Recovery of aromatic carboxylic acids and oxidation catalyst

Patent metadata

Field	Value
Publication number	US-9409849-B2
Application number	US-201113637460-A
Country	US
Kind code	B2
Filing date	Mar 16, 2011
Priority date	Mar 26, 2010
Publication date	Aug 9, 2016
Grant date	Aug 9, 2016

Abstract

The present invention relates to a process for recovery of catalyst, aromatic polycarboxylic acids and aromatic monocarboxylic acids from a residue stream from manufacture of an aromatic polycarboxylic acid.

First claim

What is claimed is:

1. A process comprising:
(a) producing a residue stream from manufacture of an aromatic polycarboxylic acid;
(b) separating the residue stream into a solid aromatic dicarboxylic acid rich stream, an aqueous stream rich in catalyst metal, acetic acid and aromatic tricarboxylic acid, and an organic stream rich in an aromatic monocarboxylic acid using a solvent extraction and
(c) separating at least one aromatic polycarboxylic acid from the dicarboxylic acid rich stream
wherein the separation process in step (b) comprises simultaneous extraction of the residue stream with two liquid phases, followed by filtration,
wherein the simultaneous extraction of residue comprises the use of water and an organic solvent comprising at least one member selected from the group consisting of toluene, benzene, cylcohexane, petroleum ether, methanol and mixtures thereof.

2. The process of claim 1 wherein the aromatic polycarboxylic acid comprises at least one member selected from the group consisting of terephthalic acid, isophthalic acid, orthophthalic acid, trimellitic acid, naphthalene dicarboxylic acid and mixtures thereof.

3. The process of claim 2 wherein the catalyst components present in the catalyst and tricarboxylic acid rich stream comprise at least one member selected from the group consisting of a cobalt salt, a manganese salt, and mixtures thereof.

4. The process of claim 2 further comprising step (a i ) removing acetic acid by evaporation from the residue stream after step (a).

5. A process comprising:
(a) producing a residue stream from manufacture of an aromatic polycarboxylic acid;
(b) separating the residue stream into a solid aromatic dicarboxylic acid rich stream, an aqueous stream rich in catalyst metal, acetic acid and aromatic tricarboxylic acid, and an organic stream rich in an aromatic monocarboxylic acid using a solvent extraction;
(c) separating at least one aromatic monocarboxylic acid from the monocarboxylic acid rich stream;
(d) separating at least one aromatic dicarboxylic acid from the dicarboxylic acid rich stream; and
(e) separating at least one catalyst from the catalyst and tricarboxylic acid rich stream
wherein the separation process in step (b) comprises simultaneous extraction of the residue stream with two liquid phases, followed by filtration,
wherein the simultaneous extraction of residue comprises the use of water and an organic solvent comprising at least one member selected from the group consisting of toluene, benzene, cyclohexane, petroleum ether, methanol and mixtures thereof.

6. The process of claim 5 wherein the aromatic polycarboxylic acid comprises at least one member selected from the group consisting of terephthalic acid, isophthalic acid, orthophthalic acid, trimellitic acid, naphthalene dicarboxylic acid and mixtures thereof.

7. The process of claim 6 wherein the aromatic monocarboxylic acid comprises at least one member selected from the group consisting of benzoic acid, paratoluic acid and its isomers, and mixtures thereof.

8. The process of claim 6 wherein the catalyst comprises at least one member selected from the group consisting of a cobalt salt, a manganese salt, and mixtures thereof.

9. The process of claim 6 further comprising step (d i ) separating trimellitic acid or its isomers from the catalyst and tricarboxylic acid rich stream after step (d).

10. The process of claim 5 further comprising step (a i ) removing acetic acid from the residue stream by evaporation after step (a).

11. A process comprising:
(a) producing a residue stream from manufacture of terephthalic acid;
(b) separating the residue stream into a solid aromatic dicarboxylic acid rich stream, an aqueous stream rich in catalyst metal, acetic acid and aromatic tricarboxylic acid, and an organic stream rich in an aromatic monocarboxylic acid using a solvent extraction;
(c) separating benzoic acid and paratoluic acid from the monocarboxylic acid rich stream;
(d) separating terephthalic acid and isophthalic acid from the dicarboxylic acid rich stream;
(e) separating trimellitic acid from the catalyst and tricarboxylic acid rich stream; and
(f) separating a cobalt salt and manganese salt from the catalyst and tricarboxylic acid rich stream
wherein the separation process in step (b) comprises simultaneous extraction of the residue stream with two liquid phases, followed by filtration,
wherein the simultaneous two phase extraction of residue comprises the use of water and an organic solvent comprising at least one member selected from the group consisting of toluene, benzene, cyclohexane, petroleum ether, methanol and mixtures thereof.

12. The process of claim 11 further comprising step (a i ) removing acetic acid from the residue stream after step (a).

13. The process of claim 11 wherein the resulting effluent from the catalyst recovery step (f) is further subjected to recovery of hydrobromic acid by acidification of the effluent using a concentrated mineral acid such as sulphuric acid.

14. The process of claim 11 wherein the separating of step (d) comprises use of an alkali selected from the group consisting of aqueous ammonia, sodium hydroxide, and potassium hydroxide.

15. The process of claim 11 wherein the separating of step (d) comprises use of a solvent, wherein isophthalic acid is soluble in the solvent and terephthalic acid is insoluble in the solvent.

16. The process of claim 11 , wherein at least one separating step comprises i) optionally, adding an aqueous solution, ii) evaporating at least some water, iii) cooling, iv) filtering out a precipitate, and v) repeating steps ii) through iv) to produce a purified stream.

17. The process of claim 16 , wherein the precipitate of step iv) comprises crude tricarboxylic acid and the crude tricarboxylic acid is further purified by adding water, evaporating at least some of the water, and cooling to produce a crystallized further purified tricarboxylic acid.

18. The process of claim 16 , wherein the precipitate of step iv) comprises crude tricarboxylic acid and the crude tricarboxylic acid is further purified by washing with a mixture of acetic acid and water, and then washing with water, to produce a further purified tricarboxylic acid.

Assignees

• Karanjgaokar C G
• Invista North America Sarl

Inventors

• Karanjgaokar C G

Classifications

• C22B7/009

  General processes for recovering metals or metallic compounds from spent catalysts (for recovering specific metals C22B11/00 - C22B61/00) · CPC title

• C07C51/48 Primary

  by liquid-liquid treatment · CPC title

• C07C51/265 Primary

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

• C07C63/307

  Monocyclic tricarboxylic acids · CPC title

• C07C63/14

  Monocyclic dicarboxylic acids · CPC title