IP Library Granted Patent US 7,214,760
Granted Patent B2
US 7,214,760 · App. 10/758,678 · Granted May 8, 2007

Process for production of a carboxylic acid/diol mixture suitable for use in polyester production

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Quick Facts
Patent No.
US 7,214,760
App. No.
10/758,678
Granted
May 8, 2007
Kind
B2
Abstract

The present invention relates to a process by which a carboxylic acid/diol mixture is obtained from a slurry or cake carboxylic acid product without isolation of a substantially dry carboxylic acid solid. More specifically, the present invention relates to a process by which a terephthalic acid/ethylene glycol mixture suitable as a starting material for polyester or co-polyester production is obtained from a slurry or cake terephthalic acid product without isolation of a substantially dry terephthalic acid solid.

Claims (86)

1. A process for producing a carboxylic acid/diol mixture, said process comprising:

(a) removing in a liquor exchange zone impurities from a carboxylic acid slurry to form a water-wet carboxylic acid cake, a mother liquor stream, a solvent mother liquor stream, and a solvent/water byproduct liquor stream;

(b) routing said water-wet carboxylic acid cake to a vapor seal zone; and

(c) adding at least one diol to said water-wet carboxylic acid cake in a carboxylic acid/diol mixing zone to form said carboxylic acid/diol mixture wherein said diol displaces water from said water-wet carboxylic acid cake; and wherein said carboxylic acid/diol mixture is produced without the isolation of a substantially dry carboxylic acid solid; and where said vapor seal zone prevents said diol from entering any zone proceeding said vapor seal zone.

2. A process according to claim 1 wherein said carboxylic acid is selected from a group consisting of terephthalic acid, isophthalic acid, naphthalene dicarboxylic acid, trimellitic acid, and mixtures thereof.

3. A process according to claim 1 or 2 wherein said diol is selected from the group consisting of ethylene glycol, diethylene glycol, n-butylene glycol, i-butylene glycol, n-propylene glycol, 1,4 butanediol, cyclohexanedimethanol, and mixtures thereof.

4. A process according to claim 1 wherein said carboxylic acid/diol mixing zone comprises at least one device selected from the group consisting of an agitated vessel, a static mixer, a screw conveyor, and a PET esterification reactor.

5. A process according to claim 1 wherein said carboxylic acid is terephthalic acid and said diol is ethylene glycol.

6. A process for producing a carboxylic acid/diol mixture, said process comprising:

(a) removing in a solvent liquor exchange zone impurities from a carboxylic acid slurry to form a carboxylic acid cake with solvent, a mother liquor stream, and a solvent mother liquor stream;

(b) adding water in a water wash zone to said carboxylic cake with solvent to produce a water-wet carboxylic acid cake and a solvent/water by product liquor stream;

(c) routing said water-wet carboxylic acid cake to a vapor seal zone; and

(d) adding at least one diol to said water-wet carboxylic acid cake in a carboxylic acid/diol mixing zone to form said carboxylic acid/diol mixture wherein said diol displaces water from said water-wet carboxylic acid cake; and wherein said carboxylic acid/diol mixture is produced without the isolation of a substantially dry carboxylic acid solid; and where said vapor seal zone prevents said diol from entering any zone proceeding said vapor seal zone.

7. A process according to claim 6 wherein said carboxylic acid is selected from a group consisting of terephthalic acid, isophthalic acid, naphthalene dicarboxylic acid, trimellitic acid and mixtures thereof.

8. A process according to claim 6 or 7 wherein said diol is selected from the group consisting of ethylene glycol, diethylene glycol, n-butylene glycol, i-butylene glycol, n-propylene glycol, 1,4 butanediol, cyclohexanedimethanol, and mixtures thereof.

9. A process according to claim 6 wherein said carboxylic acid/diol mixing zone comprises at least one device selected from the group consisting of an agitated vessel, a static mixer, a screw conveyor, and a PET esterification reactor.

