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Ionic liquid, preparation method and application

A technology of ionic liquid and cation, which is applied in the preparation of sulfate ester, sulfonate salt, carboxylate ester, etc., and can solve the problems that the strong acid catalytic performance of hexafluoroisopropanesulfonic acid cannot be reflected.

Active Publication Date: 2018-01-19
INST OF PROCESS ENG CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In the prior art, a series of new acidic ionic liquids are obtained by reacting hexafluoroisopropanesulfonic acid with imidazole or quaternary ammonium salt, but the acidity of the ionic liquid with hexafluoroisopropanesulfonate as anion is far lower than that of hexafluoroisopropanesulfonic acid. Sulfonic acid, unable to reflect the strong acidity of hexafluoroisopropanesulfonic acid in terms of catalytic performance

Method used

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  • Ionic liquid, preparation method and application
  • Ionic liquid, preparation method and application
  • Ionic liquid, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0146] Example 1 Preparation of N,N,N-dimethylbutylhexafluoroisopropanesulfonate ammonium chlorosulfonate (1# ionic liquid)

[0147] The synthetic route is:

[0148]

[0149] The specific steps are:

[0150] (1) Synthesis of N,N-dimethylhexafluoroisopropanol-based amine: Take 0.1 mol of aminohexafluoroisopropanol in a three-necked flask, add 100 mL of isopropanol, stir and heat to 35°C. Then use a constant-pressure dropping funnel to slowly add 0.5 mol of formic acid (the addition is completed in 40 minutes), and the mixture is heated to 50°C; take 0.2 mol of formaldehyde and add it with a constant-pressure dropping funnel under strong stirring (the addition is completed in 4.5 hours); The mixture was heated to 80°C and maintained at reflux for 21h. After cooling, it is alkalized with NaOH solution to pH=13, the solution is separated into layers, the upper layer is extracted with n-hexane, the solvent is evaporated using a rotary evaporator, and the maximum rotary evaporation tempe...

Embodiment 2

[0158] Example 2 Preparation of N, N, N-dimethylbutyl hexafluoroisopropanesulfonate ammonium triflate (2# ionic liquid)

[0159] Step (4) was performed after step (3) of Example 1 to combine the N,N,N-dimethylbutylhexafluoroisopropanesulfonate chlorosulfonate obtained in step (3) with trifluoromethanesulfonic acid Stirring at room temperature for 24h anion ion exchange to obtain N,N,N-dimethylbutyl hexafluoroisopropanesulfonate ammonium triflate.

[0160] Characterization:

[0161] 1 H NMR(300MHz,[D 6 ]DMSO,25℃):δ=0.89(t,3H,N(CH 2 ) 3 CH 3 ),1.3(m,2H,N(CH 2 ) 2 CH 2 CH 3 ),1.71(m,2H,NCH 2 CH 2 CH 2 CH 3 ),3.3(s,6H,N(CH 3 ) 2 ),3.22(t,2H,NCH 2 (CH 2 ) 2 CH 3 ), 4.2 (s, 1H, OH). ESI / MS: m / z (+) 348.07, m / z (-) 149.

[0162] After testing, the acidity of 2# ionic liquid is H 0 =-9.401.

Embodiment 3 6

[0163] Example 3 Preparation of hexafluoroisopropanesulfonate-disulfonate ammonium triflate (3# ionic liquid)

[0164] The synthetic route is:

[0165]

[0166] The specific steps are:

[0167] At minus 15°C, slowly add 0.1 mol (18.3g) 2-aminohexafluoroisopropanol to 0.4 mol chlorosulfonic acid dropwise and stir while adding dropwise. After the addition is complete, slowly raise the temperature to minus 5°C and stir. After 5h, the temperature was raised to 35℃ and stirred for 5h. The substrate was washed with dichloromethane after the reaction, then vacuum dried, and then slowly added dropwise with one-fold molar amount of trifluoromethanesulfonic acid to the dried bottom at room temperature. Stir while adding dropwise, react for 24h, rotary evaporate the reaction product, and obtain the target product after vacuum drying.

[0168] Characterization:

[0169] 1 H NMR(300MHz,[D 6 ]DMSO,25℃):δ=4.2(s,1H,SO 4 H),7.2(s,1H,NH),8.5(s,2H,2SO 3 H),3.3(s,6H,N(CH 3 ) 2 ),3.22(t,2H,NCH 2 (CH 2 ) 2...

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PUM

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Abstract

The invention relates to an ionic liquid. Cations of the ionic liquid contain hexafluoroisopropyl sulfonic acid groups. According to the ionic liquid provided by the invention, the hexafluoroisopropylsulfonic acid groups are introduced into the cation part of the ionic liquid to give a super acid center to the ionic liquid, through changing anion types, the ionic liquid of which the acidity is greater than that of 98% concentrated sulfuric acid is obtained, and the highest level of the hamlet acidity (H0) in the obtained ionic liquid can reach -14.13.

Description

Technical field [0001] The invention belongs to the field of ionic liquid preparation, and relates to an ionic liquid, a preparation method and application, and in particular to an ionic liquid containing a hexafluoroisopropanesulfonic acid group, and a preparation method and application thereof. Background technique [0002] Ionic liquids are composed of organic cations and inorganic anions, and are liquid at room temperature or use temperature. Compared with traditional organic solvents, ionic liquids have excellent characteristics: 1) The structure and function have ionic designability; 2) Good solubility, good solubility for organic / inorganic substances; 3) Almost no vapor pressure, Non-volatile, non-explosive, so low pollution; 4) Low melting point, stable chemical and thermodynamic properties; 5) Simple post-processing, recyclable; 6) Can be used as a reaction catalyst, ionic liquids can improve the reaction rate, increase product selectivity and The catalyst has obvious a...

Claims

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Application Information

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IPC IPC(8): C07C303/24C07C305/06C07C303/32C07C309/06C07C303/34C07C307/02C07D233/60C07D213/34B01J31/02C07C67/08C07C69/14C07D307/89
CPCB01J31/02C07C67/08C07C69/14C07C303/24C07C303/32C07C303/34C07C305/06C07C307/02C07C309/06C07D213/34C07D233/60C07D307/89
Inventor 赵国英万亚萌张锁江王傲运张振华徐子晨
Owner INST OF PROCESS ENG CHINESE ACAD OF SCI
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