Preparation method of bis-(5-formyl furfuryl) ether

A formyl furfuryl, two-component technology, applied in the field of bis-ether preparation, to achieve the effect of mild reaction conditions, easy separation and high activity

Active Publication Date: 2021-11-23
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

According to literature research, there is currently no report on the preparation of bis-(5-formyl furfuryl) ether by catalyzing the dehydration of 5-hydroxymethylfurfural under solvent-free conditions.

Method used

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  • Preparation method of bis-(5-formyl furfuryl) ether
  • Preparation method of bis-(5-formyl furfuryl) ether
  • Preparation method of bis-(5-formyl furfuryl) ether

Examples

Experimental program
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Effect test

Embodiment 1

[0059] 10mmol 5-hydroxymethylfurfural, 0.01mmol Cu(NO 3 ) 2 , 0.01 mmol VOSO 4 , 3mmol oxalic acid was added to a 50mL reaction kettle, the kettle was closed, and the air in the kettle was replaced with nitrogen gas 7 times, filled with 0.1MPa nitrogen gas, heated to 80°C, and reacted at this temperature for 0.5h. After the reaction, the reacted mixture was cooled to room temperature with water, acetonitrile was added to dissolve the solid, and then the catalyst was removed by filtration. The internal standard mesitylene was added, a sample was taken and analyzed by gas chromatography. Acetonitrile was removed by rotary evaporation, ethyl acetate was added and vacuum suction filtered, ethyl acetate was removed by rotary evaporation, and a solid was obtained by vacuum drying, with a gas chromatography (GC) purity of more than 99%.

[0060] The conversion rate of 5-hydroxymethylfurfural, the GC yield of bis-(5-formyl furfuryl) ether and the separation yield of bis-(5-formyl f...

Embodiment 2

[0062] 10mmol 5-hydroxymethylfurfural, 0.05mmol Ni(NO 3 ) 2 , 0.06mmol NaVO 3 , 2mmol of tartaric acid was added to a 50mL reaction kettle, the kettle was closed, and the air in the kettle was replaced with helium 7 times, filled with 5.0Mpa helium, heated to 50°C, and reacted at this temperature for 1h. After the reaction finished, according to the method described in Example 1, cooling and sampling analysis, the conversion rate of 5-hydroxymethylfurfural was 75%, and the GC yield of two-(5-formyl furfuryl) ether was 72%. The yield was 71%.

Embodiment 3

[0064] 10mmol 5-hydroxymethylfurfural, 0.1mmol Co(NO 3 ) 2 , 0.1 mmol VOPO 4 , 1mmol of acetylacetone was added to a 50mL reaction kettle, the kettle was closed, and the air in the kettle was replaced with nitrogen gas 7 times, filled with 3.0MPa nitrogen gas, heated to 60°C, and reacted at this temperature for 1.5h. After the reaction finished, according to the method described in Example 1, cooling and sampling analysis, the conversion rate of 5-hydroxymethylfurfural was 50%, and the GC yield of two-(5-formyl furfuryl) ether was 48%. The yield was 47%.

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Abstract

The invention discloses a preparation method of bis-(5-formyl furfuryl) ether. The preparation method at least comprises the steps of in an atmosphere containing an inert gas, carrying out a reaction on a material containing 5-hydroxymethylfurfural in the presence of a bi-component catalytic system and an organic additive to prepare the bis-(5-formyl furfuryl) ether. The method is a novel technology which is low in catalyst dosage, easy to separate, low in pollution and solvent-free, and the bis-(5-formyl furfuryl) ether is prepared by dehydrating the 5-hydroxymethylfurfural under the action of an organic additive. The method has a wide application prospect.

Description

technical field [0001] The application relates to a preparation method of bis-(5-formyl furfuryl) ether, which belongs to the field of chemical synthesis. Background technique [0002] 5-Hydroxymethylfurfural is an important furan compound, which can be prepared by dehydration of glucose or fructose. Due to its excellent chemical properties, it is widely used in medicine, chemistry, energy and other fields. It is also listed by the US Department of Energy One of the ten most important platform chemicals, its derivatives have great application prospects in the fields of fine chemicals, medicine, and degradable plastics. [0003] Bis-(5-formyl furfuryl) ether exists in a variety of plants. People have isolated this compound from hawthorn, southwest honeysuckle, ganoderma lucidum, and chuanxiong. Pharmacological experiments show that it has anti-virus, anti-nitrogenation and inhibition The role of Mycobacterium tuberculosis. According to literature research, there is no repor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/46
CPCC07D307/46Y02P20/584
Inventor 徐杰范晓萌马继平高进高鸣霞苗虹
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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