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Preparation of novel quinoline-based temperature-sensitive ionic liquids and its method for catalyzing the methylation of long-chain fatty acids

A technology for long-chain fatty acids and ionic liquids, applied in chemical instruments and methods, preparation of organic compounds, preparation of carboxylic acid esters, etc., can solve problems such as failure to meet basic standards, narrow application range, complex preparation process, etc., and achieve good technology Application prospects, significant scientific significance and high catalytic efficiency

Active Publication Date: 2016-05-25
SICHUAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the above-mentioned catalysts have limitations in practice due to their traditional preparation methods and narrow application range, showing many shortcomings: for example: too high acidity, unstable performance, complicated preparation process, high cost, etc. (Deng Youquan. Ionic Liquids—Properties, Preparation and Applications. Beijing: Sinopec Press, 2006)
The traditional synthesis of long-chain fatty acid methyl esters mostly uses concentrated sulfuric acid, benzoic acid, etc., but because many by-products are formed in the reaction, and the catalyst is not easy to recycle, it pollutes the environment very much. This method has limitations, and the products produced at the same time It is also difficult to separate and its application is limited, and it cannot meet the basic standards of modern green chemistry

Method used

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  • Preparation of novel quinoline-based temperature-sensitive ionic liquids and its method for catalyzing the methylation of long-chain fatty acids
  • Preparation of novel quinoline-based temperature-sensitive ionic liquids and its method for catalyzing the methylation of long-chain fatty acids

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Effect test

Embodiment 1

[0040] Embodiment 1 (synthetic of ionic liquid): the preparation method 1 of quinoline bisulfate ionic liquid

[0041] Add 0.1mol of quinoline into a round bottom flask, add 50mL of ethanol as a reaction solvent, cool down to 5°C in an ice bath, slowly add 0.1mol of concentrated sulfuric acid dropwise with a constant pressure titration funnel, drop it in half an hour, and then Under stirring for 2h, a white turbid liquid was obtained, and the reaction was stopped. The product was rotovaped and the ethanol was removed to give a white solid. Then wash with acetone for 3 to 4 times, and finally use absolute ethanol to recrystallize the crude product, and obtain a white powder solid after vacuum drying, which is the product quinoline hydrogen sulfate.

Embodiment 2

[0042] Embodiment 2 (synthetic of ionic liquid): the preparation method 2 of quinoline bisulfate ionic liquid

[0043] Add 0.09 mol of quinoline into a round bottom flask, add 50 ml of ethanol as a reaction solvent, cool down to 3°C in an ice bath, slowly add 0.1 mol of concentrated sulfuric acid dropwise with a constant pressure titration funnel, drop it in half an hour, and then Under stirring for 1.5h, a white turbid liquid was obtained, and the reaction was stopped. The product was rotovaped and the ethanol was removed to give a white solid. Then wash with acetone for 3 to 4 times, and finally use absolute ethanol to recrystallize the crude product, and obtain a white powder solid after vacuum drying, which is the product quinoline hydrogen sulfate.

Embodiment 3

[0044] Embodiment 3 (synthetic of ionic liquid): the preparation method 3 of quinoline bisulfate ionic liquid

[0045] Add 0.1mol of quinoline into a round bottom flask, add 50mL of ethanol as a reaction solvent, cool down to 5°C in an ice bath, slowly add 0.09mol of concentrated sulfuric acid dropwise with a constant pressure titration funnel, drop it in half an hour, and then Under stirring for 3h, a white turbid liquid was obtained, and the reaction was stopped. The product was rotovaped and the ethanol was removed to give a white solid. Then wash with acetone for 3 to 4 times, and finally use absolute ethanol to recrystallize the crude product, and obtain a white powder solid after vacuum drying, which is the product quinoline hydrogen sulfate.

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Abstract

The invention discloses a preparation method of a thermo-sensitive ionic liquid and a method for catalyzing a methyl esterification reaction of a long-chain fatty acid by adopting the thermo-sensitive ionic liquid. The structure of the thermo-sensitive ionic liquid is as shown in a general formula (I) and comprises a quinoline cation and anions such as a fluoboric acid radical, a methane sulfonic acid radical and hydrogen sulphate. The preparation method of the thermo-sensitive ionic liquid is mainly characterized in that number of phase states of a system is regulated and controlled by increasing and lowering temperature, namely the system can be in one phase at high temperature and in different phases at room temperature or low temperature after the ionic liquid is rapidly separated from products, so that the whole reaction system guarantees high catalytic efficiency in a homogeneous reaction, separation and recycling are simpler, the disadvantages of limited two-phase catalytic efficiency and difficult recycling of the ionic liquid during homogeneous catalysis are overcome, and a new thought is provided for solving the problems. The general formula (I) is as shown in the specification.

Description

technical field [0001] The invention relates to a preparation method of a temperature-sensitive ionic liquid of quinoline cations and its application in the reaction of long-chain fatty acid methyl esters, and belongs to the technical field of combining green chemistry and organic chemistry catalytic reaction methods. Background technique [0002] Esters are a class of excellent organic solvents, fine chemicals and pharmaceutical intermediates, etc., and have a wide range of applications. In order to speed up the esterification reaction rate, various types of acid-base catalysts are added. Traditionally, inorganic liquid acid and alkali catalysts are used, and its main disadvantage is that it is difficult to recycle. In recent decades, relatively new solid acid-base catalysts have been adopted to solve the problem of recycling. However, the above-mentioned catalysts have limitations in practice due to their traditional preparation methods and narrow application range, show...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/06B01J31/02C07C67/08C07C69/003C07C69/24
CPCB01J31/0284C07C67/08C07D215/06C07C69/003C07C69/24
Inventor 宋航姚舜彭琪姚田
Owner SICHUAN UNIV
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