Production and purification of phenol: hydroxyacetone removal by hydrotalcite

• US 6,486,365 B1
• Filed: 04/04/2002
• Issued: 11/26/2002
• Est. Priority Date: 04/04/2002
• Status: Expired due to Term

• Current Assignee: SABIC Global Technologies BV (Government of Saudi Arabia)
• Original Assignee: General Electric Company
• Inventors: Singh, Bharat, Tatake, Prashant Anil, Fulmer, John W., Hasyagar, Umesh, Kumbhar, Pramod
• Primary Examiner(s): Shippen, Michael L.
• Application Number:
  US10/063,258
• Time in Patent Office: 236 Days
• Field of Search: 568/754, 568/758, 568/749, 568/768, 422/189
• US Class Current: 568/768
• CPC Class Codes: C07C 2521/10 Magnesium; Oxides or hydroxides thereof
• CPC Class Codes: C07C 37/86 by treatment giving rise to a chemical modification chemisorption C07C37/82
• CPC Class Codes: C07C 39/04 Phenol

Abstract

A process for converting carbonyl-type impurities contained in a phenolic solvent to high-boiling derivatives is provided by contacting the phenolic solvent with a hydrotalcite-type material (HTM). The phenol can be separated from the high-boiling derivatives using conventional separation techniques, such as distillation, so the invention also provides a process for separating carbonyl-type impurities, such as hydroxyacetone (HA), from a phenolic solvent. The process can be applied in the conventional industrial process for converting cumene to phenol to remove carbonyl-type impurities from the phenol product. A process and a facility for producing purified phenol by converting cumene to phenol are provided. In the conversion of cumene to phenol, the phenol often contains carbonyl-type impurities. The phenol and carbonyl-type impurities are reacted in the presence of an HTM to produce phenol and high-boiling derivatives. The phenol may be further purified using conventional separation techniques, such as distillation, to remove the high-boiling derivatives.

Claims

1. A process for converting carbonyl-type impurities present in a phenolic solvent to high-boiling derivatives, which process comprises contacting the phenolic solvent with a catalyst at a catalytically-effective temperature, said catalyst comprising a layered double hydroxide composition of the formula:

2. The process of claim 1, wherein the M^II is selected from the alkaline earth metal cations alone or in combination with other divalent metal cations.

3. The process of claim 2, wherein the alkaline earth metal cation is magnesium cation.

4. The process of claim 1, wherein the M^III is selected from the Group IIIA metal cations alone or in combination with other trivalent metal cations.

5. The process of claim 4, wherein the Group IIIA metal cation is aluminum cation.

6. The process of claim 1, wherein the anion A is selected from the group consisting of CO₃²⁻

, NO₃⁻

, OH⁻

, Cl⁻

, F⁻

, or combinations thereof.

7. The process of claim 1, wherein the anion A is CO₃²⁻

.

8. The process of claim 1, wherein x is from 0.2 to 0.33.

9. The process of claim 1, wherein the catalytically-effective temperature at which the catalyst and phenolic solvent are contacted is from 40°

C. to 400°

C.

10. The process of claim 1, wherein the catalytically-effective temperature at which the catalyst and phenolic solvent are contacted is from 200°

C. to 300°

C.

11. The process of claim 1, wherein the catalytically-effective temperature at which the catalyst and phenolic solvent are contacted is from 210°

C. to 220°

C.

12. The process of claim 1, wherein the phenol-containing stream contains no more than 20 ppm of 2-methylbenzofuran (2MBF).

13. The process of claim 1, wherein the phenol-containing stream contains no more than 2 ppm of 2MBF.

14. A process for separating carbonyl-type impurities from a phenolic solvent, which process comprises contacting the phenolic solvent with a catalyst at a catalytically-effective temperature, said catalyst comprising a layered double hydroxide composition of the formula:

15. The process of claim 14, wherein the conventional separation technique is distillation.

16. The process of claim 14, wherein the M^II is selected from the alkaline earth metal cations alone or in combination with other divalent metal cations.

