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Method for preparing 2,5-diformylfuran by oxidizing 5-hydroxymethylfurfural

A technology of diformylfuran and hydroxymethylfurfural, which is applied in chemical instruments and methods, organic chemistry, chemical/physical processes, etc., can solve the problems of easy corrosion and toxicity, low product yield, unsatisfactory results, etc. Inexpensive, simple catalyst system, low catalyst consumption

Active Publication Date: 2011-03-23
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the use of molecular oxygen to oxidize 5-hydroxymethylfurfural to prepare 2,5-diformyl furan has been reported, the results are not satisfactory; some reports use catalysts containing corrosive and toxic bromine elements, such as Co / Mn / Zr / Br system (Adv.Synth.Catal., 2001, 343, 102-111); There are also methods that need to use noble metals as catalysts, such as Pd-Bi system (Top.Catal., 2000, 13, 237-242) , or use a high boiling point solvent (Org.Lett., 2003, 5, 2003-2005)
Among the methods and technologies that have been reported, the common problem is that the product yield is very low, which makes separation difficult

Method used

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  • Method for preparing 2,5-diformylfuran by oxidizing 5-hydroxymethylfurfural

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Example 1: Add 0.1mol of 5-hydroxymethylfurfural, 0.001mol of vanadyl phosphate, and 0.001mol of copper sulfate into a 100mL reaction kettle, add 5mL of acetonitrile, close the kettle, fill it with oxygen at a pressure of 0.5MPa, and then raise the temperature while stirring To 80 ℃, and keep 3h, if the oxygen partial pressure drops, add oxygen. After the reaction reached a predetermined time, the reacted mixture was cooled to room temperature. Samples were taken and analyzed by gas chromatography, and the conversion rate of raw materials was greater than 99%, and the selectivity was greater than 99%. The solvent was separated by distillation, the solid was washed with water, and a white solid was obtained by filtration. Dry in vacuo to give a white solid. The product purity reaches more than 99%. The isolated yield is 98%.

Embodiment 2

[0019] Example 2: 10-fold magnification experiment: Add 1mol 5-hydroxymethylfurfural, 0.01mol vanadyl phosphate, and 0.01mol copper sulfate to a 200mL reaction kettle, add 50mL acetonitrile, close the kettle, and fill it with oxygen at a pressure of 0.5MPa. Then the temperature was raised to 80°C under stirring, and kept for 3h, and oxygen was supplemented if the partial pressure of oxygen decreased. After the reaction reached the predetermined time, according to the method described in Example 1, the reacted mixture was cooled to room temperature for sampling analysis. The raw material conversion rate is greater than 99%, and the selectivity is greater than 99%. The isolated yield is greater than 97%.

Embodiment 3

[0020] Embodiment 3: 0.1mol 5-hydroxymethylfurfural, 0.003mol vanadyl sulfate, 0.003mol cupric chloride, 0.005mol potassium nitrite are added in the 100mL reactor, add 5mL toluene, close the still, fill in oxygen pressure is 0.1MPa, then raise the temperature to 120°C with stirring, and keep it for 12h. If the partial pressure of oxygen drops, supplement oxygen. After the reaction reaches the predetermined time, according to the method described in Example 1, cooling and sampling analysis, the conversion rate of raw materials is greater than 99%, and the selectivity is greater than 99%. The separation yield is greater than 95%.

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Abstract

The invention discloses a method for preparing 2,5-diformylfuran by selectively oxidizing 5-hydroxymethylfurfural in the presence of a catalyst. In the method, oxygen or air is used as an oxygen source, the catalyst is a composite catalyst system a composite catalyst system consisting of vanadium oxide and an auxiliary agent, and at the temperature of between 20 and 120 DEG C, the 5-hydroxymethylfurfural is selectively oxidized into the 2,5-diformylfuran. The method has high oxidation efficiency and high product yield; the catalyst is cheap and readily available; the reaction conditions are mild; the product is easy to separate and purify; and the purity of the product is over 99 percent. Therefore, the method has bright application prospect.

Description

technical field [0001] The invention relates to a method for preparing 2,5-diformyl furan by catalytic selective oxidation of 5-hydroxymethylfurfural. Specifically, it uses a composite catalyst system and uses air or oxygen as an oxygen source to oxidize 5-hydroxymethylfurfural with high activity and high yield under mild conditions to prepare 2,5-diformylfuran. Background technique [0002] With the depletion of petroleum and other fossil resources, it is of great significance to develop and utilize renewable and abundant biomass resources to replace or supplement the shortage of petroleum resources, and has received widespread attention and attention at home and abroad. 5-Hydroxymethylfurfural can be obtained by dehydration of sugar compounds, and is one of the important platform compounds in biorefinery (Science, 2006, 312, 1933-1937; Science, 2007, 316, 1597-1600; Angew.Chem .Int.Ed., 2008, 47, 9345-9348; J.Am.Chem.Soc., 2009, 131, 1979-1985). The selective oxidation o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/46B01J27/198B01J27/24B01J27/25B01J27/122B01J27/055
Inventor 徐杰马继平杜中田高进张展苗虹
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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