Styphnic acid (from

Greek Greek may refer to: Anything of, from, or related to Greece, a country in Southern Europe: *Greeks, an ethnic group *Greek language, a branch of the Indo-European language family **Proto-Greek language, the assumed last common ancestor of all kno ...

''stryphnos'' "astringent"), or 2,4,6-trinitro-1,3-benzenediol, is a yellow

astringent An astringent (sometimes called adstringent) is a chemical that shrinks or constricts body tissues. The word derives from the Latin '' adstringere'', which means "to bind fast". Astringency, the dry, puckering or numbing mouthfeel caused by t ...

acid An acid is a molecule or ion capable of either donating a proton (i.e. Hydron, hydrogen cation, H+), known as a Brønsted–Lowry acid–base theory, Brønsted–Lowry acid, or forming a covalent bond with an electron pair, known as a Lewis ...

that forms hexagonal

crystal A crystal or crystalline solid is a solid material whose constituents (such as atoms, molecules, or ions) are arranged in a highly ordered microscopic structure, forming a crystal lattice that extends in all directions. In addition, macros ...

s. It is used in the manufacture of

dye Juan de Guillebon, better known by his stage name DyE, is a French musician. He is known for the music video of the single "Fantasy Fantasy is a genre of speculative fiction that involves supernatural or Magic (supernatural), magical ele ...

pigment A pigment is a powder used to add or alter color or change visual appearance. Pigments are completely or nearly solubility, insoluble and reactivity (chemistry), chemically unreactive in water or another medium; in contrast, dyes are colored sub ...

s, inks, medicines, and

explosive An explosive (or explosive material) is a reactive substance that contains a great amount of potential energy that can produce an explosion if released suddenly, usually accompanied by the production of light, heat, sound, and pressure. An ex ...

s such as

lead styphnate Lead styphnate (lead 2,4,6- trinitroresorcinate, C6HN3O8Pb ), whose name is derived from styphnic acid, is an explosive used as a component in primer and detonator mixtures for less sensitive secondary explosives. Lead styphnate is only slight ...

. It is itself a low-sensitivity explosive, similar to

picric acid Picric acid is an organic compound with the formula (O2N)3C6H2OH. Its IUPAC name is 2,4,6-trinitrophenol (TNP). The name "picric" comes from (''pikros''), meaning "bitter", due to its bitter taste. It is one of the most acidic phenols. Like ot ...

, but explodes upon rapid heating.

History

It was discovered in 1808 by

Michel Eugène Chevreul Michel Eugène Chevreul (; 31 August 1786 – 9 April 1889) was a French chemist whose work contributed to significant developments in science, medicine, and art. Chevreul's early work with animal fats revolutionized soap and candle manufacturing ...

who was researching ways of producing colorants from tropical logwoods. Upon boiling Pernambuco wood extract with nitric acid he filtered crystals understood to be styphnic acid in an impure form. In mid-1840s chemists purified and systematically studied the substance with Rudolf Christian Böttger and Heinrich Will giving its modern name, while in 1871 J. Schreder proved that it is trinitroresorcinol.

Preparation and chemistry

It may be prepared by the nitration of

resorcinol Resorcinol (or resorcin) is a phenolic compound. It is an organic compound with the formula C6H4(OH)2. It is one of three isomeric benzenediols, the 1,3-isomer (or ''meta- (chemistry), meta''-isomer). Resorcinol crystallizes from benzene as co ...

with a mixture of nitric and

sulfuric acid Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid (English in the Commonwealth of Nations, Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen, ...

. This compound is an example of a trinitrophenol. Like picric acid, it is a moderately strong acid, capable of displacing carbon dioxide from solutions of

sodium carbonate Sodium carbonate (also known as washing soda, soda ash, sal soda, and soda crystals) is the inorganic compound with the formula and its various hydrates. All forms are white, odourless, water-soluble salts that yield alkaline solutions in water ...

, for example. It may be reacted with weakly basic oxides, such as those of lead and silver, to form the corresponding salts. The solubility of picric acid and styphnic acid in water is less than their corresponding mono- and di-nitro compounds, and far less than their non-nitrated precursor phenols, so they may be purified by fractional crystallisation.

References

{{Authority control Nitrophenols Explosive chemicals Resorcinols Organic acids