Sciencemadness Discussion Board

Oxadiazole to replace TNT - Another promising overlooked insensitive compound.

DubaiAmateurRocketry - 26-6-2018 at 21:32

If you google replace TNT, you will find a lot of coverage about the compound: Bis(1,2,4-oxadiazole)bis(methylene) Dinitrate, as published by this high-impact paper.

The author of the paper, Chavez, works at LANL has ive seen him publish about melt-castable explosives on multiple papers, direct link:

Bis(1,2,4-oxadiazole)bis(methylene) Dinitrate
IS (J) - 8.9
FS (N) - 280
Density (g cm-3) - 1.83
T melt (°C) - 85
T decomp (°C) - 183
Velocity Det (ms) - 8180
Pressure Det (GPa) - 29

However, an overlooked compound here I present oxadiazol-furoxan-
oxadiazole (OFO). OFO has signigicantly lower impact factor than the above compound (18J vs 9J, with similar detonation properties)


Note: There is a mistake within this paper where the melting point says 114, but if you check the DSC plot of this compound, it says it has a 98 melting point.

oxadiazol-furoxan- oxadiazole
IS (J) - 18
FS (N) - 120
Density (g cm-3) - 1.82
T melt (°C) - 98
T decomp (°C) - 214
Velocity Det (ms) - 8045
Pressure Det (GPa) - 27

Rocinante - 26-6-2018 at 23:44

A 8.9 J explosive is never going to replace TNT, no co-crystal... not ever. What a bunch of liars. A 18 J melt-castable one is another matter.

DubaiAmateurRocketry - 27-6-2018 at 00:10

Right, OFO has a lower impact sensitivty than TNT, although it is a 5 step synthesis, the starting materials are readily available, once industrialized, it would be within affordable range for the military.

ShotBored - 6-7-2018 at 09:41

Chavez works a lot with DMD Systems, which are owned by a few prominent names you may recognize: Mike Hiskey (RIP as of late 2017) and Darren Naud. They have some patents out that are pretty interesting for low-smoke, NC based pyro comps, but a lot of the papers the three of them published for LANL were your typicaly "fluff" papers. Difficult to synthesize chemicals with unfavorable properties just to get more grant funding for their projects.

TNT could be headed for retirement after116 years on the job

franklyn - 26-1-2020 at 10:09

Avalilable direct from the source , not the forum _

Bis(1,2,4-oxadiazole)bis(methylene) Dinitrate :
A High-Energy Melt-Castable Explosive and Energetic Propellant Plasticizing Ingredient


simply RED - 26-1-2020 at 10:59

This molecule obviously failed to replace TNT. It failed to be loadable in any (modern) weapon. Can you tell at which test it failed by just looking at the structure?

They failed once, but tried again recently.

Chemistry didn't improve....

Poetry did!

"Materials containing the furoxan moiety

have, at times,

been found to have

melt‐castable properties"

[Edited on 26-1-2020 by simply RED]

franklyn - 28-1-2020 at 05:46

The thread preceding this one is here.

The compound appears undernourished , a quality it shares with TNT. The -CH2NO3 ends are oxygen balanced leaving four carbons , four hydrogens , across the center with only two oxygens. Years ago I posted on something related , Trimethylol Isocyanurate.
Cyanuric acid readily dissolves in aqueous formaldehyde forming Trimethylol Isocyanurate.

Subjecting this to nitrolysis of mixed Sulfuric / Nitric acids would yield Trimethylenetrinitrate Isocyanurate. I dispensed with further consideration of this compound when calculations indicated expected performance to be mediocre. What other properties might result can be determined only by making it.

Energetic Materials based on Isocyanuric acid and 1,2,4-Oxadiazole Derivatives ( see page 59 ) ( then page 99 for similar structure to the compound of this thread )
The Methylenenitrate moiety -CH2NO3 readily incorporates onto any suitable organic backbone. Two joined together is Ethylene Dinitrate. Four of these on a single carbon center forms Methane Tetramethylenetetranitrate , alias PETN. Three of these on a single Nitrogen forms NitrogenTrimethylenetrinitrate , alias [Bis(Nitrooxymethyl)Amino]Methyl Nitrate ( IUPAC name , so why isn't it Tri(Nitrooxymethyl)Amine ?).
No word on it's properties but it will very likely be an ammonium analog that can form adducts with acid compounds. Trinitrophenol could be a candidate. A Nitroform adduct would provide excess oxygen to supplement that.


simply RED - 29-1-2020 at 06:48

Combining complex oxadiazole rings with the unstable -CH2NO3 group is like combing a Mercedes with an engine from Trabi...

Oxadiazole :

franklyn - 29-1-2020 at 09:50

Their Chemistry and Pharmacological Potentials

Yes , if you want it to be ' stable ' make certain it is not an explosive ! If it doesn't blow up it's just taking up space. For this reason any melt cast explosive is superior to any energetic polymer. Plastic Bonded Explosive has it's place but all those other ' Mercedes ' have shortcomings all their own. " Most of the Azoximes are very volatile substances , sublime readily , and are easily soluble in water, alcohol and benzene. Which is why it is suitable for a melt cast material. Not exactly a ' mercedes ' either.
The menu

In simple terms , so that even you can understand

Another one ( This one is actually quite good because it has lots of nitrogen and acceptable oxygen balance in a compromise for higher density )
A promising high-energy-density material


simply RED - 29-1-2020 at 10:15

From what I understand, TNT is not going to be replaced soon...

franklyn - 29-1-2020 at 13:10

The top of the line military use explosive is perhaps Octol , which is HMX , 80 - 88 % + TNT 12 - 20 %. If you have something which works well , and a history of how it performs , that's a high bar to exceed. Economics militate against introducing something else of marginal improvement and as you point out , that's arguable. But alas , there are many chemists in need of continuing employment who would otherwise be reduced to writing poetry.