IP Library Granted Patent US 7,709,681
Granted Patent B2
US 7,709,681 · App. 11/919,830 · Granted May 4, 2010

Process for the production of trimellitic acid

Assignee: Polynt S.p.A.
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Quick Facts
Patent No.
US 7,709,681
App. No.
11/919,830
Granted
May 4, 2010
Kind
B2
Abstract

Trimellitic acid is produced by oxidation of pseudocumene in acetic acid at temperatures between 130 and 240° C. in the presence of a catalyst composition containing cobalt, manganese and bromine. The process comprises the stages of: (i) simultaneously feeding pseudocumene and air or an oxygen-containing gas into a solution containing acetic acid and the catalyst composition, at an addition rate resulting in an oxygen concentration in the off-gas of less than 8 vol %, and at a temperature and a pressure sufficient to result in 5 to 25 mol % of the total amount of oxygen required to oxidize the pseudocumene to trimellitic acid being consumed, and (ii) feeding air or an oxygen-containing gas into the reaction mixture obtained in stage (i) until essentially all of the pseudocumene has been consumed and a molar yield of trimellitic acid of at least 90% has been obtained. There is no supplementation of catalyst after stage (i).

Claims (27)

1. A process for the production of trimellitic acid by oxidation of pseudocumene in acetic acid at temperatures between 130 and 240° C. in the presence of a catalyst composition containing cobalt, manganese and bromine, said process comprising the stages of

(i) gradually and simultaneously feeding pseudocumene and air or an oxygen-containing gas into a solution containing acetic acid and said catalyst composition, at an addition rate resulting in an oxygen concentration in the off-gas of less than 8 vol %, and at a temperature and a pressure sufficient to result in 5 to 25 mol % of the total amount of oxygen required to oxidize the pseudocumene to trimellitic acid being consumed, and

(ii) feeding air or an oxygen-containing gas into the reaction mixture obtained in stage (i) until essentially all of the pseudocumene has been consumed and a molar yield of trimellitic acid of at least 90% has been obtained, wherein there is no supplementation of catalyst after the completion of stage (i).

2. The process of claim 1 , wherein the reaction temperature in stage (i) is between 130° C. and 180° C.

3. The process of claim 1 , wherein in the course of stage (ii) the reaction temperature is increased to a final value between 200° C. and 240° C.

4. The process of claim 1 , wherein the pressure is between 5 and 30 bar.

5. The process of claim 1 , wherein the oxygen concentration of the off gases during stage (i) is from 2 to 6 vol %.

6. The process of claim 1 , wherein the catalyst composition further contains cerium and/or titanium.

7. The process of claim 6 , wherein the cerium content of the catalyst composition is 1 to 30 wt % relative to the total metal content.

8. The process of claim 6 , wherein the titanium content of the catalyst composition is 0.5 to 13 wt % relative to the total metal content.

9. The process of claim 1 , wherein the cobalt content of the catalyst composition is 30 to 70 wt % relative to the total metal content.

10. The process of claim 1 , wherein the manganese content of the catalyst composition is 10 to 50 wt % relative to the total metal content.

11. The process of claim 1 , wherein the total metal concentration comprising cobalt, and manganese, is 0.1 to 1.0 wt % relative to the total amount of pseudocumene employed.

12. The process of claim 6 , wherein the total metal concentration comprising cobalt, manganese and cerium and/or titanium is 0.1 to 1.0 wt % relative to the total amount of pseudocumene employed.

13. The process of claim 1 , wherein the bromine concentration is 0.05 to 0.7 wt % relative to the total amount of pseudocumene employed.

14. The process of claim 1 , wherein the weight ratio of acetic acid to total added pseudocumene is 1:1 to 4:1.

15. The process of claim 2 , wherein the reaction temperature in stage (i) is between 140° C. and 160° C.

16. The process of claim 3 , wherein in the course of stage (ii) the reaction temperature is increased to a final value between 215° C. and 230° C.

17. The process of claim 4 , wherein the pressure is between 6 and 25 bar.

18. The process of claim 7 , wherein the cerium content of the catalyst composition is 5 to 20 wt % relative to the total metal content.

19. The process of claim 8 , wherein the titanium content of the catalyst composition is 3 to 10 wt % relative to the total metal content.

20. The process of claim 9 , wherein the cobalt content of the catalyst composition is 40 to 60 wt % relative to the total metal content.

21. The process of claim 10 , wherein the manganese content of the catalyst composition is 20 to 40 wt % relative to the total metal content.

22. The process of claim 11 , wherein the total metal concentration comprising cobalt, and manganese, is 0.20 to 0.55 wt % relative to the total amount of pseudocumene employed.

23. The process of claim 12 , wherein the total metal concentration comprising cobalt, manganese and cerium and/or titanium is 0.20 to 0.55 wt % relative to the total amount of pseudocumene employed.

24. The process of claim 13 , wherein the bromine concentration is 0.1 to 0.3 wt % relative to the total amount of pseudocumene employed.

25. The process of claim 14 , wherein the weight ratio of acetic acid to total added pseudocumene is 1:5 to 3:1.

Assignments (6)
CORRECTION OF CANCELLATION OF SECURITY INTEREST Recorded Apr 16, 2021
From: U.S. BANK TRUSTEES LIMITED; ELAVON FINANCIAL SERVICES DAC, UK BRANCH; BANCA POPOLARE DI MILANO S.P.A.; COMMERZBANK AG
To: POLYNT S.P.A.
Reel/Frame 055997/0295 →
CANCELLATION OF SECURITY INTEREST Recorded Mar 25, 2021
From: U.S. BANK TRUSTEES LIMITED
To: POLYNT S.P.A.
Reel/Frame 055710/0017 →
SECURITY INTEREST Recorded Sep 21, 2017
From: POLYNT S.P.A.
To: U.S. BANK TRUSTEES LIMITED; ELAVON FINANCIAL SERVICES DAC, UK BRANCH; BANCA POPOLARE DI MILANO S.P.A.; COMMERZBANK AG
Reel/Frame 043933/0016 →
MERGER Recorded Aug 24, 2017
From: POLYNT S.P.A.
To: POLIMERI SPECIALI S.P.A.
Reel/Frame 043659/0417 →
CHANGE OF NAME Recorded Aug 24, 2017
From: POLIMERI SPECIALI S.P.A.
To: POLYNT S.P.A.
Reel/Frame 043659/0473 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 2, 2007
From: CASTIGLIONI, GIAN LUCA; PIROLA, ROBERTO; FUMAGALLI, CARLO
To: POLYINT S.P.A.
Reel/Frame 020147/0566 →
Priority Claims (1)
EP 05425324 · May 13, 2005 · regional
Continuity (1)
Related Publication 20090043124A1 · Feb 12, 2009