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A kind of method for catalyzing and synthesizing pseudo-ionone by alkaline immobilized ionic liquid

A pseudo-ionone, ionic liquid technology, applied in chemical instruments and methods, preparation of organic compounds, catalysts for physical/chemical processes, etc., can solve problems such as yield impact, product color difference, corrosion, etc., to avoid catalysts Loss, product purity, high product yield effect

Active Publication Date: 2022-07-15
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Use sodium hydroxide aqueous solution to make the problem that catalyzer exists to have: when using sodium hydroxide aqueous solution to catalyze the generation of side reaction, make the color and luster product phase of product relatively poor, productive rate is also subject to certain influence; The reaction equipment causes relatively serious corrosion, which requires regular anti-corrosion maintenance for the equipment, which increases the production cost; in the subsequent treatment process, washing and alkali removal requires a relatively large amount of water, and the treatment of sewage also increases the production cost
Considering the viscous property of the ionic liquid catalyst itself will cause catalyst loss in multiple cycle reactions, and the situation that the liquid phase catalyst is not suitable for continuous production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Example 1: Preparation of Immobilized Ionic Liquid A

[0017] In a 150 mL three-necked flask, 41.1 g (0.5 mol) of 1-methylimidazole and 53.5 g (0.5 mol) of vinyl bromide were added, respectively, and the reaction was stirred at 70 °C for 5 h. After the reaction was completed, it was cooled to room temperature to obtain a colorless sticky substance. thick liquid. After extraction with ether for 20 mL×3 times, and vacuum drying, 94.5 g of 1-vinyl-3-methylimidazolium bromide salt was obtained as a colorless viscous liquid.

[0018] Into a 250 mL three-necked flask were added 94.5 g (0.5 mol) of the 1-vinyl-3-methylimidazolium bromide ionic liquid prepared above, 22.0 g (0.55 mol) of NaOH powder, and 100 mL of dichloromethane. Stir for 24 h. After the reaction was completed, the NaBr solid and excess NaOH solid were removed by suction filtration. The filtrate was distilled under reduced pressure to remove dichloromethane to obtain the vinyl-containing ionic liquid interm...

Embodiment 2

[0020] Example 2: Preparation of Immobilized Ionic Liquid B

[0021] In a 250 mL three-necked flask, 55.6 g (0.5 mol) of N-vinylpyrrolidone, 22.0 g (0.55 mol) of NaOH powder, and 100 mL of dichloromethane were added, and the mixture was stirred at room temperature for 24 h. After the reaction was completed, the excess NaOH solid was removed by suction filtration. The filtrate was distilled under reduced pressure to remove dichloromethane to obtain the intermediate [Vnmp]OH ionic liquid, and the mass yield of the intermediate product was 99%.

[0022] Weigh 12.8 g (0.1 mol) of the intermediate prepared above, dissolve it with 100 mL of absolute ethanol, then weigh 91.2 g (0.3 mol) of styrene and 1.8 g (11 mmol) of initiator AIBN in 250 mL of The reaction was heated under reflux in a three-necked round-bottomed flask, and stirred magnetically for 24 hours. After the reaction was completed, it was cooled to room temperature to obtain a white solid. The white solid was filtered o...

Embodiment 3

[0023] Example 3: Preparation of Immobilized Ionic Liquid C

[0024] In a 150 mL three-necked flask, 50.6 g (0.5 mol) of triethylamine and 53.5 g (0.5 mol) of vinyl bromide were added, and the reaction was stirred at 70 °C for 5 h. After the reaction was completed, it was cooled to room temperature to obtain a colorless viscous liquid . After extraction with ether 20 mL×3 times, and vacuum drying, 104.1 g of N,N,N-triethylethylene bromide was obtained as a colorless viscous liquid.

[0025] Into a 250 mL three-necked flask were added 104.1 g (0.5 mol) of N,N,N-triethylethylene bromide prepared above, 22.0 g (0.55 mol) of NaOH powder, and 100 mL of dichloromethane, and stirred at room temperature for 24 h. After the reaction was completed, the NaBr solid and excess NaOH solid were removed by suction filtration. The filtrate was distilled under reduced pressure to remove dichloromethane to obtain the vinyl-containing ionic liquid intermediate [Vtea]OH, and the mass yield of t...

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PUM

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Abstract

The invention discloses a method for catalyzing and synthesizing pseudo-ionone by an alkaline immobilized ionic liquid. Slowly add acetone dropwise to react to obtain pseudo ionone; the carrier used in the alkaline immobilized ionic liquid is PS material, the PS material is polystyrene, and the alkaline immobilized ionic liquid is one of the following: . The alkaline solid-supported ionic liquid catalyst of the present invention is easy to be separated from the reaction solution, avoids the catalyst loss caused in multiple cycle reactions, and has the advantages of high product yield and clean product in the process of synthesizing pseudo-ionone. Etc.

Description

technical field [0001] The invention belongs to the field of organic synthesis fine chemicals, and particularly relates to a method for catalyzing and synthesizing pseudo ionone by an alkaline immobilized ionic liquid. Background technique [0002] The molecular formula of pseudoionone is C 13 H 20 O, the chemical name is 6,10-dimethyl-undecanotrien-2-one, which is a pale yellow transparent liquid. It is an important chemical intermediate, which can be used to synthesize fine chemicals such as ionone, vitamin A, vitamin E and β-carotene in chemical production. [0003] The preparation of pseudoionone is usually prepared by the aldol condensation reaction of citral and acetone obtained by distillation from some natural product essential oils (such as lemongrass oil and arborvitae oil) under the catalysis of catalyst. [0004] The aldol condensation reaction for the synthesis of pseudoionone needs to be carried out under the catalysis of basic catalyst. The currently widel...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/74C07C49/203B01J31/06
CPCC07C45/74B01J31/0295B01J31/0284B01J31/0279B01J31/06B01J2231/342C07C49/203
Inventor 郭红云金春晖张启源潘鹏施信
Owner ZHEJIANG UNIV OF TECH