IP Library Granted Patent US 7,763,753
Granted Patent B1
US 7,763,753 · App. 12/484,917 · Granted Jul 27, 2010

Methods for the production of 1,3,5-triamino-2,4,6-trinitrobenzene

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Quick Facts
Patent No.
US 7,763,753
App. No.
12/484,917
Granted
Jul 27, 2010
Kind
B1
Abstract

Methods of producing 1,3,5-triamino-2,4,6-trinitrobenzene are disclosed. One method comprises dissolving a 1,3,5-trialkoxy-2,4,6-trinitrobenzene compound in an organic solvent to form a 1,3,5-trialkoxy-2,4,6-trinitrobenzene compound solution. The 1,3,5-trialkoxy-2,4,6-trinitrobenzene compound solution is heated to a temperature of from approximately 30° C. to approximately 110° C. The 1,3,5-trialkoxy-2,4,6-trinitrobenzene compound is reacted with an aminating agent at a pressure of from approximately 30 pounds per square inch to approximately 120 pounds per square inch to produce a 1,3,5-triamino-2,4,6-trinitrobenzene solution.

Claims (25)

1. A method of producing 1,3,5-triamino-2,4,6-trinitro-benzene, comprising:

heating a 1,3,5-trialkoxy-2,4,6-trinitrobenzene compound solution consisting of a 1,3,5-trialkoxy-2,4,6-trinitrobenzene compound and at least one solvent to a temperature of from approximately 30° C. to approximately 110° C. in a pressure vessel; and

pressurizing the pressure vessel with an aminating agent to a pressure of from approximately 30 pounds per square inch to approximately 120 pounds per square inch to react the 1,3,5-trialkoxy-2,4,6-trinitrobenzene compound in the heated 1,3,5-trialkoxy-2,4,6-trinitrobenzene compound solution with the aminating agent to produce a 1,3,5-triamino-2,4,6-trinitrobenzene solution.

2. The method of claim 1 , wherein heating a 1,3,5-trialkoxy-2,4,6-trinitrobenzene compound solution consisting of a 1,3,5-trialkoxy-2,4,6-trinitrobenzene compound and at least one solvent to a temperature of from approximately 30° C. to approximately 110° C. in a pressure vessel comprises heating 1,3,5-trimethoxy-2,4,6-trinitrobenzene, 1,3,5-triethoxy-2,4,6-trinitrobenzene, 1,3,5-tripropoxy-2,4,6-trinitrobenzene, or combinations thereof in the at least one solvent.

3. The method of claim 1 , wherein heating a 1,3,5-trialkoxy-2,4,6-trinitrobenzene compound solution consisting of a 1,3,5-trialkoxy-2,4,6-trinitrobenzene compound and at least one solvent to a temperature of from approximately 30° C. to approximately 110° C. in a pressure vessel comprises heating the 1,3,5-trialkoxy-2,4,6-trinitrobenzene compound in toluene, mesitylene, xylene, ethyl acetate, sulfolane, or combinations thereof.

4. The method of claim 1 , wherein heating a 1,3,5-trialkoxy-2,4,6-trinitrobenzene compound solution consisting of a 1,3,5-trialkoxy-2,4,6-trinitrobenzene compound and at least one solvent to a temperature of from approximately 30° C. to approximately 110° C. in a pressure vessel comprises heating the 1,3,5-trialkoxy-2,4,6-trinitrobenzene compound solution to a temperature of from approximately 60° C. to approximately 110° C.

5. The method of claim 1 , wherein heating a 1,3,5-trialkoxy-2,4,6-trinitrobenzene compound solution consisting of a 1,3,5-trialkoxy-2,4,6-trinitrobenzene compound and at least one solvent to a temperature of from approximately 30° C. to approximately 110° C. in a pressure vessel comprises heating the 1,3,5-trialkoxy-2,4,6-trinitrobenzene compound solution to a temperature of from approximately 80° C. to approximately 100° C.

6. The method of claim 1 , wherein heating a 1,3,5-trialkoxy-2,4,6-trinitrobenzene compound solution consisting of a 1,3,5-trialkoxy-2,4,6-trinitrobenzene compound and at least one solvent to a temperature of from approximately 30° C. to approximately 110° C. in a pressure vessel comprises heating the 1,3,5-trialkoxy-2,4,6-trinitrobenzene compound solution to a temperature of approximately 90° C.

