Energetic compound embodiments and methods of making and using the same

Patent metadata

Field	Value
Publication number	US-11566009-B1
Application number	US-202016875544-A
Country	US
Kind code	B1
Filing date	May 15, 2020
Priority date	May 17, 2019
Publication date	Jan 31, 2023
Grant date	Jan 31, 2023

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.

First claim

We claim:

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.

Assignees

• Triad Nat Security Llc
• Us Army

Inventors

• Chavez David
• Sabatini Jesse
• Guzmán Pablo
• Wingard Leah
• Johnson Eric

Classifications

• C07D271/06 Primary

  1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles · CPC title

• C06B25/34

  the compound being a nitrated acyclic, alicyclic or heterocyclic amine · CPC title