IP Library › Granted Patent US 9,994,498
Granted Patent B2
US 9,994,498 · App. 13/676,541 · Granted Jun 12, 2018

Renewable high density turbine and diesel fuels from sesquiterpenes

Inventors: Benjamin G. Harvey (Ridgecrest, CA); Heather A. Meylemans (Ridgecrest, CA)
Assignee: The United States of America as Represented by the Secretary of the Navy
C07C5/13C07C5/2506C07C7/00C10G1/00C10G3/42C10G3/44C10G3/45C10G3/50C10L1/04C10L1/08C10G2300/1014C10G2400/04C10G2400/08Y02E50/13Y02P30/20Y02T50/678
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Quick Facts
Patent No.
US 9,994,498
App. No.
13/676,541
Granted
Jun 12, 2018
Kind
B2
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.

Claims (31)

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 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 14, 2012
From: HARVEY, BENJAMIN G.; MEYLEMANS, HEATHER A
To: UNITED STATES OF AMERICA AS REPRESENTED BY THE SECRETARY OF THE NAVY
Reel/Frame 029295/0702 →
Continuity (4)
Continuation In Part 12511796 · Jul 29, 2009
Provisional Application 61562681 · Nov 22, 2011
Related Publication 20150031927A1 · Jan 29, 2015
Related Publication 20150315097A9 · Nov 5, 2015