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

Patent metadata

Field	Value
Publication number	US-11434188-B2
Application number	US-201917291679-A
Country	US
Kind code	B2
Filing date	Nov 7, 2019
Priority date	Nov 9, 2018
Publication date	Sep 6, 2022
Grant date	Sep 6, 2022

Abstract

A method for manufacturing 1,4-bis(4-phenoxybenzoyl)benzene, including: providing a solvent, a Lewis acid, a first reactant and a second reactant, wherein the first reactant and the second reactant are respectively terephthaloyl chloride and diphenyl ether, or reversely; mixing the first reactant in the solvent to make a starting mixture; and, adding the second reactant to the starting mixture; wherein the Lewis acid is mixed, at least partly, to the starting mixture before adding the second reactant to the starting mixture, and/or wherein the Lewis acid is mixed, at least partly, with the second reactant and added together to the starting mixture, and wherein the temperature of the starting mixture is greater than 5° C. during at least part of the step of adding the second reactant to the starting mixture; so as to obtain 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 a solvent, a Lewis acid, a first reactant and a second reactant, wherein the first reactant and the second reactant are respectively terephthaloyl chloride and diphenyl ether, or reversely; and wherein the solvent is a separate solvent from the first reactant, the second reactant and the Lewis acid;
mixing the first reactant in the solvent to make a starting mixture; and,
adding the second reactant to the starting mixture;
wherein the Lewis acid is mixed, at least partly, to the starting mixture before adding the second reactant to the starting mixture, and/or
wherein the Lewis acid is mixed, at least partly, with the second reactant and added together to the starting mixture, and
wherein the temperature of the starting mixture is greater than 5° C. during at least part of the step of adding the second reactant to the starting mixture;
so as to obtain a product mixture comprising a 1,4-bis(4-phenoxybenzoyl)benzene-Lewis acid complex,
wherein the Lewis acid is chosen among the list 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.

2. The method of claim 1 , wherein the Lewis acid is chosen among the list consisting of: aluminum trichloride, boron trichloride, aluminum tribromide, titanium tetrachloride, antimony pentachloride, ferric chloride, gallium trichloride, and molybdenum pentachloride.

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

4. The method of claim 1 , wherein the temperature of the starting mixture is at least 15° C. during at least part of the step of adding the second reactant to the starting mixture.

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

6. The method of claim 1 , wherein the temperature of the starting mixture increases during the step of adding the second reactant to the starting mixture, from an initial temperature to a final temperature.

7. The method of claim 6 , wherein the initial temperature of the starting mixture is from 0° C. to 120° C.

8. The method of claim 6 , wherein the final temperature of the starting mixture is at least 30° C.

9. The method of claim 1 , wherein the temperature of the starting mixture does not exceed 180° C. during the step of adding the second reactant.

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

11. The method of claim 1 , wherein the second reactant is terephthaloyl chloride and, wherein the Lewis acid is mixed with terephthaloyl chloride and added together to the starting mixture.

12. The method of claim 1 , wherein the first reactant is terephthaloyl chloride and, wherein the Lewis acid is mixed with the starting mixture before adding the diphenyl ether to the starting mixture.

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

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

15. 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.

16. A method of making a polyaryletherketone 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
• Herblot Martin

Classifications

• C07C2527/125

  Compounds comprising a halogen and scandium, yttrium, aluminium, gallium, indium or thallium · CPC title

• B01J27/125

  with scandium, yttrium, aluminium, gallium, indium or thallium · CPC title

• C07C45/46 Primary

  Friedel-Crafts reactions · 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

• C08G65/4012

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