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Synthesis method using ionic liquids

A technology for ionic liquids and uses, applied in the field of synthesis using ionic liquids, can solve the problems of toxicity of diphenyl sulfone, environmental problems and the like, and achieve the effect of improving purity

Inactive Publication Date: 2012-05-23
INVISTA TECHNOLOG IES S A R L
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Diphenylsulfone is also toxic and its use has environmental concerns
However, it was not previously thought possible to use them as solvents for polymer synthesis via nucleophilic aromatic substitution routes.

Method used

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  • Synthesis method using ionic liquids

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0096] Hydroquinone (1.691 g, 15.36 mmol), 4,4-difluorobenzophenone (3.347 g, 15.34 mmol), ground potassium carbonate (2.144 g, 15.51 mmol) were purged using a Schlenk line through a vacuum / nitrogen cycle and ionic liquid bis{(trifluoromethyl)sulfonyl}amine 1-butyl-3-methylimidazole (15 mL). The mixture was stirred under a nitrogen atmosphere and heated at 200°C for 1 hour, then at 250°C for an additional 1 hour and finally at 320°C for an additional 1 hour. The obtained brown slurry was cooled to room temperature and mixed with acetone (40 mL). The resulting suspension was stirred vigorously. The resulting product powder was collected by filtration, washed with water (3 x 20 mL) and then with an acetone / methanol mixture (1:1 by weight, 3 x 20 mL). The product was next dried under a stream of air and then under high vacuum at 140 °C for 12 h to give a brown solid (3.684 g, 83%). The product was characterized by differential scanning calorimetry (DSC) under nitrogen at a h...

Embodiment 2

[0098] As in Example 1, a mixture of hydroquinone (1.652 g, 15.00 mmol), 4,4-difluorobenzophenone (3.273 g, 15.00 mmol) and ground potassium carbonate (2.103 g, 15.22 mmol) was made In the ionic liquid bis{(trifluoromethyl)sulfonyl}amine 1-butyl-3-methylimidazole as solvent (15mL). The reaction was carried out at a temperature of 200°C for 2 hours, and then at 250°C for a further 2 hours. The resulting white reaction product slurry was then treated the same as in Example 1 to give a white solid (4.090 g, 95% yield). The product was characterized as in Example 1 (m.p. = 329°C, RV = 1.32).

Embodiment 3

[0100] As in Example 1, a mixture of hydroquinone (1.003 g, 10.02 mmol), 4,4-dichlorobenzophenone (2.517 g, 10.02 mmol) and ground potassium carbonate (1.399 g, 10.12 mmol) was made In the ionic liquid bis{(trifluoromethyl)sulfonyl}amine 1-butyl-3-methylimidazole as solvent (10mL). The resulting brown product slurry was then treated the same as in Example 1 to give a white solid (2.150 g, 74% yield). The product was characterized the same as in Example 1 (RV = 1.23).

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Abstract

The disclosures herein provide a process for conducting a nucleophilic aromatic substitution reaction in an ionic liquid and forming a polymeric material.

Description

field of invention [0001] The disclosure herein relates to the preparation of polymers using nucleophilic aromatic substitution reactions in ionic liquids. The present disclosure relates to the preparation of polymers belonging to the class of polyetherketones and polyethersulfones. More specifically the present disclosure relates to the use of ionic liquids as media for the synthesis of polyetherketone, also known as polyetheretherketone (PEEK), by solution or suspension polymerization. Background of the invention [0002] Polyetheretherketone (PEEK) is known at least from Ashford's Dictionary of Industrial Chemicals, 1994, Wavelength Productions Ltd, p. 733. Victrex PLC is a repeating structure with the following Manufacturer of polyether ether ketone polymers. [0003] [0004] Known industrial techniques for the preparation of PEEK from 4,4'-difluorobenzophenone employ, for example, high temperature synthesis up to 300°C in diphenylsulfone solvent. [0005] ...

Claims

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Application Information

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IPC IPC(8): C08G65/00
CPCC08G65/4012C08G75/23C08G65/4093B01J31/02C08G65/00C08J3/00
Inventor 基思·惠斯顿查理·理查德·兰格里克肯尼斯·理查德·塞登艾伯特·V·普加
Owner INVISTA TECHNOLOG IES S A R L
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