IP Library Granted Patent US 9,650,307
Granted Patent B2
US 9,650,307 · App. 13/804,148 · Granted May 16, 2017

Methods for producing DEMN eutectic

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Quick Facts
Patent No.
US 9,650,307
App. No.
13/804,148
Granted
May 16, 2017
Kind
B2
Abstract

A method of producing DEMN eutectic comprises reacting a reactant mixture comprising ethylenediamine and diethylenetriamine with aqueous nitric acid to form a reaction mixture comprising diethylentriamine trinitrate and ethylenediamine dinitrate. The reaction mixture is combined with methylnitroguanidine and nitroguanidine to form an aqueous slurry. Water is removed from the aqueous slurry. A method of producing an energetic composition, and a system for producing DEMN eutectic are also described.

Claims (23)

1. A method of producing DEMN eutectic, comprising:

reacting a reactant mixture comprising ethylenediamine and diethylenetriamine with aqueous nitric acid to form a reaction mixture comprising diethylentriamine trinitrate and ethylenediamine dinitrate;

combining the reaction mixture with methylnitroguanidine and nitroguanidine to form an aqueous slurry; and

removing water from the aqueous slurry.

2. The method of claim 1 , wherein the aqueous nitric acid comprises from about 60 percent by weight nitric acid to about 75 percent by weight nitric acid, and from about 40 percent by weight water to about 25 percent by weight water.

3. The method of claim 1 , wherein reacting a reactant mixture comprising ethylenediamine and diethylenetriamine with aqueous nitric acid comprises reacting the reactant mixture with the aqueous nitric acid at a temperature of from about 10° C. to about 90° C.

4. The method of claim 1 , wherein reacting a reactant mixture comprising ethylenediamine and diethylenetriamine with aqueous nitric acid comprises reacting the reactant mixture with the aqueous nitric acid at a temperature of from about 35° C. to about 55° C.

5. The method of claim 1 , wherein reacting a reactant mixture comprising ethylenediamine and diethylenetriamine with aqueous nitric acid comprises controlling a ratio of the reactant mixture to the aqueous nitric acid such that the reaction mixture exhibits a pH within a range of from about 0 to about 7.

6. The method of claim 1 , wherein reacting a reactant mixture comprising ethylenediamine and diethylenetriamine with aqueous nitric acid comprises controlling a ratio of the reactant mixture to the aqueous nitric acid such that the reaction mixture exhibits a pH within a range of from about 3 to about 5.

7. The method of claim 1 , wherein combining the reaction mixture with methylnitroguanidine and nitroguanidine comprises combining at least one of methylnitroguanidine in water and nitroguanidine in water with the reaction mixture.

8. The method of claim 1 , wherein combining the reaction mixture with methylnitroguanidine and nitroguanidine comprises combining at least one of solid methylnitroguanidine and solid nitroguanidine with the reaction mixture.

9. The method of claim 1 , wherein removing water from the aqueous slurry comprises heating the aqueous slurry at a temperature of from about 50° C. to about 150° C.

10. The method of claim 1 , wherein removing water from the aqueous slurry comprises heating the aqueous slurry at a temperature of from about 90° C. to about 110° C.

11. The method of claim 1 , further comprising exposing the aqueous slurry to at least one of negative pressure and air sparge while removing water from the aqueous slurry.

12. The method of claim 1 , wherein removing water from the aqueous slurry comprises heating the aqueous slurry for a sufficient time to form a molten DEMN eutectic comprising ethylenediamine dinitrate, diethylentriamine trinitrate, methylnitroguanidine, nitroguanidine, and from about 0.1 percent by weight water to about 2 percent by weight water.

13. The method of claim 1 , wherein heating the aqueous slurry to remove water therefrom comprises heating the aqueous slurry for a sufficient time to form molten DEMN eutectic comprising ethylenediamine dinitrate, diethylentriamine trinitrate, methylnitroguanidine, nitroguanidine, and from about 0.3 percent by weight water to about 0.5 percent by weight water.

