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Chlorinated 1-vinyl-3-carboxymethyl imidazole polymerizable acidic ionic liquid and synthetic method thereof

A technology of acidic ionic liquid and carboxymethylimidazole, which is applied in the field of functional materials and its preparation, can solve the problems of low reaction yield, low solubility, and difficult removal, etc., and achieve the effect of improving yield and purity

Inactive Publication Date: 2013-08-28
NORTHWESTERN POLYTECHNICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the synthesis of 1-vinylimidazole acidic ionic liquids, due to the low solubility of reaction monomers such as 2-bromoacetic acid in some organic solvents such as acetonitrile, the reaction yield is not high
At the same time, the reaction process and the drying process are carried out at relatively high temperatures of 60°C and 70°C respectively. The presence of acidic groups can also easily promote the polymerization of vinyl double bonds, so polymer impurities are introduced into the system and are difficult to remove.

Method used

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  • Chlorinated 1-vinyl-3-carboxymethyl imidazole polymerizable acidic ionic liquid and synthetic method thereof
  • Chlorinated 1-vinyl-3-carboxymethyl imidazole polymerizable acidic ionic liquid and synthetic method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0020] Dissolve 3.00g (31.75mmol) of 2-chloroacetic acid in 9g of ethyl acetate, stir well at 50°C for 20min to obtain a clear ethyl acetate solution containing 2-chloroacetic acid, and add 0.03g of Polymerization inhibitor phenol, stir to dissolve, then add 2.99g (31.75mmol) of 1-vinylimidazole to it, react at 45°C for 48 hours, a white precipitate is obtained, wash with ethyl acetate 3 times, each time 30mL, filter , put the obtained white solid into a vacuum drying oven at 50° C. for 3 h under vacuum to obtain 4.67 g of 1-vinyl-3-carboxymethylimidazole chloride with a yield of 78%.

Embodiment 2

[0022] Dissolve 4.50g (47.62mmol) of 2-chloroacetic acid in 36g of ethyl acetate, stir well at 50°C for 20min to obtain a clear ethyl acetate solution containing 2-chloroacetic acid, and add 0.03g of Polymerization inhibitor phenol, stirred and dissolved, then added 2.99g (31.75mmol) of 1-vinylimidazole to it, reacted at 48°C for 24 hours, a white precipitate was obtained, washed 3 times with ethyl acetate, 30mL each time, filtered , put the obtained white solid into a vacuum drying oven at 50° C. for 3 h under vacuum to obtain 4.79 g of 1-vinyl-3-carboxymethylimidazole chloride with a yield of 80%.

Embodiment 3

[0024] Dissolve 6.00g (63.50mmol) of 2-chloroacetic acid in 30g of ethyl acetate, stir well at 50°C for 20min to obtain a clear ethyl acetate solution containing 2-chloroacetic acid, and add 0.03g of Polymerization inhibitor phenol, stir to dissolve, then add 2.99g (31.75mmol) of 1-vinylimidazole to it, react at 50°C for 18 hours, a white precipitate is obtained, wash with ethyl acetate 3 times, each time 30mL, filter , put the obtained white solid into a vacuum drying oven at 50° C. for 3 h under vacuum to obtain 4.93 g of 1-vinyl-3-carboxymethylimidazole chloride, with a yield of 82.3%.

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Abstract

The invention proposes a chlorinated 1-vinyl-3-carboxymethyl imidazole polymerizable acidic ionic liquid and a synthetic method thereof. The synthetic method taking 1-vinyl imidazole and 2-chloroacetic acid as materials, ethyl acetate as a solvent, and phenol as a polymerization inhibitor comprises the steps of reacting at the temperature of 45-50 DEG C so as to synthesize the chlorinated 1-vinyl-3-carboxymethyl imidazole polymerizable acidic ionic liquid, wherein the ionic liquid has Bronsted acidity; and the ionic liquid can participate in the polymerization reaction in the presence of double bonds and is immobilized. The ionic liquid has the acidity and the polymerizable characteristic, so that the ionic liquid is named as the polymerizable acidic ionic liquid. The synthetic method is simple, high in product purity, and easy to industrialize. The chlorinated 1-vinyl-3-carboxymethyl imidazole polymerizable acidic ionic liquid synthesized by the method enriches the variety of the functional ionic liquid, and can be widely applied to the fields such as separation, catalysis, material science and the like.

Description

technical field [0001] The invention relates to a chlorinated 1-vinyl-3-carboxymethylimidazole polymerizable acidic ionic liquid and a synthesis method, belonging to the technical field of functional materials and their preparation. Background technique [0002] Ionic liquids are composed of organic cations and inorganic anions or inorganic cations and organic anions, and are liquid molten salts at 100°C. Compared with commonly used molecular liquids, ionic liquids have almost no vapor pressure, are nonflammable, have higher ion density and ion conductivity, and have better solubility for inorganic and organic substances. Due to the adjustability of anions and cations, ionic liquids with desired properties can be obtained by changing the structures of anions and cations in ionic liquids. Therefore, ionic liquids have been widely used in separation chemistry, electrochemistry, organic chemistry, and even polymer chemistry in recent years. [0003] As an important branch of ...

Claims

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Application Information

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IPC IPC(8): C07D233/64
Inventor 胡小玲管萍钱立伟
Owner NORTHWESTERN POLYTECHNICAL UNIV
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