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Method for preparing 2,5-furandicarboxaldehyde oxime through autocatalysis

A technology of furandicarbaldehyde oxime and furandicarbaldehyde, which is applied in the field of autocatalytic preparation of 2,5-furandimaldehyde oxime, which can solve the problems of cumbersome separation and purification steps, increased processing costs, and harsh reaction conditions, so as to reduce pollutant emissions , improve quality, mild reaction conditions

Active Publication Date: 2021-05-25
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI +1
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  • Claims
  • Application Information

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Problems solved by technology

This method has high selectivity for preparing oxime, but it needs to use equivalent or excess hydroxylamine hydrochloride and alkali additives, and a large amount of inorganic salt by-products will be produced in the reaction process, which will bring serious pollution to the environment and lead to the improvement of treatment cost at the same time.
In addition, the reaction conditions of this method are harsh, and the separation and purification steps are cumbersome, which greatly limits its industrial application.

Method used

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  • Method for preparing 2,5-furandicarboxaldehyde oxime through autocatalysis
  • Method for preparing 2,5-furandicarboxaldehyde oxime through autocatalysis
  • Method for preparing 2,5-furandicarboxaldehyde oxime through autocatalysis

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preparation example Construction

[0036] Further, the preparation method at least includes: adding an acid to adjust the initial pH value of the solution, starting the reaction of 2,5-furandicarbaldehyde and an oximating agent in a polar solvent, and the generated 2,5-furandicarbaldehyde oxime as a catalyst The reaction process is completed by self-catalysis; after the reaction is completed, it is naturally cooled to room temperature, filtered, washed and dried to obtain the target product 2,5-furandicarbaldehyde oxime.

[0037] In some embodiments, the method for autocatalytically preparing 2,5-furandicarbaldehyde oxime includes: after adding an acid into the liquid phase reaction system, the pH of the liquid phase reaction system is 1.0-7.0.

[0038] Further, the method includes: using acid to adjust the initial pH value of the liquid phase reaction system between 3.0 and 4.0. In the present invention, the pH value is between 3.0 and 4.0, which is more conducive to the attack of the nucleophile hydroxylamine o...

Embodiment 1

[0081] Mix 1mmol 2,5-furandicarbaldehyde, 2mL water and 4.0mmol 50wt.% hydroxylamine aqueous solution evenly, heat to 30°C, then add dilute hydrochloric acid with a content of 0.1wt.%, adjust the pH of the reaction system to 3.0, and continue the heat preservation reaction 5min, after the reaction was completed, cool down to room temperature naturally, filter the reaction product to obtain a precipitate, wash the precipitate with deionized water and dry at 100°C to obtain a white powder solid, which is the target product 2,5-furandicarbaldehyde oxime. According to the test, the selectivity of the product is 99.6%, and the purity is 99.8%.

Embodiment 2

[0083] Mix 2mmol 2,5-furandicarbaldehyde, 3mL ethanol and 6mmol 70wt.% hydroxylamine aqueous solution evenly, then add dilute sulfuric acid with a content of 0.5wt.%, adjust the pH of the reaction system to 4.0, react at room temperature (25°C) for 1min, and react After the end, cool naturally to room temperature, filter the reaction product to obtain a precipitate, wash the precipitate with deionized water and dry it at 100°C to obtain a white powder solid, which is the target product 2,5-furandicarbaldehyde oxime. After testing, the product The selectivity is 99.5%, and the purity is 99.7%.

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Abstract

The invention discloses a method for preparing 2,5-furandicarboxaldehyde oxime through autocatalysis. The method comprises the following steps: triggering the reaction of 2,5-furandicarboxaldehyde and an oximation agent by using acid to generate 2,5-furandicarboxaldehyde oxime serving as a catalyst, and further reacting the rest 2,5-furandicarboxaldehyde and the oximation agent under the action of the catalyst, thereby realizing the production of 2,5-furandicarboxaldehyde oxime. According to the method, the acid is used for triggering the reaction, the 2,5-furandicarboxaldehyde oxime achieves autocatalysis to complete the reaction process, excessive alkali auxiliaries are avoided, pollutant emission is reduced, the conversion rate of the 2,5-furandicarboxaldehyde reaches 100%, the selectivity and the yield of the 2,5-furandicarboxaldehyde oxime reach 99% or above, the reaction conditions are mild, the method is simple and easy to operate, the production cost is low, and the method is suitable for industrial production.

Description

technical field [0001] The invention relates to a method for autocatalytically preparing 2,5-furandicarbaldehyde oxime, which belongs to the technical field of chemical synthesis. Background technique [0002] As the only sustainable organic carbon resource, biomass can be converted into small molecular biomass-based platform compounds with high selectivity by biological or chemical methods, and then further chemically catalyzed into high-quality fuel oil and high value-added chemical products. An important way of material transformation and utilization. Among them, 5-hydroxymethylfurfural (HMF), as an important representative product of the biomass platform, has a wide range of sources and is an important bridge connecting basic biomass raw materials and high value-added products. The nitrogen-containing heterocyclic compound-2,5-furandicarbaldehyde oxime (DFFD) synthesized by oxidation and nucleophilic substitution reaction of 5-hydroxymethylfurfural is an important inter...

Claims

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Application Information

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IPC IPC(8): C07D307/52
CPCC07D307/52
Inventor 陈金波张亚杰马中森夏长久宋亚男王乐军
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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