Method of making hydrogenated metathesis products

• US 8,115,021 B2
• Filed: 07/10/2008
• Issued: 02/14/2012
• 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: Tupy, Michael John, Amore, Francis, Kaido, Hiroki, Meng, Xiangsheng
• Primary Examiner(s): Carr, Deborah D
• Application Number:
  US12/170,818
• Publication Number:
  US 20090048459A1
• Time in Patent Office: 1,314 Days
• Field of Search: 554/146
• 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:

(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

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, wherein the metathesis composition is a polyol ester.

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

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

4. The method of claim 3, wherein the vegetable oil is soybean oil.

19. 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).

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

5. 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

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, wherein the metathesis catalyst is a metal carbene catalyst based upon a transition metal.

6. The method of claim 5, wherein the transition metal is ruthenium, molybdenum, osmium, chromium, rhenium, or tungsten.

7. The method of claim 6, wherein the transition metal is ruthenium.

8. The method of claim 7, wherein the metathesis catalyst is selected from the group of:

20. The method of claim 7, wherein the metathesis catalyst is

9. 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

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, wherein the hydrogenation catalyst is a homogeneous catalyst or a heterogeneous catalyst.

10. The method of claim 9, wherein the hydrogenation catalyst comprises nickel, copper, palladium, or platinum.

11. The method of claim 10, wherein the hydrogenation catalyst comprises nickel, copper, palladium, or platinum on a silica support.

12. The method of claim 10, wherein the hydrogenation catalyst comprises nickel, copper, palladium, or platinum on an alumina support.

13. The method of claim 10, wherein the hydrogenation catalyst comprises nickel, copper, palladium, or platinum on an alumina/silica support.

14. The method of claim 10, wherein the hydrogenation catalyst comprises nickel, copper, palladium, or platinum on a carbon support.

15. 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

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, wherein the one or more hydrogenated metathesis products contains about 100 ppm or less of the metathesis catalyst transition metal.

16. The method of claim 15, wherein the hydrogenated metathesis products contains about 10 ppm or less of the metathesis catalyst transition metal.

17. The method of claim 15, wherein the hydrogenated metathesis product contains about 1 ppm or less of the metathesis catalyst transition metal.

18. The method of claim 15, wherein the hydrogenated metathesis product contains about 0.1 ppm or less of the metathesis catalyst transition metal.

22. 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

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, wherein the hydrogenated metathesis product is partially hydrogenated or fully hydrogenated.

23. 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

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, wherein the hydrogenation step is conducted at a temperature of about 20°

C. to about 250°

C.

24. The method of claim 23, wherein the hydrogenation step is conducted at a temperature of about 120°

C. to 220°

C.

25. 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

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, wherein the hydrogenation step is conducted at a hydrogen pressure of about 15 to about 3000 psig.

26. The method of claim 25, wherein the hydrogenation step is conducted at a hydrogen gas pressure of about 40 to about 100 psig.