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Novel Friedel-Crafts reaction method and catalyst thereof

A catalyst and reaction technology, applied in physical/chemical process catalysts, chemical instruments and methods, organic chemistry, etc., can solve the problems of industrial scale and impracticality of expensive reagents

Active Publication Date: 2020-02-11
FUJIAN YONGJING TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] All of the above reactions generate large amounts of waste and wastewater, require expensive reagents or are not practical on an industrial scale

Method used

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  • Novel Friedel-Crafts reaction method and catalyst thereof
  • Novel Friedel-Crafts reaction method and catalyst thereof
  • Novel Friedel-Crafts reaction method and catalyst thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 4

[0049] Example 4 and figure 1 , and Example 5 and figure 2 Specific examples relating to the use of Friedel-Crafts reactions, including alkylation and acylation, are shown in , each of which is incorporated by reference in its entirety and full scope into this specification section of the invention.

[0050] The chemical novelty and concept of the present invention is to propose a new Friedel-Crafts process using a halogenation catalyst, which can also be combined in an advantageous manner with a fluorination process, in particular without changing the Friedel-Crafts reaction and Catalyst for both fluorination reactions. For example, in preferred embodiments, antimony (Sb) halides, which are commonly used as halogenation catalysts, are used in the present invention, and should be used as Friedel-Crafts catalysts as described herein when the concentration of HF available to activate the catalyst is "low". In an alternative of the present invention, the participation of HF ma...

example 1

[0167] Example 1: 4,4'-Dichlorobenzophenone The synthesis flow, reaction scheme and conditions in a microreactor are as follows.

[0168] 4-Chlorobenzoyl chloride is premixed with HF+catalyst mixture, preferably in a hybrid system (e.g. split and recombination system) to form at least part of chlorobenzoyl fluoride and the corresponding SbHal6-complex, which enters the microreaction in the mixture Device 1 (the material of construction is SiC) previously encountered chlorobenzene.

[0169] The reaction is carried out as a Friedel-Crafts reaction.

[0170] Chemistry (in microreactor, Friedel-Crafts acylation:

[0171]

[0172] low concentration: low concentration

[0173] If a settler of sufficient size is used, the HF-catalyst mixture will separate from the organic matter, mainly 4,4'-dichlorobenzophenone. In the next step, the HF / catalyst mixture needs to be converted into a nucleophilic fluorinating agent by adding excess HF to Sb molar ratio (which should be greater t...

example 2

[0176] CCl according to the invention 4 The pathways and reaction schemes are as follows, and the reaction conditions are as given in Example 1.

[0177] in accordance with CCl 4 This example of a pathway, with CCl 4 The Friedel-Crafts reaction, as shown in the following scheme, uses fluorobenzene as a starting material, which can be obtained by fluorinating chlorobenzene prior to the Friedel-Crafts reaction:

[0178] Chemistry in (microreactor), Friedel-Crafts acylation:

[0179]

[0180] low concentration: low concentration

[0181] The resulting product can be hydrolyzed to form 4,4'-difluorobenzophenone compounds.

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Abstract

The present invention relates to a novel method for preparing or synthesizing an acylated or alkylated aryl compound, such as acylated or alkylated benzene, through a reaction called Friedel-Crafts, and a novel catalyst for the method. The present invention particularly relates to a novel environment-friendly method for synthesizing the Friedel-Crafts reaction of the acylated or alkylated compound.

Description

technical field [0001] The invention relates to the field of Friedel-Craft reaction, in particular to a novel Friedel-Crafts reaction method and a catalyst thereof. Background technique [0002] For example, the Friedel-Crafts reaction is used in the industrial manufacture of PAEK (polyaryletherketone), especially PEEK (polyetheretherketone). [0003] For example, PEEK is made from the condensation of hydroquinone with 4,4'-difluorobenzophenone, which is made from fluorobenzene as a key raw material, as described in Victrex WO2018 / 055384, and also in Patent in CN107573500 invention patent application (2018). 4,4'-Difluorobenzophenone was prepared from 4,4'-difluorodiphenylmethane by oxidation (ChemCatChem (2018), 10(5), 1096-1106), or alternatively from fluorobenzene with CCl 4 Friedel-Crafts alkylation reaction ("Progress in Chemical Industry" (2015), 34(4), 1104-1108) or Friedel-Crafts acylation of fluorobenzene and 4-fluorobenzoyl chloride (as described in US4814508 of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/68C07C49/813C07C17/263C07C22/08C07C25/18B01J27/12
CPCC07C45/68C07C17/263B01J27/12C07C49/813C07C22/08C07C25/18C07C45/46C07C17/269C07C201/12C07C49/80C07C205/11B01J27/08C07C205/12
Inventor 崔桅龙杜宏军吴文挺
Owner FUJIAN YONGJING TECH CO LTD