TATB, triaminotrinitrobenzene or 2,4,6-triamino-1,3,5-trinitrobenzene is an

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

explosive, based on the basic six-carbon

benzene Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hyd ...

ring structure with three nitro functional groups (NO₂) and three

amine In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...

(NH₂) groups attached, alternating around the ring. TATB is a very powerful explosive (somewhat less powerful than

RDX RDX (Research Department Explosive or Royal Demolition Explosive) or hexogen, among other names, is an organic compound with the formula (CH2N2O2)3. It is white, odorless, and tasteless, widely used as an explosive. Chemically, it is classified ...

, but more than

TNT Troponin T (shortened TnT or TropT) is a part of the troponin complex, which are proteins integral to the contraction of skeletal and heart muscles. They are expressed in skeletal and cardiac myocytes. Troponin T binds to tropomyosin and helps ...

), but it is extremely insensitive to shock,

vibration Vibration () is a mechanical phenomenon whereby oscillations occur about an equilibrium point. Vibration may be deterministic if the oscillations can be characterised precisely (e.g. the periodic motion of a pendulum), or random if the os ...

fire Fire is the rapid oxidation of a fuel in the exothermic chemical process of combustion, releasing heat, light, and various reaction Product (chemistry), products. Flames, the most visible portion of the fire, are produced in the combustion re ...

, or

impact Impact may refer to: * Impact (mechanics), a large force or mechanical shock over a short period of time * Impact, Texas, a town in Taylor County, Texas, US Science and technology * Impact crater, a meteor crater caused by an impact event * Imp ...

. Because it is so difficult to detonate by accident, even under severe conditions, it has become preferred for applications where extreme

safety Safety is the state of being protected from harm or other danger. Safety can also refer to the control of recognized hazards in order to achieve an acceptable level of risk. Meanings The word 'safety' entered the English language in the 1 ...

is required, such as the explosives used in

nuclear weapon A nuclear weapon is an explosive device that derives its destructive force from nuclear reactions, either fission (fission or atomic bomb) or a combination of fission and fusion reactions (thermonuclear weapon), producing a nuclear exp ...

s, where accidental detonation during an airplane crash or rocket misfiring could potentially detonate the fissile core. All British

nuclear warhead A nuclear weapon is an explosive device that derives its destructive force from nuclear reactions, either fission (fission or atomic bomb) or a combination of fission and fusion reactions (thermonuclear weapon), producing a nuclear expl ...

s use TATB-based explosives in their primary stage. According to David Albright, South Africa's nuclear weapons used TATB to increase their safety. TATB is normally used as the explosive ingredient in

plastic bonded explosive Polymer-bonded explosives, also called PBX or plastic-bonded explosives, are explosive materials in which explosive powder is bound together in a matrix using small quantities (typically 5–10% by weight) of a synthetic polymer. PBXs are normally ...

compositions, such as PBX-9502, LX-17-0, and PBX-9503 (with 15% HMX). These formulations are described as insensitive high explosives (IHEs) in nuclear weapons literature. Though it could theoretically be mixed with other explosive compounds in castable mixtures or other use forms, the applications for such forms would be unclear since they would largely undo the insensitivity of pure TATB.

Properties

At a pressed density of 1.80, TATB has a velocity of

detonation Detonation () is a type of combustion involving a supersonic exothermic front accelerating through a medium that eventually drives a shock front propagating directly in front of it. Detonations propagate supersonically through shock waves with ...

of 7,350 meters per second. TATB has a crystal density of 1.93 grams/cm³, though most forms currently in use have no higher density than 1.80 grams/cm³. TATB melts at 350 °C. The chemical formula for TATB is C₆(NO₂)₃(NH₂)₃. Pure TATB has a bright yellow color. TATB has been found to remain stable at temperatures at least as high as 250 °C for prolonged periods of time.

Production

TATB is produced by

nitration In organic chemistry, nitration is a general class of chemical processes for the introduction of a nitro group () into an organic compound. The term also is applied incorrectly to the different process of forming nitrate esters () between Alcohol ...

of 1,3,5-trichlorobenzene to 1,3,5-trichloro-2,4,6-trinitrobenzene, then the chlorine atoms are substituted with amine groups using ammonolysis. However, it is likely that the production of TATB will be switched over to a process involving the nitration and

transamination Transamination is a chemical reaction that transfers an amino group to a ketoacid to form new amino acids.This pathway is responsible for the deamination of most amino acids. This is one of the major degradation pathways which convert essential a ...

phloroglucinol Phloroglucinol is an organic compound with the formula C6H3(OH)3. It is a colorless solid. It is used in the organic synthesis, synthesis of pharmaceuticals and explosives. Phloroglucinol is one of three isomeric benzenetriols. The other two isom ...

, since this process is milder, cheaper, and reduces the amount of

ammonium chloride Ammonium chloride is an inorganic chemical compound with the chemical formula , also written as . It is an ammonium salt of hydrogen chloride. It consists of ammonium cations and chloride anions . It is a white crystalline salt (chemistry), sal ...

salt produced in waste effluents (greener). Still, another process has been found for the production of TATB from materials that are surplus to military use. 1,1,1-trimethylhydrazinium iodide (TMHI) is formed from the rocket fuel unsymmetrical dimethylhydrazine (

UDMH Unsymmetrical dimethylhydrazine (abbreviated as UDMH; also known as 1,1-dimethylhydrazine, heptyl or Geptil) is a chemical compound with the formula H2NN(CH3)2 that is primarily used as a rocket propellant. At room temperature, UDMH is a colorle ...

) and

methyl iodide Iodomethane, also called methyl iodide, and commonly abbreviated "MeI", is the chemical compound with the formula CH3I. It is a dense, colorless, volatile liquid. In terms of chemical structure, it is related to methane by replacement of one h ...

, and acts as a vicarious nucleophilic substitution (VNS) amination reagent. When picramide, which is easily produced from Explosive D, is reacted with TMHI it is aminated to TATB. Thus, materials that would have to be destroyed when no longer needed are converted into a high value explosive.

Notes

References

* Cooper, Paul W., ''Explosives Engineering'', New York: Wiley-VCH, 1996. {{ISBN, 0-471-18636-8 Explosive chemicals Nitrobenzene derivatives Anilines

Properties

Production

See also

Notes

References