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Method for preparing chalcone and directive through multi-sulfonate ion liquid catalysis

A technology of ionic liquid and polysulfonate, which is applied in the preparation of carbon-based compounds, chemical instruments and methods, and the preparation of organic compounds, etc., can solve the difficulties of product separation, environmental pollution, catalyst usage, and large loss in recycling, etc. problem, to achieve the effect of high catalytic activity, convenient separation and high acid density

Inactive Publication Date: 2013-07-10
ANHUI UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to overcome the shortcomings of the prior art, such as serious environmental pollution, harsh reaction conditions, difficult product separation, large amount of catalyst usage and loss during recycling, and provide a catalytic preparation method of polysulfonate ionic liquid. Methods of Atones and Derivatives

Method used

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  • Method for preparing chalcone and directive through multi-sulfonate ion liquid catalysis

Examples

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Effect test

Embodiment 1

[0019] Embodiment 1: under nitrogen protection, 10mmol benzaldehyde, 10mmol acetophenone and 0.8mmol IL-SO 3 H-a was added to a 50mL three-necked flask with a stirring bar and a reflux condenser. Vigorously stir and heat up to 120°C, react for 8 hours, cool to room temperature, the reaction solution is divided into two layers after standing, the upper layer solution is separated by decantation, recrystallization and purification can obtain 1,3-diphenyl-2-propene-1 - Ketone (chalcone) yield was 94%. Contains IL-SO 3 The lower layer solution of H-a can be recycled after being vacuum-dried at 110°C for 2 hours.

Embodiment 2

[0020] Embodiment 2: under nitrogen protection, 10mmol4-methoxybenzaldehyde, 10mmol acetophenone and 1mmol IL-SO 3 H-a was added to a 50mL three-necked flask with a stirring bar and a reflux condenser. Vigorously stir and heat up to 140°C, react for 9 hours, cool to room temperature, the reaction solution is divided into two layers after standing, and the upper layer solution is separated by decantation, recrystallized and purified to obtain 4-methoxychalcone with a yield of 90% . Contains IL-SO 3 The lower layer solution of H-a can be recycled after being vacuum-dried at 110°C for 2 hours.

Embodiment 3

[0021] Embodiment 3: under argon protection, 10mmol3-chlorobenzaldehyde, 10mmol acetophenone and 1mmol IL-SO 3 H-b was added to a 50mL three-neck flask with a stirring bar and a reflux condenser. Stir vigorously and raise the temperature to 140°C, react for 8 hours, and cool to room temperature. The reaction solution is separated into two layers after standing, and the upper layer solution is separated by decantation, and the yield of 3-chlorochalcone can be obtained by recrystallization and purification. The yield is 87%. Contains IL-SO 3 The lower layer solution of H-b can be recycled after being vacuum-dried at 110°C for 2 hours.

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Abstract

The invention provides a method for preparing chalcone and a directive through multi-sulfonate ion liquid catalysis, and belongs to the technical field of organic chemistry synthesis. In the condensation reaction of the method, the mole ratio of raw material aldehyde to ketone is 1:1, the molar weight of a multi-sulfonic acid group ion liquid catalyst is 8%-10% of the used ketone or aldehyde, the reaction temperature is 120-140 DEG C, the reaction time is 8-20 hours, the reaction pressure is 1 atmospheric pressure, an upper layer product separated through standing layering after the reaction is recrystallized to obtain products, namely the chalcone and the derivative; and a separated lower layer which contains the multi-sulfonate ion liquid catalyst can be subjected to vacuum drying treatment at 110 DEG C for 2 hours and then can be recycled. Compared with the traditional preparation method which takes bronsted acid, Lewis acid and other acidic ion liquids as catalysts, the method provided by the invention has the advantages that catalytic activity is high, catalyst usage amount is small, the separation of the catalyst and the products is simple and convenient, the catalyst is recycled, and the catalytic activity of the catalyst is not obviously reduced.

Description

Technical field: [0001] The invention belongs to the technical field of organic chemical synthesis, and in particular relates to a method for preparing chalcones and derivatives by catalyzing polysulfonate ionic liquids. Background technique: [0002] Chalcone is a kind of flavonoid compound. The natural compound based on it exists in licorice, safflower and other plants. It is the precursor of flavonoid synthesis in plants. It has strong pharmacological effects, such as anti-oxidation and anti-tumor , anti-inflammatory activity, anti-hepatic virus, antibacterial and other effects. At present, this type of compound has been widely used in the treatment of common diseases such as cardiovascular disease, cancer, and immune system disease. At the same time, it is also an important intermediate in organic synthesis, which can be used in the synthesis of fine chemicals such as spices and drugs. Chalcones and their derivatives are usually prepared by Claisen-Schmidt condensation ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/74C07C49/796C07C49/84C07C49/813
CPCY02P20/584
Inventor 岳彩波储昭莲诸荣孙
Owner ANHUI UNIVERSITY OF TECHNOLOGY
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