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Method for preparing maleate by catalyzing maleic anhydride with ionic liquid

A technology of maleic anhydride and ionic liquid, which is applied in the field of ionic liquid catalyzing maleic anhydride to prepare maleic acid ester, can solve the problems of difficult complete regeneration, equipment corrosion, and many side reactions, and achieves the effect of solving equipment corrosion.

Active Publication Date: 2020-02-11
INST OF PROCESS ENG CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In the traditional production method of maleic acid ester, sulfuric acid is mainly used as catalyst. Although sulfuric acid has high catalytic activity and low price, there are many side reactions, the product is easily isomerized into fumaric acid ester, serious equipment corrosion, and complicated follow-up treatment, etc. Disadvantages: Patents CN106631784A and CN206204188U use strong acidic ion exchange resins as solid catalysts. Although such catalysts are less corrosive to equipment, the regeneration process of ion exchange resins is cumbersome, prone to secondary pollution, and difficult to completely regenerate. Low usability

Method used

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  • Method for preparing maleate by catalyzing maleic anhydride with ionic liquid
  • Method for preparing maleate by catalyzing maleic anhydride with ionic liquid
  • Method for preparing maleate by catalyzing maleic anhydride with ionic liquid

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Preparation of Dimethyl Maleate by the Reaction of Maleic Anhydride and Methanol Catalyzed by 1-Propylsulfonic Acid-3-Methylimidazolium Bisulfate Ionic Liquid

[0027] Preparation of 1-propylsulfonic acid-3-methylimidazolium bisulfate ionic liquid:

[0028] Add 4.106g (0.05moL) of methylimidazole and ethanol (50mL) into a 150mL three-necked flask, preheat it in an oil bath at 70°C, and add 1,3-propylsulfonic acid dropwise under magnetic stirring Add 6.107 g (0.05 mol) of the ester into the flask. After the dropwise addition, continue stirring for 8 h to obtain the intermediate product, 1-propylsulfonic acid-3-methylimidazole with cationic sulfonic acid function. After the reaction, the intermediate product was washed with ether for 3 to 5 times to remove unreacted raw materials, and then put into a vacuum drying oven and dried at 80° C. for 12 hours.

[0029] Add the intermediate product into a 150mL round-bottomed flask, dissolve it with an appropriate amount of deion...

Embodiment 2

[0032] Preparation of Dimethyl Maleate by Reaction of Maleic Anhydride and Methanol Catalyzed by N-Butyl Sulfonate Pyridinium Bisulfate Ionic Liquid

[0033] Preparation of N-butylsulfonic acid pyridinium bisulfate ionic liquid:

[0034] Add 3.933g (0.05mol) of pyridine and ethanol (50mL) into a 150mL three-necked flask, preheat it in an oil bath at 70°C, and add 6.8085g (0.05mol) of butyl sultone dropwise under magnetic stirring. ) into the flask, after the dropwise addition, continue to stir for 8h to obtain the intermediate product, namely the N-butylpyridinesulfonic acid function of the cationic sulfonic acid. After the reaction, the intermediate product was washed with ether for 3 to 5 times to remove unreacted raw materials, and then put into a vacuum drying oven and dried at 80° C. for 12 hours.

[0035] Add the intermediate product into a 150mL round-bottomed flask, dissolve it with an appropriate amount of deionized water, preheat it at 70°C, then add an equimolar am...

Embodiment 3

[0038] Preparation of Diethyl Maleate by Reaction of Maleic Anhydride and Ethanol Catalyzed by 1-Propylsulfonic Acid-3-Methylimidazolium Bisulfate Ionic Liquid

[0039] Preparation of 1-propylsulfonic acid-3-methylimidazolium bisulfate ionic liquid: the process is the same as in Example 1.

[0040] Esterification of maleic anhydride: Weigh maleic anhydride 0.9806g (0.01mol), ethanol 2.7642g (0.06mol), 1-propylsulfonic acid-3-methylimidazolium bisulfate ionic liquid 0.0605g (0.2mmol) ) in a glass microwave tube, set the reaction temperature to 120° C., reacted for 1 hour, the conversion rate of maleic anhydride reached 97.87%, and the yield of diethyl maleate reached 88.39%.

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Abstract

The invention discloses a method for preparing maleate by catalyzing maleic anhydride with ionic liquid. The preparation method is characterized by comprising the following steps: mixing ionic liquidwith maleic anhydride and fatty alcohol, carrying out heating to 80-140 DEG C, and performing a reaction for 0.5-4 h to obtain maleate, wherein the usage amount of the ionic liquid accounts for 0.1-10% by mol of the maleic anhydride, and a molar ratio of fatty alcohol to maleic anhydride is 2-12. A high-added-value chemical with the completely-esterified maleate as a main product is prepared in the invention. The method is simple in process, mild in conditions, friendly to environment and high in double esterification degree; and the ionic liquid is high in activity, not prone to inactivationand capable of being cyclically used.

Description

technical field [0001] The invention relates to the technical field of chemical product preparation, in particular to a method for preparing maleic acid esters from maleic anhydride catalyzed by ionic liquids. Background technique [0002] Maleic anhydride is a commonly used important basic organic chemical raw material. It is the third largest acid anhydride raw material after acetic anhydride and phthalic anhydride in the world. Maleic anhydride has a wide range of sources, and can be prepared by synthetic methods based on fossil raw materials such as benzene oxidation, butene oxidation, butane oxidation, and phthalic anhydride by-products, or by fermentation of biomass raw materials (such as: cellulose), obtained by catalytic conversion. With maleic anhydride as a platform compound, it can be used to produce a variety of high value-added chemical products such as 1,4-butanediol, tetrahydrofuran, γ-butyrolactone, and maleate. Therefore, the conversion research of maleic...

Claims

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Application Information

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IPC IPC(8): C07C67/08C07C69/60C07D233/60C07D213/20B01J31/02
CPCB01J31/0285B01J2231/49C07C67/08C07D213/20C07D233/60C07C69/60
Inventor 刘瑞霞刘玉梅张瑞锐陈圣新张婷张锁江
Owner INST OF PROCESS ENG CHINESE ACAD OF SCI
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