Acidic ionic liquid based on 1-methyl-3-benzyl imidazole cation, synthetic method and use

A technology of acidic ionic liquid and benzyl imidazolium, which is applied in the field of Brnsted acidic ionic liquid and its synthesis, can solve the problems of easily causing side reactions, strong corrosion of protonic acid, etc., and achieve convenient separation, mild conditions and high yield high effect

Inactive Publication Date: 2007-10-24
XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Benzoic acid esters are important industrial solvents and synthetic fragrances, and have a wide range of uses. The classic synthetic method is the direct esterification of benzoic acid and alcohol in the presence of protonic acid (especially sulfuric acid), or the reaction of benzoyl chloride and alcohol. Or utilize methyl benzoate and alcohol to carry out transesterification to synthesize. Protonic acid has strong corrosiveness and easily causes the generation of side reaction, and other methods also have many problems such as source of raw material, production cost, environment

Method used

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  • Acidic ionic liquid based on 1-methyl-3-benzyl imidazole cation, synthetic method and use
  • Acidic ionic liquid based on 1-methyl-3-benzyl imidazole cation, synthetic method and use
  • Acidic ionic liquid based on 1-methyl-3-benzyl imidazole cation, synthetic method and use

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] The synthesis of embodiment 1 ionic liquid 2b

[0064] Synthesis of Chloride 1a

[0065] a. In a 50ml three-neck flask equipped with mechanical stirring, first dissolve 5g of the reaction substrate 1-methylimidazole in 25ml of toluene, start stirring to make the reactant homogeneous, then place the reactant in an ice-water bath, and keep it at 0°C 1.15 equivalents of benzyl chloride was added dropwise, and the reaction was carried out for 8 hours;

[0066] b. Insulate and react overnight. After reacting at room temperature for 24 hours, heat up to 65°C and react for 24 hours. Thin-layer chromatography tracks the reaction. The reaction system is in a nitrogen environment and reacts under dark conditions;

[0067] c, post-treatment: first lower the temperature of the reaction mixture to room temperature, the reaction system will be divided into two phases, the yellow oily phase of the lower layer of the system is the crude product generated, and the upper layer is the re...

Embodiment 2

[0076] The synthesis of embodiment 2 ionic liquid 2c

[0077] Synthesis of Chloride 1a

[0078]a. In a 50ml three-neck flask equipped with mechanical stirring, first dissolve 5g of the reaction substrate 1-methylimidazole in 25ml of toluene, start stirring to make the reactant homogeneous, then place the reactant in an ice-water bath, and keep it at 0°C 1.10 equivalents of benzyl chloride was added dropwise, and the reaction was carried out for 8 hours;

[0079] b. Insulate and react overnight. After reacting at room temperature for 24 hours, heat up to 70°C and react for 24 hours. Thin-layer chromatography tracks the reaction. The reaction system is in a nitrogen environment and reacts under dark conditions;

[0080] c, post-treatment: first lower the temperature of the reaction mixture to room temperature, the reaction system will be divided into two phases, the yellow oily phase of the lower layer of the system is the crude product generated, and the upper layer is the rea...

Embodiment 3

[0087] The synthesis of embodiment 3 ionic liquid 2e

[0088] Synthesis of Chloride 1a

[0089] a. In a 50ml three-neck flask equipped with mechanical stirring, first dissolve 5g of the reaction substrate 1-methylimidazole in 25ml of xylene, start stirring to make the reactants homogeneous, place the reactants in an ice-water bath, and mix with 1 1.12 equivalents of benzyl chloride was added dropwise at ℃, and the reaction was carried out for 8 hours;

[0090] b. Insulate and react overnight. After reacting at room temperature for 24 hours, heat up to 72°C and react for 24 hours. Thin-layer chromatography tracks the reaction. The reaction system is in a nitrogen environment and reacts under dark conditions;

[0091] c, post-treatment: first lower the temperature of the reaction mixture to room temperature, the reaction system will be divided into two phases, the yellow oily phase of the lower layer of the system is the crude product generated, and the upper layer is the react...

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Abstract

The invention discloses an acid ion liquid and synthesizing method and application based on 1-methyl-3-benzyl imidazole cation, which is 1-methyl imidazole benzyl methylation organic cation, wherein the inorganic/organic anion is BF4<->,HSO4<->, H2PO4<->, p-CH3C6H4SO<3->, CF3COO<-> and ClCH2COO<->, wherein the ion liquid is liquid phase under indoor temperature, which can repair structure as mother compound due to leading functional group into structure, such as benzene ring, methylene and so on; the BrPhinsted acid can be repeating ring, reacting dielectric and reacting catalytic, which can be used to synthesize important perfume and solvent.

Description

technical field [0001] The invention relates to a Brönsted acidic ionic liquid based on 1-methyl-3-benzyl imidazolium cation and its synthesis method and application. Background technique [0002] Room temperature ionic liquid or room temperature ionic liquid or room temperature molten salt, referred to as ionic liquid. Refers to a salt composed of an organic cation and an inorganic or organic anion that is liquid at or near room temperature. Since Wilkes et al reported the first ionic liquid based on methylimidazolium cation: emimBF4 in 1992, ionic liquids have developed rapidly. As a new type, green, designable substance with special physical and chemical properties, its application has rapidly shifted from the initial electrochemistry to organic synthesis. There are a large number of research reports on the medium and reaction accelerator of organic reactions. The emergence of functionalized (or functionalized) and task-specific ionic liquids is a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/58C07C67/08
Inventor 李心琮吾满江·艾力努尔买买提
Owner XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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