METHOD OF MAKING HYDROGENATED METATHESIS PRODUCTS

• US 20090048459A1
• Filed: 07/10/2008
• Published: 02/19/2009
• Est. Priority Date: 01/10/2006
• Status: Active Grant

• Current Assignee: Wilmar Trading Pte., Ltd. (Wilmar International Limited)
• Original Assignee: Elevance Renewable Sciences Incorporated
• Inventors: Meng, Xiangsheng, Amore, Francis, Kaido, Hiroki, Tupy, Michael John
• Granted Patent: US 8,115,021 B2
• Time in Patent Office: Days
• US Class Current: 554/146
• CPC Class Codes: B01J 31/2265 Carbenes or carbynes, i.e.(image)
• CPC Class Codes: C10G 2300/1014 of vegetal origin
• CPC Class Codes: C10G 45/00 Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
• CPC Class Codes: C10G 69/02 plural serial stages only
• CPC Class Codes: C11C 3/123 using catalysts based principally on nickel or derivates
• CPC Class Codes: C11C 3/126 using catalysts based principally on other metals or derivates
• CPC Class Codes: Y02P 30/20 using bio-feedstock

Abstract

Disclosed is a method of making hydrogenated metathesis products comprising the steps of: (a) providing a metathesis composition; (b) providing a metathesis catalyst comprising a transition metal; (c) metathesizing at least a portion of the metathesis composition in the presence of the metathesis catalyst to form a first composition comprising one or more metathesis products and a transition metal; (d) hydrogenating at least a portion of the first composition in the presence of a hydrogenation catalyst to form a second composition comprising one or more hydrogenated metathesis products, transition metal, and hydrogenation catalyst; and (e) removing at least a portion of the hydrogenation catalyst from the second composition, wherein the removal of the hydrogenation catalyst removes at least a portion of the transition metal of the metathesis catalyst from the second composition.

Claims

1. A method of making hydrogenated metathesis products comprising the steps of:

providing a metathesis composition;

providing a metathesis catalyst comprising a transition metal;

metathesizing at least a portion of the metathesis composition in the presence of the metathesis catalyst to form a first composition comprising one or more metathesis products and a transition metal;

hydrogenating at least a portion of the first composition in the presence of a hydrogenation catalyst to form a second composition comprising one or more hydrogenated metathesis products, transition metal, and hydrogenation catalyst; and

removing at least a portion of the hydrogenation catalyst from the second composition, wherein the removal of the hydrogenation catalyst removes at least a portion of the transition metal of the metathesis catalyst from the second composition.

2. The method of claim 1, wherein the metathesis composition is a polyol ester.

3. The method of claim 2, wherein the metathesis composition is a triacylglyceride.

4. The method of claim 3, wherein the metathesis composition is a vegetable oil

5. The method of claim 4, wherein the vegetable oil is soybean oil.

6. The method of claim 1, wherein the metathesis catalyst is a metal carbene catalyst based upon a transition metal.

7. The method of claim 6, wherein the transition metal is ruthenium, molybdenum, osmium, chromium, rhenium, or tungsten.

8. The method of claim 7, wherein the transition metal is ruthenium.

9. The method of claim 8, wherein the metathesis catalyst is selected from the group of:

where Ph is phenyl, Mes is mesityl, py is pyridine, Cp is cyclopentyl, and Cy is cyclohexyl.

10. The method of claim 1, wherein the hydrogenation catalyst is a homogeneous catalyst.

11. The method of claim 1, wherein the hydrogenation catalyst is a heterogeneous catalyst.

12. The method of claim 1, wherein the hydrogenation catalyst comprises nickel, copper, palladium, or platinum.

13. The method of claim 12, wherein the hydrogenation catalyst comprises nickel, copper, palladium, or platinum on a silica support.

14. The method of claim 12, wherein the hydrogenation catalyst comprises nickel, copper, palladium, or platinum on an alumina support.

15. The method of claim 12, wherein the hydrogenation catalyst comprises nickel, copper, palladium, or platinum on an alumina/silica support.

16. The method of claim 12, wherein the hydrogenation catalyst comprises nickel, copper, palladium, or platinum on a carbon support.

17. The method of claim 1, wherein the hydrogenated metathesis products contains about 100 ppm or less of the metathesis catalyst transition metal.

18. The method of claim 1, wherein the hydrogenated metathesis products contains about 10 ppm or less of the metathesis catalyst transition metal.

19. The method of claim 1, wherein the hydrogenated metathesis product contains about 1 ppm or less of the metathesis catalyst transition metal.

20. The method of claim 1, wherein the hydrogenated metathesis product contains about 0.1 ppm or less of the metathesis catalyst transition metal.

21. The method of claim 1, wherein the metathesis is self-metathesis, cross-metathesis, ring-opening metathesis, ring-opening metathesis polymerizations (ROMP), ring-closing metathesis (RCM), or acyclic diene metathesis (ADMET).

22. The method of claim 1, wherein the metathesis catalyst is

where Cy is cyclohexyl.

23. The method of claim 1, wherein the hydrogenated metathesis product comprises a wax.

24. The method of claim 1, wherein the hydrogenated metathesis product is partially hydrogenated.

25. The method of claim 1, wherein the hydrogenated metathesis product is fully hydrogenated.

26. The method of claim 1, wherein the hydrogenation step is conducted at a temperature of about 20°

C. to about 250°

C.

27. The method of claim 1, wherein the hydrogenation step is conducted at a temperature of about 120°

C. to 220°

C.

28. The method of claim 1, wherein the hydrogenation step is conducted at a hydrogen pressure of about 15 to about 3000 psig.

29. The method of claim 1, wherein the hydrogenation step is conducted at a hydrogen gas pressure of about 40 to about 100 psig.

30. A hydrogenated metathesis product prepared by the method of claim 1.

31. The hydrogenated metathesis product of claim 30, wherein the hydrogenated metathesis product contains about 10 ppm or less of the metathesis catalyst transition metal.

32. The hydrogenated metathesis product of claim 30, wherein the hydrogenated metathesis product contains about 1 ppm or less of the metathesis catalyst transition metal.

33. A hydrogenated metathesis product comprising less than about 1 ppm of metathesis catalyst transition metal.