IP Library Granted Patent US 10,246,428
Granted Patent B2
US 10,246,428 · App. 15/686,195 · Granted Apr 2, 2019

Insensitive plasticizer and melt-castable energetic material

Inventors: Jesse J. Sabatini (Bel Air, MD); Gregory W. Drake (Madison, AL); Leah A. Wingard (Landenberg, PA); Eric C. Johnson (Millington, MD)
Assignee: The United States of America as represented by the Secretary of the Army
C07D261/08C06B25/00
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Quick Facts
Patent No.
US 10,246,428
App. No.
15/686,195
Granted
Apr 2, 2019
Kind
B2
Abstract

A method and compound includes mixing dichloroglyoxime with an alcohol containing an alkyne functional group in methanol to create a mixture; adding a salt compound and water to the mixture to create bis-isoxazole diol; and nitrating the bis-isoxazole diol to create 3,3′-bis-isoxazole-5,5′-bis-methylene dinitrate, which has the structural formula: The alcohol containing an alkyne functional group may include propargyl alcohol. The salt compound may include sodium bicarbonate. The method may include nitrating the bis-isoxazole diol with nitric acid. The nitric acid may include at least a concentration of 90% nitric acid in water. Alternatively, the method may include nitrating the bis-isoxazole diol with 100% nitric acid and acetic anhydride. The salt compound and the water may be added to the mixture over at least a six-hour period. The method may include mixing the mixture after adding the salt compound and the water for at least ten hours.

Claims (26)

1. A method comprising:

mixing dichloroglyoxime with an alcohol containing an alkyne functional group in methanol to create a mixture;

adding a salt compound and water to said mixture to create bis-isoxazole diol; and

nitrating said bis-isoxazole diol to create 3,3′-bis-isoxazole-5,5′-bis-methylene dinitrate.

2. The method of claim 1 , wherein said 3,3′-bis-isoxazole-5,5′-bis-methylene dinitrate has the structural formula:

3. The method of claim 1 , wherein said alcohol containing an alkyne functional group is propargyl alcohol.

4. The method of claim 1 , wherein said salt compound is comprises sodium bicarbonate.

5. The method of claim 1 , wherein said nitrating comprises nitrating said bis-isoxazole diol with nitric acid.

6. The method of claim 5 , wherein said nitric acid comprises at least a concentration of 90% nitric acid in water.

7. The method of claim 1 , wherein said nitrating comprises nitrating said bis-isoxazole diol with 100% nitric acid and acetic anhydride.

8. The method of claim 1 , wherein said salt compound and said water are added to said mixture over at least a six-hour period.

9. The method of claim 8 , further comprising mixing said mixture after adding said salt compound and said water for at least ten hours.

10. The method of claim 1 , wherein said mixing results in 0.1M dichloroglyoxime in methanol.

11. A compound having the structural formula:

12. A 3,3′-bis-isoxazole-5,5′-bis-methylene dinitrate compound formed by:

mixing dichloroglyoxime with an alcohol containing an alkyne functional group in methanol to create a mixture;

adding a salt compound and water to said mixture to create bis-isoxazole diol; and

nitrating said bis-isoxazole diol to create 3,3′-bis-isoxazole-5,5′-bis-methylene dinitrate.

13. The compound of claim 12 , wherein said alcohol containing an alkyne functional group is propargyl alcohol.

14. The compound of claim 12 , wherein said salt compound is sodium bicarbonate.

15. The compound of claim 12 , wherein the nitration occurs with nitric acid.

16. The compound of claim 15 , wherein said nitric acid comprises at least a concentration of 90% nitric acid in water.

17. The compound of claim 12 , wherein the nitration occurs with 100% nitric acid and acetic anhydride.

18. The compound of claim 12 , wherein said salt compound and said water are added to said mixture over at least a six-hour period.

19. The compound of claim 12 , wherein said mixture is mixed after adding said salt compound and said water for at least ten hours.

20. The compound of claim 12 , wherein said mixing results in 0.1M dichloroglyoxime in methanol.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 30, 2017
From: SABATINI, JESSE J; DRAKE, GREGORY W
To: THE UNITED STATES OF AMERICA AS REPRESENTED BY THE SECRETARY OF THE ARMY
Reel/Frame 043448/0740 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 30, 2017
From: WINGARD, LEAH A
To: THE UNITED STATES OF AMERICA AS REPRESENTED BY THE SECRETARY OF THE ARMY
Reel/Frame 043448/0850 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 30, 2017
From: TKC GLOBAL SOLUTIONS, LLC
To: THE UNITED STATES OF AMERICA AS REPRESENTED BY THE SECRETARY OF THE ARMY
Reel/Frame 043448/0982 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 30, 2017
From: JOHNSON, ERIC C
To: TKC GLOBAL SOLUTIONS, LLC
Reel/Frame 043449/0250 →
Continuity (1)
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