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Process for room-temperature ion liquid-catalytic preparation of ethyl linoleate

A room temperature ionic liquid, ethyl linoleate technology, applied in chemical instruments and methods, preparation of organic compounds, preparation of carboxylic acid esters, etc., can solve the problem of difficult to accurately control acidity, catalysts and esterification processes have not been reported in literature, Application limitations and other issues, to achieve the effect of maintaining efficacy, good industrial application prospects, and stable recycling performance

Inactive Publication Date: 2007-11-14
HEILONGJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Youquan Deng et al. (J Mol CatalA: Chem.2001, 165: 33-36) introduced 1-butylpyridine chloroaluminate ionic liquid ([bmim] [Cl] / AlCl 3 ) is used to catalyze the esterification reaction of acetic acid, isopropanol and benzyl alcohol, the conversion rate of acetic acid is 71.3% and 79.6% respectively, but because the chloroaluminate type ionic liquid is very sensitive to water, traces of water will It is difficult to accurately control its acidity by changing its composition and proton concentration. To ensure the esterification reaction, the ratio of aluminum trichloride to chlorobutylpyridine must be less than 1 to ensure the stability of aluminum trichloride. Alcohol must be added to the ionic liquid first, and then the organic acid is added to the reaction system
Due to the generation of water in the esterification reaction system, the application of chloroaluminate-type ionic liquids in the esterification reaction is greatly limited
Non-chloroaluminate-type ionic liquids have important research significance and application prospects due to their stability in air and water. Tetrafluoroborate (BF 4 - ) was an anionic ionic liquid once used as a solvent containing complex catalysts such as palladium and rhodium for esterification (D.Zim, R.F.De Souza, J.Dupont, et al.Tetrahedron Lett.1998, 39:7071-7075 ), and at present this type of ionic liquid is used as a catalyst for the research of esterification is also rarely reported, as the ionic liquid catalyst and esterification process of linoleic acid esterification have no bibliographical information

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] A method for preparing ethyl linoleate by catalyzing ionic liquids at room temperature, adding linoleic acid and absolute ethanol in a molar ratio of 1:2 to 6 sequentially to a device equipped with a water separator, a condensation pipe, a nitrogen protection device, a thermometer and a magnetic device. Mix in a stirred reactor, add 1-ethyl-3-methylimidazolium fluoroborate ionic liquid catalyst ([emim]BF 4 ), react at 50°C to reflux temperature, under the protection of nitrogen for 2 to 10 hours, then cool to room temperature and naturally stratify. , Collect the distillate at 158-171°C to obtain the refined ethyl linoleate product. The underlying ionic liquid can be reused. The experimental results of the esterification reaction of linoleic acid and absolute ethanol showed that the molar ratio of alkyd acid had a significant effect on the esterification rate and reaction rate of linoleic acid. With the increase of the molar ratio of alkyd, the esterification rate of ...

Embodiment 2

[0019] The method for the preparation of ethyl linoleate by room temperature ionic liquid catalysis described in embodiment 1, in the reactor with water separator, condensation pipe, nitrogen protection device, thermometer and magnetic force stirring, add linoleic acid, anhydrous Ethanol, an ionic liquid catalyst [emim]BF accounting for 42% of the mass of linoleic acid 4 , wherein the molar ratio of linoleic acid and absolute ethanol is 1:4, stirred under the protection of nitrogen, heated up to reflux temperature, reacted for 4 hours and stopped heating, cooled to room temperature, static layering, and took the upper layer product sample with 0.1mol / L KOH standard The acid value of the sample was titrated with the solution, and the esterification rate of linoleic acid was calculated to be 92.5%. Since the reaction product is immiscible with the ionic liquid, it naturally separates after cooling. After decanting the upper reaction liquid, it is rectified under reduced pressure...

Embodiment 3

[0021] The method for the preparation of ethyl linoleate by room temperature ionic liquid catalysis described in embodiment 1, in the reactor with water separator, condensation pipe, nitrogen protection device, thermometer and magnetic force stirring, add linoleic acid, anhydrous Ethanol and the room temperature ionic liquid catalyst [emim] BF that accounts for 42% of the linoleic acid quality separated after using 1 time according to the method of Example 2 4 , wherein the molar ratio of linoleic acid and absolute ethanol is 1: 4, stirred under the protection of nitrogen, heated up to reflux temperature, reacted for 4 hours and stopped heating, cooled to room temperature, static layering, took the upper layer product sample with 0.1mol / LKOH The acid value of the sample was titrated with the standard solution, and the esterification rate of linoleic acid was calculated to be 90.2%. The upper product is rectified under reduced pressure at -98.8kPa, and the fraction at 165-169°C...

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PUM

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Abstract

This invention relates to a method of ion liquid through catalysis preparing linoleic acid ethyl ester at room temperature. The invention takes linoleic acid and absolute ethyl alcohol as raw material, use 1 - alkyl- 3 - methyl glyoxaline tetra- fluoborate ion liquid through catalysis to preapre linoleic acid ethyl ester. The invention mix the linoleic acid and absolute ethyl alcohol according to mol ratio of 1 : 2 to 10, then add ion liquid catalyst about 5 to 6% linoleic acid quality to the mixture, whip and heat under nitrogen shield, takes reaction 2 to 10 hours at 40 deg circumfluence temperature,then decant upper offspring, takes underpressure rectification at minus 98.6 to minus 99.2kpa, collect fraction of 158 to 171 deg, gain refined linoleic acid ethyl ester product.

Description

Technical field: [0001] The invention relates to a method for preparing ethyl linoleate, in particular to a method for preparing ethyl linoleate by catalyzing the esterification of linoleate with room temperature ionic liquid. Background technique: [0002] Ethyl linoleate (9,12-octadecadienoic acid ethyl ester) is the main drug raw material for the prevention and treatment of heart and brain thrombosis, arteriosclerosis and other diseases. It has the functions of enhancing the body's immunity and regulating metabolism. It has been widely used in food and food fields. [0003] The industrialized method of producing ethyl linoleate is the esterification reaction of linoleic acid and absolute ethanol under the catalysis of concentrated sulfuric acid. This method not only has problems such as large amount of acid waste water discharge and serious corrosion of production equipment, but also due to the strong oxidizing property of concentrated sulfuric acid, the unsaturated bond...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/08C07C69/587B01J31/14
Inventor 吴伟武光
Owner HEILONGJIANG UNIV
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