Post by Anders Hoveland on Mar 7, 2011 10:07:53 GMT -8
Oxidation of 4-amino,5-nitro-1,2,3-triazole (ANTZ) with ammonium persulfate ("Oxone") would probably yield
N,N’-azoxy-4,4’-bis[5-nitro-1,2,3-triazole]. The compound could be further oxidized, adding an additional oxygen to one of the rings, to form a compound with the formula
C4 N10 H2 O6
A souce mentions that an initial nitration was performed at 5deg on 2-phenyl-1,2,3-triazole, adding one nitro group to the triazole ring, then further nitration at 40 degC not only added a second nitro group, but also formed the 1-N-oxide on the ring.
Another source mentions that "Oxone" can be used to oxidize
nitrotetrazole to 5-nitrotetrazole-2N-oxide. The procedure is:
12.5g of the sodium salt of 5-nitrotetrazole is dissolved in 50mL water, then reacted with 45g of potassium peroxy-monosulfate ("Oxone") and 20g of potassium acetate, which acts as a buffer. The solution is stirred for 24 hours at 50 degC.
A solution containing 0.09 moles of tertiary amine sulfate, such as Et3NH(+), Na(+), SO4(-2), dissolved in 200mL of water, is added. Then the 5-nitro tetrazole-2N-oxide is extracted using 300mL of ethyl acetate. The yellow product moves into the ethyl acetate layer. The 5-nitro tetrazole-2N-oxide product may be purified by crystallization from EtOAc or toluene, resulting in thin yellow crystals. The yield is 70%.
Oxidation of two amino groups on separate molecules can form an azoxy bridge joining the molecules into one.
Using this method under alkaline conditions, 3,5-diamino-1,2,4-triazole can be oxidized, using 30% concentrated H2O2 with sodium tungstate, to 3-amino,5-nitro-1,2,4-triazole, which can be obtained in 60% yield because the reaction rate for further oxidation is slower. The products of further oxidation are 3,5-dinitro-1,2,4-triazole and a lesser quantity of N,N’-azoxy-3,3’-bis[5-amino-1,2,4-triazole]. “Oxidation of Amino Derivatives of 1,2,4-Triazole” T.P. Kofman, E. A. Paketina. St. Petersburg State Technological Institute, Russia (1997)
Thus it seems plausible the ANTZ could be oxidized to the compound depicted below. Such a compound would be more powerful than HMX, and possibly somewhat more resistant to impact. The compound would of course be acidic, and could potentially form insensitive ammonium salts or a less sensitive adduct with 2 equivalents of nitroguanidine.
N,N’-azoxy-4,4’-bis[5-nitro-1,2,3-triazole]. The compound could be further oxidized, adding an additional oxygen to one of the rings, to form a compound with the formula
C4 N10 H2 O6
A souce mentions that an initial nitration was performed at 5deg on 2-phenyl-1,2,3-triazole, adding one nitro group to the triazole ring, then further nitration at 40 degC not only added a second nitro group, but also formed the 1-N-oxide on the ring.
Another source mentions that "Oxone" can be used to oxidize
nitrotetrazole to 5-nitrotetrazole-2N-oxide. The procedure is:
12.5g of the sodium salt of 5-nitrotetrazole is dissolved in 50mL water, then reacted with 45g of potassium peroxy-monosulfate ("Oxone") and 20g of potassium acetate, which acts as a buffer. The solution is stirred for 24 hours at 50 degC.
A solution containing 0.09 moles of tertiary amine sulfate, such as Et3NH(+), Na(+), SO4(-2), dissolved in 200mL of water, is added. Then the 5-nitro tetrazole-2N-oxide is extracted using 300mL of ethyl acetate. The yellow product moves into the ethyl acetate layer. The 5-nitro tetrazole-2N-oxide product may be purified by crystallization from EtOAc or toluene, resulting in thin yellow crystals. The yield is 70%.
Oxidation of two amino groups on separate molecules can form an azoxy bridge joining the molecules into one.
Using this method under alkaline conditions, 3,5-diamino-1,2,4-triazole can be oxidized, using 30% concentrated H2O2 with sodium tungstate, to 3-amino,5-nitro-1,2,4-triazole, which can be obtained in 60% yield because the reaction rate for further oxidation is slower. The products of further oxidation are 3,5-dinitro-1,2,4-triazole and a lesser quantity of N,N’-azoxy-3,3’-bis[5-amino-1,2,4-triazole]. “Oxidation of Amino Derivatives of 1,2,4-Triazole” T.P. Kofman, E. A. Paketina. St. Petersburg State Technological Institute, Russia (1997)
Thus it seems plausible the ANTZ could be oxidized to the compound depicted below. Such a compound would be more powerful than HMX, and possibly somewhat more resistant to impact. The compound would of course be acidic, and could potentially form insensitive ammonium salts or a less sensitive adduct with 2 equivalents of nitroguanidine.
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