US 12,258,322 B2
Methods for preparing dihydroxyammonium 5,5′-bistetrazole-1,1′diolate
Kuk Tae Kwon, Daejon (KR); Hae Wook Yoo, Daejon (KR); Seung Hee Kim, Daejon (KR); and So Jung Lee, Daejon (KR)
Assigned to AGENCY FOR DEFENSE DEVELOPMENT, Daejeon (KR)
Appl. No. 18/706,706
Filed by AGENCY FOR DEFENSE DEVELOPMENT, Daejon (KR)
PCT Filed Jun. 1, 2023, PCT No. PCT/KR2023/007481
§ 371(c)(1), (2) Date May 1, 2024,
PCT Pub. No. WO2023/239104, PCT Pub. Date Dec. 14, 2023.
Claims priority of application No. 10-2022-0068969 (KR), filed on Jun. 7, 2022.
Prior Publication US 2024/0425466 A1, Dec. 26, 2024
Int. Cl. C07D 257/04 (2006.01); C07C 249/08 (2006.01); C07C 249/12 (2006.01); C07D 309/12 (2006.01)
CPC C07D 257/04 (2013.01) [C07C 249/08 (2013.01); C07C 249/12 (2013.01); C07D 309/12 (2013.01)] 11 Claims
 
1. A method of preparing dihydroxylammonium 5,5′-bistetrazole-1,1′-diolate, the method comprising steps of:
synthesizing 5,5′-bistetrazole-1,1′-diol dihydrate (1,1′-BTO) from ditetrahydropyranyl diazidoglyoxime using a hydrochloric acid (HCl) solution in a first solvent; and
obtaining dihydroxylammonium 5,5′-bistetrazole-1,l′-diolate, and simultaneously, reacting and neutralizing the 1,1′-BTO and an amine solution,
wherein the step of synthesizing the 1, 1′-BTO comprises adding the ditetrahydropyranyl diazidoglyoxime and the first solvent to a reactor, adding an HCl solution with a concentration of 20% to 50%, and performing stirring in a temperature range of 30° C. to 60° C.,
wherein the step of obtaining the dihydroxylammonium 5,5′-bistetrazole-1,1′-diolate comprises:
forming a solution by dissolving an amine solution and an HCl solution in water and then adding sodium hydroxide (NaOH), and adding water, to prepare an amine-containing solution;
adding the 1, 1′-BTO and the amine-containing solution to the first solvent;
performing stirring for 10 minutes to 40 minutes while maintaining a temperature range of 30° C. to 50° C.; raising a temperature of a reactor to a temperature of 70° C. to 90° C. and performing stirring for 20 minutes to 60 minutes; adding an amine-containing solution;
performing stirring; performing cooling by lowering a reaction temperature of a solution to a temperature of 1° C. to 10° C.; and performing a filtration, to precipitate dihydroxylammonium 5,5′-bistetrazole-1,1′-diolate, and
wherein the first solvent comprises at least one selected from a group consisting of tetrahydrofuran (THF), dimethylformamide (DMF), dimethylacetamide (DMAc), N-methyl-2-pyrrolidone (NMP), and m-cresol.