IP Library Granted Patent US 7,154,010
Granted Patent B2
US 7,154,010 · App. 10/250,107 · Granted Dec 26, 2006

Integrated process for the production of bisphenol A from cumene hydroperoxide

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Quick Facts
Patent No.
US 7,154,010
App. No.
10/250,107
Granted
Dec 26, 2006
Kind
B2
Abstract

Use of a specific combination of catalysts for the first and second steps of the process for the conversion of CHP to BPA provides high yields of BPA and low impurity yields, without a requirement for the intermediate purification steps. In the first step, CHP is cleaved in the presence of a sulfated metal oxide catalyst such as sulfated Zirconia to produce phenol and acetone. In the second step, the phenol and acetone produced is reacted, preferably without intermediate purification, in the presence of a cation exchange resin catalyst that includes a cation exchange resin and a mercaptan or mercaptoalkanoic acid promoter to produce BPA.

Claims (36)

1. A method for production of bisphenol A comprising the steps of:

(a) cleaving cumene hydroperoxide in the presence of a sulfated metal oxide acid catalyst to substantially convert the cumene hydroperoxide to a cleavage mass comprising phenol and acetone; and

(b) reacting the cleavage mass in the presence of a cation exchange resin catalyst comprising a cation exchange resin and a mercaptan or mercaptoalkanoic acid promoter to substantially convert the phenol and acetone in the cleavage mass to bisphenol A.

2. The method of claim 1 , wherein the cleavage mass produced in step (a) is reacted in step (b) without intermediate purification.

3. The method of claim 2 , wherein the step of cleaving the cumene hydroperoxide is performed at a temperature of 55 to 65° C.

4. The method of claim 3 , further comprising the step of adding phenol to or removing acetone from the cleavage mass formed in step (a) to attain an acetone:phenol mole ratio of 1:20 to 1:10.

5. The method of claim 4 , wherein the acetone:phenol mole ratio attained is 1:13.

6. The method according to claim 3 , wherein step (b) is performed at a temperature of 40 to 100° C.

7. The method of claim 6 , further comprising the step of adding phenol to or removing acetone from the cleavage mass formed in step (a) to attain an acetone:phenol mole ratio of 1:20 to 1:10.

8. The method of claim 7 , wherein the acetone:phenol mole ratio attained is 1:13.

9. The method of claim 2 , wherein the cation exchange resin catalyst comprises pyridyl ethyl mercaptan as promoter.

10. The method of claim 9 , wherein the pyridyl ethyl mercaptan is loaded on the cation exchange resin in an amount of 20 to 70% by weight.

11. The method of claim 10 , wherein the pyridyl ethyl mercaptan is loaded on the cation exchange resin in an amount of 40% by weight.

12. The method of claim 10 , wherein the step of cleaving the cumene hydroperoxide is performed at a temperature of 55 to 65° C.

13. The method of claim 12 , further comprising the step of adding phenol to or removing acetone from the cleavage mass formed in step (a) to attain an acetone:phenol mole ratio of 1:20 to 1:10.

14. The method of claim 13 , wherein the acetone:phenol mole ratio attained is 1:13.

15. The method according to claim 12 , wherein step (b) is performed at a temperature of 40 to 100° C.

16. The method of claim 15 , further comprising the step of adding phenol to or removing acetone from the cleavage mass formed in step (a) to attain an acetone:phenol mole ratio of 1:20 to 1:10.

17. The method of claim 16 , wherein the acetone:phenol mole ratio attained is 1:13.

18. The method of claim 2 , wherein the catalyst is sulfated zirconia.

19. The method of claim 18 , wherein the step of cleaving the cumene hydroperoxide is performed at a temperature of 55 to 65° C.

20. The method of claim 18 , further comprising the step of adding phenol to or removing acetone from the cleavage mass formed in step (a) to attain an acetone:phenol mole ratio of 1:20 to 1:10.

21. The method of claim 20 , wherein the acetone:phenol mole ratio attained is 1:13.

22. The method according to claim 18 , wherein step (b) is performed at a temperature of 40 to 100° C.

23. The method of claim 22 , further comprising the step of adding phenol to or removing acetone from the cleavage mass formed in step (a) to attain an acetone:phenol mole ratio of 1:20 to 1:10.

24. The method of claim 23 , wherein the acetone:phenol mole ratio attained is 1:13.

25. The method of claim 18 , wherein the cation exchange catalyst comprises pyridyl ethyl mercaptan.

26. The method of claim 25 , wherein the pyridyl ethyl mercaptan is loaded on the cation exchange resin in an amount of 20 to 70% by weight.

27. The method of claim 25 , wherein the pyridyl ethyl mercaptan is loaded on the cation exchange resin in an amount of 40% by weight.

28. The method of claim 26 , wherein the step of cleaving the cumene hydroperoxide is performed at a temperature of 55 to 65° C.

29. The method of claim 28 , further comprising the step of adding phenol to or removing acetone from the cleavage mass formed in step (a) to attain an acetone:phenol mole ratio of 1:20 to 1:10.

30. The method of claim 29 , wherein the acetone:phenol mole ratio attained is 1:13.

31. The method according to claim 28 , wherein step (b) is performed at a temperature of 40 to 100° C.

32. The method of claim 31 , further comprising the step of adding phenol to or removing acetone from the cleavage mass formed in step (a) to attain an acetone:phenol mole ratio of 1:20 to 1:10.

33. The method of claim 32 , wherein the acetone:phenol mole ratio attained is 1:13.

34. The method of claim 1 , wherein the catalyst is sulphated zirconia.

Assignments (4)
CHANGE OF NAME Recorded Jun 6, 2016
From: SABIC INNOVATIVE PLASTICS IP B.V.
To: SABIC GLOBAL TECHNOLOGIES B.V.
Reel/Frame 038883/0791 →
RELEASE OF SECURITY INTEREST Recorded Mar 17, 2014
From: CITIBANK, N.A.
To: SABIC INNOVATIVE PLASTICS IP B.V.
Reel/Frame 032459/0798 →
SECURITY AGREEMENT Recorded Aug 18, 2008
From: SABIC INNOVATIVE PLASTICS IP B.V.
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 021423/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 30, 2008
From: GENERAL ELECTRIC COMPANY
To: SABIC INNOVATIVE PLASTICS IP B.V.
Reel/Frame 021311/0259 →