17. The process of claim 16, wherein the alkaline earth metal cation is magnesium cation.

18. The process of claim 14, wherein the M^III is selected from the Group IIIA metal cations alone or in combination with other trivalent metal cations.

19. The process of claim 18, wherein the Group IIIA metal cation is aluminum cation.

20. The process of claim 14, wherein the anion A is selected from the group consisting of CO₃²⁻

, NO₃⁻

, OH⁻

, Cl⁻

, F⁻

, or combinations thereof.

21. The process of claim 14, wherein the anion A is CO₃²⁻

.

22. The process of claim 14, wherein x is from 0.2 to 0.33.

23. The process of claim 14, wherein the catalytically-effective temperature at which the catalyst and phenolic solvent are contacted is from 40°

C. to 400°

C.

24. The process of claim 14, wherein the catalytically-effective temperature at which the catalyst and phenolic solvent are contacted is from 200°

C. to 300°

C.

25. The process of claim 14, wherein the catalytically-effective temperature at which the catalyst and phenolic solvent are contacted is from 210°

C. to 220°

C.

26. The process of claim 14, wherein the phenol-containing stream contains no more than 20 ppm of 2MBF.

27. The process of claim 14, wherein the phenol-containing stream contains no more than 2 ppm of 2MBF.

28. A process for producing phenol comprising the steps of:

converting cumene to produce a crude phenol which may contain carbonyl-type impurities;

reacting the crude phenol and any carbonyl-type impurities in the presence of a catalyst at a catalytically-effective temperature to produce a reaction product that contains phenol and may contain high-boiling derivatives of the carbonyl-type impurities and/or a small amount of 2MBF, said catalyst comprising a layered double hydroxide composition of the formula;

29. The process of claim 28, further comprising the step of separating the phenol from the reaction product using conventional separation techniques.

30. The process of claim 28, wherein the M^II is selected from the alkaline earth metal cations alone or in combination with other divalent metal cations.

31. The process of claim 30, wherein the alkaline earth metal cation is magnesium cation.

32. The process of claim 28, wherein the M^III is selected from the Group IIIA metal cations alone or in combination with other trivalent metal cations.

33. The process of claim 32, wherein the Group IIIA metal cation is aluminum cation.

34. The process of claim 28, wherein the anion A is selected from the group consisting of CO₃²⁻

, NO₃⁻

, OH⁻

, Cl⁻

, F⁻

, or combinations thereof.

35. The process of claim 28, wherein the anion A is CO₃²⁻

.

36. The process of claim 28, wherein x is from 0.2 to 0.33.

37. The process of claim 28, wherein the catalytically-effective temperature at which any carbonyl-type impurities and crude phenol are reacted is from 40°

C. to 400°

C.

38. The process of claim 28, wherein the catalytically-effective temperature at which any carbonyl-type impurities and crude phenol are reacted is from 200°

C. to 300°

C.

39. The process of claim 28, wherein the catalytically-effective temperature at which any carbonyl-type impurities and crude phenol are reacted is from 210°

C. to 220°

C.

40. The process of claim 28, wherein the reaction product contains no more than 20 ppm of 2MBF.

41. The process of claim 28, wherein the reaction product contains no more than 2 ppm of 2MBF.

42. In a process for converting cumene to phenol, wherein a crude phenol stream (CPS) which may contain carbonyl-type impurities is produced, the improvement comprising the step of contacting the CPS with a catalyst at a catalytically-effective temperature, thereby producing a phenol product that contains less of the carbonyl-type impurities, said catalyst comprising a layered double hydroxide composition of the formula:

43. The process of claim 42, wherein the M^II is selected from the alkaline earth metal cations alone or in combination with other divalent metal cations.

44. The process of claim 43, wherein the alkaline earth metal cation is magnesium cation.

45. The process of claim 42, wherein the M^III is selected from the Group IIIA metal cations alone or in combination with other trivalent metal cations.

