Trinitromethane
Encyclopedia
Trinitromethane, also referred to as nitroform, is a nitroalkane and oxidizer with chemical formula HC(NO2)3. It was first obtained as the ammonium salt by Shiskov in 1857. In 1900, it was discovered that nitroform can be produced by the reaction of acetylene
with anhydrous nitric acid
. This method went on to become the industrial process of choice during the 20th century. In the laboratory, nitroform can also be produced by hydrolysis of tetranitromethane
under mild basic conditions.
There is some evidence that the anion (which obeys the 4n+2 Hückel rule) is aromatic.
due to corrosion of iron or aluminum surfaces.
The potassium salt of nitroform, KC(NO2)3 is a lemon yellow crystalline solid that decomposes slowly at room temperatures and explodes above 95 °C. The ammonium salt is somewhat more stable, and deflagrates or explodes above 200 °C. The hydrazine salt, hydrazinium nitroformate
is thermally stable to above 125 °C and is being investigated as an ecologically friendly oxidizer for use in solid fuels for rockets.
Acetylene
Acetylene is the chemical compound with the formula C2H2. It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is unstable in pure form and thus is usually handled as a solution.As an alkyne, acetylene is unsaturated because...
with anhydrous nitric acid
Nitric acid
Nitric acid , also known as aqua fortis and spirit of nitre, is a highly corrosive and toxic strong acid.Colorless when pure, older samples tend to acquire a yellow cast due to the accumulation of oxides of nitrogen. If the solution contains more than 86% nitric acid, it is referred to as fuming...
. This method went on to become the industrial process of choice during the 20th century. In the laboratory, nitroform can also be produced by hydrolysis of tetranitromethane
Tetranitromethane
Tetranitromethane or TNM is an organic oxidizer with chemical formula C4. Its chemical structure consists of four nitro groups attached to one carbon atom...
under mild basic conditions.
Acidity
Trinitromethane exists in two forms, a colorless molecular form, HC(NO2)3, and an intensely yellow anion, (NO2)3C-. Nitroform is highly soluble in water, and the stable solution is yellow due to the presence of the anion. The pKa of trinitromethane has been measured at 0.17 ± 0.02 at 20°C, which is remarkably acidic for a methane derivative.There is some evidence that the anion (which obeys the 4n+2 Hückel rule) is aromatic.
Nitroform salts
Trinitromethane forms a series of bright yellow ionic salts. Many of these salts tend to be unstable and can be easily detonated by heat or impact. Because aqueous solutions of trinitromethane are quite acidic, this poses a handling danger similar to that of picric acidPicric acid
Picric acid is the chemical compound formally called 2,4,6-trinitrophenol . This yellow crystalline solid is one of the most acidic phenols. Like other highly nitrated compounds such as TNT, picric acid is an explosive...
due to corrosion of iron or aluminum surfaces.
The potassium salt of nitroform, KC(NO2)3 is a lemon yellow crystalline solid that decomposes slowly at room temperatures and explodes above 95 °C. The ammonium salt is somewhat more stable, and deflagrates or explodes above 200 °C. The hydrazine salt, hydrazinium nitroformate
HNF
Hydrazinium nitroformate is a salt of the hydrazinium ion and nitroformate anion . It is an energetic oxidizer, and is soluble in most solvents. Research is being conducted at ESA, to investigate its use in solid rocket propellants. It tends to produce propellants which burn very rapidly and...
is thermally stable to above 125 °C and is being investigated as an ecologically friendly oxidizer for use in solid fuels for rockets.