Method for preparing bis-(5-formylfurfuryl)ether from 5-hydroxymethylfurfural

A technology of formylfurfuryl and hydroxymethylfurfural, applied in chemical recovery, organic chemistry, etc., can solve the problems of poor hydrothermal stability, non-crystallization of pore walls, poor thermal stability, etc., and achieve easy recovery, maintain catalytic activity, strong The effect of water resistance

Active Publication Date: 2021-02-02
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in the prior art, mesoporous molecular sieves have problems such as poor hydrothermal stability, amorphous pore walls, and weak acidity, which limit their large-scale application.
Therefore, solid acids containing Lewis acid and Brφnsted acid sites were considered, such as AmberliteIR120 and Amberlyst-15, but their thermal stability during regeneration is poor

Method used

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  • Method for preparing bis-(5-formylfurfuryl)ether from 5-hydroxymethylfurfural
  • Method for preparing bis-(5-formylfurfuryl)ether from 5-hydroxymethylfurfural
  • Method for preparing bis-(5-formylfurfuryl)ether from 5-hydroxymethylfurfural

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Experimental program
Comparison scheme
Effect test

Embodiment 1-7

[0037] Add 250 mg of 5-hydroxymethylfurfural and 10 mL of toluene to a 25 mL reaction tube, heat to 90 °C under reflux, add 5 mg of catalyst (Zr(OTf) 4 、Hf(OTf) 4 , Nb(OTf) 5 、Ta(OTf) 5 , W(OTf) 6 、Sc(OTf) 3 and Yb(OTf) 3 ), and continued to stir for 6 hours. After the reaction, cool to room temperature, take samples, and send to HPLC for detection. The specific catalysts and test results are listed in Table 1, numbered 1-7. Preparation of bis-(5-formyl furfuryl) ether 1 H NMR diagram, 13 C NMR chart and HPLC chart as Figure 1-3 shown.

[0038] Table 1. The detection result of embodiment 1-7

[0039]

[0040]

Embodiment 8-11

[0042] Add 250 mg of 5-hydroxymethylfurfural and 10 mL of toluene to a 25 mL reaction tube, heat to a certain temperature under reflux, and add 5 mg of Yb(OTf) 3 , kept stirring for 6 hours. After the reaction, cool to room temperature, take samples, and send to HPLC for detection. The specific reaction temperature and detection results are listed in Table 2, and the serial numbers are 8-11.

[0043] Table 2. The detection result of embodiment 8-11

[0044]

Embodiment 12-15

[0046] Add 250mg of 5-hydroxymethylfurfural and 10mL of toluene to a 25mL reaction tube, heat to 110°C under reflux, add 5mg of Yb(OTf) 3 , keep stirring for a certain period of time. After the reaction, cool to room temperature, take samples, and send to HPLC for detection. The specific reaction time and detection results are listed in Table 3, and the serial numbers are 12-15.

[0047] Table 3. The detection result of embodiment 12-15

[0048]

[0049]

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Abstract

The invention relates to a method for preparing bis-(5-formylfurfuryl)ether from 5-hydroxymethyl furfural. The method comprises the step of dehydrating 5-hydroxymethylfurfural in the presence of a catalyst to obtain bis-(5-formylfurfuryl)ether, wherein the catalyst is metal trifluoromethanesulfonate. The 5-hydroxymethylfurfural used in the method can be conveniently obtained from biomass. The usedmetal trifluoromethanesulfonate catalyst has strong water resistance, can well maintain catalytic activity, and realizes high yield. The catalyst is easy to recover and can be repeatedly used, and the catalytic activity is not reduced. The method disclosed by the invention has the advantages of high conversion activity, high yield and excellent stability, reaction products are simple to separate,and the high-purity bis-(5-formylfurfuryl)ether can be obtained. Meanwhile, the prepared bis-(5-formylfurfuryl)ether can be used as a raw material for preparing polyamide materials.

Description

technical field [0001] The invention belongs to the technical field of producing polymer precursors from biomass, in particular to a preparation method of bis-(5-formyl furfuryl) ether. Background technique [0002] Bis-(5-formylfurfuryl) ether (OBMF) is an important bio-based chemical, which has great application prospects and has attracted extensive attention. OBMF can be used to synthesize crown ethers, polyurethanes, polyamides, and imine-based polymers with high thermal and electrical conductivity. In particular, the synthesized polyamide-based materials can be widely used in aerospace materials, microelectronic devices, auto parts, coatings and other fields. There have been studies using OBMF and 1,4-diaminobenzene to synthesize polymers with high glass transition temperature, thermal and electrical conductivity, and soluble in polar solvents. In addition, OBMF also has broad antiviral, anti-tuberculosis, and antioxidant properties, and can be used as a drug (such as...

Claims

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Application Information

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IPC IPC(8): C07D307/46
CPCC07D307/46Y02P20/584
Inventor 傅尧滕嘉楠朱瑞李兴龙
Owner UNIV OF SCI & TECH OF CHINA
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