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Sulfonic acid functionalized ionic liquid based on perfluoro alkyl sulfonic acid radical negative ion and its preparation method

A perfluoroalkane sulfonate and perfluoroalkane sulfonate technology, which is applied in the fields of sulfonic acid preparation, sulfonate preparation, organic chemistry, etc., can solve the "designable" space limitation and low activity of catalytic esterification reaction , Inconvenient operation process and other problems, to achieve good industrial application prospects, lower viscosity, reduce the effect of difficult operation

Inactive Publication Date: 2014-07-23
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The last step of this route is a standard process of making weak acid from strong acid. The use of strong acid brings inconvenience to the operation process, and it is difficult to control the physicochemical properties (acidity, viscosity, solubility, etc.) of the ionic liquid by adjusting the anion structure alone. Limiting the "designable" space of ionic liquids
In 2009, García used perfluorosultone and the -OH functional group in the cationic structure of the reactant to carry out a ring-opening reaction to introduce perfluoroalkanesulfonic acid groups to synthesize a strongly acidic ionic liquid, but due to the introduction of excess F, the ionic liquid and The solubility of the reaction raw material alcohol is reduced, resulting in a lower catalytic esterification reaction activity

Method used

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  • Sulfonic acid functionalized ionic liquid based on perfluoro alkyl sulfonic acid radical negative ion and its preparation method
  • Sulfonic acid functionalized ionic liquid based on perfluoro alkyl sulfonic acid radical negative ion and its preparation method
  • Sulfonic acid functionalized ionic liquid based on perfluoro alkyl sulfonic acid radical negative ion and its preparation method

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Experimental program
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Embodiment 1

[0030] The preparation of embodiment 1.3-(2-hydroxyethyl)-1-methylimidazolium chloride:

[0031]

[0032] Put 1.0mol methylimidazole into a 500mL three-necked flask, stir and drop 1.0mol chloroethanol at 80°C, and react at a constant temperature for 12 hours after the addition is completed. After the reaction mixture is cooled to room temperature, a white or light yellow jelly-like substance can be obtained. Wash and filter with anhydrous ether three times, and dry in vacuum for 8 hours to obtain a white or light yellow solid, dry in vacuum at 80°C for 24 hours.

Embodiment 2

[0033] The preparation of embodiment 2.N-hydroxyethylpyridine chloride:

[0034]

[0035] Put 1.0mol of pyridine into a 500mL three-necked flask, stir and add 1.0mol of chloroethanol dropwise at 80°C. After the dropwise addition, keep it warm for 12 hours. After the reaction mixture is cooled to room temperature, a white or light yellow jelly-like substance can be obtained. Wash and filter with anhydrous diethyl ether three times, and dry in vacuum for 8 hours to obtain a white or light yellow solid, dry in vacuum at 80°C for 24 hours.

Embodiment 3

[0036] The preparation of embodiment 3.2-(2-hydroxyethyl)-1-methylpyrazole chloride:

[0037]

[0038] Put 1.0mol of methylpyrazole into a 500mL three-necked flask, stir and drop 1.0mol of chloroethanol at 80°C, and keep it warm for 12 hours after the addition is completed. After the reaction mixture is cooled to room temperature, a white or light yellow jelly can be obtained. The substance was washed with anhydrous ether and filtered three times, and dried in vacuum for 8 hours to obtain a white or light yellow solid, which was dried in vacuum at 80°C for 24 hours.

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Abstract

The invention discloses a sulfonic acid functionalized ionic liquid based on a perfluoro alkyl sulfonic acid radical negative ion and its preparation method, and the structural formula of the ionic liquid is represented by a formula as shown in the specification, wherein m represents 3 or 4, n represents a 1-9 integer, and R is-CH3,-CH2CH3 or-(CH2) 3CH3. The preparation method is as follows: using a substance, which is obtained by reaction of a nitrogen-containing heterocyclic compound with ethylene chlorohydrins, or choline chloride as a precursor; then performing replacement reaction of the precursor and a perfluoro alkyl sulfonate to replace Cl<-> for CF3 (CF2) nSO3 to obtain an intermediate; using sultone and-OH in the intermediate positive ion for performing ring-opening reaction to introduce a sulfonic acid group to obtain the target ionic liquid. The ionic liquid prepared by the method is lower in viscosity, stronger in designable property, and green in synthesis process compared with sulfonic acid functionalized ionic liquids in the prior art, and can be used as a substitute for a traditional liquid acid catalyst, is wider in use range, and has good industrial application prospects.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry synthesis, in particular to a sulfonic acid functionalized ionic liquid based on perfluoroalkyl sulfonate anions and a preparation method thereof Background technique [0002] Ionic liquids have outstanding advantages such as low vapor pressure, high thermal stability, and designable structure. Using them as catalytic materials in catalytic processes has obvious advantages in improving reaction rate, conversion rate, and selectivity. Broad application prospects. In 2002, Professor Davis synthesized for the first time stable to water and air and strong Acidic sulfonic acid functionalized ionic liquid (J.Am.Chem.Soc., 2002, 124, 5962-5963), and has the dual advantages of high activity and easy separation in chemical reactions such as esterification and Pinacol rearrangement. Subsequently, Wang Tao, Wang Jun, Xu Zhenyuan and many other scientists adjusted and developed their anions and c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/60C07D213/04C07D231/12C07C309/10C07C303/02C07C303/32C07C309/06
CPCC07C303/02C07C303/32C07C309/10C07D213/04C07D231/12C07D233/60Y02P20/54
Inventor 刘秀梅王畅刘静高艳安
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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