CN101024613A - Method for catalyzing alochol acid esterization by sulfonic-acid-radical functionized ion liquid - Google Patents
Method for catalyzing alochol acid esterization by sulfonic-acid-radical functionized ion liquid Download PDFInfo
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Abstract
The invention relates to a hydroxy acid esterification method that is catalyzed by sulfonic group ion liquid. It adopts alpha-pyrrolidone positive ion that is sulfonic functionalized and ion liquid formed by inorganic or organic ion as catalyst, solvent, and dehydrating agent, the ion liquid quantity is 10-200% mol ratio of alcohol and acid, taking 0.5-8 hours reaction at 40-140 degree centigrade to gain ester. The method has the advantages of high selective, hig universality, and the ester could be automatically separated with catalyst.
Description
Technical field
The present invention relates to the organic chemical reactions method, particularly relate to a kind of method of catalyzing alochol acid esterization by sulfonic-acid-radical functionized ion liquid.
Background technology
Carboxylic acid ester compound has the wide industrial purposes, much is important chemical product.Traditional alcoholic acid esterification technology is used the inorganic acid as catalyst of severe corrosive such as the vitriol oil usually, exist that selectivity is low, product is coloured, be difficult to separate with product, problems such as etching apparatus and contaminate environment, it is therefore industrial that exploitation is had the novel alcoholic acid esterification system demand of environmental benefit and economic benefit is very urgent.Advantages such as the ionic liquid that is liquid state under the room temperature is the novel material that receives much attention in recent years, has good stability, and is non-volatile, and solvability and acidity are adjustable are showing excellent characteristic as novel green catalyst and solvent in a lot of acid catalyzed reactions.Deng You congruence (CN1247856) is used alkyl pyridine, phonetic azoles etc. contain the ionic liquid of nitric heterocyclic compound and metal or non-metallic halide formation as catalyzer and solvent, realized the alcoholic acid esterification reaction, but shortcomings such as this class ionic liquid existence is stable inadequately to water and air, the stable deficiency of repeated use; (CN1405140 is CN1528733) with ionic liquid [Hmim] BF for He Mingyuan etc.
4, Fang Yanxiong etc. (CN1880295) is cationic ionic liquid with the pyrrolidone that the N-alkyl or alkenyl replaces, and as the catalyzer and the solvent of alcoholic acid esterification, successively realized the esterification of alcohol with acid.Small molecules esters such as ethyl acetate are at [Hmim] BF
4System (CN1405140, CN1528733) in phase-splitting automatically, can not prepare by separatory.The present invention be the ionic liquid that constitutes with the alpha-pyrrolidone positively charged ion of sulfonic functional and inorganic or organic anion as catalyzer, solvent, dewatering agent, carry out the synthetic ester of alcoholic acid esterification reaction.This sulfonic functional functionalized ion liquid, be to utilize ion liquid designability, on alpha-pyrrolidone kation alkyl side chain, introduce the acidic functionality sulfonic group, the ionic liquid that obtains has and can flow, non-volatile, non-aggressive and with the immiscible special performance of some organic solvent, have higher catalytic activity and universality, the also easier and automatic phase-splitting of esterification products simultaneously, and can be recycled, catalytic activity is constant, therefore is expected to substitute in chemical industry do not meet traditional severe corrosive acid catalytic materials such as the vitriol oil that Green Chemistry requires.
Summary of the invention
The objective of the invention is to replace the reaction of traditional inorganic acids catalyst alcoholic acid esterification, realize the alcoholic acid esterification of the green high-efficient under the mild reaction conditions with acidic ion liquid.
The present invention realizes by following scheme:
In the there-necked flask that magnetic stirring apparatus, thermometer, reflux condensing tube are housed, add the ionic liquid and the alcohol, sour of certain proportioning, through reacting by heating, cooling, standing demix while stirring, processes such as separatory realize esterification; Or ionic liquid mixed with alkyd, after heating while stirring, straight run distillation goes out ester products.Ionic liquid can be reused after simply dewatering and keep catalytic activity constant.
The inventive method feature is that the ionic liquid that constitutes with the alpha-pyrrolidone positively charged ion of sulfonic functional and inorganic or organic anion is as alcoholic acid esterification catalyst for reaction, solvent, dewatering agent, the ionic liquid add-on is 10～200% of alcohol, a sour total mole number, 40～140 ℃ of temperature of reaction, normal pressure, 0.5～8 hour reaction times.
