IP Library Granted Patent US 11,566,009
Granted Patent B1
US 11,566,009 · App. 16/875,544 · Granted Jan 31, 2023

Energetic compound embodiments and methods of making and using the same

Inventors: David Chavez (Los Alamos, NM); Jesse Sabatini (Bel Air, MD); Pablo Guzmán (Bel Air, MD); Leah Wingard (Landenberg, PA); Eric Johnson (Millington, MD)
Assignees: Triad National Security, LLC; The United States of America as represented by the Secretary of the Army
C07D271/06C06B25/34
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Quick Facts
Patent No.
US 11,566,009
App. No.
16/875,544
Granted
Jan 31, 2023
Kind
B1
Abstract

Disclosed herein are embodiments of an energetic compound and methods of making and using the same. Energetic compound embodiments disclosed herein exhibit physical and chemical properties that facilitate their use in various applications, such as high energy propellant plasticizers, melt-castable explosives, and the like. Efficient and safe method embodiments for making the disclosed energetic compound embodiments are described herein.

Claims (21)

1. A compound having a structure of Formula I,

wherein

each X independently is selected from carbon, CH, nitrogen, NH, or oxygen such that each five-membered ring of Formula I independently is heteroaryl selected from an oxadiazole or an isomer thereof; an oxatriazole or an isomer thereof; or an oxazole having a formula

each Y independently is selected from aliphatic-ONO 2 wherein aliphatic is an alkyl group comprising 1 to 5 carbon atoms; and

each n independently is an integer ranging from 1 to 4.

2. The compound of claim 1 , wherein each five-membered ring of Formula I is an oxadiazole.

3. The compound of claim 1 , wherein the alkyl group is a methylene group.

4. The compound of claim 1 , wherein each Y is —CH 2 ONO 2 and each n is 1.

5. The compound of claim 1 , having a structure of Formula II or Formula III

6. The compound of claim 5 , wherein each Y independently is —CH 2 ONO 2 .

7. The compound of claim 1 , wherein the compound is

8. The compound of claim 1 , wherein the compound has a decomposition temperature ranging from 140° C. to 195° C.

9. The compound of claim 1 , wherein the compound has an onset temperature of melting that ranges from greater than 80° C. to 85° C.

10. The compound of claim 1 , wherein the compound has an explosive density ranging from greater than 1.75 g/cm 3 to 2 g/cm 3 .

11. The compound of claim 1 , wherein the compound has a detonation velocity greater than 8000 m/s to 8200 m/s.

12. A compound selected from

13. A method, comprising using an energetic compound to make a melt-castable explosive composition and/or a propellant plasticizer composition, wherein the energetic compound has a structure of Formula I,

wherein

each X independently is selected from carbon, CH, nitrogen, NH, or oxygen such that each five-membered ring of Formula I independently is heteroaryl selected from an oxadiazole or an isomer thereof; an oxatriazole or an isomer thereof; or an oxazole having a formula

each Y independently is selected from aliphatic-ONO 2 wherein aliphatic is an alkyl group comprising 1 to 5 carbon atoms; and

each n independently is an integer ranging from 1 to 4.

Assignments (3)
CONFIRMATORY LICENSE Recorded Aug 6, 2020
From: TRIAD NATIONAL SECURITY, LLC
To: U.S. DEPARTMENT OF ENERGY
Reel/Frame 053422/0617 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 29, 2020
From: CHAVEZ, DAVID
To: TRIAD NATIONAL SECURITY, LLC
Reel/Frame 052790/0569 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 29, 2020
From: SABATINI, JESSE; GUZMÁN, PABLO; WINGARD, LEAH; JOHNSON, ERIC
To: THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY OF THE ARMY
Reel/Frame 052790/0717 →
Continuity (1)
Provisional Application 62849676 · May 17, 2019