Fuel compositions comprising tetramethylcyclohexane
View Patent ↗A fuel composition comprises at least a tetramethylcyclohexane and a fuel component. The tetramethylcyclohexane can be used as a fuel component or as a fuel additive in the fuel composition. The fuel composition may further comprise a conventional fuel component selected from a petroleum-based fuel component such as diesel fuel, jet fuel, kerosene or gasoline; or a coal-based fuel component. Methods of making and using the fuel composition are also disclosed.
1. A fuel composition comprising:
(a) a tetramethylcyclohexane having a quaternary carbon atom in the cyclohexane ring in an amount of at least 5 wt. %, based on the total weight of the fuel composition; and
(b) a fuel component.
2. The fuel composition of claim 1 , wherein the tetramethylcyclohexane is
or at least one stereoisomer thereof.
3. The fuel composition of claim 1 , wherein the tetramethylcyclohexane is
or at least one stereoisomer thereof.
4. The fuel composition of claim 1 , wherein the fuel component is a petroleum-based fuel component.
5. The fuel composition of claim 4 , wherein the petroleum-based fuel component is gasoline.
6. The fuel composition of claim 4 , wherein the petroleum-based fuel component is jet fuel.
7. The fuel composition of claim 4 , wherein the petroleum-based fuel component is kerosene.
8. The fuel composition of claim 1 , wherein the fuel component is a coal-based fuel component.
9. The fuel composition of claim 1 further comprising a fuel additive.
10. The fuel composition of claim 9 , the fuel additive is selected from the group consisting of oxygenates, antioxidants, thermal stability improvers, cetane improvers, stabilizers, cold flow improvers, combustion improvers, anti-foams, anti-haze additives, corrosion inhibitors, lubricity improvers, icing inhibitors, injector cleanliness additives, smoke suppressants, drag reducing additives, metal deactivators, dispersants, detergents, demulsifiers, dyes, markers, static dissipaters, biocides and combinations thereof.
11. The fuel composition of claim 1 , wherein the amount of the tetramethylcyclohexane is at most about 30 wt. %, based on the total weight of the fuel composition.
12. The fuel composition of claim 1 , wherein the amount of the tetramethylcyclohexane is at most about 20 wt. %, based on the total weight of the fuel composition.
13. The fuel composition of claim 1 , wherein the amount of the tetramethylcyclohexane is at most about 10 wt. %, based on the total weight of the fuel composition.
14. The fuel composition of claim 1 comprising:
or at least one stereoisomer thereof;
or at least one stereoisomer thereof;
or at least one stereoisomer thereof; and
or at least one stereoisomer thereof, wherein the total amount of (a) and (b) is from about 1 wt. % to about 99 wt. %, and the total amount of (c) and (d) is from 0.5 wt. % to about 50 wt. %, based on the total weight of (a)-(d).
15. The fuel composition of claim 14 further comprising:
or at least one stereoisomer thereof;
and
or at least one stereoisomer thereof; wherein the amount of (e) is from 0 wt. % to about 50 wt. %, the amount of (0 is from about 0.1 wt. % to about 20 wt. %, and the amount of (g) is from about 0.1 wt. % to about 30 wt. %, based on the total weight of (a)-(g).
16. The fuel composition of claim 15 , wherein the total amount of (a) and (b) is from about 50 wt. % to about 99 wt. %, based on the total weight of (a)-(g).
17. The fuel composition of claim 15 , wherein the total amount of (a) and (b) is from about 80 wt. % to about 99 wt. %, based on the total weight of (a)-(g).
18. The fuel composition of claim 15 , wherein the total amount of (c) and (d) is less than about 10 wt. %, based on the total weight of (a)-(g).
19. The fuel composition of claim 1 that is an RBOB, CARBOB or AZ RBOB.
20. The fuel composition of claim 1 that has a Reid vapor pressure between 7.0 psi and 15.0 psi.
21. A method of making a fuel composition comprising contacting pinene with hydrogen in the presence of a hydrogenation catalyst to form at least a tetramethylcyclohexane.
22. The method of claim 21 , wherein the pinene is α-pinene, β-pinene or a combination thereof.
23. The method of claim 21 , wherein the hydrogenation catalyst comprises a ruthenium catalyst.
24. The method of claim 23 , wherein the ruthenium catalyst is ruthenium on a support material.
25. The method of claim 24 , wherein the support material is carbon.
26. The method of claim 21 , further comprising the step of mixing the tetramethylcyclohexane with a fuel component to make the fuel composition.
