Production of adipic acid and derivatives from carbohydrate-containing materials

• US 8,501,989 B2
• Filed: 06/11/2010
• Issued: 08/06/2013
• 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.
• Primary Examiner(s): Puttlitz, Karl J
• Application Number:
  US12/814,240
• Publication Number:
  US 20100317822A1
• Time in Patent Office: 1,152 Days
• Field of Search: None
• US Class Current: 562/590
• 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 29/149 with hydrogen or hydrogen-containing gases
• CPC Class Codes: C07C 31/20 Dihydroxylic alcohols
• 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 55/14 Adipic acid
• 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

Abstract

The present invention generally relates to processes for the chemocatalytic conversion of a carbohydrate source to an adipic acid product. The present invention includes processes for the conversion of a carbohydrate source to an adipic acid product via a furanic substrate, such as 2,5-furandicarboxylic acid or derivatives thereof. The present invention also includes processes for producing an adipic acid product comprising the catalytic hydrogenation of a furanic substrate to produce a tetrahydrofuranic substrate and the catalytic hydrodeoxygenation of at least a portion of the tetrahydrofuranic substrate 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 adipic acid comprising reacting a tetrahydrofuranic substrate comprising tetrahydrofuran-2,5-dicarboxylic acid with hydrogen, in the presence of a hydrodeoxygenation catalyst, a solvent and a source of halogen, to convert at least a portion of the tetrahydrofuran-2,5-dicarboxylic acid to adipic acid.

2. The process as set forth in claim 1 wherein the source of halogen comprises hydrogen bromide or hydrogen iodide.

3. The process as set forth in claim 1 further comprising reacting a furanic substrate comprising furan-2,5-dicarboxylic acid with hydrogen, in the presence of a hydrogenation catalyst and a solvent, but in the absence of an added source of halogen to produce the tetrahydrofuranic substrate comprising tetrahydrofuran-2,5-dicaboxylic acid.

4. The process as set forth in claim 2 further comprising reacting a furanic substrate comprising furan-2,5-dicarboxylic acid with hydrogen, in the presence of a hydrogenation catalyst and acetic acid, but in the absence of an added source of halogen to produce the tetrahydrofuranic substrate comprising tetrahydrofuran-2,5-dicaboxylic acid.

5. The process as set forth in claim 1 wherein the solvent comprises a weak carboxylic acid.

6. The process as set forth in claim 1 wherein at least a portion of the tetrahydrofuranic substrate is derived from a carbohydrate source.

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 1 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 and Pt 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 10 wherein the hydrodeoxygenation catalyst support comprises a material selected from the group consisting of carbon, silica, zirconia, and titania.

12. The process as set forth in claim 3 wherein the source of halogen comprises hydrogen bromide or hydrogen iodide.

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

14. The process as set forth in claim 1 wherein the reaction mixture is maintained at a temperature of at least about 100°

C.

15. The process as set forth in claim 3 wherein the temperature of the hydrogenation reaction mixture is from about 60°

C. to about 200°

C.

16. The process as set forth in claim 15 wherein the hydrodeoxygenation reaction is conducted under a partial pressure of hydrogen ranging from about 25 psia (172 kPa) to about 2500 psia (17237 kPa).

17. The process as set forth in claim 3 wherein at least a portion of the furanic substrate is derived from a carbohydrate source.

18. The process as set forth in claim 3 wherein the hydrogenation catalyst comprises a heterogeneous catalyst.

19. The process as set forth in claim 18 wherein the hydrogenation catalyst comprises at least one d-block metal at a surface of a support.

20. The process as set forth in claim 19 wherein the d-block metal is selected from the group consisting of Ru, Rh, Pd, Pt, Ni, Co, Fe and combinations thereof.

21. The process as set forth in claim 3 wherein the hydrogenation catalyst comprises a first metal and a second metal, wherein the first metal is selected from the group consisting of Ru, Rh, Pd, Pt, Ni, Co and Fe, 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.

22. The process a set forth in claim 20 wherein the hydrogenation catalyst support comprises a material selected from the group consisting of carbon, zirconia, zeolite and silica.

23. The process of in claim 3 wherein the hydrogenation catalyst and the hydrodeoxygenation catalyst are the same.

24. The process of claim 3 wherein the hydrogenation reaction and the hydrodeoxygenation reaction are carried out in different reactors.

25. The process of claim 3 wherein the hydrogenation reaction and the hydrodeoxygenation reaction are carried out in the same reactor.

26. The process of claim 1 wherein the reaction temperature is at least about 140°

C.

27. The process of claim 1 wherein the yield of adipic acid is at least about 90%.

28. The process of claim 2 wherein adipic acid is produced at a yield of at least about 90%.

29. The process of claim 28 wherein the reaction temperature is at least about 140°

C.