IP Library Granted Patent US 10,618,863
Granted Patent B2
US 10,618,863 · App. 15/981,284 · Granted Apr 14, 2020

Method for manufacturing 1,4-bis (4-phenoxybenzoylbenzene) at an elevated temperature

Inventors: Julien Jouanneau (Corneville sur Risle, FR); Guillaume Le (Herouville Saint Clair, FR); Jérome Amstutz (Charly, FR)
Assignee: ARKEMA FRANCE
C07C45/46C07C45/80C08G61/127C08G65/4012C08G65/4093C08G2261/3442C08G2261/45C08G2650/62
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Quick Facts
Patent No.
US 10,618,863
App. No.
15/981,284
Granted
Apr 14, 2020
Kind
B2
Abstract

A method for manufacturing 1,4-bis 4-phenoxybenzoyl) benzene, including: providing a reactant mixture including terephthaloyl chloride and diphenyl ether in a solvent; adding a Lewis acid to the reactant mixture, so as to obtain a product mixture; wherein the temperature of the reactant mixture is greater than 5° C. during at least part of the step of adding the Lewis acid to the reactant mixture.

Claims (27)

1. A method for manufacturing 1,4-bis(4-phenoxybenzoyl)benzene, comprising:

providing a reactant mixture comprising terephthaloyl chloride and diphenyl ether in a solvent; and

adding a Lewis acid to the reactant mixture, so as to obtain a product mixture;

wherein the temperature of the reactant mixture is greater than 5° C. during at least part of the step of adding the Lewis acid to the reactant mixture.

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

3. The method of claim 1 , wherein the temperature of the reactant mixture is at least 15° C. during at least part of the step of adding the Lewis acid to the reactant mixture.

4. The method of claim 1 , wherein the temperature of the reactant mixture is at least 30° C. after 20% by weight of Lewis acid that has been added to the reactant mixture, relative to the total weight of Lewis acid added to the reactant mixture.

5. The method of claim 1 wherein the temperature of the reactant mixture increases during the step of adding the Lewis acid to the reactant mixture, from an initial temperature to a final temperature.

6. The method of claim 5 , wherein the initial temperature is from 0 to 80° C.

7. The method of claim 5 , wherein the final temperature is at least 30° C.

8. The method of claim 1 , wherein the temperature of the reactant mixture does not exceed 100° C. during the step of adding the Lewis acid.

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

10. The method of claim 1 , wherein a temperature difference between a final temperature and an initial temperature is from 1 to 120° C.

11. The method of claim 1 , wherein the solvent is a separate solvent from the diphenyl ether.

12. The method of claim 1 , wherein the concentration of terephthaloyl chloride relative to a sum of the solvent, the terephthaloyl chloride, the diphenyl ether and the Lewis acid is from 2 to 25%.

13. The method of claim 1 , wherein the concentration of diphenyl ether relative to a sum of the solvent, the terephthaloyl chloride, the diphenyl ether and the Lewis acid is from 2 to 42%.

14. The method of claim 1 , wherein the weight ratio of terephthaloyl chloride to diphenyl ether introduced into the reactor is from 0.05 to 0.6.

15. The method of claim 1 , further comprising steps of:

mixing the product mixture with a protic solvent so as to provide a product slurry; and

separating 1,4-bis(4-phenoxybenzoyl)benzene from the product slurry and optionally washing.

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 ; and

reacting said 1,4-bis(4-phenoxybenzoyl)benzene with at least one difunctional aromatic acyl chloride.

17. A method for manufacturing 1,4-bis(4-phenoxybenzoyl)benzene, comprising:

providing terephthaloyl chloride, diphenyl ether, a solvent and a Lewis acid;

reacting the terephthaloyl chloride with the diphenyl ether in the solvent, and in the presence of the Lewis acid, so as to obtain a product mixture, wherein the temperature of the reacting mixture is greater than 5° C. during at least part of the duration of the reaction; and

recovering the product mixture comprising a 1,4-bis(4-phenoxybenzoyl)benzene-Lewis acid complex.

Assignments (3)
CHANGE OF ADDRESS Recorded Jul 4, 2025
From: ARKEMA FRANCE
To: ARKEMA FRANCE
Reel/Frame 071814/0739 →
CORRECTIVE ASSIGNMENT TO CORRECT THE FIRST NAME OF THE THIRD-LISTED INVENTOR PREVIOUSLY RECORDED ON REEL 045821 FRAME 0389. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Mar 5, 2020
From: JOUANNEAU, JULIEN M.; LE, GUILLAUME M.; AMSTUTZ, JÉROME M.
To: ARKEMA FRANCE
Reel/Frame 052094/0872 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 16, 2018
From: JOUANNEAU, JULIEN M.; LE, GUILLAUME M.; AMSTUTZ, JAN M.
To: ARKEMA FRANCE
Reel/Frame 045821/0389 →
Priority Claims (1)
EP 17305559 · May 16, 2017 · regional
Continuity (1)
Related Publication 20180334418A1 · Nov 22, 2018