10. A process according to claim 6 wherein said carboxylic acid is terephthalic acid and said diol is ethylene glycol.

11. A process for producing a carboxylic acid/diol mixture, said process comprising:

(a) removing in a solid-liquid separation zone impurities from a carboxylic acid slurry to form a slurry or cake carboxylic acid product and a mother liquor stream;

(b) removing in a solvent-water liquor exchange zone residual impurities from said slurry or cake carboxylic acid product to form a water-wet carboxylic acid cake, a solvent mother liquor stream, and a solvent/water byproduct liquor stream;

(c) routing said water-wet carboxylic acid cake to a vapor seal zone; and

(d) adding at least one diol to said water-wet carboxylic acid cake in a carboxylic acid/diol mixing zone to form said carboxylic acid/diol mixture wherein said diol displaces water from said water-wet carboxylic acid cake; and wherein said carboxylic acid/diol mixture is produced without the isolation of a substantially dry carboxylic acid solid; and where said vapor seal zone prevents said diol from entering any zone proceeding said vapor seal zone.

12. A process according to claim 11 wherein said carboxylic acid is selected from a group consisting of terephthalic acid, isophthalic acid, naphthalene dicarboxylic acid, trimellitic acid and mixtures thereof.

13. A process according to claim 11 or 12 wherein said diol is selected from the group consisting of ethylene glycol, diethylene glycol, n-butylene glycol, i-butylene glycol, n-propylene glycol, 1,4 butanediol, cyclohexanedimethanol, and mixtures thereof.

14. A process according to claim 11 wherein said carboxylic acid/diol mixing zone comprises at least one device selected from the group consisting of an agitated vessel, a static mixer, a screw conveyor, and a PET esterification reactor.

15. A process according to claim 11 wherein said carboxylic acid is terephthalic acid and said diol is ethylene glycol.

16. A process for producing a carboxylic acid/diol mixture, said process comprising the following steps:

(a) removing a solvent from a slurry or cake carboxylic acid product in a solvent-water liquor exchange zone; wherein a substantial portion of the solvent in said slurry or cake carboxylic acid product is replaced with water to form a water-wet carboxylic acid cake;

(b) routing said water-wet carboxylic acid cake to a vapor seal zone; and

(c) adding at least one diol to said water-wet carboxylic acid cake in a carboxylic acid/diol mixing zone to form said carboxylic acid/diol mixture wherein said diol displaces water from said water-wet carboxylic acid cake; and wherein said carboxylic acid/diol mixture is produced without the isolation of a substantially dry carboxylic acid solid; and where said vapor seal zone prevents said diol from entering any zone proceeding said vapor seal zone.

17. A process according to claim 16 wherein said carboxylic acid is selected from a group consisting of terephthalic acid, isophthalic acid, naphthalene dicarboxylic acid, trimellitic and mixtures thereof.

18. A process according to claim 16 or 17 wherein said diol is selected from the group consisting of ethylene glycol, diethylene glycol, n-butylene glycol, i-butylene glycol, n-propylene glycol, 1,4 butanediol, cyclohexanedimethanol, and mixtures thereof.

19. A process according to claim 16 wherein said carboxylic acid/diol mixing zone comprises at least one device selected from the group consisting of an agitated vessel, a static mixer, a screw conveyor, and a PET esterification reactor.

20. A process for producing a terephthalic acid/diol mixture, said process comprising:

(a) removing in a solvent wash zone residual impurities from a slurry or cake terephthalic acid product to form a terephthalic acid cake with acetic acid;

(b) removing a substantial portion of a solvent in a water wash zone from said terephthalic acid cake with acetic acid to form a water-wet terephthalic acid cake; and

(c) routing said water-wet terephthalic acid cake to a vapor seal zone; and

(d) adding at least one diol to said water-wet terephthalic acid cake in a carboxylic acid/diol mixing zone to form said terephthalic acid/diol mixture wherein said diol displaces water from said water-wet terephthalic acid cake; and wherein said terephthalic acid/diol mixture is produced without the isolation of a substantially dry carboxylic acid solid; and where said vapor seal zone prevents said diol from entering any zone proceeding said vapor seal zone.

21. A process according to claim 20 wherein said solvent wash zone comprises a solid-liquid separation device that is operated at a temperature between about 40° C. to about 155° C.

22. A process according to claim 21 wherein said water wash zone comprises a solid-liquid separation device that is operated at a temperature between about 40° C. to about 155° C.

23. A process according to claim 20 or 21 wherein said adding occurs at a temperature between about 40° C. to about 290° C.