The alpha-pyrrolidone cationic structural general formula of the described sulfonic functional of the inventive method is as follows:
N=1～6 wherein.
The described inorganic or organic anion of the inventive method is chlorine, bromine, iodine, sulfate radical, bisulfate ion, nitrate radical, tosic acid root, trifluoromethanesulfonic acid root, trifluoroacetic acid radical ion.
The described reactant alcohol of the inventive method is C
1～C
12The saturated or unsaturated fatty alcohol of the monobasic of straight or branched, aromatic alcohol, polyvalent alcohol, C
3～C
12Alicyclic ring alcohol.
The general formula of the described aromatic alcohol of the inventive method is:
Wherein R is C
1～C
4Alkyl.
The described polyvalent alcohol of the inventive method is ethylene glycol, glycerol, tetramethylolmethane.
Monocarboxylic acid, di-carboxylic acid, lactic acid, citric acid that the described reactant acid of the inventive method is straight or branched, phenylformic acid, salicylic acid, m-Salicylic acid, P-hydroxybenzoic acid, 0-chloro-benzoic acid, m-chlorobenzoic acid, Chlorodracylic acid, o-bromobenzoic acid, m-bromobenzoic acid, parabromobenzoic acid.
The monocarboxylic general formula of the described straight or branched of the inventive method is R ' COOH, and R is H atom, C
1～C
17Alkyl, C
2～C
17Thiazolinyl; The general formula of di-carboxylic acid is HOOC (CH
2)
nCOOH, n=0,1-6.
In the method for the invention, the addition sequence in the reaction process between alcohol, acid and the ionic liquid three without limits.
In the method for the invention, stir reflux certain hour down in the reaction process, reaction afterreaction liquid leaves standstill separatory, tells upper organic phase and gets esterified prod; Or reaction afterreaction liquid directly distill esterified prod.
The inventive method is compared with background technology, and beneficial effect is:
1. used acidic ion liquid promotes medium as alcoholic acid esterification catalyst for reaction or reaction, the phase-splitting automatically of esterification reaction product and ionic liquid, and the purity height is simplified separation process.
2. transformation efficiency height, selectivity 100%.
3. reacted ionic-liquid catalyst can use repeatedly through simple vaccum dewatering, and catalytic activity is constant, and product is colourless.When the catalyzer usage quantity is big, can dewater and use repeatedly continuously.Thereby total production cost can reduce.Because the ionic liquid steam forces down, and is non-volatile, so this catalyst system is eco-friendly.
4. universality is good.Saturated fatty acid, unsaturated fatty acids, alpha hydroxy acid, diprotic acid, aromatic acid, phenylformic acid, substituted benzoic acid can generate ester with above-mentioned reactant alcohol.
Embodiment
Following embodiment is to the further specifying of the inventive method, and is not limitation of the invention.
Embodiment one: take by weighing acetate 0.1mol respectively, methyl alcohol 0.1mol, ionic liquid N-(3-sulfonic group) propyl pyrrole alkane ketone hydrosulfate 0.05mol; Ionic liquid, methyl alcohol, acetate are added in the round-bottomed flask that has agitator, thermometer, reflux condensing tube successively, magnetic agitation, and 40 ℃ of heating reflux reactions 1 hour; Standing demix pipettes the upper strata esterification products, and transformation efficiency is 71.2%, selectivity 100%; Ionic liquid is reused after vacuum hydro-extraction.
Embodiment two: take by weighing acetate 0.1mol respectively, ethanol 0.1mol, ionic liquid N-(3-sulfonic group) propyl pyrrole alkane ketone hydrosulfate 0.02mol; Ionic liquid, ethanol, acetate are added in the round-bottomed flask that has agitator, thermometer, reflux condensing tube successively, magnetic agitation, and 80 ℃ of heating reflux reactions 0.5 hour; Standing demix pipettes the upper strata esterification products, and transformation efficiency is 91.1%, selectivity 100%; Ionic liquid is reused after vacuum hydro-extraction.
Embodiment three: take by weighing acetate 0.1mol respectively, propyl carbinol 0.1mol, ionic liquid N-(3-sulfonic group) propyl pyrrole alkane ketone hydrosulfate 0.01mol; Ionic liquid, propyl carbinol, acetate are added in the round-bottomed flask that has agitator, thermometer, reflux condensing tube successively, and 100 ℃ of lower magnetic force stirring reactions 1 hour; Standing demix pipettes the upper strata esterification products, and transformation efficiency is 82.5%, selectivity 100%; Ionic liquid is reused after vacuum hydro-extraction.
