Method for catalysis-synthesizing 2,5-dicarbaldehyde by carbohydrate

A technology of carbohydrates and furandicarbaldehyde, applied in the direction of organic chemistry, can solve the problems of high energy consumption, high cost, low yield, etc., and achieve the effect of simple operation, short reaction time and less reaction by-products

Inactive Publication Date: 2010-07-07
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The purpose of the present invention is to provide a kind of synthetic method more economical and practical, can synthesize the method for DFF

Method used

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  • Method for catalysis-synthesizing 2,5-dicarbaldehyde by carbohydrate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Add 0.08g glucose (0.45mmol), 1mLDMA, 0.007g CrCl 3 ·6H 2 O and 0.08g NaBr. After connecting the condenser tube, place it in an oil bath, raise the temperature of the oil bath to 100°C, keep the temperature constant, stir, and reflux for 6 hours to stop the reaction. The reaction system was naturally cooled to room temperature, and the CrCl was separated by centrifugation. 3 ·6H 2 O and NaBr, GC analysis indicated a 74% yield of HMF. Add 0.096mmolNaVO to the reaction solution 3 2H 2 O, air was bubbled through the mixture at a flow rate of 24 mL / min, the temperature of the oil bath was raised to 110° C., the temperature was kept constant, stirred, and the reaction was refluxed for 10 hours to stop the reaction. The reaction system was naturally cooled to room temperature, and NaVO was separated by centrifugation. 3 2H 2 O, GC analysis shows that the selectivity of DFF calculated with HMF is 70%, the yield is 69%, and the yield of DFF calculated with glucose is 51...

Embodiment 2-5

[0018] Prepare four reaction solutions containing HMF according to the method of Example 1, and add NaVO respectively 3 2H 2 O0.032mmol, 0.064mmol, 0.128mmol, 0.160mmol, and air was bubbled through the four mixtures at a flow rate of 24mL / min, and the oil bath was heated to 110°C, kept at constant temperature, stirred, and refluxed for 10 hours After stopping the reaction. The reaction system was naturally cooled to room temperature, and NaVO was separated by centrifugation. 3 2H 2 O. The reaction solution was detected by GC, and the results of the reaction under different amounts of catalysts are listed in Table 1.

[0019] Table 1

[0020] Implementation column

Embodiment 6-9

[0022] Prepare four reaction solutions containing HMF according to the method of Example 1, add 0.096mmol NaVO 3 2H 2 O, and the air is bubbled through the four mixed liquids at a flow rate of 8mL / min, 16mL / min, 32mL / min, and 40mL / min respectively, and the oil bath is heated to 110°C, constant temperature, stirring, and reflux reaction The reaction stopped after 10 hours. The reaction system was naturally cooled to room temperature, and NaVO was separated by centrifugation. 3 2H 2 O. The reaction solution was detected by GC, and the results obtained from the reaction at different air flow rates are listed in Table 2.

[0023] Table 2

[0024] Implementation column

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Abstract

The invention relates to a method for catalysis-synthesizing 2,5-dicarbaldehyde by carbohydrate; carbohydrate is used as raw material, N,N-dimethylacetylamide is used as reaction medium, sodium bromide is used as additive, 5-hydroxymethylfurfural is dehydrated under acid catalysis, vandic salt is added as the catalyst, and air flows in under normal pressure to carry out oxidizing reaction, so as to synthesize 2,5-dicarbaldehyde; in the method, the reaction condition is mild, the raw materials and the catalyst are obtained easily, the method has high 2,5-dicarbaldehyde yield and the reaction process is easily operated.

Description

Technical field: [0001] The present invention relates to a two-step catalytic process for the preparation of 2,5-furandicarbaldehyde from carbohydrates. Background technique: [0002] 2,5-furandicarbaldehyde (DFF) is a versatile intermediate in organic synthesis. DFF itself can be used as a raw material to synthesize drugs, macrocyclic ligands, antifungal agents and furans. It can also be used as a polymerized monomer to form various high polymers, such as polypinacol and polyethylene. In addition, it can be used as a synthetic pharmaceutical intermediates. [0003] At present, using 5-hydroxymethylfurfural (HMF) as a raw material to synthesize DFF through oxidation reaction is considered to be the only industrially feasible method for preparing DFF. However, because obtaining HMF requires complex separation procedures, the high price of HMF makes the production cost of DFF very high, so the production of DFF has not been industrialized so far. Carbohydrates are regarded ...

Claims

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Application Information

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IPC IPC(8): C07D307/46
Inventor 胡常伟向西杨宇郭滨童冬梅祝良芳
Owner SICHUAN UNIV
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