Catalysis of styrene oxide alcoholysis ring-opening reaction by phosphotungstic acid ionic liquid

A technology of styrene oxide and ionic liquid, which is applied in alcoholysis preparation, physical/chemical process catalyst, organic compound/hydride/coordination complex catalyst, etc., to achieve high catalyst activity, mild reaction conditions, and environmental friendliness Effect

Inactive Publication Date: 2013-10-02
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the ring-opening reaction temperature is 60-70°C, and the reaction time is 24-48h, so there is a certain energy consumption problem (Organic Chemistry, 2009, 29(5): 794-797)

Method used

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  • Catalysis of styrene oxide alcoholysis ring-opening reaction by phosphotungstic acid ionic liquid
  • Catalysis of styrene oxide alcoholysis ring-opening reaction by phosphotungstic acid ionic liquid
  • Catalysis of styrene oxide alcoholysis ring-opening reaction by phosphotungstic acid ionic liquid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] In a 10mL round bottom flask, add 0.05g (0.014mmol) [MIMPS] 3 PW 12 o 40 , 3 mL (48 mmol) ethanol. After stirring evenly at room temperature, 0.24 mL (2 mmol) of styrene oxide was added dropwise to start the reaction at room temperature. After reacting for a period of time, a certain amount of reaction solution was taken, and the progress of the ring-opening reaction of styrene oxide was monitored by gas chromatography. The results of the catalytic reactions are shown in Table 1.

Embodiment 2

[0024] In a 10mL round bottom flask, add 0.048g (0.014mmol) [PyPS] 3 PW 12 o 40 , 3 mL (48 mmol) ethanol. After stirring evenly at room temperature, 0.24 mL (2 mmol) of styrene oxide was added dropwise to start the reaction at room temperature. After reacting for a period of time, a certain amount of reaction solution was taken, and the progress of the ring-opening reaction of styrene oxide was monitored by gas chromatography. The results of the catalytic reactions are shown in Table 1.

Embodiment 3

[0026] In a 10mL round bottom flask, add 0.049g (0.014mmol) [TEAPS] 3 PW 12 o 40 , 3 mL (48 mmol) ethanol. After stirring evenly at room temperature, 0.24 mL (2 mmol) of styrene oxide was added dropwise to start the reaction at room temperature. After reacting for a period of time, a certain amount of reaction solution was taken, and the progress of the ring-opening reaction of styrene oxide was monitored by gas chromatography. The results of the catalytic reactions are shown in Table 1.

[0027] Table 1 Catalyst activity evaluation results

[0028]

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Abstract

The invention discloses a use of a phosphotungstic acid ionic liquid as a catalyst in catalysis of a styrene oxide alcoholysis ring-opening reaction. The catalyst is an ionic liquid containing phosphotungstic acid anions and alkyl sulfonic acid-modified 1-methylimidazole-pyridine-triethylamine salt structure cations. Styrene oxide and an alcohol compound as reaction raw materials undergo a ring-opening reaction in the presence of the catalyst. The phosphotungstic acid ionic liquid can be prepared conveniently, has high catalytic activity and a small use amount, cannot be dissolved in a reaction system and can be recycled. In the reaction, an emulsification phenomenon is produced so that dispersity of the catalyst in the reaction system is improved and the reaction can be promoted. In the catalysis of a styrene oxide alcoholysis ring-opening reaction by the phosphotungstic acid ionic liquid, reaction conditions are mild; environmental friendliness is obtained; and the phosphotungstic acid ionic liquid has an industrial application prospect.

Description

technical field [0001] The invention relates to the application of phosphotungstic acid ionic liquid as a catalyst in catalyzing the ring-cleaving reaction of styrene oxide by alcohol, and belongs to the field of chemical technology, especially the ring-cleaving reaction of styrene oxide by alcohol. Background technique [0002] Epoxy compounds refer to ethers containing three-membered rings and their derivatives, which are important and widely used intermediates in organic synthesis reactions. Its chemical properties are active, and many difficult-to-synthesize multifunctional compounds can be synthesized through ring opening, and it can also be used to provide protective groups and stereoscopically and regioselectively synthesize various organic compounds. [0003] β-alkoxy alcohols are compounds produced by the ring-opening reaction of epoxy compounds and alcohols, usually under acidic or alkaline conditions. Compared with base-catalyzed, acid-catalyzed ring-opening react...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C33/26C07C29/128B01J31/02
Inventor 陈静江春涛侯文华胡晨晖张荣李猛杨惠
Owner NANJING UNIV OF TECH
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