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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This makes the synthesis of aromatic

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

Examples

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Example Embodiment

[0017] Example 1: 2 mmol 2,5-furandicarbaldehyde, 3.5 mL of 1.5 mol / L hydroxylamine aqueous solution, and 10 mL of water were added to a 25 mL round-bottomed flask. Stir and warm up to 100 ℃, react for 6h. After completion, cool to room temperature. The 2,5-furandicarbaldehyde dioxime product was obtained by filtration, and the isolated yield was 95%. Then 1 mmol of 2,5-furandicarbaldehyde dioxime, 30 mg of MgO, 8 mL of N,N-dimethylformamide was added to a 25 mL round bottom flask. Stir and warm up to 150 ℃, and react for 1 h. After completion, cool to room temperature. After the reaction solution was evaporated to remove the solvent, 2,5-dicyanofuran was obtained as a white solid by column chromatography, and the isolated yield was 96%.

Example Embodiment

[0018] Example 2: 2 mmol of 2,5-furandicarbaldehyde, 3.5 mL of 1.5 mol / L hydroxylamine aqueous solution, and 10 mL of methanol were added to a 25 mL round-bottomed flask. Stir and warm up to 60 ℃, react for 14h. After completion, cool to room temperature. The 2,5-furandicarbaldehyde dioxime product was obtained by filtration, and the isolated 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 warm up to 140 ℃, react for 3h. After completion, cool to room temperature. After the reaction solution was evaporated to remove the solvent, 2,5-dicyanofuran was obtained as a white solid by column chromatography, and the isolated yield was 98%.

Example Embodiment

[0019] Example 3: 2 mmol 2,5-furandicarbaldehyde, 3.5 mL of 1.5 mol / L hydroxylamine aqueous solution, and 10 mL of ethanol were added to a 25 mL round-bottomed flask. Stir and warm up to 80 ℃, and react for 12h. After completion, cool to room temperature. The 2,5-furandicarbaldehyde dioxime product was obtained by filtration, and the isolated yield was 99%. See the HPLC and GC-MS spectra respectively. figure 1 and image 3 . Then 1mmol 2,5-furandicarbaldehyde dioxime, 50mg α-MnO 2 , 8mL of toluene was added to a 25mL round bottom flask. Stir and warm up to 110 ℃, react for 8h. After completion, cool to room temperature. After the reaction solution was evaporated to remove the solvent, 2,5-dicyanofuran was obtained as a white solid by column chromatography. The isolated yield was 99%. The HPLC and GC-MS spectra were 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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