IP Library Granted Patent US 9,109,175
Granted Patent B2
US 9,109,175 · App. 13/883,987 · Granted Aug 18, 2015

Isoprenoid based alternative diesel fuel

Inventors: Taek Soon Lee (Albany, CA); Pamela Peralta-Yahya (Atlanta, GA); Jay D. Keasling (Berkeley, CA)
Assignee: The Regents of the University of California
C10L1/1608C10L1/04C10L1/08F02B43/04
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Quick Facts
Patent No.
US 9,109,175
App. No.
13/883,987
Granted
Aug 18, 2015
Kind
B2
Abstract

Fuel compositions are provided comprising a hydrogenation product of a monocyclic sesquiterpene (e.g., hydrogenated bisabolene) and a fuel additive. Methods of making and using the fuel compositions are also disclosed.

Claims (30)

1. A fuel composition, said fuel composition comprising:

(a) a hydrogenation product of a monocyclic sesquiterpene comprising a cyclohexene moiety and a branched alkene moiety; and

(b) a fuel additive,

wherein the hydrogenation product comprises a bisabolane compound of Formula I:

or a stereoisomer thereof.

2. The fuel composition in accordance with claim 1 , wherein said monocyclic sesquiterpene is a member selected from the group consisting of α-zingiberene, β-sesquiphellandrene, α-bisabolene, β-bisabolene, γ-bisabolene, curcumene, gossonorol and mixtures thereof.

3. The fuel composition in accordance with claim 2 , wherein said monocyclic sesquiterpene is α-zingiberene, α-bisabolene, β-bisabolene, γ-bisabolene, curcumene and mixtures thereof.

4. The fuel composition in accordance with claim 2 , wherein said monocyclic sesquiterpene is α-bisabolene or α-zingiberene.

5. The fuel composition in accordance with claim 2 , wherein said monocyclic sesquiterpene is a mixture of α-bisabolene and α-zingiberene.

6. The fuel composition in accordance with claim 1 , wherein the fuel additive is at least one additive selected from the group consisting of an antioxidant, a cetane improver, a stabilizer, a lubricity improver and combinations thereof.

7. The fuel composition in accordance with claim 1 , wherein the fuel composition further comprises a conventional fuel component.

8. The fuel composition in accordance with claim 7 , wherein the conventional fuel component is a petroleum-based fuel.

9. The fuel composition in accordance with claim 8 , wherein the petroleum-based fuel is a member selected from the group consisting of kerosene, Jet A, Jet A-1, Jet B and combinations thereof.

10. The fuel composition in accordance with claim 7 , wherein the conventional fuel component is a petrodiesel or a Fischer-Tropsch-based fuel.

11. The fuel composition in accordance with claim 1 , wherein said fuel additive is selected from the group consisting of an antioxidant, an oxygenate, a thermal stability improver, a stabilizer, a cold flow improver, a combustion improver, an anti-foam additive, an anti-haze additive, a corrosion inhibitor, a lubricity improver, an icing inhibitor, an injector cleanliness additive, a smoke suppressant, a drag reducing additive, a metal deactivator, a dispersant, a detergent, a de-emulsifier, a dye, a marker, a static dissipater, a biocide, a cetane improver and combinations thereof; or said fuel additive is at least one additive selected from the group consisting of an antioxidant, a cetane improver, a stabilizer, a lubricity improver and combinations thereof.

12. A vehicle comprising an internal combustion engine, a fuel tank connected to the internal combustion engine, and a fuel composition in the fuel tank, wherein the fuel composition is the fuel composition of claim 1 , wherein the fuel combustion is used to power the internal combustion engine.

13. A method of powering an engine comprising the step of combusting the fuel composition of claim 1 in the engine.

14. The method of claim 13 , wherein, the engine is a diesel engine.

15. The method of claim 13 , wherein the engine is a jet engine.

16. The fuel composition of claim 1 , wherein the hydrogenation product comprises a bisabolane compound of Formula I:

and stereoisomers thereof.

17. The fuel composition in accordance with claim 16 , wherein the bisabolane compound is produced by chemically converting a monocyclic sesquiterpene starting material from a biological source to the bisabolane compound of Formula I.

18. The fuel composition in accordance with claim 16 , wherein the fuel additive is at least one additive selected from the group consisting of an antioxidant, a cetane improver, a stabilizer, a lubricity improver and combinations thereof.

19. A method of making a fuel composition, said method comprising adding a fuel additive to a hydrogenation product of a monocyclic sesquiterpene comprising a cyclohexene moiety and a branched alkene moiety, wherein the hydrogenation product comprises a bisabolane compound of Formula I:

or a stereoisomer thereof.

20. The method in accordance with claim 19 , wherein said monocyclic sesquiterpene is a member selected from the group consisting of α-zingiberene, β-sesquiphellandrene, α-bisabolene, β-bisabolene, γ-bisabolene, curcumene, gossonorol and mixtures thereof.

21. The method in accordance with claim 20 , wherein said monocyclic sesquiterpene is α-zingiberene, α-bisabolene, β-bisabolene, γ-bisabolene, curcumene and mixtures thereof.

22. The method in accordance with claim 21 , wherein said monocyclic sesquiterpene is α-bisabolene or α-zingiberene.

23. The method in accordance with claim 21 , wherein said monocyclic sesquiterpene is a mixture of α-bisabolene and α-zingiberene.

24. A method of making a fuel component, said method comprising: hydrogenating a monocyclic sesquiterpene, and recovering the hydrogenation product to produce the fuel component, wherein said monocyclic sesquiterpene is a member selected from the group consisting of α-zingiberene, β-sesquiphellandrene, α-bisabolene, β-bisabolene, γ-bisabolene, curcumene, gossonorol and mixtures thereof.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 18, 2013
From: LEE, TAEK SOON; PERALTA-YAHYA, PAMELA; KEASLING, JAY D.
To: THE REGENTS OF THE UNIVERSITY OF CALIFORNIA
Reel/Frame 031621/0325 →
CONFIRMATORY LICENSE Recorded Jun 3, 2013
From: REGENTS OF THE UNIVERSITY OF CALIFORNIA, THE
To: ENERGY, UNITED STATES DEPARTMENT OF
Reel/Frame 030530/0483 →
Continuity (2)
Provisional Application 61411347 · Nov 8, 2010
Related Publication 20130298861A1 · Nov 14, 2013