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Method for preparing 2,5-diformylfuran

A technology of furandiformaldehyde and hydroxymethyl furfural, applied in directions such as organic chemistry, can solve problems such as difficulty in product separation, and achieve the effects of low economic and environmental cost, easy reuse, and low amount of by-products

Inactive Publication Date: 2015-04-01
合肥利夫生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, since the solvent used in the reaction system is a high boiling point solvent, it is difficult to separate the product in this system.

Method used

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  • Method for preparing 2,5-diformylfuran
  • Method for preparing 2,5-diformylfuran
  • Method for preparing 2,5-diformylfuran

Examples

Experimental program
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Effect test

Embodiment 1

[0031] In this example, 2,5-furandicarbaldehyde (2,5-DFF) was prepared according to the following steps:

[0032] Dissolve 63 mg of 5-HMF (total 0.5 mmol) in 2 mL of dichloroethane, then add 10.1 mg of Fe(NO 3 ) 3 9H 2 O (a total of 0.025mmol, accounting for 5% of the amount of 5-HMF substances), 7.8mg of TEMPO (a total of 0.025mmol, accounting for 5% of the amount of 5-HMF substances) and 1.5mg NaCl (a total of 0.025mol, accounting for 5- 5% of the amount of the HMF substance) to obtain a mixed liquid of the raw material group, and stirred and reacted in the air at room temperature and pressure for 4 hours to obtain a reaction mixture.

[0033] The GC detection result of reaction mixture is as follows figure 2 shown, from figure 2 It can be seen that the product 2,5-furandicarbaldehyde (internal standard: 5-methylfurfural) was successfully obtained in this implementation, and the yield of 2,5-DFF in this example was 92%.

[0034] Conditions for GC detection:

[0035] ...

Embodiment 2

[0039]This embodiment prepares the raw material group as shown in Table 1, and in addition to the raw materials covered by Table 1, also contains 0.5mmol of 5-HMF and 2mL of organic solvent dichloromethane, the preparation method is: 0.5mmol 5-HMF is added to In 2mL of dichloromethane, add TEMPO, catalyst activator (Fe(NO 3 ) 3 9H 2 O, Cu(NO 3 ) 2 ·3H 2 O, AgNO 3 , Pd(NO 3 ) 3 ·3H 2 O or FeCl 3 ) and additives (NaCl) to form a raw material mixture, stirring the raw material mixture at room temperature and pressure for 4 hours, so that 5-hydroxymethylfurfural can The oxidation reaction is carried out to obtain the product 2,5-furandicarbaldehyde. The yields of the products obtained are shown in Table 1.

[0040] Table 1 The table of raw materials used in embodiment 2

[0041]

[0042] As can be seen from the yield in the table, no target compound can be obtained without adding TEMPO (Example 2) or without adding iron nitrate nonahydrate (Example 3). Adding a sma...

Embodiment 3

[0044] This embodiment prepares the raw material group as shown in Table 2, and in addition to the raw materials covered by Table 2, it also contains 0.5mmol of 5-HMF and 2mL of organic solvent dichloromethane. The preparation method is: 0.5mmol 5-HMF is added to In 2mL of dichloromethane, add TEMPO, catalyst activator (Fe(NO 3 ) 3 9H 2 O) and additives (NaBr, KCl, NaF or NaCl) to form a raw material mixture, and stir the raw material mixture for 4 hours at room temperature and normal pressure, so that 5-hydroxymethylfurfural is catalyzed by the piperidine nitrogen oxide catalyst and the catalyst activator. 1. Carry out the oxidation reaction under the oxidation of air to obtain the product 2,5-furandicarbaldehyde. The yields of the products obtained are shown in Table 2.

[0045] Table 2 The table of raw materials used in embodiment 3

[0046]

[0047] It can be seen from the yield in the table that adding a small amount of alkali metal halide can affect the yield of 2...

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Abstract

The invention discloses a method for preparing 2,5-diformulfuran. The method is characterized in that 5-hydroxymethylfurfural, a piperidine nitrogen oxide catalyst and a catalyst activating agent serve as raw materials, 5-hydroxymethylfurfural is added into an organic solvent, then the piperidine nitrogen oxide catalyst and the catalyst activating agent are added into the organic solvent, and raw material mixed liquor is formed; 5-hydroxymethylfurfural has an oxidation reaction under the catalyst action of the piperidine nitrogen oxide catalyst and the catalyst activating agent at the temperature of 10-100 DEG C for 1-24 hours with molecular oxygen as an oxidation agent, and the product of 2,5-diformulfuran is obtained. The catalyst used in the preparation method is low in price and easy to obtain, the reaction time is short, and the method is efficient and energy-saving; the yield of the target product reaches as high as 92%, and a few of by-products are produced; air serves as an oxygen source, and the economic and environment cost are low.

Description

technical field [0001] The invention relates to a preparation method of 2,5-furandicarbaldehyde. Background technique [0002] Petroleum has been an important dependence of human development since the 20th century. With the reduction of petroleum reserves and the increase of people's demand for petroleum products, the search for renewable petroleum substitutes has attracted much attention in recent years. Biomass has attracted extensive attention as the only renewable organic carbon resource. 5-Hydroxymethylfurfural (5-HMF) is an important platform molecule that can be obtained from biomass and converted into a variety of liquid fuels and chemicals. Through oxidation, 5-HMF can be converted into 2,5-furandicarbaldehyde (2,5-DFF), which is a chemical intermediate with important potential application value, such as medicine, polymer monomer, adhesive Agents and many other fields. However, due to the abundant functional groups of 5-HMF, a series of side reactions such as per...

Claims

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Application Information

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IPC IPC(8): C07D307/46
CPCC07D307/46
Inventor 邓晋徐海汪鹏徐强丁帆丁飞焦许圣春
Owner 合肥利夫生物科技有限公司
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