14. The method of claim 1 , wherein reacting a reactant mixture comprising ethylenediamine and diethylenetriamine with aqueous nitric acid and combining the reaction mixture with methylnitroguanidine and nitroguanidine comprises reacting the reactant mixture with aqueous nitric acid and combining the reaction mixture with methylnitroguanidine and nitroguanidine in a single vessel.

15. A method producing DEMN eutectic, comprising:

reacting a reactant mixture comprising ethylenediamine and diethylenetriamine with an aqueous solution comprising from about 60 percent by weight nitric acid to about 75 percent by weight nitric acid at a temperature of from about 10° C. to about 90° C. to form a reaction mixture comprising ethylenediamine dinitrate and diethylentriamine trinitrate and exhibiting a pH within a range of from about 0 to about 7;

combining the reaction mixture with methylnitroguanidine and nitroguanidine to form an aqueous slurry; and

heating the aqueous slurry at a temperature of from about 50° C. to about 150° C. and under at least one of negative pressure and air sparge to form a eutectic composition comprising ethylenediamine dinitrate, diethylentriamine trinitrate, methylnitroguanidine, nitroguanidine, and from about 0.1 percent by weight water to about 2 percent by weight water.

16. The method of claim 15 , further comprising cooling the eutectic composition to form a solid eutectic composition.

17. The method of claim 15 , further comprising forming particles from the eutectic composition.

Assignments (9)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 8, 2021
From: NORTHROP GRUMMAN INNOVATION SYSTEMS LLC
To: NORTHROP GRUMMAN SYSTEMS CORPORATION
Reel/Frame 055256/0892 →
CHANGE OF NAME Recorded Feb 4, 2021
From: NORTHROP GRUMMAN INNOVATION SYSTEMS, INC.
To: NORTHROP GRUMMAN INNOVATION SYSTEMS LLC
Reel/Frame 055223/0425 →
CHANGE OF NAME Recorded Nov 1, 2018
From: ORBITAL ATK, INC.
To: NORTHROP GRUMMAN INNOVATION SYSTEMS, INC.
Reel/Frame 047400/0381 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded Jun 6, 2018
From: WELLS FARGO BANK, NATIONAL ASSOCIATION, AS ADMINISTRATIVE AGENT
To: ORBITAL ATK, INC.
Reel/Frame 046477/0874 →
RELEASE OF SECURITY INTEREST Recorded Oct 8, 2015
From: BANK OF AMERICA, N.A.
To: ALLIANT TECHSYSTEMS INC.; FEDERAL CARTRIDGE CO.; EAGLE INDUSTRIES UNLIMITED, INC.; AMMUNITION ACCESSORIES, INC.; ORBITAL ATK, INC. (F/K/A ALLIANT TECHSYSTEMS INC.)
Reel/Frame 036816/0624 →
SECURITY AGREEMENT Recorded Sep 30, 2015
From: ORBITAL ATK, INC.; ORBITAL SCIENCES CORPORATION
To: WELLS FARGO BANK, NATIONAL ASSOCIATION, AS ADMINISTRATIVE AGENT
Reel/Frame 036732/0170 →
CHANGE OF NAME Recorded May 22, 2015
From: ALLIANT TECHSYSTEMS INC.
To: ORBITAL ATK, INC.
Reel/Frame 035752/0471 →
SECURITY AGREEMENT Recorded Nov 26, 2013
From: ALLIANT TECHSYSTEMS INC.; CALIBER COMPANY; EAGLE INDUSTRIES UNLIMITED, INC.; FEDERAL CARTRIDGE COMPANY; SAVAGE ARMS, INC.; SAVAGE RANGE SYSTEMS, INC.; SAVAGE SPORTS CORPORATION
To: BANK OF AMERICA, N.A.
Reel/Frame 031731/0281 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT SUPPLEMENT Recorded Aug 26, 2013
From: ALLIANT TECHSYSTEMS INC.
To: BANK OF AMERICA, N.A.
Reel/Frame 031081/0622 →