Production of glutaric acid and derivatives from carbohydrate-containing materials

• US 8,785,683 B2
• Filed: 06/11/2010
• Issued: 07/22/2014
• 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.
• Primary Examiner(s): Zucker, Paul A
• Application Number:
  US12/814,216
• Publication Number:
  US 20100317825A1
• Time in Patent Office: 1,502 Days
• US Class Current: 562/515
• 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 51/313 with molecular oxygen
• 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 55/12 Glutaric 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
• CPC Class Codes: C08G 69/36 derived from amino acids, polyamines and polycarboxylic acids

Abstract

The present invention generally relates to processes for the chemocatalytic conversion of a pentose source to a glutaric acid product. The present invention includes processes for the conversion of pentose to a glutaric acid product via pentaric acid or derivatives thereof. The present invention also includes processes comprising the catalytic oxidation of pentose to pentaric acid and catalytic hydrodeoxygenation of pentaric acid or derivatives thereof to a glutaric acid product.

Claims

1. A process for preparing a glutaric acid product, the process comprising:

reacting, in the presence of a heterogeneous hydrodeoxygenation catalyst comprising at least one d-block metal selected from the group consisting of Co, Ni, Ru, Rh, Pd, Os, Ir, Pt, and combinations thereof at a surface of a support and a halogen source, a C5-backbone substrate and hydrogen to convert at least a portion of the C5-backbone substrate to a glutaric acid product, wherein the C5-backbone substrate comprises a compound of formula I

2. The process as set forth in claim 1 wherein the C5-backbone 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 C5-backbone substrate comprises a pentaric acid.

4. The process as set forth in claim 1 wherein the C5-backbone substrate comprises a chemical selected from the group consisting of xylaric acid, arabinaric acid, derivatives of such acids, and mixtures thereof.

5. The process as set forth in claim 3 wherein the pentaric acid comprises an acid selected from the group consisting of xylaric and arabinaric acid.

6. The process as set forth in claim 4 wherein at least a portion of the C5-backbone substrate is solubilized with a weak carboxylic acid.

7. The process as set forth in claim 6 wherein the weak carboxylic acid is acetic acid.

8. The process as set forth in claim 1 wherein the d-block metal is selected from the group consisting of Ru, Rh, Pd, Pt, and combinations thereof.

9. 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, 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.

10. The process as set forth in claim 1 wherein the hydrodeoxygenation catalyst support comprises a material selected from the group consisting of carbon, silica and zirconia.

11. The process as set forth in claim 6 wherein the halogen source comprises ionic, atomic, and/or molecular forms of bromine or iodine.

12. The process as set forth in claim 4 wherein the halogen source comprises hydrogen bromide.

13. The process as set forth in claim 1 wherein the molar ratio of the halogen source to C5-backbone substrate is equal to or less than about 1.

14. The process as set forth in claim 5 wherein the reaction is maintained at a temperature of at least about 80°

C.

15. The process as set forth in claim 4 wherein the temperature of the reaction is from about 100°

C. to about 200°

C.

16. The process as set forth in claim 15 wherein the 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 1 wherein at least a portion of the C5-backbone substrate is derived from a pentose.

33. The process as set forth in claim 7 wherein the d-block metal is selected from the group consisting of Ru, Rh, Pd, Pt, and combinations thereof.

34. The process as set forth in claim 10 wherein the d-block metal is selected from the group consisting of Ru, Rh, Pd, Pt, and combinations thereof.

35. The process as set forth in claim 1 wherein the glutaric acid product comprises glutaric acid.

18. A process for preparing a glutaric acid product, the process comprising:

a) converting at least a portion of a pentose source to a C5-backbone substrate comprising pentaric acid or derivative thereof, and

b) converting, in the presence of a heterogeneous hydrodeoxygenation catalyst comprising at least one d-block metal selected from the group consisting of Co, Ni, Ru, Rh, Pd, Os, Ir, Pt, and combinations thereof at a surface of a support, at least a portion of the pentaric acid or derivative thereof to a glutaric acid product of formula II

19. The process as set forth in claim 18 wherein the glutaric acid product comprises glutaric acid.

20. The process as set forth in claim 18 wherein the process further comprises converting a source of carbohydrates to the pentose source.

21. A process for preparing a glutaric acid product, the process comprising:

a) reacting a pentose with oxygen, in the presence of a solvent, and an oxidation catalyst and in the absence of added base, to convert at least a portion of the pentose to at least one pentaric acid and/or derivative thereof, and

b) reacting, in the presence of a heterogeneous hydrodeoxygenation catalyst comprising at least one d-block metal selected from the group consisting of Co, Ni, Ru, Rh, Pd, Os, Ir, Pt, and combinations thereof at a surface of a support and a halogen source, at least a portion of the at least one pentaric acid and/or derivative thereof and hydrogen, to convert at least a portion of the at least one pentaric acid and/or derivative thereof to a glutaric acid product of formula II

22. The process as set forth in claim 21 wherein a solvent is added to step b) to solubilize the at least one pentaric acid and/or derivative thereof.

28. A process of claim 21 wherein the oxygen is supplied to the reaction as air, oxygen-enriched air, oxygen alone, or oxygen with one or more other constituents substantially inert to the reaction.

29. The process as set forth in claim 21 wherein at least a portion of the at least one pentaric acid and/or derivative is solubilized with a weak carboxylic acid.

30. The process as set forth in claim 21 wherein the hydrodeoxygenation catalyst comprises a d-block metal selected from the group consisting of Ru, Rh, Pd, Pt, and combinations thereof.

31. The process as set forth in claim 21 wherein the halogen source comprises ionic, atomic, and/or molecular forms of bromine or iodine.

32. The process as set forth in claim 29 wherein the halogen source comprises hydrogen bromide.

36. The process as set forth in claim 21 wherein the glutaric acid product comprises glutaric acid.

23. A process for producing a glutaric acid product from a pentose, the process comprising:

converting by heterogeneous chemocatalysis at least a portion of the pentose to the glutaric acid product in the presence of a heterogeneous hydrodeoxygenation catalyst comprising at least one d-block metal selected from the group consisting of Co, Ni, Ru, Rh, Pd, Os, Ir, Pt, and combinations thereof at a surface of a support, wherein the glutaric acid product is of formula II

24. The process as set forth in claim 23 wherein the process comprises:

a) converting by chemocatalysis at least a portion of the pentose to pentaric acid or derivative thereof, and

b) converting by heterogeneous chemocatalysis at least a portion of the pentaric acid or derivative thereof to the glutaric acid product.

25. The process as set forth in claim 24 wherein the glutaric acid product comprises glutaric acid.

26. The process of claim 24 wherein the pentose comprises xylose and the pentaric acid or derivative thereof comprises xylaric acid or derivative thereof.

27. The process of claim 24 wherein the pentaric acid is xylaric acid.