Production of adipic acid and derivatives from carbohydrate-containing materials

• US 9,156,766 B2
• Filed: 01/13/2014
• Issued: 10/13/2015
• Est. Priority Date: 06/13/2009
• Status: Active Grant

• Current Assignee: Archer Daniels Midland Company
• Original Assignee: Rennovia Inc.
• Inventors: Boussie, Thomas R., Dias, Eric L., Fresco, Zachary M., Murphy, Vincent J., Shoemaker, James, Archer, Raymond, Jiang, Hong
• Primary Examiner(s): Katakam, Sudhakar
• Assistant Examiner(s): Sawyer, Jennifer C
• Application Number:
  US14/153,248
• Publication Number:
  US 20140256982A1
• Time in Patent Office: 638 Days
• Field of Search: None
• US Class Current: 1/1
• CPC Class Codes: B01J 21/063 Titanium; Oxides or hydroxides thereof
• CPC Class Codes: B01J 21/066 Zirconium or hafnium; Oxides or hydroxides thereof
• CPC Class Codes: B01J 21/08 Silica
• CPC Class Codes: B01J 21/16 Clays or other mineral silicates
• CPC Class Codes: B01J 21/18 Carbon
• CPC Class Codes: B01J 23/40 of the platinum group metals
• CPC Class Codes: B01J 23/44 Palladium
• CPC Class Codes: B01J 23/462 Ruthenium
• CPC Class Codes: B01J 23/464 Rhodium
• CPC Class Codes: B01J 23/468 Iridium
• CPC Class Codes: B01J 23/52 Gold
• CPC Class Codes: B01J 23/6525 Molybdenum
• CPC Class Codes: B01J 23/6562 Manganese
• CPC Class Codes: B01J 23/6567 Rhenium
• CPC Class Codes: B01J 23/8906 Iron and noble metals
• CPC Class Codes: B01J 23/8913 Cobalt and noble metals
• CPC Class Codes: B01J 23/8926 Copper and noble metals
• CPC Class Codes: B01J 35/393 Metal or metal oxide crystallite size
• CPC Class Codes: B01J 37/0205 in several steps
• CPC Class Codes: C07B 2200/07 Optical isomers
• CPC Class Codes: C07C 201/08 : by substitution of hydrogen atoms by nitro groups
• CPC Class Codes: C07C 209/00 : Preparation of compounds containing amino groups bound to a carbon skeleton
• CPC Class Codes: C07C 211/12 : 1,6-Diaminohexanes
• CPC Class Codes: C07C 253/00 : Preparation of carboxylic acid nitriles of cyanogen or compounds thereof C01C3/00
• CPC Class Codes: C07C 255/04 : containing two cyano groups bound to the carbon skeleton
• CPC Class Codes: C07C 51/235 : of —CHO groups or primary alcohol groups
• CPC Class Codes: C07C 51/31 : of cyclic compounds with ring-splitting
• CPC Class Codes: C07C 51/377 : by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups C07C51/36 - C07C51/373 take precedence
• CPC Class Codes: C07C 51/412 : by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
• CPC Class Codes: C07C 55/14 : Adipic acid
• CPC Class Codes: C07D 201/08 : from carboxylic acids or derivatives thereof, e.g. hydroxy carboxylic acids, lactones or nitriles
• CPC Class Codes: C07D 223/10 : attached in position 2
• CPC Class Codes: C07D 309/30 : Oxygen atoms, e.g. delta-lactones
• CPC Class Codes: C08G 63/16 : Dicarboxylic acids and dihydroxy compounds
• CPC Class Codes: C08G 69/14 : Lactams
• CPC Class Codes: C08G 69/26 : derived from polyamines and polycarboxylic acids
• CPC Class Codes: C08G 69/36 : derived from amino acids, polyamines and polycarboxylic acids
• CPC Class Codes: Y02P 20/582 : Recycling of unreacted starting or intermediate materials

Abstract

The present invention generally relates to processes for the chemocatalytic conversion of a glucose source to an adipic acid product. The present invention includes processes for the conversion of glucose to an adipic acid product via glucaric acid or derivatives thereof. The present invention also includes processes comprising catalytic oxidation of glucose to glucaric acid or derivative thereof and processes comprising the catalytic hydrodeoxygenation of glucaric acid or derivatives thereof to an adipic acid product. The present invention also includes products produced from adipic acid product and processes for the production thereof from such adipic acid product.

