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Protonation alkyl imidazole tungstate ionic liquid and preparation method thereof

A technology of alkylimidazole tungstate and alkylimidazole tetrafluoroborate, which is applied in the field of preparation of protonated alkylimidazole tungstate ionic liquid, can solve research lag, few characteristic studies, melting point and viscosity increase and other issues, to achieve the effect of excellent thermal stability

Inactive Publication Date: 2009-04-29
EAST CHINA UNIV OF SCI & TECH
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  • Abstract
  • Description
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Problems solved by technology

[0004] However, most of the newly synthesized functionalized ionic liquids only involve the functionalization of cations. An important reason is that the functional design of cations is relatively simple. However, after functionalization of cations, the melting point and viscosity of ionic liquids often increase. Among them, viscosity is critical for applications in large-scale chemical processes and related processes.
It has been found that after the functionalization of anions, the viscosity and melting point of some ionic liquids will decrease instead. Functionalized anions are one of the decisive factors affecting the properties of ionic liquids, but the research reports on functionalization of anions are very rare. Compared with ionic liquids, there are only a small number of anion-functionalized ionic liquids at present, and their research is relatively lagging behind, and there are not many studies on their characteristics, so that the application research of ionic liquids based on functionalized anions in the field of catalysis is at an important stage. In the initial stage, there is an urgent need for exploration and research

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  • Protonation alkyl imidazole tungstate ionic liquid and preparation method thereof
  • Protonation alkyl imidazole tungstate ionic liquid and preparation method thereof
  • Protonation alkyl imidazole tungstate ionic liquid and preparation method thereof

Examples

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example 1

[0037] Example 1: Protonated hexylimidazole tungstate ionic liquid [C 6 Im] 2 [WO 4 ] preparation

[0038] 1) Synthesis of hexyl methanesulfonate: all operations were carried out under nitrogen atmosphere. Under the condition of strong stirring in an ice bath, dissolve 3.7 ml of methanesulfonyl chloride (46 mmol) in anhydrous CH 2 Cl 2The solution was added dropwise to 30ml CH containing 5.0ml hexanol (40mmol) and 8ml triethylamine (56mmol) 2 Cl 2 middle. Stir at room temperature for 2 hours, stop the reaction and add ice cubes to cool, then add 20ml of ice water to the reaction solution to dilute. use CH 2 Cl 2 After extraction, the organic layer was washed with saturated ammonium chloride solution and distilled water respectively, and then the water in the organic phase was removed with sodium carbonate, and the solvent was removed by vacuuming under reduced pressure to obtain a nearly colorless oily hexyl methanesulfonate.

[0039] 2) Synthesis of hexylimidazole: ...

example 2

[0042] Example 2: Protonated octyl imidazolium tungstate ionic liquid [C 8 Im] 2 [WO 4 ] preparation

[0043] 1) Synthesis of octyl mesylate: all operations were carried out under nitrogen atmosphere. Under the condition of strong stirring in an ice bath, dissolve 3.7 ml of methanesulfonyl chloride (46 mmol) in anhydrous CH 2 Cl 2 The solution was added dropwise to 30 ml CH containing 6.3 ml octanol (40 mmol) and 8 ml triethylamine (56 mmol) 2 Cl 2 middle. Stir at room temperature for 2 hours, stop the reaction and add ice cubes to cool, then add 20ml of ice water to the reaction solution to dilute. use CH 2 Cl 2 After extraction, the organic layer was washed with saturated ammonium chloride solution and distilled water respectively, and then the water in the organic phase was removed with sodium carbonate, and the solvent was removed by vacuuming under reduced pressure to obtain a nearly colorless oily hexyl methanesulfonate.

[0044] 2) Synthesis of octylimidazole:...

example 3

[0047] Example 3: Protonated dodecyl imidazolium tungstate ionic liquid [C 12 Im] 2 [WO 4 ] preparation

[0048] 1) Synthesis of dodecyl methanesulfonate: all operations were carried out under nitrogen atmosphere. Under the condition of strong stirring in an ice bath, dissolve 3.7 ml of methanesulfonyl chloride (46 mmol) in anhydrous CH 2 Cl 2 The solution was added dropwise to 30ml CH containing 7.45g dodecanol (40mmol) and 8ml triethylamine (56mmol) 2 Cl 2 middle. Stir at room temperature for 2 hours, stop the reaction and add ice cubes to cool, then add 20ml of ice water to the reaction solution to dilute. use CH 2 Cl 2 After extraction, the organic layer was washed with saturated ammonium chloride solution and distilled water, and then the water in the organic phase was removed with sodium carbonate, and the solvent was removed by vacuuming under reduced pressure to obtain a colorless oily dodecyl methanesulfonate.

[0049] 2) Synthesis of dodecyl imidazole: 2.7 ...

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Abstract

The invention belongs to an ionic liquid of protonated alkyl imidazole tungstate and a method for preparing the same, wherein the ionic liquid comprises protonated alkyl imidazole cations and tungstate radicle or isopolytungstic anions. The method for preparing the ionic liquid comprises the following steps: 1) reacting alkyl alcohol with methyl sulfonyl chloride to obtain alkyl mesylate; 2) reacting the alkyl mesylate with imidazole under the action of sodium hydride to obtain alkyl imidazole; 3) adding a tetrafluoroborate aqueous solution into an ether solution of the alkyl imidazole, stirring the mixture, draining the solvent to obtain an ionic liquid of protonated alkyl imidazole tetrafluoroborate; and 4) adding a corresponding aqueous solution of sodium tungstate or a hoevellite solution of isopolytungstic acid into an aqueous solution of the protonated alkyl imidazole tetrafluoroborate, stirring the mixture at room temperature to split phase of the mixture soon, and then washing, draining the solvent to obtain the corresponding ionic liquid of the protonated alkyl imidazole tungstate. The invention develops the protonated alkyl imidazole cations and the tungstate into the ionic liquid for the first time, the synthetic steps are simple, and the ionic liquid can be obtained with high yield.

Description

Technical field: [0001] The present invention relates to a protonated alkylimidazole tungstate ionic liquid, in particular to an ionic liquid in which the cation is a protonated alkylimidazole and the anion is a tungstate or isopolytungstate; the present invention also relates to a protonated alkyl The preparation method of imidazole tungstate ionic liquid. Background technique: [0002] In recent years, the research and application of room temperature ionic liquids (referred to as ionic liquids) has attracted great attention. Ionic liquids are substances composed of cations and anions that are liquid at or near room temperature. Compared with organic solvents, it has the characteristics of thermal stability, non-flammability, non-volatility, non-oxidation, non-explosion, and low toxicity, so it is clean and friendly for catalytic synthesis reactions. The development of ionic liquids has gone through three stages: (1) In the late 1980s, aluminum halide salt-type acidic ion...

Claims

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Application Information

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IPC IPC(8): C07D233/58
Inventor 侯震山乔云香李欢胡玉汪向锐冯博
Owner EAST CHINA UNIV OF SCI & TECH
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