Paraxylene extraction of purification mother liquor with heat integration

Patent metadata

Field	Value
Publication number	US-9975839-B2
Application number	US-201515513373-A
Country	US
Kind code	B2
Filing date	Sep 23, 2015
Priority date	Sep 24, 2014
Publication date	May 22, 2018
Grant date	May 22, 2018

Abstract

The present invention provides a process for the production of an aromatic dicarboxylic acid comprising the catalytic oxidation of a hydrocarbon precursor in an organic solvent, comprising the steps of: i) separating a vent gas from an oxidation stage into an organic solvent-rich liquid stream and a water-rich vapor stream in a distillation stage; and ii) separating an aqueous purification mother liquor comprising organic compounds from purified aromatic dicarboxylic acid crystals in a separation stage, characterized in that the process further comprises the steps of: iii) transferring the aqueous purification mother liquor from the separation stage to an extraction stage; iv) extracting said organic compounds from the aqueous purification mother liquor by contacting the aqueous purification mother liquor at a temperature of at least 90° C. with an organic liquid in the extraction stage to form an aqueous phase and an organic phase, wherein the concentration of said organic compounds in the aqueous phase is lower than the concentration of said organic compounds in the aqueous purification mother liquor; and v) transferring the aqueous phase to said distillation stage. The present invention further provides an apparatus for carrying out the process.

First claim

The invention claimed is:

1. A process for the production of an aromatic dicarboxylic acid comprising the catalytic oxidation of a hydrocarbon precursor in an organic solvent, comprising the steps of:
i) separating a vent gas from an oxidation stage into an organic solvent-rich liquid stream and a water-rich vapour stream in a distillation stage; and
ii) separating an aqueous purification mother liquor comprising organic compounds from purified aromatic dicarboxylic acid crystals in a separation stage,
characterised in that the process further comprises the steps of:
iii) transferring the aqueous purification mother liquor from the separation stage to an extraction stage;
iv) extracting said organic compounds from the aqueous purification mother liquor by contacting the aqueous purification mother liquor at a temperature of at least 90° C. with an organic liquid in the extraction stage to form an aqueous phase and an organic phase, wherein the concentration of said organic compounds in the aqueous phase is lower than the concentration of said organic compounds in the aqueous purification mother liquor; and
v) transferring the aqueous phase to said distillation stage.

2. The process of claim 1 , further comprising heating the organic liquid prior to its contact with the aqueous purification mother liquor.

3. The process of claim 1 , wherein step iii) further comprises diluting the aqueous purification mother liquor with an aqueous liquid.

4. The process of claim 1 , wherein step iii) further comprises heating the aqueous purification mother liquor.

5. The process of claim 1 , wherein the aqueous purification mother liquor is transferred in step iii) from the separation stage to the extraction stage without being subject to an intermediate cooling step followed by an intermediate separation step.

6. The process of claim 1 , wherein the distillation stage comprises a first distillation column.

7. The process of claim 6 , wherein the distillation stage further comprises a second distillation column, wherein the first and second distillation columns are connected in series.

8. The process of claim 6 , wherein the aqueous phase is transferred in step v) to an upper region of the first distillation column.

9. The process of claim 8 , wherein the first distillation column comprises a plurality of theoretical stages and the aqueous phase is transferred in step v) to the top theoretical stage of the first distillation column.

10. The process of claim 8 , wherein the first distillation column comprises a plurality of trays and the aqueous phase is transferred in step v) to the top tray of the first distillation column.

11. The process of claim 1 , wherein the extraction stage comprises an extraction column.

12. The process of claim 11 , wherein the extraction column contains structured packing.

13. The process of claim 1 , wherein the organic liquid comprises the hydrocarbon precursor.

14. The process of claim 1 , further comprising the step of:
vi) transferring the organic phase to the oxidation stage.

15. The process of claim 1 , wherein the organic liquid comprises p-xylene.

16. The process of claim 1 , wherein the aromatic dicarboxylic acid is terephthalic acid.

17. The process of claim 1 , wherein said organic compounds comprise p-toluic acid, terephthalic acid, benzoic acid or a mixture thereof.

