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Novel method for preparing oxygen heterocyclic compound through ionic liquid catalysis

A technology of ionic liquids and compounds, applied in the field of catalysis, can solve problems such as unreported, and achieve the effects of no by-products, no metal participation, and simple separation

Active Publication Date: 2020-07-24
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Under metal-free conditions, the research and technology of preparing tetrahydrofuran, tetrahydropyran and other oxygen heterocyclic compounds and their derivatives from aliphatic diethers catalyzed by ionic liquids have not been reported.

Method used

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  • Novel method for preparing oxygen heterocyclic compound through ionic liquid catalysis
  • Novel method for preparing oxygen heterocyclic compound through ionic liquid catalysis
  • Novel method for preparing oxygen heterocyclic compound through ionic liquid catalysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1, [1-butylsulfonic acid group-3-methylimidazole] trifluoromethanesulfonate catalyzed 1,5-dimethoxypentane to prepare tetrahydropyran

[0040] Mix 2 mmol 1,5-dimethoxypentane with 0.2 mmol ionic liquid [1-butylsulfono-3-methylimidazole] trifluoromethanesulfonate ([SO 3 H-BMIm][OTf]) was placed in a 20 ml stainless steel reaction kettle, sealed; moved to an oil bath at 120°C, stirred and heated for 15 hours; the reaction kettle was immersed in ice water to terminate the reaction, and then left at room temperature for a period of time. The reaction solution was transferred to a separatory funnel and divided into upper and lower layers. Take the upper organic phase, use 1 H and 13 C NMR analysis of its composition and determination of material structure. According to the analysis results, it is determined that the conversion rate of raw materials is 94%, and the product is tetrahydropyran, and its separation yield is 94%.

[0041] reaction product 1 H and 13 ...

Embodiment 2

[0045] Example 2, [1-butylsulfonic acid group-3-methylimidazole] trifluoromethanesulfonate catalyzed 1,5-dimethoxypentane to prepare tetrahydropyran

[0046] Mix 0.1mol 1,5-dimethoxypentane with 0.1mol ionic liquid [SO 3 H-BMIm][OTf] was placed in a 50 ml stainless steel reactor and sealed; moved to an oil bath at 120°C, stirred and heated for 10 hours; the reactor was immersed in ice water to terminate the reaction, and then left at room temperature for a period of time. The reaction solution was transferred to a separatory funnel and divided into upper and lower layers. Take the upper organic phase, use 1 H and 13 C NMR analysis of its composition and determination of material structure. According to the analysis results, it is determined that the conversion rate of raw materials is >99.9%, the product is tetrahydropyran, and the separation yield is >99%.

Embodiment 3

[0047] Example 3, [1-propylsulfonate-3-methylimidazole] triflate catalyzes the preparation of tetrahydropyran from 1,5-dimethoxypentane

[0048] Mix 2 mmol 1,5-dimethoxypentane with 0.2 mmol ionic liquid [1-propylsulfono-3-methylimidazole] trifluoromethanesulfonate ([SO 3 H-PrMIm][OTf]) was placed in a 20 ml stainless steel reaction kettle, sealed; moved to an oil bath at 120°C, stirred and heated for 10 hours; the reaction kettle was immersed in ice water to terminate the reaction, and then left at room temperature for a period of time. The reaction solution was transferred to a separatory funnel and divided into upper and lower layers. Take the upper organic phase, use 1 H and 13 C NMR analysis of its composition and determination of material structure. According to the analysis results, it is determined that the conversion rate of raw materials is 90%, and the product is tetrahydropyran, and its separation yield is 90%.

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Abstract

The invention discloses a novel method for preparing an oxygen heterocyclic compound through ionic liquid catalysis. The ionic liquid catalytic system has the advantages of high efficiency, simplicity, mild reaction conditions, no metal participation, no by-product, simple separation and the like and can efficiently catalyze fatty diether metathesis cyclization to prepare an oxygen heterocyclic compound and has very high industrial application value.

Description

technical field [0001] The invention belongs to the field of catalysis, and in particular relates to a new method for preparing oxygen heterocyclic compounds by catalyzing ionic liquids. Background technique [0002] Oxygen heterocyclic compounds such as tetrahydrofuran and tetrahydropyran and their derivatives are important chemicals and are widely used in chemical production. This type of compound can be obtained by the fatty diether metathesis reaction represented by formula (1). However, the catalytic system currently used is mainly a metal Lewis acid catalyst, such as Fe(OTf) 3 , AlCl 3 , FeCl 3 , FeBr 3 Wait. There are defects such as low reaction efficiency, low selectivity of target products, difficult separation, and metal residues. In order to meet the needs of green and sustainable development, it is of great significance to develop a new method for the preparation of the above-mentioned oxygen heterocyclic compounds through the metathesis reaction of alipha...

Claims

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Application Information

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IPC IPC(8): C07D307/06C07D307/08C07D309/04C07D319/12C07D295/26B01J31/02
CPCC07D307/06C07D307/08C07D309/04C07D319/12C07D295/26B01J31/0284B01J2231/4288
Inventor 刘志敏王欢赵燕飞韩布兴
Owner INST OF CHEM CHINESE ACAD OF SCI
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