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Preparation method of 2,5-dihydrofuran

A technology of dicyanofuran and furandicarboxaldehyde, applied in the direction of organic chemistry and the like, can solve the problems such as the difficulty of synthesizing aromatic heterocyclic nitrile compounds, and achieve the effects of avoiding the generation of polymerization by-products, the reaction process is efficient, and the product purity is high.

Pending Publication Date: 2019-05-21
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This makes the synthesis of aromatic heterocyclic nitriles more difficult.

Method used

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

Examples

Experimental program
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Embodiment 1

[0017] Example 1: 2mmol 2,5-furandicarbaldehyde, 3.5mL 1.5mol / L aqueous hydroxylamine solution, and 10mL water were added to a 25mL round bottom flask. Stir and heat up to 100°C, react for 6h. When finished, cool to room temperature. The 2,5-furandicarbaldehyde dioxime product was obtained by filtration, and the separation yield was 95%. Add 1 mmol of 2,5-furandicarbaldehyde dioxime, 30 mg of MgO, and 8 mL of N,N-dimethylformamide into a 25 mL round bottom flask. Stir and heat up to 150°C, react for 1h. When finished, cool to room temperature. After evaporating the solvent from the reaction liquid, a white solid of 2,5-dicyanofuran was obtained by column chromatography separation, and the separation yield was 96%.

Embodiment 2

[0018] Example 2: 2mmol 2,5-furandicarbaldehyde, 3.5mL 1.5mol / L aqueous solution of hydroxylamine, and 10mL methanol were added to a 25mL round bottom flask. Stir and heat up to 60°C, react for 14h. When finished, cool to room temperature. The 2,5-furandicarbaldehyde dioxime product was obtained by filtration, and the separation yield was 97%. Then 1mmol 2,5-furandicarbaldehyde dioxime, 30mg CeO 2 , 8mL o-xylene was added to a 25mL round bottom flask. Stir and heat up to 140°C, react for 3h. When finished, cool to room temperature. After evaporating the solvent from the reaction liquid, a white solid of 2,5-dicyanofuran was obtained by column chromatography separation, and the separation yield was 98%.

Embodiment 3

[0019] Example 3: 2mmol 2,5-furandicarbaldehyde, 3.5mL 1.5mol / L aqueous hydroxylamine solution, and 10mL ethanol were added to a 25mL round bottom flask. Stir and heat up to 80°C, react for 12h. When finished, cool to room temperature. The 2,5-furandicarbaldehyde dioxime product was obtained by filtration, the separation yield was 99%, and the HPLC and GC-MS spectra were shown in figure 1 and image 3 . Then add 1 mmol 2,5-furandicarbaldehyde dioxime, 50 mg α-MnO 2 , 8mL of toluene was added to a 25mL round bottom flask. Stir and heat up to 110°C, react for 8h. When finished, cool to room temperature. After evaporating the solvent from the reaction solution, the column chromatography separation method was used to obtain 2,5-dicyanofuran as a white solid with a separation yield of 99%. The HPLC spectrum and GC-MS spectrum are shown in figure 2 and Figure 4 .

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Abstract

The invention discloses a preparation method of 2,5-dihydrofuran. The method comprises the following steps: taking hydroxylamine or hydroxylammonium salt as a nitrogen source, taking 2,5-furandiformaldehyde as a raw material, dehydrating through 2,5-furandiformaldehyde dioxime intermediate under the catalyst effect, thereby efficiently preparing 2,5-dihydrofuran. The method realizes efficient synthesis of the active biomass-based furans dinitrile compound, thereby avoiding the polymerization side effect of the intermediate imide by taking the ammonia gas as the nitrogen source. Furthermore, the acid is used as dehydration catalyst, thereby prohibiting the condition that the nitrile is further hydrolyzed to generate the amide and like byproducts. The reaction condition is mild in conditionand simple in operation, and the manufactured 2,5-dihydrofuran product is high in purity.

Description

technical field [0001] The invention relates to a preparation method of 2,5-dicyanofuran. The method uses hydroxylamine or hydroxylamine salt as a nitrogen source, 2,5-furandicarbaldehyde as a raw material, and 2,5-furandicarbaldehyde dioxime as an intermediate body and dehydration under the action of a catalyst to efficiently prepare 2,5-dicyanofuran. Background technique [0002] Dinitrile compounds are a class of molecules with homobifunctional groups, which have important applications in the fields of fine chemicals and biomedicine. Dinitriles can be used to synthesize diamine monomers and diamide drugs, and can also be used to further synthesize materials such as covalent triazine skeleton polymers, polybenzimidazoles, and polyamidines, which are widely used. At present, dinitriles can be prepared from hydrocarbon compounds through ammoxidation reaction, but because the C-H bonds in hydrocarbon molecules are relatively stable, the reaction conditions are harsh and the ...

Claims

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Application Information

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IPC IPC(8): C07D307/68
Inventor 徐杰徐永明马继平贾秀全高进苗虹李晓芳
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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