24. A process according to claim 20 wherein said diol is selected from the group consisting of ethylene glycol, diethylene glycol, n-butylene glycol, i-butylene glycol, n-propylene glycol, 1,4 butanediol, cyclohexanedimethanol, and mixtures thereof.

25. A process according to claim 20 wherein said diol is ethylene glycol.

26. A process according to claim 20 wherein said carboxylic acid/diol mixing zone comprises a device selected from the group consisting of an agitated vessel, a static mixer, a screw conveyor, and a PET esterification reactor.

27. A process for producing a terephthalic acid/diol mixture, said process comprising:

(a) removing a solvent from a slurry or cake terephthalic acid product in a solvent-water liquor exchange zone; wherein a substantial portion of the solvent in said slurry or cake terephthalic acid product is replaced with water to form a water-wet terephthalic acid cake;

(b) routing said water-wet terephthalic acid cake to a vapor seal zone; and

(c) adding at least one diol to said water-wet terephthalic acid cake in a carboxylic acid/diol mixing zone to form said terephthalic acid/diol mixture wherein said diol displaces water from said water-wet terephthalic acid cake; and wherein said terephthalic acid/diol mixture is produced without the isolation of a substantially dry carboxylic acid solid; and where said vapor seal zone prevents said diol from entering any zone proceeding said vapor seal zone.

28. A process according to claim 27 wherein said solvent liquor exchange zone comprises a solid-liquid separation device that is operated at a temperature between about 40° C. to about 155° C.

29. A process according to claim 27 wherein said adding occurs at a temperature between about 40° C. and 290° C.

30. A process according to claim 27 wherein said diol is selected from the group consisting of ethylene glycol, diethylene glycol, n-butylene glycol, i-butylene glycol, n-propylene glycol, 1,4 butanediol, cyclohexanedimethanol, and mixtures thereof.

31. A process according to claim 27 wherein said diol is ethylene glycol.

32. A process according to claim 27 wherein said carboxylic acid/diol mixing zone comprises a device selected from the group consisting of an agitated vessel, a static mixer, a screw conveyor, and a PET esterification reactor.

33. A process for producing a terephthalic acid/diol mixture, said process comprising:

(a) removing in a solvent wash zone residual impurities from a slurry or cake terephthalic acid product from a terephthalic acid cake with acetic acid; wherein said solvent wash zone comprises at least one solid-liquid separation device that is operated at a temperature between about 40° C. to about 155° C.

(b) removing a substantial portion of a solvent in a water wash zone from said terephthalic acid cake with acetic acid to form a water-wet terephthalic acid cake; wherein said water wash zone comprises at least one solid-liquid separation device that is operated at a temperature between about 40° C. to about 155° C.;

(c) routing said water-wet terephthalic acid cake to a vapor seal zone; and

(d) adding at least one diol to said water-wet terephthalic acid cake in a carboxylic acid/diol mixing zone to form said terephthalic acid/diol mixture; wherein said adding occurs at a temperature between about 40° C. to about 290° C.; wherein said diol displaces water from said water-wet terephthalic acid cake; wherein said terephthalic acid/diol mixture is produced without the the isolation of a substantially dry carboxylic acid solid; and wherein said vapor seal zone prevents said diol from entering any zone proceeding said vapor seal zone; and wherein said diol is ethylene glycol.

34. A process for producing a carboxylic acid/diol mixture, said process comprising:

(a) removing in a solid-liquid separation zone impurities from a carboxylic acid slurry to form a slurry or cake carboxylic acid product and a mother liquor stream;

(b) adding solvent to a slurry or cake carboxylic acid product in a solvent wash zone to said slurry or cake carboxylic acid product to produce a carboxylic acid cake with solvent and a solvent mother liquor stream;

(c) optionally, adding water in a water wash zone to said carboxylic cake with solvent to produce a water-wet carboxylic acid cake and a solvent/water by product liquor stream;

(d) routing said water-wet carboxylic acid cake or said carboxylic acid cake with solvent to a vapor seal zone; and

(e) adding at least one diol to said water-wet carboxylic acid cake in a carboxylic acid/diol mixing zone to form said carboxylic acid/diol mixture wherein said diol displaces water from said water-wet carboxylic acid cake; and wherein said carboxylic acid/diol mixture is produced without the isolation of a substantially dry carboxylic acid solid; and where said vapor seal zone prevents said diol from entering any zone proceeding said vapor seal zone.