Embodiment four: take by weighing acetate 0.1mol respectively, n-Octanol 0.1mol, ionic liquid N-(3-sulfonic group) propyl pyrrole alkane keto hydrochloride 0.01mol; Ionic liquid, n-Octanol, acetate are added in the round-bottomed flask that has agitator, thermometer, reflux condensing tube successively, magnetic agitation, and under 130 ℃, reacted 2 hours; Standing demix pipettes the upper strata esterification products, and transformation efficiency is 62.4%, selectivity 100%; Ionic liquid is reused after vacuum hydro-extraction.
Embodiment five: take by weighing acetate 0.1mol respectively, lauryl alcohol (lauryl alcohol) 0.1mol, ionic liquid N-(3-sulfonic group) propyl pyrrole alkane ketone hydrosulfate 0.1mol; Ionic liquid, lauryl alcohol, acetate are added in the round-bottomed flask that has agitator, thermometer, reflux condensing tube successively, magnetic agitation, and under 130 ℃, reacted 2 hours; Standing demix pipettes the upper strata esterification products, and transformation efficiency is 63.7%, selectivity 100%.Ionic liquid is reused after vacuum hydro-extraction.
Embodiment six: take by weighing acetate 0.1mol respectively, phenylcarbinol 0.1mol, ionic liquid N-(4-sulfonic group) butyl pyrrolidine ketone hydrosulfate 0.05mol; Ionic liquid, phenylcarbinol, acetate are added in the round-bottomed flask that has agitator, thermometer, reflux condensing tube successively, magnetic agitation, and under 110 ℃, reacted 2 hours; Standing demix pipettes the upper strata esterification products, and transformation efficiency is 85.2%, selectivity 100%; Ionic liquid is reused after vacuum hydro-extraction.
Embodiment seven: take by weighing acetate 0.1mol respectively, phenylpropyl alcohol 0.1mol, ionic liquid bromination N-(3-sulfonic group) propyl pyrrole alkane ketone 0.02mol; Ionic liquid, phenylpropyl alcohol, acetate are added in the round-bottomed flask that has agitator, thermometer, reflux condensing tube successively, magnetic agitation, and under 120 ℃, reacted 8 hours; Standing demix pipettes the upper strata esterification products, and transformation efficiency is 61.0%, selectivity 100%; Ionic liquid is reused after vacuum hydro-extraction.
Embodiment eight: take by weighing acetate 0.1mol respectively, 4-phenyl-2-butanols 0.1mol, ionic liquid N-(3-sulfonic group) propyl pyrrole alkane ketone trifluoroacetate 0.02mol; Ionic liquid, 4-phenyl-2-butanols, acetate are added in the round-bottomed flask that has agitator, thermometer, reflux condensing tube successively, magnetic agitation, and under 140 ℃, reacted 8 hours; Standing demix pipettes the upper strata esterification products, and transformation efficiency is 46.3%, selectivity 100%; Ionic liquid is reused after vacuum hydro-extraction.
Embodiment nine: take by weighing acetate 0.2mol respectively, ethylene glycol 0.1mol, ionic liquid N-(3-sulfonic group) propyl pyrrole alkane ketone hydrosulfate 0.02mol; Ionic liquid, ethylene glycol, acetate are added in the round-bottomed flask that has agitator, thermometer, reflux condensing tube successively, magnetic agitation, and under 120 ℃, reacted 1 hour; Standing demix pipettes the upper strata esterification products, and transformation efficiency is 61.5%, selectivity 100%; Ionic liquid is reused after vacuum hydro-extraction.
Embodiment ten: take by weighing propionic acid 0.1mol respectively, n-propyl alcohol 0.1mol, ionic liquid N-(3-sulfonic group) propyl pyrrole alkane ketone fluoroform sulphonate 0.01mol; Ionic liquid, n-propyl alcohol, propionic acid are added in the round-bottomed flask that has agitator, thermometer, reflux condensing tube successively, magnetic agitation, and under 90 ℃, reacted 2 hours; Standing demix pipettes the upper strata esterification products, and transformation efficiency is 68.7%, selectivity 100%; Ionic liquid is reused after vacuum hydro-extraction.
