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Method for efficiently preparing high-content 1, 3-dialkyl imidazole ionic liquid

A technology of dialkylimidazole and ionic liquid, which is applied in the preparation of carboxylate, carboxylate, sulfonate, etc., which can solve the problem of high specificity of solvent, reduction of production efficiency of ionic liquid, instability of methyl carbonate anion, etc. problems, to achieve the effect of improving purity, reducing the amount of reaction solvent used, and improving production efficiency

Pending Publication Date: 2022-06-07
浙江肯特催化材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At the same time, the patent WO2009040242A1 stated that this reaction will produce 1,3-dialkyl-3-carboxylate as a by-product. When the amount of solvent methanol is increased, the production of carboxylate can be reduced. It is recommended that the amount of solvent methanol exceeds 2.5-5% of the total mass of raw materials. times is optimal, at this time the content of by-products is 0.5-1.0%; in Chemical Engineering Journal 368 (2019) 649-658, Andreas Oligschlager and others also researched and discussed this reaction, and 1 , The formation of 3-dialkyl-3-carboxylate has been studied in detail. The research shows that the methyl carbonate anion is extremely unstable. It can only be stable when it is surrounded by a large amount of methanol and forms a hydrogen bond with methanol, otherwise it is easy to form Carboxylate by-products, so in the reaction, the greater the amount of solvent methanol, the less carboxylate by-products, but too large a solvent specific gravity will reduce the production efficiency of ionic liquids

Method used

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  • Method for efficiently preparing high-content 1, 3-dialkyl imidazole ionic liquid
  • Method for efficiently preparing high-content 1, 3-dialkyl imidazole ionic liquid
  • Method for efficiently preparing high-content 1, 3-dialkyl imidazole ionic liquid

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] (1) In the autoclave, add N-ethylimidazole 41.05g (0.50mol), dimethyl carbonate 67.56g (0.75mol) and solvent ethylene glycol 86.89g (solvent addition amount is N-ethylimidazole and carbonic acid two 0.8 times the total mass of methyl ester), close the autoclave, replace with nitrogen for 6 min, then heat to 130 ° C, stir at 500 r / min, monitor the reaction progress by GC, after 32 h of reaction, no N-ethylimidazole can be detected, stop the reaction, and obtain 186.71 g of 46.5% pale yellow 1-ethyl-3-methylimidazole carbonate monomethyl carbonate solution in alcohol.

[0029] (2) 40.04g of 1-ethyl-3-methylimidazole monomethyl carbonate alcohol solution with a content of 46.5% and 15.31g of trifluoromethanesulfonic acid with a content of 98.0% were added to the reaction flask, and after stirring at 60°C for 4 hours, the solution The pH value remained unchanged, the reaction was stopped, the solvent ethylene glycol was evaporated under reduced pressure at 90 °C, and then m...

Embodiment 2

[0031] (1) 41.05g (0.50mol) of N-ethylimidazole, 58.55g (0.65mol) of dimethyl carbonate and 109.56g of solvent 1,4-butanediol (the amount of solvent added is N-ethyl) were added to the autoclave 1.1 times the total mass of imidazole and dimethyl carbonate), close the autoclave, replace with nitrogen for 6 min, then heat to 135 ° C, stir at 500 r / min, monitor the reaction progress by GC, after 30 h of reaction, no N-ethylimidazole can be detected, The reaction was stopped to obtain 195.66 g of a light yellow 1-ethyl-3-methylimidazole carbonate monomethyl carbonate alcoholic solution with a content of 43.71%.

[0032] (2) 42.60g of 1-ethyl-3-methylimidazole carbonate monomethyl carbonate alcohol solution with a content of 43.71% and 6.06g of acetic acid with a content of 99.0% were added to the reaction flask, and the pH value of the solution remained unchanged after stirring at 60°C for 6 hours. , stop the reaction, evaporate the solvent 1,4-butanediol under reduced pressure at...

Embodiment 3

[0034](1) N-butylimidazole 49.67g (0.4mol), dimethyl carbonate 46.84g (0.52mol) and solvent 3-methyl-1,3-butanediol 86.86g (solvent addition amount) were added to the autoclave is 0.9 times the total mass of N-butylimidazole and dimethyl carbonate), close the autoclave, replace with nitrogen for 6 minutes, then heat to 140 ° C, stir at 500 r / min, monitor the reaction progress by GC, after 48 hours of reaction, no N can be detected -Butylimidazole, stop the reaction, and obtain 171.23 1-butyl-3-methylimidazole monomethyl carbonate alcoholic solution with a content of 45.98%.

[0035] (2) 46.60g of 1-butyl-3-methylimidazole carbonate monomethyl carbonate alcohol solution with a content of 45.98% and 21.95g of tetrafluoroboric acid with a content of 40.0% were added to the reaction flask, and after stirring at 75°C for 6 hours, the pH of the solution The value remains unchanged, the reaction is stopped, the solvent 3-methyl-1,3-butanediol is evaporated under reduced pressure at 1...

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Abstract

The invention discloses a method for efficiently preparing a high-content 1, 3-dialkyl imidazole ionic liquid. The method comprises the following steps: (1) by taking N-alkyl imidazole and dimethyl carbonate as raw materials and glycol as a solvent, heating and reacting in a pressure kettle to obtain an intermediate 1-alkyl-3-methylimidazole monomethyl carbonate salt; and (2) carrying out heating reaction on the obtained intermediate and acid containing target anions, and then carrying out reduced pressure distillation and vacuum drying twice to obtain the high-content 1-alkyl-3-methylimidazolium salt. The method has the advantages that the imidazole ionic liquid is synthesized by taking diol as a solvent, and compared with a traditional method of trying methanol as the solvent, the method has the advantages that the use amount of the solvent during reaction can be greatly reduced, the production efficiency can be improved, meanwhile, the content of a byproduct carboxylate can be reduced, and the high-content ionic liquid can be obtained.

Description

technical field [0001] The present invention relates to a method, in particular to a method for efficiently preparing high-content 1,3-dialkylimidazolium ionic liquid. Background technique [0002] Ionic liquids are salts composed of large cations and anions that do not easily form ordered crystals and thus remain liquid at or near room temperature. Commonly used organic cations are dialkylimidazoles, alkylpyridines, dialkylpyrrolidones and tetraoxanes Phosphine, etc., common anions are F-, Cl-, Br - , SO 4 2- , CH 3 SO 3 - , CF 3 SO 3 - , PF 6 - Wait. Ionic liquids have the advantages of large heat capacity, high density, good thermal conductivity, and at the same time, they are non-flammable, low vapor pressure, good thermal stability, and wide temperature range. They are a good environment-friendly green solvent. At the same time, it has a wide electrochemical window (usually 3-5V), which can be used in battery electrolytes and has broad prospects in green ene...

Claims

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Application Information

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IPC IPC(8): C07D233/58C07C51/41C07C53/10C07C303/32C07C309/06
CPCC07D233/58C07C68/06C07C51/412C07C303/32C07C69/96C07C53/10C07C309/06Y02P20/54
Inventor 卓广澜王高郑琪杨建锋方黎锋
Owner 浙江肯特催化材料科技有限公司
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