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Multifunctional imidazolium surfactant and preparation method thereof

A surfactant and multi-functionality technology, applied in chemical instruments and methods, organic chemistry, dissolution, etc., can solve problems such as difficulty in forming densely arranged structures, large electrostatic repulsion, and increased usage, and achieve easy separation, purification, and enhancement Hydrophilicity and the effect of less by-products

Active Publication Date: 2020-06-30
LASER FUSION RES CENT CHINA ACAD OF ENG PHYSICS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, traditional surfactants usually only have one hydrophilic group and one hydrophobic group, and the hydrophilic groups are usually anions and cations, resulting in a large electrostatic repulsion between the hydrophilic groups in the solution, making it difficult to form a close arrangement. structure, greatly reducing its surfactant capacity
However, the hydrophobic group is usually a straight chain of aliphatic chain with a short length, which can provide limited hydrophobic effect, and it is difficult to obtain a high-efficiency surfactant.
In addition, with the rapid development of science and technology and economy, the application fields of surfactants will become wider and wider, and their usage will also increase significantly, which will bring an increasingly serious burden to the earth's environment and do not meet the requirements of green and sustainable development.

Method used

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  • Multifunctional imidazolium surfactant and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Step 1. Dissolve 0.68g imidazole (10mmol) in dimethyl sulfoxide (20mL), heat to 50°C, add 0.6g sodium hydroxide (15mmol) under stirring, continue stirring for 15min, then add 1.49g methyl iodide dropwise (10.5mmol), after the dropwise addition is completed, continue to react for 12h, cool to room temperature, dilute with water, extract 3 times with dichloromethane, combine the organic phases, wash 3 times with water, add water-removing agent anhydrous sulfuric acid in the organic phase Sodium, after standing still for 1h, suction filtration, after removing the solvent, N-methylimidazole was obtained with a yield of 98%;

[0027] Step 2, under the protection of nitrogen, add 3.12g styrene (30mmol) deoxygenated in advance in the reaction flask, then add 0.357g s-tris(bromomethyl)benzene (1mmol), 0.432g cuprous bromide (3mmol) successively ) and 0.468g of bipyridine (3mmol), stirred at room temperature for 10min, heated to 110°C, stirred for 12h, cooled to room temperature...

Embodiment 2

[0031] Step 1. Dissolve 0.82g 2-methylimidazole (10mmol) in N,N-dimethylformamide (20mL), heat to 40°C, add 0.84g potassium hydroxide (15mmol) while stirring, and continue stirring After 15 minutes, add 1.438 g of bromobutane (10.5 mmol) dropwise. After the dropwise addition, continue the reaction for 12 hours, cool to room temperature, dilute with water, extract 3 times with dichloromethane, combine the organic phases, and wash 3 times with water , adding a dehydrating agent, anhydrous sodium sulfate, to the organic phase, and after standing still for 1 hour, suction filtration, after removing the solvent, 1-butyl-2-methylimidazole was obtained with a yield of 97%;

[0032] Step 2, under the protection of nitrogen, add 1.77g of α-methylstyrene (15mmol) deoxygenated in advance to the reaction flask, and then add 0.357g of s-tris(bromomethyl)benzene (1mmol), 0.432g of ethylene bromide Copper (3mmol) and 0.468g bipyridine (3mmol), stirred at room temperature for 10min, heated to...

Embodiment 3

[0036] Step 1. Dissolve 1.442g 2-phenylimidazole (10mmol) in N,N-dimethylacetamide (20mL), control the temperature at 20°C, add 0.36g sodium hydride (15mmol) under stirring, and continue stirring After 15min, add 1.144g bromoethane (10.5mmol) dropwise. After the dropwise addition, continue the reaction for 12h, cool to room temperature, dilute with water, extract 3 times with dichloromethane, combine the organic phases, wash 3 times with water, and A dehydrating agent, anhydrous sodium sulfate, was added to the organic phase, and after standing still for 1 hour, it was suction filtered, and after removing the solvent, 1-ethyl-2-phenylimidazole was obtained with a yield of 98%;

[0037]Step 2, under the protection of nitrogen, add 2.1g methyl methacrylate (21mmol) deoxygenated in advance to the reaction flask, then add 0.357g s-tris(bromomethyl)benzene (1mmol), 0.432g ethylene bromide successively Copper (3mmol) and 0.468g bipyridine (3mmol), stirred at room temperature for 10m...

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Abstract

The invention discloses a multifunctional imidazolium surfactant and a preparation method thereof, comprising: (1) preparation of an alkyl-substituted imidazole intermediate; (2) preparation of a brominated oligomer intermediate; (3) Under nitrogen protection, the alkyl-substituted imidazole intermediate, brominated oligomer intermediate and acetonitrile were added to the reaction flask, stirred, heated to reflux, reacted, cooled to room temperature, and the solvent was removed to obtain a triimidazolium surface active agent. Compared with the prior art, the triimidazolium surfactant provided by the present invention has excellent performance, has three imidazolium groups, and greatly enhances the hydrophilicity of the surfactant; the triimidazolium surfactant of the present invention, By adjusting the amount of monomers, the size of the hydrophobic group in the surfactant molecule can be effectively controlled, which is conducive to regulating the performance of the surfactant; the preparation method and process of the triimidazolium surfactant of the present invention are simple, and the obtained product is easy to separate Purification, less by-products, and environment-friendly.

Description

technical field [0001] The invention belongs to the technical field of fine chemical surfactants, and relates to a preparation method of a trimidazolium surfactant. Background technique [0002] Surfactant is an important class of chemical reagents. Its molecules are composed of hydrophilic and hydrophobic parts. It can form an aligned structure in the solution, which can significantly reduce the surface tension of the solution. It has the functions of emulsification, solubilization, antistatic and wetting. , Sterilization, decontamination and many other properties, it has important application value in many fields such as petroleum industry, medical and health, daily chemical industry, scientific research and so on. At present, traditional surfactants usually only have one hydrophilic group and one hydrophobic group, and the hydrophilic groups are usually anions and cations, resulting in a large electrostatic repulsion between the hydrophilic groups in the solution, making ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/61B01F17/32C09K23/32
CPCC07D233/61C09K23/00
Inventor 张帅李娃尹强陈素芬李婧李洁刘梅芳刘一杨李波
Owner LASER FUSION RES CENT CHINA ACAD OF ENG PHYSICS
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