Insensitive plasticizer and melt-castable energetic material

Patent metadata

Field	Value
Publication number	US-10246428-B2
Application number	US-201715686195-A
Country	US
Kind code	B2
Filing date	Aug 25, 2017
Priority date	Aug 25, 2017
Publication date	Apr 2, 2019
Grant date	Apr 2, 2019

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.

First claim

What is claimed is:

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.

Assignees

• The Us Secretary Of The Army U S Army Research Laborator
• Us Army

Inventors

• Sabatini Jesse J
• Drake Gregory W
• Wingard Leah A
• Johnson Eric C

Classifications

• C06B25/00

  Compositions containing a nitrated organic compound · CPC title

• C07D261/08 Primary

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title

• C06B45/105

  The resin being a polymer bearing energetic groups or containing a soluble organic explosive · CPC title