1,3,5-Trinitrobenzene
Colorless rhombic- bipyramidal Papers
Fixed
1.76 g · cm -3 ( 20 ° C)
315 ° C
- Very poor in water ( 330 mg · l-1 at 20 ° C)
- Bad in ethanol, diethyl ether and benzene
Risk
275 mg · kg -1 ( LD50, rat, oral)
Template: Infobox chemical / molecular formula search available
Trinitrobenzene ( TNB ) is an explosive. The explosive force of TNB is comparable to that of TNT. Despite a slightly higher explosive power than TNT, the use of TNB for economic reasons does not take place. It consists of a benzene ring with three nitro groups (- NO2) as a substituent. There are three structural isomers of TNB (1,2,3 -, 1,2,4 - and 1,3,5- trinitrobenzene ), the abbreviation is, however, mostly used for the 1,3,5 - isomer.
Representation
Producing trinitrobenzene carried by nitration of m-dinitrobenzene with a mixture of fuming nitric acid and concentrated sulfuric acid. Also possible is the representation of 2,4,6 - trinitrotoluene, which is followed by a decarboxylation in boiling water after oxidation to 2,4,6- trinitrobenzoic with potassium dichromate and sulfuric acid.
Properties
Trinitrobenzene occurs in five polymorphic forms. The thermodynamically stable Form I melts at 125.3 ° C with a melting enthalpy of 15.0 kJ mol -1. The metastable forms II and III show melting points at 107.2 ° C and 109.8 ° C with enthalpies of fusion of 14.8 kJ · mol -1 and 13.2 kJ · mol -1. Both forms are monotropic to form I. Forms II and III are enantiotropically each other. The transition point between form II and III is about 97 ° C. Two other forms with melting points at 109 ° C and 88 ° C have so far been only thermo observed microscopically.
The connection is resistant to acids and reacts with bases. It is insoluble in water, slightly soluble in alcohol, ether and benzene, very soluble in acetone or ethyl acetate. With polycyclic aromatic hydrocarbons such as naphthalene, anthracene, carbazole and charge-transfer complexes are formed. The 1:1 stoichiometric complexes have defined melting points, such as naphthalene with at 157.6 ° C, with anthracene at 165.4 ° C and 204.4 ° C. for carbazole
The connection exceeds trinitrotoluene in terms of explosive force. Important explosion indicators are:
Use
TNB is slightly more sensitive to impacts than TNT, but this would not carry weight in the application. Complicated due to the manufacture, it is much more expensive than TNT and therefore is not practically used.