IP Library Granted Patent US 7,226,986
Granted Patent B2
US 7,226,986 · App. 11/077,481 · Granted Jun 5, 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 7,226,986
App. No.
11/077,481
Granted
Jun 5, 2007
Kind
B2
Abstract

The present invention relates to a process by which a carboxylic acid/diol mixture is obtained from a carboxylic acid/solvent slurry 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 is obtained from a terephthalic acid/solvent slurry without isolation of a substantially dry terephthalic acid solid.

Claims (40)

1. A process for producing a carboxylic acid/diol mixture suitable for the production of polyesters, said process comprising adding a diol to a water-wet carboxylic acid cake in a carboxylic acid/diol mixing zone to remove at least a portion of the water from said water-wet carboxylic acid cake to form said carboxylic acid/diol mixture; wherein said carboxylic acid/diol mixture is produced without the isolation of a substantially dry carboxylic acid solid; wherein said water is displaced from said water-wet carboxylic acid cake by the addition of said diol.

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, and a screw conveyor.

5. A process for producing a carboxylic acid/diol mixture suitable for the production of polyesters, said process comprising the following steps:

(a) removing in a first solid-liquid separation device impurities from a carboxylic acid/solvent slurry to form a carboxylic acid cake with acetic acid and a solvent mother liquor stream;

(b) removing a portion of a solvent in a second solid-liquid separation device from said carboxylic acid cake with acetic acid to form a water-wet carboxylic acid cake and a solvent/water byproduct liquor;

(c) adding a diol to said water-wet carboxylic acid cake in a carboxylic acid/diol mixing zone to remove at least a portion of the water from said water-wet carboxylic acid cake to form said carboxylic acid/diol mixture; wherein said carboxylic acid/diol mixture is produced without the isolation of a substantially dry carboxylic acid solid; wherein said water is displaced from said water-wet carboxylic acid cake by the addition of said diol.

6. A process according to claim 5 wherein said carboxylic acid is selected from a group consisting of terephthalic acid, isophthalic acid, naphthalene dicarboxylic acid, trimellitic acid and mixtures thereof.

7. A process according to claim 5 or 6 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.

8. A process according to claim 5 wherein said diol/carboxylic acid mixing zone comprises at least one device selected from the group consisting of an agitated vessel, a static mixer, and a screw conveyor.

9. A process for producing a carboxylic acid/diol mixture suitable for the production of polyesters, said process comprising the following steps:

(a) removing a solvent from a carboxylic acid/solvent slurry in a solid-liquid separation zone; wherein a portion of the solvent in said carboxylic acid/solvent slurry is replaced with water to form a water-wet carboxylic acid cake;

(b) adding a diol to said water-wet carboxylic acid cake in a carboxylic acid/diol mixing zone to remove at least a portion of the water from said water-wet carboxylic acid cake to form said carboxylic acid/diol mixture; wherein said carboxylic acid/diol mixture is produced without the isolation of a substantially dry carboxylic acid solid; wherein said water is displaced from said water-wet carboxylic acid cake by the addition of said diol.

10. A process according to claim 9 wherein said carboxylic acid is selected from a group consisting of terephthalic acid, isophthalic acid, naphthalene dicarboxylic acid, trimellitic and mixtures thereof.

11. A process according to claim 9 or 10 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.

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

13. A process for producing a terephthalic acid/diol mixture, said process comprising adding a diol to a water-wet terephthalic acid cake in a terephthalic acid/diol mixing zone to remove a portion of the water to form said terephthalic acid/diol mixture.

14. A process according to claim 13 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.

15. A process according to claim 13 wherein said diol is ethylene glycol.

16. A process according to claim 13 , 14 or 15 wherein said adding occurs at a temperature between about 40° C. and about 290° C.

17. A process according to claim 13 wherein said terephthalic 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.

18. A process for producing a terephthalic acid/diol mixture suitable for the production of polyesters, said process comprising the following steps:

(a) removing in a first solid-liquid separation device impurities from a terephthalic acid/solvent slurry to form a terephthalic acid cake with acetic acid;

(b) removing a portion of a solvent in a second solid-liquid separation device from said terephthalic acid cake with acetic acid to form a water-wet terephthalic acid cake; and

(c) adding a diol to said water-wet terephthalic acid cake in a terephthalic acid/diol mixing zone to remove at least a portion of the water from said water-wet carboxylic acid cake to form said terephthalic acid/diol mixture; wherein said carboxylic acid/diol mixture is produced without the isolation of a substantially dry carboxylic acid solid; wherein said water is displaced from said water-wet carboxylic acid cake by the addition of said diol.

19. A process according to claim 18 wherein said first solid-liquid separation device is operated at a temperature between about 40° C. to about 155° C.

20. A process according to claim 19 wherein said second solid-liquid separation device is operated at a temperature between about 40° C. to about 155° C.

21. A process according to claim 18 or 20 wherein said adding occurs at a temperature between about 40° C. and about 290° C.

22. A process according to claim 18 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.

23. A process according to claim 18 wherein said diol is ethylene glycol.

24. A process according to claim 18 wherein said terephthalic acid/diol mixing zone comprises a device selected from the group consisting of an agitated vessel, a static mixer, and a screw conveyor.

25. A process for producing a terephthalic acid/diol mixture suitable for the production of polyesters, said process comprising the following steps:

(a) removing a solvent from a terephthalic acid/solvent slurry in a solid-liquid separation zone; wherein a portion of the solvent in said terephthalic acid/solvent slurry is replaced with water to form a water-wet terephthalic acid cake;

(b) adding a diol to said water-wet terephthalic acid cake in a terephthalic acid/diol mixing zone to remove at a portion the water from said water-wet carboxylic acid cake to form said terephthalic acid/diol mixture; wherein said carboxylic acid/diol mixture is produced without the isolation of a substantially dry carboxylic acid solid; wherein said water is displaced from said water-wet carboxylic acid cake by the addition of said diol.

26. A process according to claim 25 wherein said solid-liquid displacement zone is operated at a temperature between about 40° C. to about 155° C.

27. A process according to claim 25 wherein said adding occurs at a temperature between about 40° C. and 290° C.

28. A process according to claim 25 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.

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

30. A process according to claim 25 wherein said diol/terephthalic acid mixing zone comprises a device selected from the group consisting of an agitated vessel, a static mixer, and a screw conveyor.

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 Aug 9, 2005
From: LIN, ROBERT; UPSHAW, TIMOTHY ALAN; HALL, DUANE ALAN; PARKER, KENNY RANDOLPH
To: EASTMAN CHEMICAL COMPANY
Reel/Frame 016622/0473 →