Hexanitroethane (HNE) is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

with

chemical formula In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, ...

C₂N₆O₁₂ or (O₂N)₃C-C(NO₂)₃. It is a solid matter with a melting point of 135 °C. Hexanitroethane is used in some

pyrotechnic composition A pyrotechnic composition is a substance or mixture of substances designed to produce an effect by heat, light, sound, gas/smoke or a combination of these, as a result of non-detonative self-sustaining exothermic reaction, exothermic chemical reac ...

s as a nitrogen-rich oxidizer, e.g. in some

decoy flare A flare or decoy flare is an aerial infrared countermeasure used by a plane or helicopter to counter an infrared homing ("heat-seeking") surface-to-air missile or air-to-air missile. Flares are commonly composed of a pyrotechnic composition b ...

compositions and some

propellant A propellant (or propellent) is a mass that is expelled or expanded in such a way as to create a thrust or other motive force in accordance with Newton's third law of motion, and "propel" a vehicle, projectile, or fluid payload. In vehicles, the e ...

s. Like

hexanitrobenzene Hexanitrobenzene, also known as HNB, is a high-density explosive compound with chemical formula , obtained by oxidizing the amine group of pentanitroaniline with hydrogen peroxide in sulfuric acid. Properties HNB has the undesirable property ...

, HNE is investigated as a gas source for explosively pumped

gas dynamic laser A gas dynamic laser (GDL) is a laser based on differences in relaxation velocities of molecular vibrational states. The lasing medium gas has such properties that an energetically lower vibrational state relaxes faster than a higher vibrational st ...

. A composition of HNE as oxidizer with

boron Boron is a chemical element with the symbol B and atomic number 5. In its crystalline form it is a brittle, dark, lustrous metalloid; in its amorphous form it is a brown powder. As the lightest element of the ''boron group'' it has th ...

as fuel is being investigated as a new explosive.

Preparation

The first synthesis was described by Wilhelm Will in 1914, using the reaction between the potassium salt of tetranitroethane with

nitric acid Nitric acid is the inorganic compound with the formula . It is a highly corrosive mineral acid. The compound is colorless, but older samples tend to be yellow cast due to decomposition into oxides of nitrogen. Most commercially available nitri ...

. :C₂(NO₂)₄K₂ + 4 HNO₃ → C₂(NO₂)₆ + 2 KNO₃ + 2 H₂O A practicable method for industrial use starts with

furfural Furfural is an organic compound with the formula C4H3OCHO. It is a colorless liquid, although commercial samples are often brown. It has an aldehyde group attached to the 2-position of furan. It is a product of the dehydration of sugars, as occurs ...

, which first undergoes oxidative ring-opening by bromine to mucobromic acid. In the following step, mucobromic acid is reacted with

potassium nitrite Potassium nitrite (distinct from potassium nitrate) is the inorganic compound with the chemical formula . It is an ionic salt of potassium ions K+ and nitrite ions NO2−, which forms a white or slightly yellow, hygroscopic crystalline powder that ...

at just below room temperature to form the dipotassium salt of 2,3,3-trinitropropanal. The final product is obtained by

nitration In organic chemistry, nitration is a general class of chemical processes for the introduction of a nitro group into an organic compound. The term also is applied incorrectly to the different process of forming nitrate esters between alcohols and ...

with nitric acid and sulfuric acid at −60 °C. : Hexanitroethane_synthesis

Properties

The thermal decomposition of hexanitroethane has been detected at 60 °C upwards in both the solid and solution phases. Above 140 °C, this can occur explosively. The decomposition is first order and is significantly faster in solution than in the solid. For the solid, the following reaction can be formulated: :C₂(NO₂)₆ → 3 NO₂ + NO + N₂O + 2 CO₂ For the decomposition is solution, tetranitroethylene is first formed and can be trapped and detected as a Diels–Alder adduct, for example with

anthracene Anthracene is a solid polycyclic aromatic hydrocarbon (PAH) of formula C14H10, consisting of three fused benzene rings. It is a component of coal tar. Anthracene is used in the Economic production, production of the red dye alizarin and other dyes ...

cyclopentadiene Cyclopentadiene is an organic compound with the chemical formula, formula C5H6.LeRoy H. Scharpen and Victor W. Laurie (1965): "Structure of cyclopentadiene". ''The Journal of Chemical Physics'', volume 43, issue 8, pages 2765-2766. It is often ab ...

.{{Cite journal, last1=Tzeng, first1=Dongjaw, last2=Baum, first2=Kurt, date=1983, title=Reactions of hexanitroethane with alcohols, journal=The Journal of Organic Chemistry, language=en, volume=48, issue=26, pages=5384–5385, doi=10.1021/jo00174a053, issn=0022-3263 : Hexanitroethane_reactions01

References

External links

WebBook page for C2N6O12
Nitroalkanes Explosive chemicals Pyrotechnic oxidizers