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Novel disulfonic acid type alkyl imidazole ionic liquid, preparation and uses thereof

A technology of alkylimidazole and ionic liquid, which is applied in the field of new bissulfonic acid acidic ionic liquid and its preparation, can solve the problems that the reaction conditions are not very friendly to the environment and cannot be surpassed, and achieve high reaction yield and low dosage , good catalytic activity

Active Publication Date: 2009-08-19
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At the same time, we noticed that common monosulfonic acid-based ionic liquids cannot surpass traditional inorganic or organic strong acids in acidity, so some reactions cannot really replace these traditional proton strong acids. In addition, in the synthesis of such monosulfonic acid-based ionic liquids In the first stage of synthesizing amphoteric compounds, organic solvents such as toluene and acetonitrile are often used as reaction solvents, and the reaction conditions are not very friendly to the environment.

Method used

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  • Novel disulfonic acid type alkyl imidazole ionic liquid, preparation and uses thereof
  • Novel disulfonic acid type alkyl imidazole ionic liquid, preparation and uses thereof
  • Novel disulfonic acid type alkyl imidazole ionic liquid, preparation and uses thereof

Examples

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Effect test

Embodiment 1

[0061] [(HSO 3 -p) 2 im][HSO 4 ] (n=1, Y=HSO 4 )Synthesis:

[0062] Trimethylsilimidazole (14.0g0.1mol) was added to a 100mL three-necked flask, and 1,3-propane sultone (24.4g0.2mol) was slowly added dropwise under ice-bath conditions. Stirring was continued for half an hour under ice-bath conditions, about 1.8 mL (0.1 mol) of water was added dropwise, stirring was continued for 2 hours, and water and trimethylsilanol were distilled off under reduced pressure to obtain an intermediate zwitterionic compound. Add sulfuric acid (10.0g0.1mol) dropwise to the about 2mol / L aqueous solution of the obtained zwitterionic compound, reflux for 8 hours after the dropwise addition, and finally remove the solvent water by precipitation under reduced pressure at 90°C to obtain a light yellow transparent ion Liquid 38.9g, yield 95%.

Embodiment 2

[0064] [(HSO 3 -p) 2 im][HSO 4 ] (n=1, Y=HSO 4 )Synthesis:

[0065] Trimethylsilimidazole (14.0g0.1mol) was added to a 100mL three-necked flask, and 1,3-propane sultone (24.4g0.19mol) was slowly added dropwise under ice-bath conditions. Stirring was continued for half an hour under ice-bath conditions, about 1.8 mL (0.1 mol) of water was added dropwise, stirring was continued for 2 hours, and water and trimethylsilanol were distilled off under reduced pressure to obtain an intermediate zwitterionic compound. Add sulfuric acid (9.0g0.09mol) dropwise to the about 2mol / L aqueous solution of the obtained zwitterionic compound, reflux for 8 hours after the dropwise addition, and finally remove the solvent water by precipitation under reduced pressure at 80°C to obtain a light yellow transparent ion Liquid 32.76g, yield 80%.

Embodiment 3

[0067] [(HSO 3 -b) 2 im][HSO 4 ] (n=2, Y=HSO 4 )Synthesis

[0068] Add trimethylsilimidazole (14.0g0.1mol) into a 100ml three-necked flask, and slowly add 1,4-butyl sultone (27.2g0.2mol) dropwise under ice-bath conditions. Stirring was continued for half an hour under ice-bath conditions, about 1.8ml (0.1mol) of deionized water was added dropwise, stirring was continued for 2h, and water and trimethylsilanol were distilled off under reduced pressure to obtain an intermediate zwitterionic compound. Add 50ml of deionized water to the obtained zwitterionic compound and stir evenly, and add sulfuric acid (10.0g0.1mol) dropwise. After the dropwise addition, heat and reflux at 90°C for 6 hours, and finally remove it by precipitation under reduced pressure at 90°C. Solvent water to obtain 40.7 g of light yellow transparent ionic liquid with a yield of 94%.

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Abstract

The invention discloses a novel disulfonate type alkyl imidazole ionic liquid as well as a preparation method and application thereof. Structure of the ionic liquid is shown as formula (I), and the preparation method of the ionic liquid comprises the followings steps: trimethylsilylimidazole with structure shown as formula (II) is dropwise added to sultones with the structure shown as formula (III) for heat insulation reaction at the temperature of minus 20 DEG C to 30 DEG C, then water is dropwise added for continuing the heat insulation reaction to obtain an intermediate product (a zwitterionic compound) with the structure shown as formula (IV); an HY acid is dropwise added to aqueous solution of the zwitterionic compound to obtain a target product after full reaction at the temperature of 60-100 DEG C. The designed ionic liquid is hydrostable, almost has no steam pressure, especially has strong acidic properties, exhibits good catalytic activity when being applied to pechmann reaction, and a synthetic method thereof has environment-friendly feature, thus being expected to be applied to organic synthesis and catalysis fields as an environment-friendly solvent and catalyst.

Description

(1) Technical field [0001] The invention relates to a novel disulfonic acid type acidic ionic liquid and its preparation method and application, in particular to a bissulfonic acid type alkylimidazole ionic liquid and its preparation method and application. (2) Background technology [0002] As an emerging substance, ionic liquids have a series of outstanding advantages compared with traditional organic solvents: wide liquid range, better chemical and thermal stability, lower vapor pressure, and ionic liquids have adjustable acidity, and High ionic conductivity and wide electrochemical window. It has catalytic activity and certain selectivity for some reactions. [0003] In recent years, functionalized ionic liquids have begun to attract people's interest, especially ionic liquids with acidic groups on cations, which have been widely designed and studied. It can replace some traditional protonic acids as catalysts and achieve good catalytic effects. At the same time, we n...

Claims

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Application Information

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IPC IPC(8): C07D233/60B01J31/02C07D311/06
Inventor 许丹倩吴健罗书平徐振元
Owner ZHEJIANG UNIV OF TECH
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