18. The process of claim 17 , wherein the purified aromatic dicarboxylic acid crystals comprise less than or equal to 200 ppm p-toluic acid.

19. An apparatus for the production of an aromatic dicarboxylic acid comprising:
a) a distillation stage configured to separate a vent gas from an oxidation stage into an organic solvent-rich liquid stream and a water-rich vapour stream; and
b) a separation stage configured to separate an aqueous purification mother liquor comprising organic compounds from purified aromatic dicarboxylic acid crystals;
characterised in that the apparatus further comprises:
c) an extraction stage configured to receive the aqueous purification mother liquor from the separation stage and to extract said organic compounds from the aqueous purification mother liquor by contacting the aqueous purification mother liquor at a temperature of at least 90° C. with an organic liquid to form an aqueous phase and an organic phase, wherein the concentration of said organic compounds in the aqueous phase is lower than the concentration of said organic compounds in the aqueous purification mother liquor; wherein the extraction stage is further configured to transfer the aqueous phase to said distillation stage.

20. The apparatus of claim 19 , further comprising means to heat the organic liquid prior to its contact with the aqueous purification mother liquor.

21. The apparatus of claim 19 , further comprising means to dilute the aqueous purification mother liquor with an aqueous liquid before it is received by the extraction stage.

22. The apparatus of claim 19 , further comprising means to heat the aqueous purification mother liquor before it is received by the extraction stage.

23. The apparatus of claim 19 , wherein the extraction stage is configured to receive the aqueous purification mother liquor from the separation stage without an intermediate cooling step followed by an intermediate separation step.

24. The apparatus of claim 19 , wherein the distillation stage comprises a first distillation column.

25. The apparatus of claim 24 , wherein the distillation stage comprises a second distillation column, wherein the first and second distillation columns are connected in series.

26. The apparatus of claim 24 , wherein the extraction stage is configured to transfer the aqueous phase to an upper region of the first distillation column.

27. The apparatus of claim 26 , wherein the first distillation column comprises a plurality of theoretical stages and the extraction stage is configured to transfer the aqueous phase to the top theoretical stage of the first distillation column.

28. The apparatus of claim 26 , wherein the first distillation column comprises a plurality of trays and the extraction stage is configured to transfer the aqueous phase to the top tray of the first distillation column.

29. The apparatus of claim 19 , wherein the extraction stage comprises an extraction column.

30. The apparatus of claim 29 , wherein the extraction column contains structured packing.

31. The apparatus of claim 19 , wherein the organic liquid comprises a hydrocarbon precursor for forming the aromatic dicarboxylic acid.

32. The apparatus of claim 19 , wherein the extraction stage is configured to transfer the organic phase to the oxidation stage.

33. The apparatus of claim 19 , wherein the organic liquid comprises p-xylene.

34. The apparatus of claim 19 , wherein the aromatic dicarboxylic acid is terephthalic acid.

35. The apparatus of claim 19 , wherein said organic compounds comprise p-toluic acid, terephthalic acid, benzoic acid or a mixture thereof.

36. The apparatus of claim 35 , wherein the purified aromatic dicarboxylic acid crystals comprise less than or equal to 200 ppm p-toluic acid.

Assignees

• Invista Tech Sarl
• Invista North America Sarl

Inventors

• Ure Alan Macpherson
• Limbach Antony Peter John

Classifications

• C07C51/265 Primary

  having alkyl side chains which are oxidised to carboxyl groups · CPC title

• B01D11/0492

  Applications, solvents used · CPC title

• C07C51/48

  by liquid-liquid treatment · CPC title

• B01D11/043

  with stationary contacting elements, sieve plates or loose contacting elements · CPC title

• B01D3/143

  by two or more of a fractionation, separation or rectification step · CPC title