Embodiment 11: take by weighing butanic acid 0.1mol respectively, ethanol 0.1mol, ionic liquid iodate N-(4-sulfonic group) butyl pyrrolidine ketone 0.02mol; Ionic liquid, ethanol, butanic acid are added in the round-bottomed flask that has agitator, thermometer, reflux condensing tube successively, magnetic agitation, and under 80 ℃, reacted 2 hours; Standing demix pipettes the upper strata esterification products, and transformation efficiency is 76.8%, selectivity 100%; Ionic liquid is reused after vacuum hydro-extraction.
Embodiment 12: take by weighing butanic acid 0.1mol respectively, the about 0.1mol of hexalin, ionic liquid N-(4-sulfonic group) butyl pyrrolidine ketone tosilate 0.04mol; Ionic liquid, hexalin, butanic acid are added in the round-bottomed flask that has agitator, thermometer, reflux condensing tube successively, magnetic agitation, and under 120 ℃, reacted 2 hours; Standing demix pipettes the upper strata esterification products, and transformation efficiency is 65.9%, selectivity 100%; Ionic liquid is reused after vacuum hydro-extraction.
Embodiment 13: take by weighing positive enanthic acid 0.1mol respectively, methyl alcohol 0.1mol, ionic liquid bromination N-(3-sulfonic group) propyl pyrrole alkane ketone 0.002mol; Ionic liquid, methyl alcohol, positive enanthic acid are added in the round-bottomed flask that has agitator, thermometer, reflux condensing tube successively, magnetic agitation, and under 70 ℃ of stream temperature, reacted 4 hours; Standing demix pipettes the upper strata esterification products, and transformation efficiency is 62.6%, selectivity 100%; Ionic liquid is reused after vacuum hydro-extraction.
Embodiment 14: take by weighing stearic acid (octadecanoic acid) 0.1mol respectively, ethanol 0.1mol, ionic liquid N-(4-sulfonic group) butyl pyrrolidine ketone nitrate 0.1mol; Ionic liquid, ethanol, stearic acid are added in the round-bottomed flask that has agitator, thermometer, reflux condensing tube successively, magnetic agitation, and under 90 ℃, reacted 8 hours; Standing demix pipettes the upper strata esterification products, and transformation efficiency is 51.5%, selectivity 100%; Ionic liquid is reused after vacuum hydro-extraction.
Embodiment 15: take by weighing vinylformic acid 0.1mol respectively, propyl carbinol 0.1mol, ionic liquid N-(3-sulfonic group) propyl pyrrole alkane ketone fluoroform sulphonate 0.05 mol; Ionic liquid, propyl carbinol, vinylformic acid are added in the round-bottomed flask that has agitator, thermometer, reflux condensing tube successively, magnetic agitation, and under 100 ℃, reacted 2 hours; Standing demix pipettes the upper strata esterification products, and transformation efficiency is 81.9%, selectivity 100%; Ionic liquid is reused after vacuum hydro-extraction.
Embodiment 16: take by weighing oleic acid (Octadec-9-enoic Acid) 0.1mol respectively, propyl carbinol 0.1mol, ionic liquid N-(3-sulfonic group) propyl pyrrole alkane ketone fluoroform sulphonate 0.05 mol; Ionic liquid, propyl carbinol, oleic acid are added in the round-bottomed flask that has agitator, thermometer, reflux condensing tube successively, magnetic agitation, and under 100 ℃, reacted 2 hours; Standing demix pipettes the upper strata esterification products, and transformation efficiency is 53.2%, selectivity 100%; Ionic liquid is reused after vacuum hydro-extraction.
Embodiment 17: take by weighing oxalic acid 0.1mol respectively, ethanol 0.1mol, ionic liquid N-(4-sulfonic group) butyl pyrrolidine ketone trifluoroacetate 0.1mol; Ionic liquid, ethanol, oxalic acid are added in the round-bottomed flask that has agitator, thermometer, reflux condensing tube successively, magnetic agitation, and under 80 ℃, reacted 4 hours; Standing demix pipettes the upper strata esterification products, and transformation efficiency is 78.5%, selectivity 100%; Ionic liquid is reused after vacuum hydro-extraction.
Embodiment 18: take by weighing Succinic Acid (succsinic acid) respectively (0.1mol), ethanol (0.1mol), ionic liquid N-(3-sulfonic group) propyl pyrrole alkane ketone hydrosulfate 0.1mol; Ionic liquid, ethanol, Succinic Acid are added in the round-bottomed flask that has agitator, thermometer, reflux condensing tube successively, magnetic agitation, and under 80 ℃, reacted 2 hours; Standing demix pipettes the upper strata esterification products, and transformation efficiency is 80.5%, selectivity 100%; Ionic liquid is reused after vacuum hydro-extraction.
