Dissociation of a 1,4-bis (4-phenoxybenzoyl)benzene-lewis acid complex in an aqueous solution

Patent metadata

Field	Value
Publication number	US-11358924-B2
Application number	US-201815982625-A
Country	US
Kind code	B2
Filing date	May 17, 2018
Priority date	May 18, 2017
Publication date	Jun 14, 2022
Grant date	Jun 14, 2022

Abstract

A method for manufacturing 1,4-bis(4-phenoxybenzoyl)benzene, including: reacting terephthaloyl chloride with diphenyl ether in a reaction solvent and in the presence of a Lewis acid, so as to obtain a product mixture including a 1,4-bis(4-phenoxybenzoyl)benzene-Lewis acid complex; contacting the product mixture with an aqueous solution, so as to obtain an aqueous phase containing the Lewis acid and an organic phase containing 1,4-bis(4-phenoxybenzoyl)benzene; heating at least the second phase up to a maximum temperature, followed by cooling the second phase down to a separation temperature; subjecting at least the second phase to a solid/liquid separation step at the separation temperature, so as to recover solid 1,4-bis(4-phenoxybenzoyl)benzene.

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 a reaction solvent and in the presence of a Lewis acid, so as to obtain a product mixture comprising a 1,4-bis(4-phenoxybenzoylbenzene)-Lewis acid complex, wherein the reaction solvent is ortho-dichlorobenzene and wherein the Lewis acid is aluminum trichloride; and
contacting the product mixture with an aqueous solution, so as to obtain an aqueous phase containing the Lewis acid and an organic phase containing 1,4-bis(4-phenoxybenzoyl)benzene,
wherein the concentration of Lewis acid in the product mixture is from 10 to 25%, and wherein the aqueous phase contains at least 90% of the Lewis acid from the product mixture, and wherein the relative weight ratio of product mixture and aqueous solution put in contact is from 3 to 0.5.

2. The method of claim 1 , wherein the aqueous solution has a pH of not more than 5.

3. The method of claim 1 , wherein the product mixture is poured into a vessel containing the aqueous solution.

4. The method of claim 1 , further comprising:
separating the aqueous phase from the organic phase; and/or
heating the organic phase up to a maximum temperature, followed by cooling the organic phase down to a separation temperature.

5. The method of claim 4 , wherein from 30 to 99.9 wt. % of the 1,4-bis(4-phenoxybenzoyl)benzene contained in the organic phase is dissolved in the organic phase at the maximum temperature.

6. The method of claim 4 , wherein the maximum temperature is from 90 to 150° C.

7. The method of claim 4 , wherein the separation temperature is at least 20° C.

8. The method of claim 4 , wherein the organic phase is cooled down at a rate of from 10 to 50° C./h.

9. The method of claim 1 , wherein at least the organic phase is subjected to a solid/liquid separation step so as to recover solid 1,4-bis(4-phenoxybenzoyl)benzene.

10. The method of claim 9 , wherein the solid/liquid separation step is performed at a temperature of at least 20° C.

11. The method of claim 9 , comprising one or more steps of washing the recovered solid 1,4-bis(4-phenoxybenzoyl)benzene in a protic solvent and subjecting it to a further solid/liquid separation.

12. The method of claim 11 , wherein at least one of the steps of washing the solid 1,4-bis(4-phenoxybenzoyl)benzene in a protic solvent is performed at a temperature of at least 20° C.

13. The method of claim 1 , wherein the organic phase comprises at least 50% of the 1,4-bis(4-phenoxybenzoyl)benzene in the product mixture.

14. A method of making a polyether 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.

Assignees

• Arkema France

Inventors

• Le Guillaume
• Jouanneau Julien

Classifications

• C08G2261/45

  Friedel-Crafts-type · CPC title

• C08G65/4093

  characterised by the process or apparatus used · 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

• C07C45/85

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

• C08G2261/3442

  Polyetherketones · CPC title