Sulfonic acid functionalized pyrrolidone ionic liquid catalyst, and preparation method and application thereof

A technology of sulfonic acid functionalization and pyrrolidone, which is applied in the direction of sulfonate preparation, organic compound preparation, physical/chemical process catalysts, etc., can solve problems such as industrial production obstacles, achieve the effect of improving conversion rate and overcoming single types

Active Publication Date: 2021-12-14
NANCHANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There are certain shortcomings in these catalysts in industrial production, and there are certain obstacles to industrial production.

Method used

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  • Sulfonic acid functionalized pyrrolidone ionic liquid catalyst, and preparation method and application thereof
  • Sulfonic acid functionalized pyrrolidone ionic liquid catalyst, and preparation method and application thereof
  • Sulfonic acid functionalized pyrrolidone ionic liquid catalyst, and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] 1. Preparation of ionic liquid precursor: Dissolve 2-pyrrolidone and hexanesulfonic acid in the solvent ethyl acetate at a molar ratio of 1:1.5, gradually raise the temperature to 50°C and stir for 8 hours, wash with ethyl acetate after the reaction Unreacted materials were removed and dried under vacuum at 60 °C for 4 h.

[0030] 2. Preparation of ionic liquid: Mix the washed ionic liquid precursor and p-toluenesulfonic acid at a molar ratio of 1:2.05, stir at 80°C for 8h, evaporate at 80°C for 1h after the reaction to obtain a yellow color Viscous liquid.

[0031] In the obtained sulfonic acid functionalized pyrrolidone ionic liquid catalyst, containing mass fraction is 45% pyrrolidone, 50% hexanesulfonic acid, 5% p-toluenesulfonate; the electric pH of ionic liquid catalyst is 1.5, and conductivity is 0.45 S / m; viscosity is 360mPa·s.

Embodiment 2

[0033] 1. Preparation of ionic liquid precursor: Dissolve N-methylpyrrolidone and hexanesulfonic acid in the solvent toluene at a molar ratio of 1:1.1, gradually raise the temperature to 60°C and stir for 7 hours, wash with toluene after the reaction to remove untreated The reacted material was dried under vacuum at 50° C. for 6 h.

[0034] 2. Preparation of ionic liquid: Mix the washed ionic liquid precursor and methanesulfonic acid at a molar ratio of 1:1.8, stir at 60°C for 8h, evaporate at 60°C for 1h after the reaction to obtain a yellow color Viscous liquid.

[0035] In the obtained sulfonic acid functionalized pyrrolidone ionic liquid catalyst, containing mass fraction is 35% pyrrolidone, 55% hexanesulfonic acid, 10% methanesulfonate; the electric pH of ionic liquid catalyst is 1.9, and conductivity is 1.35 S / m; viscosity is 450mPa·s.

Embodiment 3

[0037] 1. Preparation of ionic liquid precursor: Dissolve N-ethylpyrrolidone and hexanesulfonic acid in diethyl ether as a molar ratio of 1:1.5, gradually raise the temperature to 55°C and stir for 8 hours, wash with diethyl ether to remove untreated The reacted material was dried under vacuum at 50° C. for 6 h.

[0038] 2. Preparation of ionic liquid: mix the washed ionic liquid precursor with concentrated sulfuric acid at a molar ratio of 1:1.5, stir at 80°C for 10h, evaporate at 80°C for 0.5h after the reaction to obtain a yellow viscous thick liquid.

[0039] In the obtained sulfonic acid functionalized pyrrolidone ionic liquid catalyst, containing mass fraction is 37% pyrrolidone, 55% hexanesulfonic acid, 8% bisulfate; the electric pH of ionic liquid catalyst is 1.1, and conductivity is 1.30S / m; the viscosity is 520 mPa·s.

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Abstract

The invention discloses a sulfonic acid functionalized pyrrolidone ionic liquid catalyst, and a preparation method and application thereof. The technical problem of preparing the sulfonic acid functionalized pyrrolidone ionic liquid in the prior art is mainly solved in the invention. The preparation method comprises the following steps: heating pyrrolidone and alkyl sulfonic acid at 40-330 DEG C through a two-step synthesis process; and adding an acid into the previous step, fully reacting at the temperature of 30-350 DEG C, and purifying to obtain the target product. The technical problem is well solved by the scheme. The sulfonic acid functionalized pyrrolidone ionic liquid catalyst comprises pyrrolidone, alkyl sulfonic acid and acid radical ions, and the pyrrolidone accounts for 35-55% of the total weight; the alkyl sulfonic acid accounts for 20-50% of the total weight; and the acid radical ions account for 1-20% of the total weight. The ionic liquid catalyst designed by the invention is applied to esterification reaction of acid or acid anhydride and alcohol, has relatively high catalytic activity, high stability, high reaction rate and few byproducts, and is beneficial to industrial application.

Description

technical field [0001] The invention belongs to the technical field of liquid catalysts, and in particular relates to a sulfonic acid functionalized pyrrolidone ionic liquid catalyst and a preparation method and application thereof. Background technique [0002] Ester compounds can be used as important chemical intermediates and are widely used in food additives, plasticizers, spices, medical supplies, coatings and other fields. In the field of esterification catalysis, commonly used catalysts are mainly inorganic acid catalysts, solid superacids, enzyme catalysts, acidic ion exchange resins, heteropolyacids, and some metal catalysts, such as titanium-based catalysts and aluminum-based catalysts. These catalysts have certain shortcomings in industrial production, and there are certain obstacles to industrial production. With the country's continuous requirements for environmental protection and the prospect of sustainable development. Ionic liquid catalysis has become a re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/26B01J31/02C07C309/30C07C309/04C07C303/32C07C67/08C07C69/80C07C69/76C07C69/82C07C69/14
CPCC07D207/26B01J31/0285B01J31/0298C07C309/30C07C309/04C07C303/32C07C67/08C07C69/80C07C69/76C07C69/82C07C69/14B01J2231/49Y02P20/584
Inventor 冯刚张雪张荣斌
Owner NANCHANG UNIV
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