Embodiment 19: take by weighing citric acid 0.04mol respectively, ethanol 0.12mol, ionic liquid N-(4-sulfonic group) butyl pyrrolidine ketone trifluoroacetate 0.02mol; Ionic liquid, ethanol, citric acid are added in the round-bottomed flask that has agitator, thermometer, reflux condensing tube successively, magnetic agitation, and under 80 ℃, reacted 2 hours; Standing demix pipettes the upper strata esterification products, and transformation efficiency is 78.5%, selectivity 100%; Ionic liquid is reused after vacuum hydro-extraction.
Embodiment 20: take by weighing lactic acid (alpha-hydroxypropionic acid) 0.1mol respectively, propyl carbinol 0.1mol, ionic liquid N-(3-sulfonic group) propyl pyrrole alkane ketone fluoroform sulphonate 0.05mol; Ionic liquid, propyl carbinol, lactic acid are added in the round-bottomed flask that has agitator, thermometer, reflux condensing tube successively, magnetic agitation, and under 100 ℃, reacted 2 hours; Standing demix pipettes the upper strata esterification products, and transformation efficiency is 70.2%, selectivity 100%; Ionic liquid is reused after vacuum hydro-extraction.
Embodiment 21: take by weighing phenylformic acid (M-nitro benzoic acid) 0.1mol respectively, ethanol 0.1mol, ionic liquid N-(4-sulfonic group) butyl pyrrolidine ketone trifluoroacetate 0.1mol; Ionic liquid, ethanol, phenylformic acid are added in the round-bottomed flask that has agitator, thermometer, reflux condensing tube successively, magnetic agitation, and under 80 ℃, reacted 4 hours; Standing demix pipettes the upper strata esterification products, and transformation efficiency is 76.3%, selectivity 100%; Ionic liquid is reused after vacuum hydro-extraction.
Embodiment 22: take by weighing salicylic acid 0.1mol respectively, propyl carbinol 0.1mol, ionic liquid N-(3-sulfonic group) propyl pyrrole alkane ketone hydrosulfate 0.05mol; Ionic liquid, propyl carbinol, salicylic acid are added in the round-bottomed flask that has agitator, thermometer, reflux condensing tube successively, magnetic agitation, and under 110 ℃, reacted 8 hours; Standing demix pipettes the upper strata esterification products, and transformation efficiency is 68.1%, selectivity 100%; Ionic liquid is reused after vacuum hydro-extraction.
Embodiment 23: take by weighing adjacent bromobenzene formic acid 0.1mol respectively, propyl carbinol 0.1mol, ionic liquid N-(3-sulfonic group) propyl pyrrole alkane ketone hydrosulfate 0.05mol; Ionic liquid, propyl carbinol, adjacent bromobenzene formic acid are added in the round-bottomed flask that has agitator, thermometer, reflux condensing tube successively, magnetic agitation, and under 110 ℃, reacted 8 hours; Standing demix pipettes the upper strata esterification products, and transformation efficiency is 56.8%, selectivity 100%; Ionic liquid is reused after vacuum hydro-extraction.
Claims (10)
1. the method for a catalyzing alochol acid esterization by sulfonic-acid-radical functionized ion liquid, it is characterized in that the alpha-pyrrolidone positively charged ion of sulfonic functional and ionic liquid that inorganic or organic anion constitutes are as alcoholic acid esterification catalyst for reaction, solvent, dewatering agent, 10～200% of the total mole number that above-mentioned ionic liquid add-on is pure and mild acid, 40～140 ℃ of temperature of reaction, normal pressure, 0.5～8 hour reaction times.
2. in the method for claim 1, it is characterized in that the alpha-pyrrolidone cationic structural general formula of described sulfonic functional is as follows:
N=1～6 wherein.
3. in the method for claim 1, it is characterized in that described inorganic or organic anion is chlorine, bromine, iodine, sulfate radical, bisulfate ion, nitrate radical, tosic acid root, trifluoromethanesulfonic acid root, trifluoroacetic acid radical ion.
