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Trinitrophenol

Picric acid
Pikrinsäure.svg
Picric-acid-3D.png
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Names
Preferred IUPAC name
2,4,6-Trinitrophenol
Other names
Picric acid
Carbazotic acid
Phenol trinitrate
Picronitric acid
Trinitrophenol
2,4,6-Trinitro-1-phenol
2-Hydroxy-1,3,5-trinitrobenzene
TNP
Melinite
Identifiers
3D model (Jmol)
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.001.696
PubChem CID
RTECS number TJ7875000
UNII
Properties
C6H3N3O7
Molar mass 229.10 g·mol−1
Appearance Colorless to yellow solid
Density 1.763 g·cm−3, solid
Melting point 122.5 °C (252.5 °F; 395.6 K)
Boiling point > 300 °C (572 °F; 573 K) Explodes
12.7 g·L−1
Vapor pressure 1 mmHg (195 °C)
Acidity (pKa) 0.38
-84.34·10−6 cm3/mol
Hazards
Main hazards explosive
Toxic T Explosive E Extremely Flammable F+
R-phrases R1 R4 R11 R23 R24 R25
S-phrases S28 S35 S37 S45
NFPA 704
Flammability code 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g., propane Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 4: Readily capable of detonation or explosive decomposition at normal temperatures and pressures. E.g., nitroglycerin Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 150 °C; 302 °F; 423 K
Lethal dose or concentration (LD, LC):
100 mg/kg (guinea pig, oral)
250 mg/kg (cat, oral)
120 mg/kg (rabbit, oral)
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 0.1 mg/m3 [skin]
REL (Recommended)
TWA 0.1 mg/m3 ST 0.3 mg/m3 [skin]
IDLH (Immediate danger)
75 mg/m3
Explosive data
Detonation velocity 7,350 m·s−1 at ρ 1.70
RE factor 1.20
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

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 the Greek πικρός (pikros), meaning "bitter", reflecting its bitter taste. It is one of the most acidic phenols. Like other highly nitrated organic compounds, picric acid is an explosive, which was once its primary use. It has also been used in medicine (antiseptic, burn treatments) and dyes.

Picric acid was probably first mentioned in the alchemical writings of Johann Rudolf Glauber in 1742. Initially, it was made by nitrating substances such as animal horn, silk, indigo, and natural resin, the synthesis from indigo first being performed by Peter Woulfe in 1771. Its synthesis from phenol, and the correct determination of its formula, were successfully accomplished in 1841. Not until 1830 did chemists think to use picric acid as an explosive. Before then, chemists assumed that only the salts of picric acid were explosive, not the acid itself. In 1871 Hermann Sprengel proved it could be detonated and most military powers used picric acid as their main high explosive material. Picric acid is also used in the analytical chemistry of metals, ores, and minerals.

Picric acid was the first high explosive nitrated organic compound widely considered suitable to withstand the shock of firing in conventional artillery. Nitroglycerine and guncotton were available earlier but shock sensitivity sometimes caused detonation in the artillery barrel at the time of firing. In 1885, based on research of Hermann Sprengel, French chemist Eugène Turpin patented the use of pressed and cast picric acid in blasting charges and artillery shells. In 1887 the French government adopted a mixture of picric acid and guncotton under the name Melinite. In 1888, Britain started manufacturing a very similar mixture in Lydd, Kent, under the name Lyddite. Japan followed with an "improved" formula known as shimose powder. In 1889, a similar material, a mixture of ammonium cresylate with trinitrocresol, or an ammonium salt of trinitrocresol, started to be manufactured under the name ecrasite in Austria-Hungary. By 1894 Russia was manufacturing artillery shells filled with picric acid. Ammonium picrate (known as Dunnite or explosive D) was used by the United States beginning in 1906. However, shells filled with picric acid become highly unstable if the compound reacts with metal shell or fuze casings to form metal picrates which are more sensitive than the parent phenol. The sensitivity of picric acid was demonstrated in the Halifax Explosion. Picric acid was used in the Battle of Omdurman,Second Boer War, the Russo-Japanese War, and World War I. Germany began filling artillery shells with TNT in 1902. Toluene was less readily available than phenol, and TNT is less powerful than picric acid, but improved safety of munitions manufacturing and storage caused replacement of picric acid by TNT for most military purposes between the World Wars.


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