Method for synthesis of TKX-50 using insensitive intermediate

Patent metadata

Field	Value
Publication number	US-11434209-B2
Application number	US-201916969177-A
Country	US
Kind code	B2
Filing date	Aug 5, 2019
Priority date	Aug 21, 2018
Publication date	Sep 6, 2022
Grant date	Sep 6, 2022

Abstract

The present disclosure relates to a method for synthesis of TKX-50 using an insensitive intermediate, and more specifically, to a method of manufacturing TKX-50 which includes: preparing DCG as a starting material; forming a THP-DAG intermediate from the DCG; and synthesizing TKX-50 through the THP-DAG intermediate.

First claim

The invention claimed is:

1. A method of manufacturing

the method comprising:
preparing

as a starting material;
forming a

from the DCG; and
synthesizing TKX-50 through the THP-DAG intermediate.

2. The method of claim 1 , wherein the TKX-50 is free of

that is an intermediate byproduct.

3. The method of claim 1 , wherein the method comprises:
synthesizing DCG;
synthesizing

through the DCG;
synthesizing THP-DAG through the THP-DCG; and
synthesizing TKX-50 through the THP-DAG.

4. The method of claim 3 , wherein the synthesizing of the DCG comprises:
synthesizing glyoxime; and
reacting the glyoxime with N-chlorosuccinimide.

5. The method of claim 3 , wherein the synthesizing of the THP-DCG through the DCG is performed by reacting the DCG with 3,4-dihydro-2H-pyran in the presence of a p-toluenesulfonic acid (p-TsOH) catalyst.

6. The method of claim 5 , wherein the synthesizing of the THP-DCG through the DCG is performed by stirring and reacting the DCG, the p-TsOH and the 3,4-dihydro-2H-pyran at a weight ratio of 1:3 to 4:1.6.

7. The method of claim 6 , wherein stirring of the DCG, the p-TsOH and the 3,4-dihydro-2H-pyran is performed at room temperature.

8. The method of claim 3 , wherein the synthesizing of the THP-DAG through the THP-DCG is performed through an azidation reaction.

9. The method of claim 8 , wherein the synthesizing of the THP-DAG through the THP-DCG is performed by reacting the THP-DCG with sodium azide (NaN 3 ).

10. The method of claim 9 , wherein the THP-DCG and the sodium azide are stirred at a weight ratio of 1:0.4 to 0.8 and reacted.

11. The method of claim 10 , wherein stirring of the THP-DCG and the sodium azide is performed at a temperature of 95° C. to 100° C.

12. The method of claim 3 , wherein the synthesizing of the TKX-50 through the THP-DAG comprises:
synthesizing 5,5′-bistetrazole-1,1′-diol by reacting the THP-DAG with a hydrochloric acid gas; and
synthesizing the TKX-50 by reacting the 5,5′-bistetrazole-1,1′-diol with hydroxylamine.

13. The method of claim 12 , wherein the synthesizing of the 5,5′-bistetrazole-1,1′-diol by reacting the THP-DAG with the hydrochloric acid gas is performed by stirring the THP-DAG and the hydrochloric acid under a temperature condition of room temperature.

14. The method of claim 12 , wherein the synthesizing of the TKX-50 by reacting the 5,5′-bistetrazole-1,1′-diol with the hydroxylamine is performed by stirring and reacting the 5,5′-bistetrazole-1,1′-diol and the hydroxylamine at a weight ratio of 1:0.5 to 0.7.

15. The method of claim 14 , wherein stirring of the 5,5′-bistetrazole-1,1′-diol and the hydroxylamine is performed at a temperature of 40° C. to 60° C.

Assignees

• Agency Defense Dev

Inventors

• Kwon Kuk Tae
• Lee Woong Hee
• Shim Jeong Sub
• Lee So Jung

Classifications

• C07D257/04 Primary

  Five-membered rings · CPC title

• C06B25/34

  the compound being a nitrated acyclic, alicyclic or heterocyclic amine · CPC title

• C06B49/00 Primary

  Use of single substances as explosives · CPC title