Claims

1. A process for preparing glucaric acid or derivative thereof, the process comprising:

reacting glucose with oxygen in the presence of a heterogeneous oxidation catalyst comprising a metal selected from the group consisting of Pd, Pt, and a combination thereof to convert at least a portion of the glucose to glucaric acid or derivative thereof, wherein the pH of the reaction mixture is less than 7 and the weight ratio of glucose to Pd and/or Pt is no greater than about 200;

1 and wherein the reaction is conducted in the substantial absence of added base.

2. The process of claim 1 wherein the weight ratio of glucose to Pd and/or Pt is no greater than about 90:

1.

3. The process of claim 1 wherein the weight ratio of glucose to Pd and/or Pt is from about 40:

1 to about 200;

1.

4. The process of claim 1 wherein the at least a portion of the glucose is converted to glucaric acid.

5. The process as set forth in claim 1 wherein at least about 50% of the glucose is converted to glucaric acid.

6. The process as set forth in claim 1 wherein at least about 60% of the glucose is converted to glucaric acid.

7. The process of claim 1 wherein the at least a portion of the glucose is converted to a glucarolactone.

8. The process as set forth in claim 1 wherein the reaction mixture is maintained at a temperature of at least about 60°

C.

9. The process as set forth in claim 1 wherein the temperature of the reaction mixture is from about 60°

C. to about 150°

C.

10. The process as set forth in claim 1 wherein the reaction is conducted under a partial pressure of oxygen in the range of from about 15 psia (104 kPa) to about 2000 psia (13790 kPa).

11. The process as set forth in claim 1 wherein the heterogeneous oxidation catalyst comprises Pt.

12. The process as set forth in claim 1 wherein the heterogeneous oxidation catalyst further comprises a second metal besides Pd and/or Pt.

13. The process as set forth in claim 1 wherein the heterogeneous oxidation catalyst is a supported catalyst and the catalyst support comprises a material selected from the group consisting of carbon, alumina, silica, titania, zirconia, and zeolite.

14. The process as set forth in claim 13 wherein the catalyst support comprises carbon.

15. The process as set forth in claim 13 wherein the heterogeneous oxidation catalyst comprises Pt and the support comprises carbon black.

16. The process as set forth in claim 1 wherein the heterogeneous oxidation catalyst comprises Pt and Au.

17. The process as set forth in claim 1 wherein at least a portion of the glucose is solubilized with a weak carboxylic acid.

18. The process as set forth in claim 1 wherein the temperature of the reaction mixture is from about 70°

C. to about 150°

C.

19. The process as set forth in claim 1 wherein at least a portion of the glucose is obtained from a carbohydrate source.

20. The process of claim 1 wherein the temperature of the reaction mixture is from about 80°

C. to about 120°

C.

21. A process for preparing glucaric acid or derivative thereof, the process comprising:

reacting glucose with oxygen in the presence of a heterogeneous oxidation catalyst comprising a metal selected from the group consisting of Pd, Pt, and a combination thereof to convert at least a portion of the glucose to glucaric acid or derivative thereof, wherein the reaction is conducted under a partial pressure of oxygen of at least about 25 psia (172 kPa), the pH of the reaction mixture is less than 7 and is maintained at a temperature of at least 60°

C., the glucaric acid yield is at least about 15%, and the weight ratio of glucose to Pd and/or Pt is no greater than about 200;

1.

22. The process of claim 21 wherein the glucaric acid yield is at least about 30%.

23. The process of claim 21 wherein the weight ratio of glucose to Pd and/or Pt is no greater than about 90:

1.

24. The process of claim 21 wherein the weight ratio of glucose to Pd and/or Pt is from about 40:

1 to about 200;

1.

46. The process as set forth in claim 21 wherein the glucaric acid yield is in excess of 50%.

47. The process as set forth in claim 21 wherein the glucaric acid yield is in excess of 60%.

48. The process as set forth in claim 21 wherein the at least a portion of the glucose is converted to a glucarolactone.

49. The process as set forth in claim 21 wherein the reaction is conducted in the substantial absence of added base.

50. The process as set forth in claim 46 wherein the reaction is conducted in the substantial absence of added base.

51. The process as set forth in claim 50 wherein the temperature of the reaction mixture is from about 70°

C. to about 150°

C.

