Method for the recovery of compounds deriving from the synthesis of poly aryl ether ketone polymers

Patent metadata

Field	Value
Publication number	US-10731001-B2
Application number	US-201816185485-A
Country	US
Kind code	B2
Filing date	Nov 9, 2018
Priority date	Nov 9, 2018
Publication date	Aug 4, 2020
Grant date	Aug 4, 2020

Abstract

A method for treating a shear-thinning residue composition deriving from the synthesis of an aryl ether ketone, the residue composition including a liquid fraction and solid residues, the method including the steps of: passing said shear-thinning residue composition through a shear-generating evaporating device, between a rotating part and a stationary part; and recovering a condensed liquid fraction and separately recover concentrated solid residues.

First claim

The invention claimed is:

1. A method for treating a shear-thinning residue composition deriving from the synthesis of a aryl ether ketone, said residue composition comprising a liquid fraction and solid residues, the method comprising the steps of:
(i) passing said shear-thinning residue composition through a shear-generating evaporating device, between a rotating part and a stationary part; and
(ii) recovering a condensed liquid fraction and separately recovering concentrated solid residues.

2. The method according to claim 1 , wherein a shear rate is applied to the shear-thinning residue composition by the shear-generating evaporating device, the shear rate being equal to or greater than 10 s −1 .

3. The method according to claim 1 , wherein the shear-thinning residue composition has a zero shear viscosity at 25° C. from 1 to 10000 Pa·s.

4. The method according to claim 1 , wherein the minimum distance between the rotating part and the stationary part of the shear-generating evaporating device is from 0.03 to 5 mm.

5. The method according to claim 1 , wherein the aryl ether ketone is chosen from 1,4-bis(4-phenoxybenzoyl)benzene and/or a poly ether ketone ketone polymer.

6. The method according to claim 1 , wherein the liquid fraction of the shear-thinning residue composition comprises at least one residual solvent and/or at least one residual reactant.

7. The method according to claim 6 , wherein the liquid fraction of the shear-thinning residue composition comprises at least one residual solvent, wherein the residual solvent is chosen from carbon disulfide, ortho-dichlorobenzene, meta-dichlorobenzene, para-dichlorobenzene, 1,2,4-trichlorobenzene, 1,2,3-trichlorobenzene, ortho-difluorobenzene, 1,1-dichloroethane, 1,2-dichloroethane, 1,1,2,2-tetrachloroethane, tetrachloroethylene, dichloromethane, nitrobenzene and mixtures thereof.

8. The method according to claim 6 , wherein the liquid fraction of the shear-thinning residue composition comprises at least one residual reactant, wherein the residual reactant is diphenyl ether.

9. The method according to claim 1 , wherein the solid residues comprise aryl ether ketone particles such as 1,4-bis(4-phenoxybenzoyl)benzene and/or a poly ether ketone ketone polymer, and/or reaction by-products resulting from an incomplete conversion to the reaction products and/or by-products resulting from a side reaction.

10. The method according to claim 1 , wherein the shear-generating evaporating device is chosen from a horizontal thin-film evaporator, a vertical thin-film evaporator, a horizontal wiped-film evaporator, a vertical wiped-film evaporator, a scraped-surface heat exchanger, a single-screw devolatilizing extruder, and a twin-screw devolatilizing extruder.

11. The method according to claim 1 , wherein the method is carried out as a batch process, or a semi-batch process, or a continuous process.

12. The method according to claim 1 , wherein the shear-thinning residue composition has a solids concentration before step (i) from 5 to 25 wt. %.

13. The method according to claim 1 , wherein during step (i) the shear-thinning residue composition is brought to a temperature equal to or greater than 160° C.

14. The method according to claim 1 , further comprising a subsequent step of:
(iii) using the concentrated solid residues as a fuel source.

15. The method according to claim 1 , wherein the condensed liquid fraction recovered in step (ii) is recycled in the synthesis of the aryl ether ketone.

16. The method according to claim 15 , wherein the condensed liquid fraction recovered in step (ii) comprises at least one residual solvent and at least one residual reactant which are separated prior to recycling and are recycled separately.