27. The method of claim 26 , wherein the fuel component is a petroleum-based fuel component.
28. The method of claim 27 , wherein the petroleum-based fuel component is gasoline.
29. The method of claim 27 , wherein the petroleum-based fuel component is jet fuel.
30. The method of claim 27 , wherein the petroleum-based fuel component is kerosene.
31. 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 comprises at least 5 wt. % of a tetramethylcyclohexane having a quaternary carbon atom in the cyclohexane ring, based on the total weight of the fuel composition, and a fuel component, and wherein the fuel composition is used to power the internal combustion engine.
32. The vehicle of claim 31 , wherein the internal combustion engine is a gasoline engine.
33. The vehicle of claim 31 , wherein the tetramethylcyclohexane is
or at least one stereoisomer thereof.
34. The vehicle of claim 31 , wherein the tetramethylcyclohexane is
or at least one stereoisomer thereof.
35. 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 prepared by contacting pinene with hydrogen in the presence of a hydrogenation catalyst, and wherein the fuel composition is used to power the internal combustion engine.
36. The vehicle of claim 35 , wherein the pinene is α-pinene, β-pinene or a combination thereof.
37. The vehicle of claim 35 , wherein the internal combustion engine is a gasoline engine.
38. A method of making a fuel composition comprising:
(a) contacting a cell capable of making pinene with a sugar under conditions suitable for making pinene;
(b) converting the pinene to pinane;
(c) converting the pinane to at least a tetramethylcyclohexane; and
(d) mixing the tetramethylcyclohexane with a fuel component to make the fuel composition.
39. The method of claim 38 , wherein the pinene is converted to pinane by hydrogen in the presence of a first hydrogenation catalyst.
40. The method of claim 38 , wherein the pinane is converted to tetramethylcyclohexane by hydrogen in the presence of a second hydrogenation catalyst.
41. A method of making an RBOB comprising mixing a gasoline with a fuel composition comprising a tetramethylcyclohexane having a quaternary carbon atom in the cyclohexane ring, wherein the RBOB has a Reid vapor pressure from about 7.0 psi to about 15.0 psi, and wherein the amount of the tetramethylcyclohexane is from about 1 wt. % to about 50 wt. %, based on the total weight of the fuel composition.
42. The method of claim 41 , wherein the tetramethylcyclohexane is
or at least one stereoisomer thereof.
43. The method of claim 41 , wherein the tetramethylcyclohexane is
or at least one stereoisomer thereof.
44. A fuel tank containing a fuel composition, wherein the fuel composition comprises at least 5 wt. % of a tetramethylcyclohexane having a quaternary carbon atom in the cyclohexane ring, based on the total weight of the fuel composition, and a fuel component.
45. The fuel tank of claim 44 , wherein the tetramethylcyclohexane is
or at least one stereoisomer thereof.
46. The fuel tank of claim 44 , wherein the tetramethylcyclohexane is
or at least one stereoisomer thereof.
47. The fuel tank of claim 44 , wherein the fuel tank is a vehicle fuel tank.
48. A fuel composition comprising a gasoline and at least one tetramethylcyclohexane having a quaternary carbon atom in the cyclohexane ring, wherein the amount of the tetramethylcyclohexane is from about 1 wt. % to about 50 wt. %, based on the total weight of the fuel composition.
49. The fuel composition of claim 48 , wherein the tetramethylcyclohexane is
or at least one stereoisomer thereof.
50. The fuel composition of claim 48 , wherein the tetramethylcyclohexane is
or at least one stereoisomer thereof.
51. The fuel composition of claim 50 further comprising a fuel additive.
52. The fuel composition of claim 51 , the fuel additive is selected from the group consisting of oxygenates, antioxidants, thermal stability improvers, cetane improvers, stabilizers, cold flow improvers, combustion improvers, anti-foams, anti-haze additives, corrosion inhibitors, lubricity improvers, icing inhibitors, injector cleanliness additives, smoke suppressants, drag reducing additives, metal deactivators, dispersants, detergents, demulsifiers, dyes, markers, static dissipaters, biocides and combinations thereof.