Bis-oxadiazole, or more formally known as bis(1,2,4-oxadiazole)bis(methylene) dinitrate, is a nitrated heterocyclic compound of the

oxadiazole Oxadiazoles are a class of heterocyclic aromatic chemical compound of the azole family; with the molecular formula C2H2N2O. There are four isomers of oxadiazole: File:1,2,3-oxadiazole.svg, 1,2,3-oxadiazole File:1,2,4-oxadiazole.svg, 1,2,4-oxadiazo ...

family. Bis-oxadiazole is related to bis-isoxazole tetranitrate (BITN), which was developed at the

United States Army Research Laboratory The U.S. Army Combat Capabilities Development Command Army Research Laboratory (DEVCOM ARL) is the U.S. Army's foundational research laboratory. ARL is headquartered at the Adelphi Laboratory Center (ALC) in Adelphi, Maryland. Its largest sing ...

(ARL). With a high

nitrogen Nitrogen is the chemical element with the symbol N and atomic number 7. Nitrogen is a nonmetal and the lightest member of group 15 of the periodic table, often called the pnictogens. It is a common element in the universe, estimated at se ...

content, these compounds are poised to release a large volume of very stable N₂. It is a “melt-cast” explosive material that is potentially both more powerful and environmentally friendly alternative to

TNT Trinitrotoluene (), more commonly known as TNT, more specifically 2,4,6-trinitrotoluene, and by its preferred IUPAC name 2-methyl-1,3,5-trinitrobenzene, is a chemical compound with the formula C6H2(NO2)3CH3. TNT is occasionally used as a reagen ...

Synthesis

Glyoxal Glyoxal is an organic compound with the chemical formula OCHCHO. It is the smallest dialdehyde (a compound with two aldehyde groups). It is a crystalline solid, white at low temperatures and yellow near the melting point (15 °C). The liquid ...

condenses Condensation is the change of the state of matter from the gas phase into the liquid phase, and is the reverse of vaporization. The word most often refers to the water cycle. It can also be defined as the change in the state of water vapor to ...

with

hydroxylamine Hydroxylamine is an inorganic compound with the formula . The material is a white crystalline, hygroscopic compound.Greenwood and Earnshaw. ''Chemistry of the Elements.'' 2nd Edition. Reed Educational and Professional Publishing Ltd. pp. 431–43 ...

to yield diaminoglyoxime (DAG). Treating DAG with methyl glycolate in the presence of base at high temperature yields bis(1,2,4-oxadiazole).

Replacement for TNT

TNT is attractive explosive because it is a melt-castable. A low

melting point The melting point (or, rarely, liquefaction point) of a substance is the temperature at which it changes state from solid to liquid. At the melting point the solid and liquid phase exist in equilibrium. The melting point of a substance depen ...

of about 80 °C and high

decomposition temperature Thermal decomposition, or thermolysis, is a chemical decomposition caused by heat. The decomposition temperature of a substance is the temperature at which the substance chemically decomposes. The reaction is usually endothermic as heat is req ...

of 295 °C allows manufacturers to safely pour TNT into molds. The production of TNT generates hazardous waste, e.g. red water and

pink water Trinitrotoluene (), more commonly known as TNT, more specifically 2,4,6-trinitrotoluene, and by its preferred IUPAC name 2-methyl-1,3,5-trinitrobenzene, is a chemical compound with the formula C6H2(NO2)3CH3. TNT is occasionally used as a reage ...

. Bis-oxadiazole, which is also melt-castable, is about 1.5 times more powerful than TNT and yet produces less hazardous wastes. A major challenge in the production of bis-oxadiazole is its low yield.

References

{{reflist Military technology Explosive chemicals Oxadiazoles