cellulose is treated with formic acid for acidolysis and formylation to obtain cellulose formate, and aluminum chloride hydrochloride is used as a combined catalyst to directly and efficiently catalyze cellulose formate in a dimethyl sulfoxide water cosolvent system to prepare 5-hydroxymethylfurfural.

Description

technical field [0001] The invention relates to the technical field of energy and chemical industry, in particular to a method for obtaining cellulose formate by treating cellulose with formic acid for acidolysis and formylation, and catalyzing cellulose formate in a dimethyl sulfoxide-water co-solvent system to prepare 5-hydroxy Methylfurfural method. Background technique [0002] In recent years, with the continuous consumption of non-renewable fossil resources, the use of biomass such as cellulose as a rich source of renewable organic carbon to produce high value-added chemicals and fuels has attracted much attention. Cellulose is a class of natural products that widely exist in nature. It is considered to be one of the most potential "green" materials in the world due to its excellent renewability and biocyclability, good biodegradability and biocompatibility. . [0003] In the conversion process of biomass such as cellulose, 5-hydroxymethylfurfural is known as an impo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/46C08B3/04C08B3/26
CPCC07D307/46C08B3/04C08B3/26
Inventor 张玺铭金才迪盛奎川钱湘群
Owner ZHEJIANG UNIV
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