7. The method of claim 1 , wherein pressurizing the pressure vessel with an aminating agent to a pressure of from approximately 30 pounds per square inch to approximately 120 pounds per square inch comprises pressurizing the pressure vessel with the aminating agent at a pressure of from approximately 40 pounds per square inch to approximately 100 pounds per square inch.

8. The method of claim 1 , wherein pressurizing the pressure vessel with an aminating agent to a pressure of from approximately 30 pounds per square inch to approximately 120 pounds per square inch comprises pressurizing the pressure vessel with the aminating agent at a pressure of from approximately 40 pounds per square inch to approximately 60 pounds per square inch.

9. The method of claim 1 , wherein pressurizing the pressure vessel with an aminating agent to a pressure of from approximately 30 pounds per square inch to approximately 120 pounds per square inch comprises pressurizing the pressure vessel with the aminating agent at a pressure of approximately 60 pounds per square inch.

10. The method of claim 1 , wherein pressurizing the pressure vessel with an aminating agent comprises pressurizing the pressure vessel with ammonia or ammonium hydroxide.

11. The method of claim 1 , further comprising cooling the 1,3,5-triamino-2,4,6-trinitrobenzene solution to precipitate the 1,3,5-triamino-2,4,6-trinitrobenzene.

12. The method of claim 11 , further comprising washing the 1,3,5-triamino-2,4,6-trinitrobenzene with water or isopropanol.

13. A method of producing 1,3,5-triamino-2,4,6-trinitro-benzene, comprising:

heating a 1,3,5-triethoxy-2,4,6-trinitrobenzene solution consisting of 1,3,5-triethoxy-2,4,6-trinitrobenzene and toluene to a temperature of approximately 90° C. in a pressure vessel; and

pressurizing the pressure vessel with ammonia to a pressure of approximately 60 pounds per square inch to react the 1,3,5-triethoxy-2,4,6-trinitrobenzene in the heated 1,3,5-triethoxy-2,4,6-trinitrobenzene solution to produce 1,3,5-triamino-2,4,6-trinitrobenzene.

14. A method of producing 1,3,5-triamino-2,4,6-trinitro-benzene, comprising:

introducing a 1,3,5-triethoxy-2,4,6-trinitrobenzene solution consisting of 1,3,5-triethoxy-2,4,6-trinitrobenzene and at least one solvent into a pressure vessel;

sealing the pressure vessel;

heating the 1,3,5-triethoxy-2,4,6-trinitrobenzene solution to a temperature of approximately 90° C.;

pressurizing the pressure vessel with ammonia to a total reactor pressure of approximately 60 pounds per square inch; and

reacting the 1,3,5-triethoxy-2,4,6-trinitrobenzene with the ammonia to produce 1,3,5-triamino-2,4,6-trinitrobenzene.

15. The method of claim 3 , wherein the at least one solvent further comprises water.

16. The method of claim 1 , further comprising adding seed crystals to the pressure vessel.

Assignments (10)
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 →
RELEASE OF SECURITY INTEREST Recorded Jun 6, 2018
From: BANK OF AMERICA, N.A.
To: ALLIANT TECHSYSTEMS INC.; ATK/PHYSICAL SCIENCES, INC.; ORBITAL SCIENCES CORPORATION; ORBITAL ATK, INC.
Reel/Frame 045998/0801 →
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 →
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 035753/0373 →
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 →
SECURITY AGREEMENT Recorded Nov 4, 2010
From: ALLIANT TECHSYSTEMS INC.; AMMUNITION ACCESSORIES INC.; ATK COMMERCIAL AMMUNITION COMPANY INC.; ATK COMMERCIAL AMMUNITION HOLDINGS COMPANY; ATK LAUNCH SYSTEMS INC.; ATK SPACE SYSTEMS INC.; FEDERAL CARTRIDGE COMPANY; EAGLE INDUSTRIES UNLIMITED, INC.; EAGLE MAYAGUEZ, LLC; EAGLE NEW BEDFORD, INC.
To: BANK OF AMERICA, N.A.
Reel/Frame 025321/0291 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 15, 2009
From: PARASKOS, ALEXANDER J.; KRAMER, MICHAEL P.
To: ALLIANT TECHSYSTEMS INC.
Reel/Frame 022828/0209 →