17. The method according to claim 1 , wherein from 65 to 99 wt. % of the liquid fraction of the shear-thinning residue composition is recovered in the recovered condensed liquid fraction.

18. The method according to claim 1 , comprising a preliminary step of providing the shear-thinning residue composition, said preliminary step comprising recovering a mother liquor from the synthesis of an aryl ether ketone, distilling said mother liquor, and recovering the shear-thinning residue composition as a distillation residue.

19. A method for manufacturing an aryl ether ketone, comprising:
reacting a reactant A with a reactant B in a reaction solvent, so as to obtain a product mixture comprising the aryl ether ketone, wherein reactant A is a difunctional aromatic molecule containing one or more oxygen atoms, wherein reactant B is a difunctional aromatic molecule containing one or more halogen atoms;
subjecting the product mixture to a solid/liquid separation so as to recover a purified aryl ether ketone and separately recover a mother liquor; and
either:
subjecting the mother liquor to a method for treating a shear-thinning residue composition, said mother liquor forming part or all of the shear-thinning residue composition; or
distilling said mother liquor, recovering a shear-thinning residue composition as a distillation residue, and subjecting said recovered shear-thinning residue composition to the method for treating a shear-thinning residue composition,

wherein the method for treating a shear-thinning residue composition is the method of claim 1 .

20. The method of claim 19 , wherein the aryl ether ketone is 1,4-bis(4-phenoxybenzoyl)benzene, reactant A is terephthaloyl chloride, and reactant B is diphenyl ether.

21. The method of claim 19 , wherein the aryl ether ketone is a poly ether ketone ketone polymer, reactant A is a difunctional aromatic acyl chloride, and reactant B is 1,4-bis(4-phenoxybenzoyl)benzene.

22. The method according to claim 19 , wherein the reaction solvent is chosen from carbon disulfide, ortho-dichlorobenzene, meta-dichlorobenzene, para-dichlorobenzene, 1,2,4-trichlorobenzene, 1,2,3-trichlorobenzene, ortho-difluorobenzene, 1,1-dichloroethane, 1,2-dichloroethane, 1,1,2,2-tetrachloroethane, tetrachloroethylene, dichloromethane, nitrobenzene and mixtures thereof.

23. The method according to claim 19 , wherein the solid/liquid separation step comprises a filtration step.

24. A method for manufacturing a poly ether ketone ketone polymer, comprising:
reacting terephthaloyl chloride with diphenyl ether in a reaction solvent, so as to obtain a product mixture comprising 1,4-bis(4-phenoxybenzoyl)benzene;
subjecting the product mixture to a solid/liquid separation so as to recover a purified 1,4-bis(4-phenoxybenzoyl)benzene and separately recover a mother liquor; and
either:
subjecting the mother liquor to a method for treating a shear-thinning residue composition, said mother liquor forming part or all of the shear-thinning residue composition; or
distilling said mother liquor, recovering a shear-thinning residue composition as a distillation residue, and subjecting said recovered shear-thinning residue composition to the method for treating a shear-thinning residue composition,

reacting a difunctional aromatic acyl chloride with the 1,4-bis(4-phenoxybenzoyl)benzene in a reaction solvent, so as to obtain a product mixture comprising the poly ether ketone ketone polymer;
subjecting the product mixture to a solid/liquid separation so as to recover a purified poly ether ketone ketone polymer and separately recover a mother liquor; and
either:
subjecting the mother liquor to a method for treating a shear-thinning residue composition, said mother liqu

Assignees

• Arkema France

Inventors

• Schon Steven Gabriel
• Goddard Andrew Richard
• Jouanneau Julien

Classifications

• C08G65/4093

  characterised by the process or apparatus used · CPC title

• B01D1/223

  containing a rotor · CPC title

• C08G65/4018

  (I) or (II) containing halogens other than as leaving group (X) · CPC title

• C08G65/46 Primary

  Post-polymerisation treatment, e.g. recovery, purification, drying · CPC title

• Y02P20/582

  Recycling of unreacted starting or intermediate materials · CPC title