35. A process according to claim 34 wherein said carboxylic acid is selected from a group consisting of terephthalic acid, isophthalic acid, naphthalene dicarboxylic acid, trimellitic acid and mixtures thereof.

36. A process according to claim 34 or 35 wherein said diol is selected from the group consisting of ethylene glycol, diethylene glycol, n-butylene glycol, i-butylene glycol, n-propylene glycol, 1,4 butanediol, cyclohexanedimethanol, and mixtures thereof.

37. A process according to claim 34 wherein said carboxylic acid/diol mixing zone comprises at least one device selected from the group consisting of an agitated vessel, a static mixer, a screw conveyor, and a PET esterification reactor.

38. A process according to claim 34 wherein said carboxylic acid is terephthalic acid and said diol is ethylene glycol.

39. A process for producing a terephthalic acid/diol mixture, said process comprising:

(a) removing in a solid-liquid separation zone impurities from a terephthalic acid slurry to form a slurry or cake terephthalic acid product and a mother liquor stream;

(b) adding solvent in a solvent wash zone to said slurry or cake terephthalic acid product to produce a terephthalic acid cake with solvent and a solvent mother liquor stream;

(c) optionally, adding water in a water wash zone to said terephthalic acid cake with solvent to produce a water-wet terephthalic acid cake and a solvent/water by product liquor stream;

(d) routing said water-wet terephthalic acid cake or said carboxylic acid cake with solvent to a vapor seal zone; and

(e) adding at least one diol to said water-wet terephthalic acid cake in a carboxylic acid/diol mixing zone to form said terephthalic acid/diol mixture wherein said diol displaces water from said water-wet terephthalic acid cake; and wherein said terephthalic acid/diol mixture is produced without the isolation of a substantially dry carboxylic acid solid; and where said vapor seal zone prevents said diol from entering any zone proceeding said vapor seal zone.

40. A process according to claim 39 wherein said solvent wash zone comprises a solid-liquid separation device that is operated at a temperature between about 40° C. to about 155° C.

41. A process according to claim 40 wherein said water wash zone comprises a solid-liquid separation device that is operated at a temperature between about 40° C. to about 155° C.

42. A process according to claim 39 or 40 wherein said adding occurs at a temperature between about 40° C. and about 290° C.

43. A process according to claim 39 wherein said diol is selected from the group consisting of ethylene glycol, diethylene glycol, n-butylene glycol, i-butylene glycol, n-propylene glycol, 1,4 butanediol, cyclohexanedimethanol, and mixtures thereof.

44. A process according to claim 39 wherein said diol is ethylene glycol.

45. A process according to claim 39 wherein said carboxylic acid/diol mixing zone comprises a device selected from the group consisting of an agitated vessel, a static mixer, a screw conveyor, and a PET esterification reactor.

46. A process according to claim 34 or 39 wherein said solvent is added counter current to the flow of said slurry or cake carboxylic acid product.

47. A process according to claim 34 or 39 wherein said water is added counter current to the flow of said carboxylic acid cake with solvent.

48. A process according to claim 46 wherein said water is added counter current to the flow of said carboxylic acid cake with solvent.

49. A process according to claim 48 wherein said water wash zone comprises from about 2 to about 4 stages of water counter current washes.

50. A process according to claim 46 wherein said solvent wash zone comprises from about 2 to about 4 stages of solvent counter current washes.

51. A process according to claim 47 wherein said water wash zone comprises from about 2 to about 4 stages of water counter current washes.

Assignments (3)
CHANGE OF NAME Recorded Jan 11, 2022
From: GRUPO PETROTEMEX, S.A. DE C.V.
To: ALPEK POLYESTER, S.A. DE C.V.
Reel/Frame 058691/0337 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 1, 2011
From: EASTMAN CHEMICAL COMPANY
To: GRUPO PETROTEMEX, S.A. DE C.V.
Reel/Frame 025727/0820 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 11, 2004
From: PARKER, KENNY RANDOLPH; LIN, ROBERT; GIBSON, PHILIP EDWARD
To: EASTMAN CHEMICAL COMPANY
Reel/Frame 014616/0460 →