Base oils and methods for making the same

Patent metadata

Field	Value
Publication number	US-9862906-B2
Application number	US-201214112238-A
Country	US
Kind code	B2
Filing date	Feb 13, 2012
Priority date	Apr 13, 2011
Publication date	Jan 9, 2018
Grant date	Jan 9, 2018

Abstract

Provided herein are isoparaffins derived from hydrocarbon terpenes such as myrcene, ocimene and farnesene, and methods for making the same. In certain variations, the isoparaffins have utility as lubricant base stocks.

First claim

What is claimed is:

1. A method for making a base oil, the method comprising:
coupling a hydrocarbon terpene feedstock obtained from a renewable carbon source with one or more non-terpene olefin co-monomers in the presence of a catalyst to form one or more branched alkenes comprising one or more hydrocarbon terpene:olefin adducts;
hydrogenating the branched alkenes to form one or more isoparaffins; and
making a base oil from at least a portion of the isoparaffins, wherein the base oil has at least 25% renewable carbon content.

2. The method of claim 1 , wherein the one or more non-terpene olefin co-monomers comprise one or more alpha-olefins.

3. The method of claim 1 , wherein the one or more non-terpene olefin co-monomers are a linear alkene or a branched alkene containing at most two branches.

4. The method of claim 1 , adapted for making a base oil with a kinematic viscosity at 100° C. of about 2-3 cSt, about 4-5 cSt, about 6-8 cSt, or about 9-10 cSt.

5. The method of claim 1 , adapted for making a base oil with a viscosity index of at least about 120, about 130, or about 140.

6. The method of claim 1 , comprising one of the following:
selecting the one or more non-terpene olefin co-monomers and/or a coupling mechanism to modulate a degree of branching in the base oil;
tuning coupling conditions to form predominantly 1:1 hydrocarbon terpene:olefin adducts;
tuning coupling conditions to form a mixture of 1:1 hydrocarbon terpene:olefin adducts and 1:2 hydrocarbon terpene:olefin adducts;
distilling the isoparaffins to form one or more distillation cuts, and making the base oil from at least one of the distillation cuts;
adding a pour point depressant to the at least a portion of the isoparaffins to make the base oil; and
adding a viscosity modifier to the at least a portion of the isoparaffins to make the base oil.

7. The method of claim 2 , comprising increasing a carbon chain length of the one or more alpha-olefins to increase a viscosity index of the base oil.

8. The method of claim 2 , wherein the hydrocarbon terpene feedstock comprises a conjugated diene moiety, and the coupling comprises a hydrovinylation reaction between the conjugated diene moiety and the alpha-olefin.

9. The method of claim 8 , wherein the catalyst comprises a Co(I) catalyst.

10. The method of claim 1 , wherein the hydrocarbon terpene feedstock comprises a partially hydrogenated terpene, and the catalyst comprises a cationic initiator.

11. The method of claim 10 , wherein the cationic initiator comprises a protic acid preferrably sulfuric acid.

12. The method of claim 10 , wherein the catalyst comprises a Lewis acid, a first co-catalyst and a second co-catalyst.

13. The method of claim 12 , wherein the Lewis acid comprises BF 3 , the first co-catalyst comprises an alcohol having the formula R 1 OH, and the second co-catalyst comprises an ester having the formula R 2 CO 2 R 1 , with R 1 being a C 1 -C 10 linear or branched alkyl group and R 2 being a C 1 -C 4 linear or branched alkyl group; preferably the first co-catalyst comprises n-butanol; or the first co-catalyst comprises n-butanol and the second co-catalyst comprises n-butyl acetate.

14. The method of claim 13 , capable of forming isoparaffins in which branching originates predominantly from the hydrocarbon terpene feedstock, or branching comprises predominantly methyl groups.

15. The method of claim 1 , wherein the hydrocarbon terpene feedstock comprises β-farnesene.

16. The method of claim 1 , wherein the hydrocarbon terpene feedstock comprises partially hydrogenated hydrocarbon terpene, preferably partially hydrogenated β-farnesene.

17. The method of claim 2 , wherein the one or more alpha-olefins are selected from the group consisting of 1-hexene, 1-octene, 1-decene, 1-dodecene, 1-tetradecene, 1-hexadecene, 1-octadecene, 1-eicosene, and any combination of two or more thereof.

