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Bifunctional ionic liquid, preparation method thereof and application of bifunctional ionic liquid in catalytic synthesis of bisphenol compounds

An ionic liquid, dual-function technology, applied in the field of ionic liquid applications, to achieve the effects of increasing productivity, simplifying the use process, and reducing production costs

Pending Publication Date: 2021-08-13
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The ionic liquid-mercapto compound composite catalytic system is used to catalyze the synthesis of bisphenol fluorene. The raw material 9-fluorenone can be completely reacted. The disadvantage is that the cocatalyst thioglycolic acid is used in the reaction.

Method used

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  • Bifunctional ionic liquid, preparation method thereof and application of bifunctional ionic liquid in catalytic synthesis of bisphenol compounds
  • Bifunctional ionic liquid, preparation method thereof and application of bifunctional ionic liquid in catalytic synthesis of bisphenol compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Accurately weigh 0.1mol (11.7g) of 1-methyl-2-mercaptoimidazole into a 250mL round bottom flask, then add 70mL of absolute ethanol to the flask, heat up to 60°C, and stir to completely dissolve the solid. Slowly add 0.1mol (12.2g) of 1,3-propane sultone dropwise. After the dropwise addition, continue to stir and reflux at 60°C for 8 hours. Washed three times respectively and dried in vacuum to obtain 21.2 g of 3-(sulfopropyl)-1-methyl-2-mercaptoimidazole with a yield of 89%.

[0050] Add 0.05 mol (11.8 g) of the above-prepared 3-(sulfopropyl)-1-methyl-2-mercaptoimidazole and 40 mL of deionized water into a 100 mL round bottom flask in turn, and stir to completely dissolve the zwitterions; Slowly add 0.05mol (8.6g) of p-toluenesulfonic acid dropwise. After the dropwise addition, the temperature is raised to 80° C. for 6 hours. The water was distilled off under reduced pressure, washed three times with ether, and dried in vacuo to obtain 3-(sulfopropyl)-1-methyl-2-mercap...

Embodiment 2

[0052] Accurately weigh 0.1mol (13.2g) of 2-methyl-5-mercapto-1,3,4-thiadiazole in a 250ml round bottom flask, add 125ml of ethyl acetate into the flask, heat up to 95°C, and stir to The solid dissolved completely. Slowly add 0.1mol (13.6g) of 1,4-butane sultone dropwise. After the dropwise addition, continue to stir and reflux at 90°C for 12 hours. The cake was washed three times and dried in vacuum to obtain 18.8 g of 3-(sulfobutyl)-5-methyl-2-mercapto-1,3,4-thiadiazole with a yield of 70%.

[0053] Add 0.05mol (13.4g) of 3-(sulfobutyl)-5-methyl-2-mercapto-1,3,4-thiadiazole prepared above and 40mL deionized water into a 100mL round bottom flask in sequence , stir to completely dissolve the zwitterions; slowly add 0.05mol (7.8g) of 3-mercaptopropanesulfonic acid dropwise, and after the dropwise addition, raise the temperature to 60°C for 12h. The water was distilled off under reduced pressure, washed three times with ether, and dried in vacuo to obtain a bifunctional ionic ...

Embodiment 3

[0055] Accurately weigh 0.1mol (15.0g) of 2,5-dimercapto-1,3,4-thiadiazole into a 250ml round bottom flask, add 120ml of ethyl acetate into the flask, heat up to 95°C, and stir to make the solid completely dissolve. Slowly add 0.2mol (24.4g) of 1,3-propane sultone dropwise. After the dropwise addition, continue to stir and reflux at 95°C for 12 hours. Washed three times respectively and dried in vacuum to obtain 3,4-di(sulfopropyl)-2,5-dimercapto-1,3,4-thiadiazole, 25.6g, yield 65%

[0056] Add 0.05mol (19.7g) of 3,4-bis(sulfopropyl)-2,5-dimercapto-1,3,4-thiadiazole prepared above and 40mL of deionized water into a 100mL round-bottomed In the flask, stir to completely dissolve the zwitterions; slowly add 0.1 mol (15.8 g) of benzenesulfonic acid dropwise, and after the dropwise addition, raise the temperature to 90° C. for 10 h. Distilled off water under reduced pressure, washed three times with ether, and dried in vacuo to obtain 3,4-di(sulfopropyl)-2,5-dimercapto-1,3,4-thia...

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Abstract

The invention discloses a bifunctional ionic liquid, a preparation method thereof and application of the bifunctional ionic liquid in catalytic synthesis of bisphenol compounds, and belongs to the field of application of ionic liquid catalysts. The bifunctional ionic liquid is composed of heterocyclic quaternary ammonium cations containing sulfonic groups and sulfydryl and organic strong acid anions containing or not containing sulfydryl. The bifunctional ionic liquid has the functions of strong protonic acid and a -SH-containing compound, is used for catalytic synthesis of diphenolic acid, bisphenol A, bisphenol fluorene and the like, and has the characteristics of high reaction rate, high target product yield and good selectivity. The bifunctional ionic liquid is a green catalyst which is stable in performance and can be recycled, and compared with a protonic acid and sulfhydryl compound composite catalyst used in a traditional production process, the production process is simplified, equipment corrosion is reduced, and the production cost is reduced.

Description

technical field [0001] The invention belongs to the application field of ionic liquids, and in particular relates to a bifunctional ionic liquid, a preparation method thereof and an application in catalytically synthesizing bisphenol compounds. Background technique [0002] Bisphenol compounds mainly include bisphenol acid, bisphenol A and bisphenol fluorene, which are formed through the condensation of carbonyl compounds and phenol. They are an important class of fine chemicals and polymer synthesis monomers. [0003] Bisphenol fluorene is obtained by the condensation reaction of 9-fluorenone and phenol. Because it has a Cardo ring structure, the polymer using bisphenol fluorene as a monomer has good rigidity and heat resistance. Bisphenol A is obtained by the reaction of acetone and phenol, and the reaction raw materials of acetone and phenol are joint products of industrial production, which are simple and easy to obtain. At present, bisphenol A is one of the chemicals w...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/84C07D285/125C07C303/32C07C309/30C07C319/12C07C323/66C07C309/29C07C309/06B01J31/02C07C51/367C07C59/52C07C37/20C07C39/16C07C39/17
CPCC07D233/84C07D285/125C07C303/32C07C309/30C07C319/12C07C323/66C07C309/29C07C309/06B01J31/0289B01J31/0291B01J31/0298C07C51/367C07C37/20B01J2231/4205C07C2601/08C07C2603/18C07C59/52C07C39/16C07C39/17
Inventor 于丽梅高占先魏佳伦鲁鑫鑫闫磊
Owner DALIAN UNIV OF TECH
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