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Method for preparing 5-hydroxymethyl-furfural

A technology of methyl and substituents, which is applied in the field of preparation of 5-hydroxymethylfurfural, can solve the problems that the research situation has not been reported, the ionic liquid is not recycled, and the principle of green chemistry is hindered, and the separation method of the product is simple. Ease of operation, less catalyst and solvent consumption, less demanding effects on corrosion resistance

Inactive Publication Date: 2009-03-18
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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Problems solved by technology

However, this method still has some economic and environmental defects. These processes use ionic liquids without recycling, and the cost is relatively high. It is necessary to effectively reduce the cost of product separation and purification. The use of chromium-based catalysts hinders the principles of green chemistry.
[0007] In short, the existing HMF preparation methods are either too expensive, and the production cost needs to be further reduced; or the reaction selectivity is low, and a better catalytic system needs to be found
So far, the detailed research on the use of protonic acids to catalyze the dehydration of six-carbon sugars to produce HMF in ionic liquids has not been reported.

Method used

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  • Method for preparing 5-hydroxymethyl-furfural
  • Method for preparing 5-hydroxymethyl-furfural

Examples

Experimental program
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Effect test

Embodiment 1

[0038] 4 g of ionic liquid [C 4 MIm]Cl was added to a 10 ml round bottom flask, heated to 80°C, and 0.4 g of fructose was slowly added under vigorous stirring, and stirred until dissolved. At this point, 0.02 g of concentrated hydrochloric acid was quickly added to the reaction system, and reacted at 80° C. for 8 minutes under normal pressure to stop the reaction. Get 0.01 gram sample and quench reaction immediately with cold water, this sample pH value is adjusted to 7.0 with the NaOH of 0.05mol / L, gained aqueous solution measures HMF productive rate at 282nm place with ultraviolet-visible spectrophotometer by standard curve method and is 97%.

[0039] The remaining part in the reaction system was separated by column chromatography (using silica gel as filler, eluent: petroleum ether / ethyl acetate=4:2 (v / v)), to obtain 0.269 g of dark yellow liquid product HMF, The isolated yield was 96%. The product is analyzed by nuclear magnetic resonance spectroscopy, and the data are: ...

Embodiment 2

[0041] 4 g of ionic liquid [C 4 MIm]Cl was added to a 10 ml round bottom flask, heated to 80°C, and 4 g of fructose was slowly added under vigorous stirring, and stirred until dissolved. At this point, 0.2 g of concentrated hydrochloric acid was quickly added to the reaction system, and reacted at 80° C. for 25 minutes under normal pressure. Reaction finishes, quenches reaction with cold water, with the NaOH of 0.05mol / L the pH value of reaction solution is adjusted to 7.0, gained aqueous solution measures HMF productive rate at 282nm place by standard curve method and is 77% with ultraviolet-visible spectrophotometer, isolates product The rate is 75%.

Embodiment 3

[0043] 4 g of ionic liquid [C 4 MIm]Cl was added to a 10 ml round bottom flask, heated to 80°C, and 8 g of fructose was slowly added under vigorous stirring, and stirred until dissolved. At this point, 0.4 g of concentrated hydrochloric acid was quickly added to the reaction system, and reacted at 80° C. for 120 minutes under normal pressure. Reaction finishes, quenches reaction with cold water, with the NaOH of 0.05mol / L the pH value of reaction solution is adjusted to 7.0, gained aqueous solution measures HMF productive rate at 282nm place by standard curve method and is 58% with ultraviolet-visible spectrophotometer, isolates product The rate is 55%.

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Abstract

The invention relates to a method for transforming biomass sugar source into 5-hydroxymethyl-furfural, in particular to a method for preparing the 5-hydroxymethyl-furfural. The method comprises the following steps: using ionic liquid as a solvent, hexose or hexose source biomass as raw material substrates, and 0.5 to 50 percent (relative to the mass of the biomass sugar source) of acidic ionic liquid, inorganic acid or organic acid as a catalyst, and performing the reaction of materials for 1.5 minutes to 23 hours at normal pressure and at a temperature of between 80 DEG C and 100 DEG C to efficiently generate HMF. The method has the advantages of high HMF selectivity, less acid consumption, moderate operating conditions, fast reaction, reusable ionic liquid, simple process, environment protection and the like, and opens up a new approach for preparing commodity chemicals and replacing fuels starting from renewable biological resources.

Description

technical field [0001] The present invention relates to the preparation of 5-hydroxymethylfurfural, specifically a kind of high-efficiency conversion of biomass sugar source (six-carbon sugar or biomass rich in six-carbon sugar) into 5-hydroxymethylfurfural in ionic liquid (HMF) method. Background technique [0002] Using biomass energy to replace petroleum to prepare chemicals, plastics and fuels is a feasible solution to the world's energy crisis. The research on the preparation of general-purpose chemicals from renewable biological resources has become a research hotspot in the field of resources and energy at home and abroad. Abundant biomass resources can be converted under suitable conditions into valuable intermediate compounds such as furfural, HMF, and levulinic acid, which are highly reactive and can synthesize a series of valuable chemicals, so they have recently been regarded as biomass-based A new platform compound for resources. [0003] Among them, HMF is pa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/46C07D307/48
Inventor 赵宗保李昌志张泽会杜昱光
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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