Method for manufacturing 1,4-bis (4-phenoxybenzoyl)benzene using substantially non-hydrolyzed terephthaloyl chloride

Patent metadata

Field	Value
Publication number	US-10807933-B2
Application number	US-201816613587-A
Country	US
Kind code	B2
Filing date	May 16, 2018
Priority date	May 16, 2017
Publication date	Oct 20, 2020
Grant date	Oct 20, 2020

Abstract

A method for manufacturing 1,4-bis(4-phenoxybenzoyl)benzene, including: providing terephthaloyl chloride, diphenyl ether, a solvent and a Lewis acid, wherein the terephthaloyl chloride is of a purity grade such that, 10 minutes after introducing it at a reference concentration of 6.5 wt. % into said solvent, at a temperature of 20° C., a solution is obtained having a turbidity of less than 500 NTU; mixing the terephthaloyl chloride, the diphenyl ether and the solvent so as to make a reactant mixture; adding the Lewis acid to the reactant mixture so as to effect the reaction of the terephthaloyl chloride with the diphenyl ether; recovering a product mixture comprising a 1,4-bis(4-phenoxybenzoyl)benzene-Lewis acid complex.

First claim

The invention claimed is:

1. A method for manufacturing 1,4-bis(4-phenoxybenzoyl)benzene, comprising:
providing terephthaloyl chloride, diphenyl ether, a solvent and a Lewis acid, wherein the terephthaloyl chloride is of a purity grade such that, 10 minutes after introducing it at a reference concentration of 6.5 wt. % into said solvent, at a temperature of 20° C., a solution is obtained having a turbidity of less than 500 NTU;
reacting terephthaloyl chloride with diphenyl ether in the solvent and in the presence of the Lewis acid; and
recovering a product mixture comprising a 1,4-bis(4-phenoxybenzoyl)benzene-Lewis acid complex.

2. The method of claim 1 , wherein the terephthaloyl chloride is of a purity grade such that:
10 minutes after introducing it at a reference concentration of 6.5 wt. % into said solvent, at a temperature of 20° C., a solution is obtained having a turbidity of less than 200 NTU.

3. The method of claim 1 , reacting terephthaloyl chloride with diphenyl ether in the solvent and in the presence of the Lewis acid comprises:
mixing the terephthaloyl chloride, the diphenyl ether and the solvent so as to make a reactant mixture; and
adding the Lewis acid to the reactant mixture so as to effect the reaction of the terephthaloyl chloride with the diphenyl ether.

4. The method of claim 3 , wherein the terephthaloyl chloride is kept in a sealed container without contact with ambient air prior to making the reactant mixture.

5. The method of claim 1 , wherein the diphenyl ether and solvent, in combination, contain less than 500 ppm by weight of water.

6. The method of claim 1 , wherein the diphenyl ether and solvent, in combination, contain from 1 to 250 ppm by weight of water.

7. The method of claim 3 , comprising a step of drying the solvent or of drying the solvent combined with the diphenyl ether prior to adding the terephthaloyl chloride to the solvent.

8. 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 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 reaction of the terephthaloyl chloride with the diphenyl ether.

9. 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 reaction of the terephthaloyl chloride with the diphenyl ether.

10. 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 reaction of the terephthaloyl chloride with the diphenyl ether.

11. 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 reaction of the terephthaloyl chloride with the diphenyl ether.

12. The method of claim 3 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.

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

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

15. 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.

16. 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

• Le Guillaume
• Jouanneau Julien

Classifications

• C08G2650/40

  containing ketone groups, e.g. polyarylethylketones, PEEK or PEK · CPC title

• C08G65/4012

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

• 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

• C07C45/80

  by liquid-liquid treatment · CPC title

• C07C45/46 Primary

  Friedel-Crafts reactions · CPC title