Production of adipic acid and derivatives from carbohydrate-containing materials

• US 8,669,397 B2
• Filed: 06/11/2010
• Issued: 03/11/2014
• 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): Richter, Johann R
• Assistant Examiner(s): Sawyer, Jennifer C
• Application Number:
  US12/814,188
• Publication Number:
  US 20100317823A1
• Time in Patent Office: 1,369 Days
• Field of Search: None
• US Class Current: 562/592
• 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 an adipic acid product, the process comprising:

reacting, in the presence of a hydrodeoxygenation catalyst and a halogen source, a hydrodeoxygenation substrate and hydrogen gas to convert at least a portion of the hydrodeoxygenation substrate to an adipic acid product, wherein the hydrodeoxygenation substrate comprises a compound of formula I

2. The process as set forth in claim 1 wherein the hydrodeoxygenation substrate comprises a compound of formula I, wherein X is hydroxyl and R¹ is independently a salt-forming ion, hydrogen, hydrocarbyl, or substituted hydrocarbyl.

3. The process as set forth in claim 1 wherein the hydrodeoxygenation substrate comprises glucaric acid.

4. The process as set forth in claim 1 wherein the adipic acid product comprises adipic acid.

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

6. The process as set forth in claim 5 wherein the pKa of the weak carboxylic acid is at least about 4.5.

7. The process as set forth in claim 1 wherein the hydrodeoxygenation catalyst comprises a heterogeneous catalyst.

8. The process as set forth in claim 7 wherein the hydrodeoxygenation catalyst comprises at least one d-block metal at a surface of a support.

9. The process as set forth in claim 8 wherein the d-block metal is selected from the group consisting of Ru, Rh, Pd, Pt, and combinations thereof.

10. The process as set forth in claim 7 wherein the hydrodeoxygenation catalyst comprises a first metal and a second metal, wherein the first metal is selected from the group consisting of Ru, Rh, Pd, Pt, and combinations thereof, and the second metal is selected from the group consisting of Mo, Ru, Rh, Pd, Ir, Pt, and Au, and wherein the second metal is not the same as the first metal.

11. The process as set forth in claim 9 wherein the hydrodeoxygenation catalyst support is selected from the group consisting of carbon, silica and zirconia.

12. The process as set forth in claim 5 wherein the halogen source comprises an ionic, atomic, and/or a molecular form of bromine.

13. The process as set forth in claim 12 wherein the halogen source comprises hydrogen bromide.

14. The process as set forth in claim 3 wherein the molar ratio of halogen source to hydrodeoxygenation substrate is equal to or less than about 1.

15. The process as set forth in claim 1 wherein the reaction mixture is maintained at a temperature of at least about 80°

C.

16. The process as set forth in claim 1 wherein the temperature of the reaction mixture is from about 100°

C. to about 200°

C.

17. The process as set forth in claim 1 wherein the reaction is conducted under a partial pressure of hydrogen ranging from about 25 psia (172 kPa) to about 2500 psia (17237 kPa).

18. The process as set forth in claim 1 wherein the hydrodeoxygenation substrate of formula I is prepared by

reacting glucose with oxygen to convert at least a portion of the glucose to the hydrodeoxygenation substrate of formula I.

19. The process of claim 12 wherein the hydrodeoxygenation catalyst comprises Pt and Rh on a support comprising silica.

20. The process of claim 12 wherein the reaction is conducted at a temperature of at least about 140°

C.

21. The process of claim 1 wherein the hydrodeoxygenation substrate comprises glucaric acid, the hydrodeoxygenation catalyst comprises a heterogeneous catalyst comprising at least one d-block metal selected from the group consisting of Ru, Rh, Pd, Pt, and combinations thereof at a surface of a support, and the halogen source comprises an ionic, atomic, and/or a molecular form of bromine.

22. The process of claim 5 wherein the hydrodeoxygenation substrate comprises glucaric acid, the hydrodeoxygenation catalyst comprises a heterogeneous catalyst comprising at least one d-block metal selected from the group consisting of Ru, Rh, Pd, Pt, and combinations thereof at a surface of a support, and the halogen source comprises an ionic, atomic, and/or a molecular form of bromine.

23. The process of claim 1 wherein at least a portion of the hydrodeoxygenation substrate is solubilized with a weak carboxylic acid, the hydrodeoxygenation catalyst comprises a heterogeneous catalyst comprising at least one d-block metal selected from the group consisting of Ru, Rh, Pd, Pt, and combinations thereof at a surface of a support, and the halogen source comprises an ionic, atomic, and/or a molecular form of bromine.

24. The process of claim 23 wherein the hydrodeoxygenation substrate comprises glucaric acid.

25. The process of claim 1 wherein at least a portion of the hydrodeoxygenation substrate is solubilized with a weak carboxylic acid, the hydrodeoxygenation catalyst comprises a heterogeneous catalyst comprising at least one d-block metal selected from the group consisting of Ru, Rh, Pd, Pt, and combinations thereof at a surface of a support, and the halogen source comprises hydrogen bromide.

26. The process of claim 25 wherein the hydrodeoxygenation substrate comprises glucaric acid.

27. The process as set forth in claim 1 wherein the halogen source comprises an ionic, atomic, and/or a molecular form of bromine.

28. The process as set forth in claim 3 wherein the adipic acid product comprises adipic acid.

29. The process as set forth in claim 24 wherein the adipic acid product comprises adipic acid.

30. The process as set forth in claim 6 wherein the halogen source comprises an ionic, atomic, and/or a molecular form of bromine.

31. The process as set forth in claim 1 wherein the temperature of the reaction mixture is from about 100°

C. to about 200°

C. and wherein the reaction is conducted under a partial pressure of hydrogen ranging from about 25 psia (172 kPa) to about 2500 psia (17237 kPa).

32. The process as set forth in claim 26 wherein the temperature of the reaction mixture is from about 100°

C. to about 200°

C. and wherein the reaction is conducted under a partial pressure of hydrogen ranging from about 25 psia (172 kPa) to about 2500 psia (17237 kPa).

33. The process as set forth in claim 23 wherein the pKa of the weak carboxylic acid is at least about 4.5.

34. The process as set forth in claim 26 wherein the pKa of the weak carboxylic acid is at least about 4.5.

35. The process of claim 19 wherein the reaction is conducted at a temperature of at least about 140°

C.

36. The process of claim 18 wherein at least a portion of the glucose and the hydrodeoxygenation substrate of formula I are solubilized with a weak carboxylic acid.

37. The process of claim 18 wherein glucose is reacted with oxygen in the presence of an oxidation catalyst.

38. The process of claim 18 wherein glucose is reacted with oxygen in the substantial absence of added base.

39. The process as set forth in claim 36 wherein the weak carboxylic acid comprises acetic acid.

40. The process as set forth in claim 36 wherein the pKa of the weak carboxylic acid is at least about 4.5.