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Method for preparing 2,5-diformyl furan by catalyzing 5-hydroxy methyl furfural

A technology of diformylfuran and hydroxymethylfurfural, applied in chemical instruments and methods, physical/chemical process catalysts, organic compound/hydride/coordination complex catalysts, etc., can solve the problem of low product yield and reaction temperature High, difficult separation and other problems, to achieve the effect of high product yield, simple separation, high separation yield

Active Publication Date: 2011-06-22
中科化物(大连)科技实业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the relevant literature also has molecular oxygen as the report of oxidant research, most of the reaction temperature is higher (more than 150 ℃), the product yield is low (less than 61%), and separation is difficult

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Add 0.63g of 5-hydroxymethylfurfural, 0.0078g of TEMPO, 0.0163g of vanadyl sulfate, and 0.0069g of sodium nitrite into a 50mL reaction kettle, add 2mL of acetonitrile, close the kettle, and fill it with oxygen at a pressure of 0.5MPa. Stir at ℃ for 0.5h, then raise the temperature to 80℃ with stirring, and keep it for 3h. If the partial pressure of oxygen drops, supplement oxygen. After the reaction, cool to room temperature. Sampling is analyzed by gas chromatography, the conversion rate is greater than 99%, and the selectivity is greater than 99%. The solvent was removed under reduced pressure by a water pump, the solid was washed thoroughly with water, and filtered to obtain a white solid. Dry in vacuo to give a white solid. The product purity reaches more than 99%. The isolated yield is 98%.

Embodiment 2

[0021] 10 times magnification experiment: Add 6.3g 5-hydroxymethylfurfural, 0.078g TEMPO, 0.163g vanadyl sulfate, 0.069g sodium nitrite into a 100mL reaction kettle, add 20mL acetonitrile, close the kettle, and fill it with oxygen at a pressure of 0.5 MPa, first stir at 30°C for 0.5h, then raise the temperature to 80°C under stirring, and keep it for 3h, if the partial pressure of oxygen drops, supplement oxygen. After the reaction, it was cooled to room temperature and analyzed. The conversion rate is greater than 99%, and the selectivity is greater than 99%. The solvent was removed under reduced pressure by a water pump, the solid was washed thoroughly with water, and filtered to obtain a white solid. Dry in vacuo to give a white solid. The isolated yield is 97%.

Embodiment 3

[0023] Add 0.63g 5-hydroxymethylfurfural, 0.0085g 4-methoxy-2,2,6,6-tetramethylpiperidine-oxyl radical, 0.0163g vanadyl phosphate, 0.0040g potassium nitrite to 50mL Add 5mL of acetone to the reaction kettle, close the kettle, fill it with oxygen at a pressure of 0.05MPa, first stir at 20°C for 0.5h, then raise the temperature to 80°C while stirring, and keep it for 12h. If the oxygen partial pressure drops, add oxygen. After the reaction, it was cooled to room temperature and analyzed. The conversion rate is greater than 99%. The solvent was removed under reduced pressure by a water pump, the solid was washed thoroughly with water, and filtered to obtain a white solid. Dry in vacuo to give a white solid. The isolated yield is 96%.

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Abstract

The invention provides a method for preparing 2,5-diformyl furan by catalytic oxidation of 5-hydroxy methyl furfural. The method comprises the following steps: taking air or oxygen as an oxygen source, taking a mixture of inorganic vanadium oxides, 2,2,6,6-4-pipecolate-oxygen radicals and derivatives and nitrites of the 2,2,6,6-4-pipecolate-oxygen radicals as a compound catalyst system, and oxidizing the 5-hydroxy methyl furfural into the 2,5-diformyl furan at a temperature of between 50 and 120 DEG C. The method has the advantages of high oxidizing efficiency, few byproducts, mild reaction conditions, easy separation and purification of products and quite high practicability.

Description

technical field [0001] The invention relates to a method for preparing 2,5-diformyl furan by catalytically oxidizing 5-hydroxymethylfurfural. Specifically, it uses a three-component catalyst system, uses air or oxygen as the oxygen source, and oxidizes 5-hydroxymethylfurfural with high activity and high yield under mild conditions to prepare 2,5-diformylfuran. Background technique [0002] With the depletion of fossil resources such as petroleum, the search for chemicals that can replace fossil resources has increasingly become the focus of research in various countries. 5-Hydroxymethylfurfural obtained from carbohydrates is an important platform compound in biorefinery. (Angew.Chem.Int.Ed.2007,46,7164-7183; Chem.Rev.2007,107,2411-2502) Selective oxidation of 5-hydroxymethylfurfural to prepare 2,5-diformylfuran is its important One of the downstream product development processes. As a key intermediate, 2,5-diformylfuran has important potential applications in synthetic fi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/46B01J31/02
Inventor 徐杰杜中田马继平苗虹
Owner 中科化物(大连)科技实业有限公司
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