Renewable high density turbine and diesel fuels from sesquiterpenes

Patent metadata

Field	Value
Publication number	US-9994498-B2
Application number	US-201213676541-A
Country	US
Kind code	B2
Filing date	Nov 14, 2012
Priority date	Jul 29, 2009
Publication date	Jun 12, 2018
Grant date	Jun 12, 2018

Abstract

A fuel and method for conversion of sesquiterpenes to high density fuels. The sesquiterpenes can be either extracted from plants or specifically produced by bioengineered organisms from waste biomass. This approach allows for the synthesis of high performance renewable fuels.

First claim

What is claimed is:

1. A method for manufacturing jet and diesel fuels, comprising:
providing sesquiterpenes isolated from plant extracts and/or biosynthesized from biomass;
purifying said sesquiterpenes to produce purified sesquiterpenes;
converting said purified sesquiterpenes to non-aromatic multicyclic sesquiterpenes by isomerization with at least one heterogeneous acid catalyst;
hydrogenating said non-aromatic multicyclic sesquiterpenes isomers to produce hydrogenated multicyclic sesquiterpenes; and
distilling said hydrogenated non-aromatic multicyclic sesquiterpenes to produce high density fuels, wherein said fuels having a minimum density of 0.85 g/mL and a minimum net heat of combustion of 132,700 btu/gal.

2. The method according to claim 1 , wherein said sesquiterpenes are selected from the group consisting of valencene, premnaspirodiene, caryophyllene, humulene, clovene, neoclovene, panasinsene, thujopsene, longifolene, cubebene, zizaene, santalene, longipinene, isomers of sesquiterpenes, and any mixtures thereof.

3. The method according to claim 1 , wherein said sesquiterpenes are selected from the group consisting of caryophyllene, valencene, premnaspirodiene, or any mixture thereof.

4. The method according to claim 1 , wherein said non-aromatic multicyclic sesquiterpene isomers are at least one isomer selected from the group consisting of α-neoclovene, clovene, or any mixture thereof.

5. The method according to claim 1 , wherein said hydrogenating catalyst having at least one metal selected from the group consisting of Ni, Cu, Pd, Pt, PtO 2 , Ru and the reaction is conducted without a solvent.

6. The method according to claim 1 , wherein said heterogeneous acid catalyst are selected from the group consisting of at least one of Nafion (perfluorinated sulfonic acid resins), Amberlyst (cross-linked sulfonic acid resins), Montmorillonite K-10, polyphosphoric acids, cation exchange resins, Lewis acid catalysts, supported Bronsted acid catalysts, mineral acids including H 2 SO 4 and H 3 PO 4 , and any mixtures thereof.

7. The method according to claim 1 , wherein said plant extracts are selected from the group consisting of clove oil or any essential oil having significant quantities of cyclic sesquiterpenes, and mixtures of said oils.

8. The method according to claim 1 , wherein said biomass includes at least one of sucrose, glucose, fructose, cellobiose, other reducing sugars, cellulose, and hemicelluloses in any proportion.

9. The method according to claim 1 , wherein said high density fuels are pure sesquiterpanes or prepared by selective fractional distillation of hydrogenated multicyclic sesquiterpane mixtures with density >0.90 g/mL and net heat of combustion >137,000 Btu/gal).

10. The method according to claim 1 , wherein said high density diesel fuels are pure sesquiterpanes or generated by selective fractional distillation of hydrogenated multicyclic sesquiterpane mixtures with cetane number >30.

11. The method according to claim 1 , wherein said high density diesel fuels are generated by blending hydrogenated multicyclic sesquiterpane mixtures with known cetane enhancers.

12. The method according to claim 1 , wherein said high density fuels are generated by blending hydrogenated multicyclic sesquiterpene fuels with petroleum-based fuels including JP-10, RJ-4, JP-8, JP-5, F-76, Diesel #2, Jet A, and any renewable fuel.

13. The method according to claim 1 , wherein said high density missile/turbine fuels are blends of hydrogenated multicyclic sesquiterpanes with JP-10 in a desired proportion.

14. The method according to claim 1 , wherein said high density jet fuels are blends of hydrogenated multicyclic sesquiterpanes with jet fuels including JP-5, JP-8, and Jet A.

15. The method according to claim 1 , wherein said high density diesel fuels are blends of hydrogenated multicyclic sesquiterpanes with petroleum-derived diesel fuel.

16. The method according to claim 1 , wherein said high density jet/diesel fuels are blends of hydrogenated multicyclic sesquiterpanes with fuels generated by ethylene oligomerization.

17. The method according to claim 1 , wherein said high density jet/diesel fuels are blends of hydrogenated multicyclic sesquiterpanes with fuels generated by butene oligomerization.

18. The method according to claim 1 , wherein said high density jet/diesel fuels are blends of hydrogenated multicyclic sesquiterpanes with fuels generated by hexene oligomerization.

19. The method according to claim 1 , wherein said high density jet/diesel fuels are blends of hydrogenated multicyclic sesquiterpanes with diesel fuels produced from natural gas.

20. High density fuels produced from the methods of claim 1 .

21. A method for manufacturing jet and diesel fuels, comprising:
providing sesquiterpenes isolated from plant extracts and/or biosynthesized from biomass;
purifying said sesquiterpenes to purified sesquiterpenes;
converting said purified sesquiterpenes to non-aromatic multicyclic sesquiterpenes with at least one heterogeneous acid catalyst to produce non-aromatic multicyclic sesquiterpene isomers; and
distilling said non-aromatic multicyclic sesquiterpene isomers producing a set of fuels.

22. A set of fuels produced from the methods of claim 21 .

Assignees

• Us Navy

Inventors

• Harvey Benjamin G
• Meylemans Heather A

Classifications

• C10G3/45

  containing iron group metals or compounds thereof · CPC title

• C07C5/2506

  Catalytic processes · CPC title

• C10G3/50

  in the presence of hydrogen, hydrogen donors or hydrogen generating compounds · CPC title

• Y02T50/678

  Aviation using fuels of non-fossil origin · CPC title

• C10L1/04 Primary

  essentially based on blends of hydrocarbons · CPC title