4. in the method for claim 1, it is characterized in that above-mentioned reactant alcohol is C
1～C
12The saturated or unsaturated fatty alcohol of the monobasic of straight or branched, aromatic alcohol, polyvalent alcohol, C
3～C
12Alicyclic ring alcohol.
5. in the method as claimed in claim 4, it is characterized in that the general formula of above-mentioned aromatic alcohol is:
Wherein R is the alkyl of C1～C4.
6. in the method as claimed in claim 4, it is characterized in that above-mentioned polyvalent alcohol is ethylene glycol, glycerol, tetramethylolmethane.
7. in the method for claim 1, it is characterized in that above-mentioned reactant acid is the monocarboxylic acid of straight or branched, di-carboxylic acid, lactic acid, citric acid, phenylformic acid, salicylic acid, m-Salicylic acid, P-hydroxybenzoic acid, 0-chloro-benzoic acid, m-chlorobenzoic acid, Chlorodracylic acid, o-bromobenzoic acid, m-bromobenzoic acid, parabromobenzoic acid.
8. in the method as claimed in claim 7, the monocarboxylic general formula that it is characterized in that above-mentioned straight or branched is R ' COOH, and R is H atom, C
1～C
17Alkyl, C
2～C
17Thiazolinyl; The general formula of di-carboxylic acid is HOOC (CH
2)
nCOOH, n=0,1-6.
9. in the method for claim 1, it is characterized in that between alcohol in the above-mentioned reaction process, acid and the ionic liquid three addition sequence without limits.
10. in the method for claim 1, it is characterized in that stirring in the above-mentioned reaction process reflux certain hour down, reaction afterreaction liquid leaves standstill separatory, tells upper organic phase and gets esterified prod; Or reaction afterreaction liquid directly distill esterified prod.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101985423A (en) * | 2009-12-18 | 2011-03-16 | 镇江高鹏药业有限公司 | Method for catalytic synthesis of salicylate alkyl ester by using ionic liquid under microwave promotion |
| CN103467556A (en) * | 2013-09-04 | 2013-12-25 | 江南大学 | Preparation method of phytosterol cinnamate |
| WO2014063582A1 (en) * | 2012-10-23 | 2014-05-01 | Wu Feng | Ionic liquid catalyst and fatty acid preparation method |
| CN107954874A (en) * | 2016-10-14 | 2018-04-24 | 中国石油化工股份有限公司 | A kind of method for preparing benzoic ether |
| PL423578A1 (en) * | 2017-11-24 | 2019-06-03 | Grupa Azoty Zakl Azotowe Kedzierzyn Spolka Akcyjna | Method for obtaining dialkyl succinates |
| CN113788775A (en) * | 2021-09-03 | 2021-12-14 | 南昌大学 | Sulfonic acid functionalized pyrrolidone ionic liquid catalyst and preparation method and application thereof |
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| CN1880295A (en) * | 2005-06-17 | 2006-12-20 | 广东工业大学 | Method for catalyzing alcohol acid esterification using ion liquid |
| CN100404495C (en) * | 2005-09-30 | 2008-07-23 | 清华大学 | Tributyl citrate preparation method using ion liquid catalysis |
| CN1903824A (en) * | 2006-08-03 | 2007-01-31 | 青岛科技大学 | Clean esterification method for producing bialkyl ortho phthalate |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101985423A (en) * | 2009-12-18 | 2011-03-16 | 镇江高鹏药业有限公司 | Method for catalytic synthesis of salicylate alkyl ester by using ionic liquid under microwave promotion |
| WO2014063582A1 (en) * | 2012-10-23 | 2014-05-01 | Wu Feng | Ionic liquid catalyst and fatty acid preparation method |
| CN103467556A (en) * | 2013-09-04 | 2013-12-25 | 江南大学 | Preparation method of phytosterol cinnamate |
| CN103467556B (en) * | 2013-09-04 | 2015-08-12 | 江南大学 | A kind of preparation method of phytosterol cinnamate |
| CN107954874A (en) * | 2016-10-14 | 2018-04-24 | 中国石油化工股份有限公司 | A kind of method for preparing benzoic ether |
| PL423578A1 (en) * | 2017-11-24 | 2019-06-03 | Grupa Azoty Zakl Azotowe Kedzierzyn Spolka Akcyjna | Method for obtaining dialkyl succinates |
| CN113788775A (en) * | 2021-09-03 | 2021-12-14 | 南昌大学 | Sulfonic acid functionalized pyrrolidone ionic liquid catalyst and preparation method and application thereof |
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