46. The process of claim 45, wherein the Group IIIA metal cation is aluminum cation.

47. The process of claim 42, wherein the anion A is selected from the group consisting of CO₃²⁻

, NO⁻

, OH⁻

, Cl⁻

, F⁻

, or combinations thereof.

48. The process of claim 42, wherein the anion A is CO₃²⁻

.

49. The process of claim 42, wherein x is from 0.2 to 0.33.

50. The process of claim 42, wherein the catalytically-effective temperature at which the catalyst and CPS are contacted is from 40°

C. to 400°

C.

51. The process of claim 42, wherein the catalytically-effective temperature at which the catalyst and CPS are contacted is from 200°

C. to 300°

C.

52. The process of claim 42, wherein the catalytically-effective temperature at which the catalyst and CPS are contacted is from 210°

C. to 220°

C.

53. The process of claim 42, wherein the phenol product contains no more than 20 ppm of 2MBF.

54. The process of claim 42, wherein the phenol product contains no more than 2 ppm of 2MBF.

55. A facility for converting cumene to phenol, said facility comprising:

a vessel containing cumene;

a first reaction vessel connected to the vessel containing cumene, wherein in said first reaction vessel the cumene is oxidized to form a cumene hydroperoxide (CHP) mixture;

a second reaction vessel connected to the first reaction vessel, wherein in said second reaction vessel the CHP mixture is cleaved to form a crude cleavage mass mixture;

a third reaction vessel connected to the second reaction vessel, wherein in the third reaction vessel a base is added to the crude cleavage mass mixture to form a neutralized crude cleavage mass mixture;

a separation section connected to receive the neutralized crude cleavage mass mixture, wherein the neutralized crude cleavage mass mixture is separated into streams, wherein one of those streams is a crude phenol stream (CPS) comprising phenol and which may contain carbonyl-type impurities;

a temperature control mechanism connected to receive the CPS; and

a catalyst bed connected to receive the CPS, after it passes through the temperature control mechanism, and to produce a purified phenol-containing product, said catalyst bed comprising a layered double hydroxide composition of the formula;

56. The facility of claim 55, wherein the separation section comprises one or more distillation apparatuses.

57. The facility of claim 56, wherein the separation section comprises three distillation columns.

58. The facility of claim 55, wherein the temperature control mechanism can maintain a temperature in the catalyst bed of 40°

C. to 400°

C.

59. The facility of claim 55, further comprising a second separation section connected to the catalyst bed, wherein the purified phenol-containing product is separated into two or more streams wherein one of the streams is a phenol stream having greater purity than the purified phenol-containing stream.

60. The facility of claim 59, wherein the second separation section comprises a distillation apparatus.

61. The facility of claim 59, wherein the second separation section comprises a single distillation column.

62. The facility of claim 55, wherein the M^II is selected from the alkaline earth metal cations alone or in combination with other divalent metal cations.

63. The facility of claim 62, wherein the alkaline earth metal cation is magnesium cation.

64. The facility of claim 55, wherein the M^III is selected from the Group IIIA metal cations alone or in combination with other trivalent metal cations.

65. The facility of claim 64, wherein the Group IIIA metal cation is aluminum cation.

66. The facility of claim 55, wherein the anion A is selected from the group consisting of CO₃²⁻

, NO₃⁻

, OH⁻

, Cl⁻

, F⁻

, or combinations thereof.

67. The facility of claim 55, wherein the anion A is CO₃²⁻

.

68. The facility of claim 55, wherein x is from 0.2 to 0.33.

69. The facility of claim 55, wherein the temperature control mechanism can maintain a temperature in the catalyst bed of 200°

C. to 300°

C.

70. The facility of claim 55, wherein the temperature control mechanism can maintain a temperature in the catalyst bed of 210°

C. to 220°

C.

71. The facility of claim 55, wherein the purified phenol-containing product contains no more than 20 ppm of 2MBF.

72. The facility of claim 55, wherein the purified phenol-containing product contains no more than 2 ppm of 2MBF.