# US 10,246,428 B2 · Insensitive plasticizer and melt-castable energetic material

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- Number: US 10,246,428 B2
- Document ID: US10246428B2
- Status: Granted
- Kind: B2
- Application number: 15/686,195
- Filed: 2017-08-25
- Published: 2019-02-28
- Granted: 2019-04-02
- Earliest claimed: 2017-08-25
- Assignees: The United States of America as represented by the Secretary of the Army
- Applicants: The United States of America AS Represented By the Secretary of the Army-U.S. Army Research Laborator
- Inventors: Jesse J. Sabatini; Gregory W. Drake; Leah A. Wingard; Eric C. Johnson
- Web page: https://patentgrep.com/patent/US10246428B2

## CPC

- C07D 261/08: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C06B 25/00: Compositions containing a nitrated organic compound
- C06B 45/105: {The resin being a polymer bearing energetic groups or containing a soluble organic explosive}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C06B: EXPLOSIVES OR THERMIC COMPOSITIONS (blasting F42D); MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES (compounds in general C01, C07 or C08; {demolition agents based on cementitious or like materials C04B41/0009})

## 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

### Claim 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.

### Claim 2 (depends on 1)

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

### Claim 3 (depends on 1)

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

### Claim 4 (depends on 1)

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

### Claim 5 (depends on 1)

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

### Claim 6 (depends on 5)

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

### Claim 7 (depends on 1)

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

### Claim 8 (depends on 1)

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

### Claim 9 (depends on 8)

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

### Claim 10 (depends on 1)

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

### Claim 11

A compound having the structural formula:

### Claim 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.

### Claim 13 (depends on 12)

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

### Claim 14 (depends on 12)

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

### Claim 15 (depends on 12)

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

### Claim 16 (depends on 15)

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

### Claim 17 (depends on 12)

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

### Claim 18 (depends on 12)

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

### Claim 19 (depends on 12)

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

### Claim 20 (depends on 12)

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