IP Library Granted Patent US 8,894,782
Granted Patent B2
US 8,894,782 · App. 10/365,102 · Granted Nov 25, 2014

Hypergolic hydrocarbon fuels

Inventors: Thomas A. Dobbins (Howard, OH); David B. Wiley (Warsaw, OH)
Assignee: Wiley Organics, Inc.
C06B43/00
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Quick Facts
Patent No.
US 8,894,782
App. No.
10/365,102
Granted
Nov 25, 2014
Kind
B2
Abstract

Reduced toxicity fuels containing hydrocarbons having both strained rings and internal, conjugated triple bonds are disclosed. The fuels described herein are hypergolic with nitrogen tetroxide and/or inhibited red fuming nitric acid.

Claims (27)

1. A fuel composition comprising a conventional fuel and a compound represented by the formula (I):

wherein R 1 and R 2 are the same or different and represent an alkyl group having from 1 to 5 carbon atoms, provided at least one of R 1 and R 2 represents a cycloalkyl group having from 3 to 4 carbon atoms, wherein said fuel composition is hypergolic when brought into contact with an oxidizer selected from the group consisting of nitrogen tetroxide and inhibited red fuming nitric acid.

2. The fuel composition of claim 1 wherein said compound is selected from the group consisting of 1-methyl-4-cyclopropyl-butadi-yne and 1-ethyl-4-cyclopropyl-butadi-yne.

3. The fuel composition of claim 1 wherein R 1 and R 2 are the same or different and represent a cycloalkyl group having from 3 to 4 carbon atoms.

4. The fuel composition of claim 3 wherein said compound is selected from the group consisting of 1,4-dicyclopropyl-1,3-butadiyne, 1-cyclobutyl-4-cyclopropyl-1,3-butadiyne, and 1,4-dicyclobutyl-1,3-butadi-yne.

5. The fuel composition of claim 1 wherein said conventional fuel is selected from the group consisting of saturated hydrocarbons, unsaturated hydrocarbons, alcohols, organoamines, hydrazines and mixtures thereof.

6. The fuel composition of claim 5 wherein said fuel is selected from the group consisting of kerosene and exo-tetrahydro-dicyclopentadiene.

7. A propellant comprising a fuel composition and an oxidizer wherein said fuel composition comprises a compound represented by the formula (I):

wherein R 1 and R 2 are the same or different and represent an alkyl group having from 1 to 5 carbon atoms, provided at least one of R 1 and R 2 represents a cycloalkyl group having from 3 to 4 carbon atoms and said oxidizer is selected from the group consisting of nitrogen tetroxide and inhibited red fuming nitric acid wherein the fuel composition is hypergolic with the oxidizer.

8. The propellant of claim 7 wherein said compound is selected from the group consisting of 1-methyl-4-cyclopropyl-butadi-yne and 1-ethyl-4-cyclopropyl-butadi-yne.

9. The propellant of claim 7 where R 1 and R 2 are the same or different and represent a cycloalkyl group having from 3 to 4 carbon atoms.

10. The propellant of claim 9 wherein said compound is selected from the group consisting of 1,4-dicyclopropyl-1,3-butadiyne, 1-cyclobutyl-4-cyclopropyl-1,3-butadiyne and 1,4-dicyclobutyl-1,3-butadi-yne.

11. The propellant of claim 7 wherein said fuel composition further comprises a fuel selected from the group consisting of saturated hydrocarbons, unsaturated hydrocarbons, alcohols, organoamines, hydrazines and combinations thereof.

12. The propellant of claim 11 wherein said fuel composition further comprises a fuel selected from the group consisting of hexane, heptane, octane, decane, gasoline, kerosene, ethylene, propylene, butadiene, methanol, ethanol, propanol, and combinations thereof.

13. The propellant of claim 7 wherein said propellant has an oxidizer-to-fuel ratio in the range of about 2:1 to 10:1.

14. The propellant of claim 7 wherein said fuel composition comprises from about 40 percent to 100 percent by weight of the compound represented by formula (I).

15. A method for producing a propellant comprising contacting a fuel with an oxidizer wherein said fuel comprises a compound represented by the formula (I):

where R 1 and R 2 are the same or different and represent an alkyl group having from 1 to 5 carbon atoms, provided at least one of R 1 and R 2 represents a cycloalkyl group having from 3 to 4 carbon atoms and the oxidizer is selected from the group consisting of nitrogen tetroxide and inhibited red fuming nitric acid wherein the fuel is hypergolic with the oxidizer.

16. The method of claim 15 wherein said compound is selected from the group consisting of: 1-methyl-4-cyclopropyl-butadi-yne and 1-ethyl-4-cyclopropyl-butadi-yne.

17. The method of claim 15 wherein R 1 and R 2 are the same or different and represent an alkyl group having from 3 to 4 carbon atoms.

18. The method of claim 17 wherein said compound is selected from the group consisting of 1,4-dicyclopropyl-1,3-butadiyne, 1-cyclobutyl-4-cyclopropyl-1,3-butadiyne, and 1,4-dicyclobutyl-1,3-butadi-yne.

19. The method of claim 15 wherein said fuel further comprises a fuel selected from the group consisting of saturated hydrocarbons, unsaturated hydrocarbons, alcohols, organoamines, hydrazines and combinations thereof.

20. The method of claim 15 wherein said fuel comprises about 40 percent to 100 percent by weight of the compound represented by formula (I).

21. The method of claim 15 wherein said propellant has an oxidizer-to-fuel ratio in the range of about 2:1 to 10:1.

22. The fuel composition of claim 1 wherein the fuel composition comprises from about 40 percent to about 80 percent by weight of the compound represented by formula (I).

23. The fuel composition of claim 22 wherein the compound is selected from the group consisting of 1,4-dicyclopropyl-1,3-butadiyne, 1-cyclobutyl-4-cyclopropyl-1,3-butadiyne, and 1,4-dicyclobutyl-1,3-butadi-yne.

24. The fuel composition of claim 23 wherein the fuel is selected from the group consisting of kerosene and exo-tetrahydro-dicyclopentadiene.

Assignments (2)
CHANGE OF NAME Recorded Jul 20, 2023
From: WILEY ORGANICS, INC.
To: WILEY COMPANIES
Reel/Frame 064353/0966 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 12, 2003
From: DOBBINS, THOMAS A.; WILEY, DAVID B.
To: WILEY ORGANICS, INC.
Reel/Frame 013770/0712 →
Continuity (3)
Provisional Application 60407888 · Sep 3, 2002
Provisional Application 60421370 · Oct 25, 2002
Related Publication 20140209224A1 · Jul 31, 2014