18. The method of claim 2 , wherein the hydrocarbon terpene feedstock comprises β-farnesene or partially hydrogenated β-farnesene; and the one or more alpha-olefins are selected from the group consisting of 1-decene, 1-dodecene, 1-tetradecene, 1-hexadecene, 1-octadecene, and any combination of two or more thereof, preferably selected from the group consisting of 1-tetradecene, 1-hexadecene, or a mixture of 1-tetradecene and 1-hexadecene, more preferably a mixture of 1-tetradecene and 1-hexadecene.

19. The method of claim 1 , comprising distilling the isoparaffins to form one or more distillation cuts, and making the base oil from at least one of the distillation cuts; wherein a first lighter distillation cut of the isoparaffins is used to make a first base oil and a second heavier distillation cut of the isoparaffins is to make a second base oil.

20. A base oil comprising hydrocarbon terpene feedstock:non-terpene olefin adducts, hydrogenated, wherein the hydrocarbon terpene feedstock is obtained from a renewable carbon source, and wherein the base oil has at least 25% renewable carbon content.

21. The base oil of claim 20 , comprising 1:1 hydrocarbon terpene feedstock:non-terpene olefin adducts, hydrogenated; 1:2 hydrocarbon terpene feedstock:non-terpene olefin adducts, hydrogenated; or 2:1 hydrocarbon terpene feedstock:non-terpene olefin adducts, hydrogenated.

22. The base oil of claim 20 , having a viscosity index of at least about 120, about 130, or about 140.

23. The base oil of claim 20 , having a kinematic viscosity at 100° C. of about 4 cSt, about 5 cSt, or about 3 cSt and a viscosity index of about 120 or higher.

24. The base oil of claim 20 , comprising β-farnesene:alpha-olefin adducts or partially hydrogenated β-farnesene:alpha-olefin adducts, hydrogenated.

25. The base oil of claim 24 , comprising
β-farnesene:1-decene adducts or partially hydrogenated β-farnesene:1-decene adducts, hydrogenated;
β-farnesene:1-dodecene adducts or partially hydrogenated β-farnesene:1-dodecene adducts, hydrogenated;
β-farnesene:1-tetracene adducts or partially hydrogenated β-farnesene:1-tetracene adducts, hydrogenated; β-farnesene:1-hexadecene adducts or partially hydrogenated β-farnesene:1-hexadecene adducts, hydrogenated;
β-farnesene:1-octadecene adducts or partially hydrogenated β-farnesene:1-octadecene adducts, hydrogenated;
β-farnesene:1-tetradecene adducts, hydrogenated and β-farnesene:1-hexadecene adducts, hydrogenated; or
partially hydrogenated β-farnesene:1-tetradecene adducts and partially hydrogenated β-farnesene:1-hexadecene adducts, hydrogenated.

26. The base oil of claim 20 , comprising a pour point depressant and/or a viscosity modifier.

27. The base oil of claim 20 , wherein the hydrocarbon terpene feedstock comprises a partially hydrogenated hydrocarbon terpene.

28. The base oil of claim 27 , wherein the hydrocarbon terpene feedstock comprises partially hydrogenated β-farnesene.

29. The base oil of claim 28 , wherein the non-terpene olefin comprises 1-tetradecene, 1-hexadecene, or a mixture of 1-tetradecene and 1-hexadecene.

30. The base oil of claim 20 , comprising at least about 85% 1:1 hydrocarbon terpene feedstock:non-terpene olefin adducts; or at least about 70% trimeric hydrocarbon terpene feedstock:non-terpene olefin adducts.

31. The base oil of claim 20 , having at least about 50% renewable carbon content; or about 100% renewable carbon content.

Assignees

• Ohler Nicholas
• Fisher Karl
• Tirmizi Shakeel
• Amyris Inc

Inventors

• Ohler Nicholas
• Fisher Karl
• Tirmizi Shakeel

Classifications

• C07C5/03

  of non-aromatic carbon-to-carbon double bonds · CPC title

• C10M2205/083

  used as base material · CPC title

• C10M2203/024

  unsaturated · CPC title

• C10M107/14

  containing conjugated diene · CPC title

• C07C2523/44

  Palladium · CPC title