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Method for preparing 2,5-furandicarboxaldehyde from 5-hydroxymethylfurfural

A technology of hydroxymethylfurfural and furandicarbaldehyde, which is applied in the field of preparation of 2,5-furandicarbaldehyde by catalyzing the oxidation of 5-hydroxymethylfurfural, which can solve the limitation of noble metal ruthenium for further application, and there is no catalytic oxidation preparation method, etc. problems, to achieve the effect of high selectivity, mild reaction conditions and simple operation

Active Publication Date: 2020-04-28
YANTAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the system obtained a higher DFF yield under milder conditions, the use of noble metal ruthenium limits its further application.
[0005]Although 2,5-furandicarbaldehyde can be obtained by catalytic oxidation of 5-hydroxymethylfurfural, there is no relatively economical, reasonable and efficient preparation method for catalytic oxidation

Method used

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Examples

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Comparison scheme
Effect test

preparation example Construction

[0023] CeCu(OH) 6 Mo 6 o 18 Preparation example of

[0024] (1) Preparation of Cu(II) polyanions (NH 4 ) 4 Cu(OH) 6 Mo 6 o 18 :

[0025] Add CuSO dropwise 4 • 5H 2 O(3×10-3 mol) mixed aqueous solution (20 cm 3 ) to boiling heptamolybdic acid aqueous solution (wherein, heptamolybdic acid is in 80 cm 3 The amount in water is 4.2×10 -3 mol), the resulting solution was refluxed for 10 min, and then the obtained yellow insoluble precipitate was filtered off while hot.

[0026] The filtrate was transferred to a petri dish, left standing for 12h to form light blue crystals, the crystals were filtered and vacuum-dried at 60°C for 8 hours to obtain (NH 4 ) 4 Cu(OH) 6 Mo 6 o 18 .

[0027] (2) CeCu(OH) 6 Mo 6 o 18 was prepared as follows:

[0028] The excess Ce(NH 4 ) 2 (NO 3 ) 6 Aqueous solution was added dropwise to (NH 4 ) 4 Cu(OH) 6 Mo 6 o 18 aqueous solution and stirred at room temperature, wherein, Ce(NH 4 ) 2 (NO 3 ) 6 with (NH 4 ) 4 Cu(OH) ...

Embodiment 1

[0031] The preparation of 2,5-furandicarbaldehyde by oxidation of 5-hydroxymethylfurfural comprises the following steps:

[0032] (1) Add 0.0504 g HMF into 7 mL p-chlorotoluene solution, stir and then add 40 mg CeCu(OH) 6 Mo 6 o 18 Catalyst, at 110 o Continuously feed oxygen (20 mL / min, 8 h) at C to carry out HMF oxidation reaction to obtain a mixed liquid;

[0033] (2) The mixture was diluted with the same solvent and analyzed by high performance liquid chromatography. The standard solution was used to identify the product type, showing that the conversion rate of HMF was 33%, and the yield of DFF reached 33%.

[0034] It shows that HMF reacts with oxygen, and the reason for the reaction is that CeCu(OH) 6 Mo 6 o 18 Acts as a catalyst, but at 110 o C, the optimal catalytic temperature cannot be reached, and the DFF yield is not high, only 33%.

Embodiment 2

[0036] The preparation of 2,5-furandicarbaldehyde by oxidation of 5-hydroxymethylfurfural comprises the following steps:

[0037] (1) Add 0.0504 g HMF into 7 mL p-chlorotoluene solution, stir and then add 40 mg CeCu(OH) 6 Mo 6 o 18 Catalyst, at 120 o Continuously feed oxygen (20 mL / min, 8 h) at C to carry out HMF oxidation reaction to obtain a mixed liquid;

[0038] (2) The mixture was diluted with the same solvent and analyzed by high performance liquid chromatography. The standard solution was used to identify the product type, showing that the conversion rate of HMF was 39%, and the yield of DFF reached 39%.

[0039] It shows that HMF reacts with oxygen, and the reason for the reaction is that CeCu(OH) 6 Mo 6 o 18 acts as a catalyst, but at 120 o C, the optimal catalytic temperature cannot be reached, and the DFF yield is not high, only 39%.

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Abstract

The invention relates to a method for preparing 2,5-furandicarboxaldehyde through oxidation of 5-hydroxymethylfurfural, particularly a method for catalyzing oxidation of 5-hydroxymethylfurfural (HMF)by adopting an Anderson type CeCu(OH)6Mo6O18 heteropolyacid salt as a catalyst to prepare 2,5-furandicarboxaldehyde (DFF). The method comprises the following steps: 1) adding 0.0504 g of HMF into 7 mLof an aromatic hydrocarbon solvent solution, stirring, then adding 40-120 mg of the Anderson type heteropolyacid salt CeCu(OH)6Mo6O18 catalyst; 2) introducing oxygen, carrying out an HMF oxidation reaction at the temperature of 110 to 150 DEG C to obtain a liquid mixture containing DFF; (3) diluting the liquid mixture and analyzing a product by using a high performance liquid chromatograph. The DFF can be efficiently synthesized by the method (the yield is up to 99%), the reaction conditions are mild, and the catalyst can be recycled, so that the method is a cheap and efficient DFF preparation method. Moreover, compared with a catalyst in the prior art, the catalyst used in the method has higher DFF selectivity and is more economical.

Description

technical field [0001] The invention relates to the technical field of catalysts, in particular to a preparation method for catalyzing the oxidation of 5-hydroxymethylfurfural to prepare 2,5-furandicarbaldehyde. Background technique [0002] Biomass is an available and renewable non-fossil carbon source, and it has been hailed as one of the new energy sources most likely to replace fossil fuels and organic molecules. 5-Hydroxymethylfurfural (HMF), an important intermediate linking biomass resources to fossil carbon sources, has attracted considerable attention. HMF can synthesize many high value-added chemical materials, such as 2,5-furandicarboxylic acid (FDCA) and 2,5-formylfuran (DFF), etc. [0003] Due to its unique dialdehyde properties, DFF has been widely used in the synthesis of various useful compounds, including pharmaceutical intermediates, antifungal drugs, organic conductors, macrocyclic ligands, and furan resins, etc. Therefore, the selective oxidation of HMF...

Claims

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Application Information

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IPC IPC(8): C07D307/46B01J31/16B01J27/19
CPCC07D307/46B01J27/19B01J23/887Y02P20/584
Inventor 吕宏缨徐佳佳朱治国苏婷廖卫平
Owner YANTAI UNIV
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