Method for manufacturing 1,4-bis (4-phenoxybenzoyl)benzene in supersaturation conditions

Patent metadata

Field	Value
Publication number	US-10428002-B2
Application number	US-201815981439-A
Country	US
Kind code	B2
Filing date	May 16, 2018
Priority date	May 16, 2017
Publication date	Oct 1, 2019
Grant date	Oct 1, 2019

Abstract

A method for manufacturing 1,4-bis(4-phenoxybenzoylbenzene), including: providing a reactant mixture including terephthaloyl chloride, diphenyl ether and a Lewis acid in a solvent; reacting terephthaloyl chloride with diphenyl ether, so as to obtain a product mixture including a 1,4-bis(4-phenoxybenzoylbenzene)-Lewis acid complex; wherein the 1,4-bis(4-phenoxybenzoylbenzene)-Lewis acid complex is dissolved in the solvent at a 1,4-bis(4-phenoxybenzoylbenzene) weight concentration in the solvent which is higher than the saturation limit of the 1,4-bis(4-phenoxybenzoylbenzene)-Lewis acid complex during at least part of the step of reacting terephthaloyl chloride with diphenyl ether.

First claim

The invention claimed is:

1. A method for manufacturing 1,4-bis(4-phenoxybenzoyl)benzene, comprising:
providing a reactant mixture comprising terephthaloyl chloride, diphenyl ether and a Lewis acid in a solvent;
reacting the terephthaloyl chloride with the diphenyl ether, so as to obtain a product mixture comprising a 1,4-bis(4-phenoxybenzoyl)benzene-Lewis acid complex;

wherein the 1,4-bis(4-phenoxybenzoyl)benzene-Lewis acid complex is dissolved in the solvent at a 1,4-bis(4-phenoxybenzoyl)benzene weight concentration in the solvent which is higher than the saturation limit of the 1,4-bis(4-phenoxybenzoyl)benzene-Lewis acid complex during at least part of the step of reacting terephthaloyl chloride with diphenyl ether.

2. The method of claim 1 , wherein the 1,4-bis(4-phenoxybenzoyl)benzene-Lewis acid complex is dissolved in the solvent at a 1,4-bis(4-phenoxybenzoyl)benzene weight concentration which is higher by at least 5% than the saturation limit of the 1,4-bis(4-phenoxybenzoyl)benzene-Lewis acid complex, during part of the step of reacting terephthaloyl chloride with diphenyl ether.

3. The method of claim 1 , wherein the 1,4-bis(4-phenoxybenzoyl)benzene-Lewis acid complex is dissolved in the solvent at a 1,4-bis(4-phenoxybenzoyl)benzene weight concentration of more than 5 wt. % during part of the step of reacting terephthaloyl chloride with diphenyl ether.

4. The method of claim 1 , wherein the 1,4-bis(4-phenoxybenzoyl)benzene-Lewis acid complex is dissolved in the solvent during at least 75% of the duration of the step of reacting terephthaloyl chloride with diphenyl ether.

5. The method of claim 1 , wherein the 1,4-bis(4-phenoxybenzoyl)benzene-Lewis acid complex is dissolved in the solvent when an amount of 1,4-bis(4-phenoxybenzoyl)benzene of 75 mol. %, relative to the initial amount of terephthaloyl chloride, is present in the reactant mixture.

6. The method of claim 1 , wherein the step of reacting terephthaloyl chloride with diphenyl ether is performed in a reactor, and wherein:
the reactor comprises internal walls having a rugosity of less than 1 μm; and/or
the method comprises a preliminary step of washing the reactor; and/or
the method comprises a step of eliminating solid particles from the reactant mixture, before or after the step of reacting terephthaloyl chloride with diphenyl ether; and/or
the shear stress of the reactant mixture remains below 100 s −1 during at least part of the step of reacting terephthaloyl chloride with diphenyl ether.

7. The method of claim 1 , wherein the Lewis acid is aluminum trichloride.

8. The method of claim 1 , wherein the temperature of the reactant mixture is at least 5° C. during at least part of the step of reacting terephthaloyl chloride with diphenyl ether.

9. The method of claim 1 , wherein the Lewis acid is progressively added to a mixture of terephthaloyl chloride and diphenyl ether in the solvent, and the temperature of the reactant mixture is at least 30° C. after 30% by weight of Lewis acid has been added, relative to the total weight of Lewis acid.

10. The method of claim 1 , wherein the temperature of the reactant mixture increases during the step of reacting terephthaloyl chloride with diphenyl ether, from an initial temperature to a final temperature.

11. The method of claim 1 , wherein the solvent is ortho-dichlorobenzene.

12. The method of claim 1 , comprising the additional steps of:
mixing the product mixture with a protic solvent so as to provide a product slurry;
separating 1,4-bis(4-phenoxybenzoyl)benzene from the product slurry and optionally washing.

13. A method of making a polyether ketone ketone polymer, comprising:
manufacturing 1,4-bis(4-phenoxybenzoyl)benzene according to the method of claim 1 ;
reacting said 1,4-bis(4-phenoxybenzoyl)benzene with at least one difunctional aromatic acyl chloride.

Assignees

• Arkema France

Inventors

• Jouanneau Julien
• Le Guillaume
• Vincent Guillaume

Classifications

• C07C49/84

  containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups · CPC title

• C08G2261/45

  Friedel-Crafts-type · CPC title

• C08G65/4012

  Other compound (II) containing a ketone group, e.g. X-Ar-C(=O)-Ar-X for polyetherketones · CPC title

• C08G2650/62

  characterised by the nature of monomer used · CPC title

• C08G2261/3442

  Polyetherketones · CPC title