Trinitromethane, also referred to as nitroform, is a nitroalkane and

oxidizer An oxidizing agent (also known as an oxidant, oxidizer, electron recipient, or electron acceptor) is a substance in a redox chemical reaction that gains or " accepts"/"receives" an electron from a (called the , , or ''electron donor''). In ot ...

with chemical formula HC(NO₂)₃. It was first obtained in 1857 as the ammonium salt by the Russian chemist (1830–1908). In 1900, it was discovered that nitroform can be produced by the reaction of

acetylene Acetylene (Chemical nomenclature, systematic name: ethyne) is a chemical compound with the formula and structure . It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is u ...

with anhydrous

nitric acid Nitric acid is an inorganic compound with the formula . It is a highly corrosive mineral acid. The compound is colorless, but samples tend to acquire a yellow cast over time due to decomposition into nitrogen oxide, oxides of nitrogen. Most com ...

. 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 or TNM is an organic oxidizer with chemical formula . Its chemical structure consists of four nitro groups attached to one carbon atom. In 1857 it was first synthesised by the reaction of sodium cyanoacetamide with nitric aci ...

under mild basic conditions.

Acidity

Trinitromethane as a neutral molecule is colorless. It is highly acidic, easily forming an intensely yellow anion, (NO₂)₃C⁻ (nitroformate). The p''K''_a of trinitromethane has been measured at 0.17 ± 0.02 at 20 °C, which is remarkably acidic for a methane derivative. Trinitromethane easily dissolves in water to form an acidic yellow solution. There is some evidence that the anion, which obeys the 4''n''+2 Hückel rule, displays Y-aromaticity, a form of

aromaticity In organic chemistry, aromaticity is a chemical property describing the way in which a conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibits a stabilization stronger than would be expected from conjugation alone. The e ...

disputed among chemists.

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. 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.

Condensation with formaldehyde

As found by British chemists Hurd and Starke during

WWII World War II or the Second World War (1 September 1939 – 2 September 1945) was a World war, global conflict between two coalitions: the Allies of World War II, Allies and the Axis powers. World War II by country, Nearly all of the wo ...

, trinitromethane reacts with

paraformaldehyde Paraformaldehyde (PFA) is the smallest polyoxymethylene, the polymerization product of formaldehyde with a typical degree of polymerization of 8–100 units. Paraformaldehyde commonly has a slight odor of formaldehyde due to decomposition. Par ...

, giving . This compound is a solvent to

nitrocellulose Nitrocellulose (also known as cellulose nitrate, flash paper, flash cotton, guncotton, pyroxylin and flash string, depending on form) is a highly flammable compound formed by nitrating cellulose through exposure to a mixture of nitric acid and ...

and a precursor to high explosives such as

trinitroethylorthoformate Trinitroethylorthoformate also known as TNEOF is an explosive with excellent chemical stability. It does not have hygroscopicity, does not dissolve in water, and does not react with acids. It decomposes in aqueous sodium hydroxide solution to rele ...

and

trinitroethylorthocarbonate Trinitroethylorthocarbonate, also known as TNEOC, is an organic compound with the chemical formula . It is an oxidizer with excellent chemical stability. Its explosion point is 238 °C, and it begins to be decomposed at 200 °C. Its expl ...

Acidity

Nitroform salts

Condensation with formaldehyde

References

Further reading