52. The process as set forth in claim 21 wherein the temperature of the reaction mixture is from about 80°

C. to about 120°

C.

53. The process as set forth in claim 21 wherein the partial pressure of oxygen is in the range of from about 15 psia (104 kPa) to about 2000 psia (13790 kPa).

54. The process as set forth in claim 51 wherein the heterogeneous oxidation catalyst comprises Pt.

55. The process as set forth in claim 21 wherein the heterogeneous oxidation catalyst further comprises a second metal besides Pd and/or Pt.

56. The process as set forth in claim 51 wherein the heterogeneous oxidation catalyst is a supported catalyst and the catalyst support comprises a material selected from the group consisting of carbon, alumina, silica, titania, zirconia, and zeolite.

57. The process as set forth in claim 21 wherein the catalyst support comprises carbon.

58. The process as set forth in claim 56 wherein the heterogeneous oxidation catalyst comprises Pt and the support comprises carbon black.

59. The process as set forth in claim 21 wherein the heterogeneous oxidation catalyst comprises Pt and Au.

60. The process as set forth in claim 21 wherein at least a portion of the glucose is solubilized with a weak carboxylic acid.

61. The process as set forth in claim 21 wherein at least a portion of the glucose is obtained from a carbohydrate source.

25. A process for preparing an adipic acid product, the process comprising:

a) reacting glucose with oxygen in the presence of a heterogeneous oxidation catalyst comprising a metal selected from the group consisting of Pd, Pt, and a combination thereof to convert at least a portion of the glucose to glucaric acid or derivative thereof, wherein the pH of the reaction mixture is less than 7, wherein the weight ratio of glucose to Pd and/or Pt is no greater than about 200;

1; and

b) reacting, in the presence of a hydrodeoxygenation catalyst, a halogen source and hydrogen, at least a portion of the glucaric acid or derivative thereof, to convert at least a portion of the glucaric acid or derivative thereof to an adipic acid product.

26. The process of claim 25 wherein the at least a portion of the glucose is converted to glucaric acid.

27. The process as set forth in claim 25 wherein at least a portion of the glucose and glucaric acid or derivative thereof is solubilized in a weak carboxylic acid.

28. The process of claim 25 wherein the weight ratio of glucose to Pd and/or Pt is no greater than about 90:

1.

29. The process of claim 25 wherein the weight ratio of glucose to Pd and/or Pt is from about 40:

1 to about 200;

1.

30. The process as set forth in claim 25 wherein at least about 50% of the glucose is converted to glucaric acid.

31. The process as set forth in claim 25 wherein at least about 60% of the glucose is converted to glucaric acid.

32. The process as set forth in claim 25 wherein the at least a portion of the glucose is converted to a glucarolactone.

33. The process as set forth in claim 25 wherein the reaction is conducted in the substantial absence of added base.

34. The process as set forth in claim 25 wherein the reaction mixture is maintained at a temperature of at least about 60°

C.

35. The process as set forth in claim 25 wherein the temperature of the reaction mixture is from about 60°

C. to about 150°

C.

36. The process as set forth in claim 25 wherein the temperature of the reaction mixture is from about 70°

C. to about 150°

C.

37. The process as set forth in claim 25 wherein the temperature of the reaction mixture is from about 80°

C. to about 120°

C.

38. The process as set forth in claim 25 wherein the partial pressure of oxygen is in the range of from about 15 psia (104 kPa) to about 2000 psia (13790 kPa).

39. The process as set forth in claim 25 wherein the heterogeneous oxidation catalyst comprises Pt.

40. The process as set forth in claim 25 wherein the heterogeneous oxidation catalyst further comprises a second metal besides Pd and/or Pt.

41. The process as set forth in claim 25 wherein the heterogeneous oxidation catalyst is a supported catalyst and the catalyst support comprises a material selected from the group consisting of carbon, alumina, silica, titania, zirconia, and zeolite.

42. The process as set forth in claim 41 wherein the catalyst support comprises carbon.

43. The process as set forth in claim 41 wherein the heterogeneous oxidation catalyst comprises Pt and the support comprises carbon black.

44. The process as set forth in claim 25 wherein the heterogeneous oxidation catalyst comprises Pt and Au.

45. The process as set forth in claim 25 wherein at least a portion of the glucose is obtained from a carbohydrate source.