Dissociation of 1,4-bis (4-phenoxybenzoyl)benzene—Lewis acid complex in a protic solvent

Patent metadata

Field	Value
Publication number	US-10793500-B2
Application number	US-201816186039-A
Country	US
Kind code	B2
Filing date	Nov 9, 2018
Priority date	May 16, 2017
Publication date	Oct 6, 2020
Grant date	Oct 6, 2020

Abstract

A method for manufacturing 1,4-bis(4-phenoxybenzoyl)benzene, including: reacting terephthaloyl chloride with diphenyl ether in the presence of a Lewis acid, so as to obtain a product mixture including 1,4-bis(4-phenoxybenzoyl)benzene-Lewis acid complex, wherein the 1,4-bis(4-phenoxybenzoyl)benzene-Lewis acid complex is, at least partly, in the form of a precipitate; carrying out a solid/liquid separation of the product mixture to obtain a cake comprising the 1,4-bis(4-phenoxybenzoyl)benzene-Lewis acid complex precipitate; putting the cake in contact with a decomplexing solvent, wherein the decomplexing solvent is a protic solvent, so as to dissociate the 1,4-bis(4-phenoxybenzoyl)benzene-Lewis acid complex into 1,4-bis(4-phenoxybenzoyl)benzene; and, recovering the 1,4-bis(4-phenoxybenzoyl)benzene. Also, a method for manufacturing a polyaryletherketone polymer starting from 1,4-bis(4-phenoxybenzoyl)benzene manufactured by the above method.

First claim

The invention claimed is:

1. A method for manufacturing 1,4-bis(4-phenoxybenzoyl)benzene, comprising:
reacting terephthaloyl chloride with diphenyl ether in the presence of a Lewis acid, so as to obtain a product mixture comprising 1,4-bis(4-phenoxybenzoyl)benzene-Lewis acid complex, wherein the 1,4-bis(4-phenoxybenzoyl)benzene-Lewis acid complex is, at least partly, in the form of a precipitate;
carrying out a solid/liquid separation of the product mixture to obtain a cake comprising the 1,4-bis(4-phenoxybenzoyl)benzene-Lewis acid complex precipitate;
putting the cake in contact with a decomplexing solvent, wherein the decomplexing solvent is a protic solvent, so as to dissociate the 1,4-bis(4-phenoxybenzoyl)benzene-Lewis acid complex into 1,4-bis(4-phenoxybenzoyl)benzene; and,
recovering the 1,4-bis(4-phenoxybenzoyl)benzene.

2. The method of claim 1 , wherein reacting terephthaloyl chloride with diphenyl ether in the presence of a Lewis acid is carried out in a reaction solvent, wherein the reaction solvent is separate from the terephthaloyl chloride, the diphenyl ether, and the Lewis acid.

3. The method of claim 1 , wherein the 1,4-bis(4-phenoxybenzoyl)benzene-Lewis acid complex precipitate has a density between 1.34 and 2.40, measured by a pycnometer at 23° C.

4. The method of claim 1 , wherein the cake has a solid content of at least 40 wt. %.

5. The method of claim 1 , wherein the decomplexing solvent is chosen from the group consisting of: methanol, acetic acid, formic acid, ethanol, isopropanol, benzyl alcohol, aqueous solutions and mixtures thereof.

6. The method of claim 5 , wherein the decomplexing solvent is an aqueous solution.

7. The method of claim 1 , wherein the decomplexing solvent has a pH of no more than 6.

8. The method of claim 1 , wherein the decomplexing solvent has a pH of more than 9.

9. The method of claim 6 , wherein the aqueous solution is an aqueous solution of HCl.

10. The method of claim 1 , wherein the temperature when carrying out the solid/liquid separation of the product mixture does not exceed 79° C.

11. The method of claim 1 wherein the solid/liquid separation is carried out in one or more successive steps, each step being chosen from the group consisting of: centrifugal filtration, sedimentation, centrifugal decanting, filtration under vacuum, filtration under pressure and gravity filtration.

12. The method of claim 1 , wherein the Lewis acid is selected from the group consisting of: aluminum trichloride, aluminum tribromide, antimony pentachloride, antimony pentafluoride, indium trichloride, gallium trichloride, boron trichloride, boron trifluoride, zinc chloride, ferric chloride, stannic chloride, titanium tetrachloride, and molybdenum pentachloride.

13. The method of claim 1 , wherein before carrying out a solid/liquid separation of the product mixture, the product mixture is cooled down and/or submitted to shear stress and/or subject to the elimination by distillation of part of the reaction solvent, and/or subject to the addition of a compound in solid form acting as a seed in order to foster the 1,4-bis(4-phenoxybenzoyl)benzene-Lewis acid complex precipitation.

14. The method of claim 1 , wherein reacting terephthaloyl chloride with diphenyl ether in the presence of a Lewis acid is carried out, at least partly, at a temperature greater than 5° C.

15. 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 500 NTU.

16. The method of claim 2 , wherein the 1,4-bis(4-phenoxybenzoyl)benzene-Lewis acid complex is dissolved in the reaction 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.

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

Assignees

• Arkema France

Inventors

• Jouanneau Julien
• Le Guillaume
• Schon Steven
• Richardson John
• Vincent Guillaume
• Amstutz Jér{Hacek Over (O)}Me

Classifications

• C07C45/81

  by change in the physical state, e.g. crystallisation · CPC title

• C07C45/85

  by treatment giving rise to a chemical modification (by chemisorption C07C45/79) · CPC title

• C08G2261/45

  Friedel-Crafts-type · CPC title

• C08G2261/3442

  Polyetherketones · CPC title

• C08G61/127

  derived from carbon dioxide, carbonyl halide, carboxylic acids or their derivatives · CPC title