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Preparation method of 2,5-furandicarboxylate

A technology of furandicarboxylic acid and furandiformaldehyde, applied in the direction of organic chemistry, etc., can solve the problems of equipment corrosion, low unit production capacity, low raw material concentration, etc.

Active Publication Date: 2015-04-22
INST OF ADVANCED TECH UNIV OF SCI & TECH OF CHINA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this method can directly precipitate the product FDCA, it still has the disadvantages of low raw material concentration and low unit production capacity. At the same time, high-pressure air or oxygen must be used, and the equipment cost is high; in addition, the introduction of bromine also seriously corrodes the equipment.

Method used

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  • Preparation method of 2,5-furandicarboxylate
  • Preparation method of 2,5-furandicarboxylate
  • Preparation method of 2,5-furandicarboxylate

Examples

Experimental program
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Effect test

Embodiment 1

[0026] This embodiment prepares FDCA according to the following steps:

[0027] Add 0.5mmol (62mg) of 2,5-DFF to 0.5mL of 70% tert-butanol peroxy aqueous solution, stir and react at 110°C for 6h, then cool naturally to room temperature to obtain the reaction product, and centrifuge the reaction product The precipitate was separated, washed with 5 mL of water and dried at 105°C to obtain 70 mg of white solid, which was the target product 2,5-furandicarboxylic acid. The molar yield of the product was 90% after testing.

Embodiment 2

[0029] a. 5-HMF (63mg, 0.5mmol) was added to 2mL of dichloroethane, and then TEMPO (7.8mg, 0.025mmol, 5mol%), Fe(NO 3 ) 3 9H 2 O (10.1mg, 0.025mmol, 5mol%) and NaCl (1.5mg, 0.025mol, 5mol%) were stirred and reacted at room temperature in air for 4h to obtain a reaction mixture containing 2,5-furandicarbaldehyde; GC test results such as figure 1 shown, from figure 1 It can be seen that the product 2,5-furandicarbaldehyde (internal standard: 5-methylfurfural) was successfully obtained in this step.

[0030] b. Add 0.5 mL of 70% tert-butanol peroxy aqueous solution to the reaction mixture, stir and react at 110°C for 6 hours, then cool naturally to room temperature to obtain the reaction product, centrifuge the reaction product to obtain a precipitate, add 5 mL The precipitate was washed with water and dried at 105° C. to obtain 62 mg of white solid, which is the target product FDCA. The molar yield of the product was 80% after testing.

Embodiment 3

[0032] This embodiment prepares FDCA according to the following steps:

[0033] a. Add 5-HMF into 2mL of dichloroethane, and the prepared mass concentrations are 25g / L, 50g / L, 100g / L, 120g / L, 140g / L, 160g / L, 180g / L, 200g / L The 5-hydroxymethyl furfural solution of L, 250g / L, 300g / L, then add catalyzer tetramethyl piperidine nitroxide (the amount of its substance is 5% of 5-HMF), catalyst activator Fe(NO 3 ) 3 9H 2 O (the amount of its substance is 5% of 5-HMF) and additive NaCl (the amount of its substance is 5% of 5-HMF), stirred and reacted at room temperature in air for 4h to obtain a reaction mixture containing 2,5-DFF solution; the reaction mixture was tested, and the yield of 2,5-DFF was shown in Table 1.

[0034] b. Add 0.5 mL of 70% tert-butanol peroxy aqueous solution to the reaction mixture, stir and react at 110°C for 6 hours, then cool naturally to room temperature to obtain the reaction product, centrifuge the reaction product to obtain a precipitate, add 5 mL ...

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Abstract

The invention discloses a method for preparing 2,5-furandicarboxylate. The preparation method is characterized by comprising the following steps of: mixing 2,5-dicarboxaldehyde with the aqueous solution of t-butylhydroperoxide, and stirring to enable 2,5-dicarboxaldehyde to react with the aqueous solution of t-butylhydroperoxide for 4-8 hours at the temperature of 100-120 DEG C, naturally cooling to the room temperature to obtain a reaction product, separating the reaction product centrifugally to obtain precipitate, and washing precipitate and drying to obtain the target product which is 2,5-furandicarboxylate. The method disclosed by the invention has the advantages of mild reaction condition, low cost, environment friendliness and high product yield.

Description

technical field [0001] The invention relates to a preparation method of 2,5-furandicarboxylic acid. Background technique [0002] 2,5-furandicarboxylic acid (FDCA) is one of the 12 "platform compounds" of the US Department of Energy, and has broad application prospects. For example, it can replace the polymerization reaction of terephthalic acid (PTA) and ethylene glycol to produce plastics for beverage bottle packaging. This plastic is called furan polyester (PEF) plastic, which can not only directly replace the existing The polyethylene terephthalate (PET) plastic produced from petroleum resources has the advantages of being from renewable resources, degradable in the natural environment, and does not produce white pollution. [0003] Lin Lu et al. (Chemical Reagent, 33, 2011, 11-12) reported the preparation of FDCA by oxidizing 5-hydroxymethylfurfural (5-HMF) with alkaline potassium permanganate aqueous solution. The method has low raw material concentration and low uni...

Claims

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Application Information

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IPC IPC(8): C07D307/68
CPCC07D307/68
Inventor 邓晋徐海汪鹏徐强丁帆丁飞焦许圣春
Owner INST OF ADVANCED TECH UNIV OF SCI & TECH OF CHINA
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