Copper-chromium catalyzed hydrogenation of polyunsaturated oils

• US 6,716,155 B2
• Filed: 12/18/2002
• Issued: 04/06/2004
• Est. Priority Date: 01/11/2002
• Status: Active Grant

• Current Assignee: Archer Daniels Midland Company
• Original Assignee: Archer Daniels Midland Company
• Inventors: Sleeter, Ronald
• Primary Examiner(s): Carr, Deborah D.
• Application Number:
  US10/321,728
• Publication Number:
  US 20030158433A1
• Time in Patent Office: 475 Days
• Field of Search: 554/141, 554/144
• US Class Current: 554/144
• CPC Class Codes: A23D 9/00 Other edible oils or fats, e.g. shortenings, cooking oils
• CPC Class Codes: A23D 9/02 characterised by the production or working-up
• CPC Class Codes: B01J 23/868 copper and chromium
• CPC Class Codes: C11C 3/126 using catalysts based principally on other metals or derivates

Abstract

A process for the hydrogenation of a polyunsaturated oil, wherein said oil is reacted with hydrogen in the presence of a copper-chromium containing catalyst at a temperature of from about 200 to 300° C. and a pressure of from about 300 to 500 psig, for 3-8 hours. The reaction results in a product having a monounsaturated fatty acid percent conversion (i.e., monounsaturated fatty acid content) of from about 60-90%, preferably from about 70-90% and most preferably, from about 80-90%. The copper-chromium catalyst may also be recovered and reused without regeneration or further treatment prior to reuse.

Claims

1. A process for hydrogenating a polyunsaturated oil, comprising:

(a) reacting said polyunsaturated oil with hydrogen in the presence of a copper-chromium containing catalyst, at a temperature of from about 200-300°

C. and a pressure of from about 300-500 psig, for about 3-8 hours;

(b) removing said catalyst from a product obtained in (a); and

(c) recycling said removed catalyst obtained from (b) to a subsequent hydrogenation reaction, wherein said hydrogenation reaction is carried out as described in (a).

2. The process according to claim 1, wherein the reaction is carried out at a temperature from about 225°

C.

3. The process according to claim 1, wherein the reaction is carried out at a pressure from about 320 psig.

4. The process according to claim 1, wherein the reaction is carried out for about 5 hours.

5. The process according to claim 1, wherein the catalyst is removed by filtration or centrifugation.

6. The process according to claim 5, wherein the catalyst is removed by filtration.

7. The process according to claim 1, wherein said catalyst recycled to step (c) displays essentially no loss of catalytic activity or selectivity, as compared to step (a).

8. The process according to claim 1, wherein said catalyst is fixed on a support material.

9. The process according to claim 8, wherein said catalyst is incorporated within a fixed bed catalyst system.

10. The process according to claim 1, wherein said recycled catalyst is not subjected to further treatment before being recycled to step (a).

11. The process according to claim 1, further comprising:

(d) removing said recycled catalyst from a product obtained in (c).

12. The process of according to claim 11, further comprising:

recycling said catalyst from (d) to subsequent hydrogenation reactions, where said subsequent hydrogenation reactions are carried out as in (a); and

further wherein (a) through (d) are repeated until a loss of greater than 50% catalytic selectivity or catalytic activity is obtained.

13. The process according to claim 11, wherein said catalyst is not subjected to further treatment prior to being recycled.

14. The process according to claim 1, wherein said product is further subjected to fractionation.

15. The hydrogenated oil obtained from the process according to claim 1, having a total percent monounsaturated acid content of from about 60-90%.

16. The hydrogenated oil obtained from the process according to claim 1, having a total percent monounsaturated acid content of from about 70-90%.

17. The hydrogenated oil obtained from the process according to claim 1, having a total percent monounsaturated acid content of from about 80-90%.

18. The hydrogenated oil obtained from the process according to claim 1, wherein said hydrogenated oil is a reactant in a process to make compounds selected from the group consisting of:

diesters of diols, fatty acid alcohols, polyol polyesters, aldehydes, imines and amines.

19. The process according to claim 1, wherein the copper-chromium containing catalyst comprises a mixture of CuO and Cr₂O₃ or CuO and CuCr₂O₄.

20. The process according to claim 19, wherein said copper-chromium containing catalyst further comprises a metal oxide promoter.

21. The process according to claim 20, wherein said promoter is BaO.

22. The hydrogenated oil obtained from the process according to claim 1, wherein said hydrogenated oil is separated into liquid and solid fractions.

23. The hydrogenated oil obtained from the process according to claim 22, wherein said liquid fraction is further subjected to a winterization process.

24. The hydrogenated oil obtained from the process according to claim 22, wherein said liquid fraction is further subjected to fractionation to separate cis and trans isomers in said hydrogenated oil.

25. The process according to claim 1, wherein said polyunsaturated oil is obtained from an animal or a plant.

26. The process according to claim 25, wherein said polyunsaturated oil is obtained from a plant.

27. The process according to claim 26, wherein said plant is genetically engineered or modified.

28. The process according to claim 27, wherein said plant further comprises a fatty acid compositional content which is different than that of the non-genetically engineered or non-modified plant of the same species.

29. The process according to claim 26, wherein said polyunsaturated oil is selected from the group consisting of soybean oil, sunflower oil, rapeseed oil, canola oil and corn oil.

30. The process according to claim 29, wherein said polyunsaturated oil is soybean oil.