Method for preparing 5-formyloxy methylfurfural from fructose

A technology of formyloxymethylfurfural and fructose, applied in the direction of organic chemistry, etc., can solve the problems of low yield and small feeding amount, and achieve the effects of low preparation cost, high feeding amount and mild reaction conditions

Inactive Publication Date: 2017-08-01
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method has a wide range of sources of raw materials and a simple process, but it needs to use a large amount of catalyst sodium bromide, and the amount of feed is small and the yield is low.

Method used

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  • Method for preparing 5-formyloxy methylfurfural from fructose
  • Method for preparing 5-formyloxy methylfurfural from fructose

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Add 1.08g of choline chloride and 0.27g of fructose into a 50mL round bottom flask, shake and mix properly. Another 10 mL of tetrahydrofuran and 2 μL of hydrochloric acid (38%) were added. The flask was placed in an oil bath for magnetic stirring, and the reaction was heated at a temperature of 100° C., and the reaction time was 4 hours. After the reaction was completed, it was cooled naturally. Take out the upper reaction solution, add anhydrous formic acid (anhydrous formic acid:reaction solution volume ratio is 1:2), heat the reaction in an oil bath, the temperature is 100°C, and react for 6h. After the reaction, the reaction solvent was distilled off under reduced pressure, the residue was extracted several times with 5 mL of methyl tert-butyl ether, the extracts were combined, and the extractant was recovered by distillation under reduced pressure. Rectify at 125-130°C under a pressure of 2000 Pa, wash the distillate with saturated aqueous sodium bicarbonate solu...

Embodiment 2

[0028] Add 1.08g of choline chloride and 0.27g of fructose into a 50mL round bottom flask, shake and mix properly. Another 10 mL of acetonitrile and 2 μL of hydrochloric acid (38%) were added. The flask was placed in an oil bath for magnetic stirring, and the reaction was heated at a temperature of 100° C., and the reaction time was 4 hours. After the reaction was completed, it was cooled naturally. Take out the upper reaction solution, add anhydrous formic acid (anhydrous formic acid:reaction solution volume ratio is 1:2), heat the reaction in an oil bath, the temperature is 100°C, and react for 6h. After the reaction, the reaction solvent was distilled off under reduced pressure, the residue was extracted several times with 5 mL of methyl tert-butyl ether, the extracts were combined, and the extractant was recovered by distillation under reduced pressure. Rectify at 125-130°C under a pressure of 2000 Pa, wash the distillate with saturated aqueous sodium bicarbonate solutio...

Embodiment 3

[0030] Add 1.08g of choline chloride and 0.27g of fructose into a 50mL round bottom flask, shake and mix properly. Another 20 mL of methyl isobutyl ketone and 2 μL of hydrochloric acid (38%) were added. The flask was placed in an oil bath for magnetic stirring, and the reaction was heated at a temperature of 100° C., and the reaction time was 4 hours. After the reaction was completed, it was cooled naturally. Take out the upper reaction solution, add anhydrous formic acid (anhydrous formic acid:reaction solution volume ratio is 1:4), heat the reaction in an oil bath, the temperature is 80°C, and react for 6h. After the reaction was over, the reaction solvent was distilled off under reduced pressure, and the residue was extracted several times with a mixture of 5 mL of ethyl acetate and n-hexane (volume ratio 1:1) continuously, the extracts were combined, and the extractant was recovered by distillation under reduced pressure. Rectify at 125-130°C under a pressure of 2000 Pa,...

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Abstract

The invention discloses a method for preparing 5-formyloxy methylfurfural from fructose, and relates to 5-formyloxy methylfurfural. The method specifically comprises the following steps of mixing the fructose and choline chloride into a reaction container, using hydrochloric acid as a catalyst, using a polarity organic solvent as a reaction extracting agent, and heating to react; after reaction is finished, naturally cooling, fetching out reaction liquid, adding a certain amount of anhydrous formic acid into the reaction liquid, and continuing to heat to react; after reaction is finished, relieving pressure and distilling to remove the solvent, using the extracting agent to continuously extract the residues, combining the extracting agent, and relieving pressure and distilling to recycle the extracting agent; under the certain condition, distilling the residual liquid, using a saturated sodium bicarbonate water solution to wash distilling matter, and drying anhydrous magnesium sulfate, so as to obtain the 5-formyloxy methylfurfural with purity more than 99%. The method has the advantages that the reaction condition is mild, the reaction system is green and recyclable, the feeding amount is high, the yield rate is high, a new path is provided for preparation of the 5-formyloxy methylfurfural, and the added value of biomass raw materials is further improved.

Description

technical field [0001] The present invention relates to 5-formyloxymethylfurfural, in particular to a method for preparing 5-formyloxymethylfurfural from fructose. Background technique [0002] 5-Hydroxymethylfurfural (5-HMF) is considered to be the most promising platform chemical because of its unique chemical structure, which can be converted into various furanic substances with high added value, such as 2,5-di Methylfuran (DMF), 2,5-furandimethanol (FDM), 2,5-furandicarbaldehyde (DFF), 2,5-furandicarboxylic acid (FDCA), etc. HMF is widely used in the chemical industry and has attracted much attention. Its research mainly focuses on the improvement of yield and separation and purification. Studies have found that ionic liquid is an effective reaction medium for preparing 5-HMF. Using fructose as raw material, the yield of 5-HMF can reach more than 90%, but its cost is high, and the prepared 5-HMF is difficult to separate and purify. In recent years, deep eutectic melt (...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/50
CPCC07D307/50
Inventor 孙勇熊彩霞唐兴林鹿曾宪海
Owner XIAMEN UNIV
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