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TATB, triaminotrinitrobenzene or 2,4,6-triamino-1,3,5-trinitrobenzene is an
aromatic In chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to satur ...
explosive, based on the basic six-carbon
benzene Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, ...
ring structure with three
nitro functional group In organic chemistry, nitro compounds are organic compounds that contain one or more nitro functional groups (). The nitro group is one of the most common explosophores (functional group that makes a compound explosive) used globally. The nitr ...
s (NO2) and three
amine In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituen ...
(NH2) groups attached, alternating around the ring. TATB is a very powerful explosive (somewhat less powerful than
RDX RDX (abbreviation of "Research Department eXplosive") or hexogen, among other names, is an organic compound with the formula (O2N2CH2)3. It is a white solid without smell or taste, widely used as an explosive. Chemically, it is classified as a ...
, but more than
TNT Trinitrotoluene (), more commonly known as TNT, more specifically 2,4,6-trinitrotoluene, and by its preferred IUPAC name 2-methyl-1,3,5-trinitrobenzene, is a chemical compound with the formula C6H2(NO2)3CH3. TNT is occasionally used as a reagen ...
), but it is extremely insensitive to
shock Shock may refer to: Common uses Collective noun *Shock, a historic commercial term for a group of 60, see English numerals#Special names * Stook, or shock of grain, stacked sheaves Healthcare * Shock (circulatory), circulatory medical emergen ...
,
vibration Vibration is a mechanical phenomenon whereby oscillations occur about an equilibrium point. The word comes from Latin ''vibrationem'' ("shaking, brandishing"). The oscillations may be periodic function, periodic, such as the motion of a pendulum ...
,
fire Fire is the rapid oxidation of a material (the fuel) in the exothermic chemical process of combustion, releasing heat, light, and various reaction Product (chemistry), products. At a certain point in the combustion reaction, called the ignition ...
, or
impact Impact may refer to: * Impact (mechanics), a high force or shock (mechanics) over a short time period * Impact, Texas, a town in Taylor County, Texas, US Science and technology * Impact crater, a meteor crater caused by an impact event * Impac ...
. 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 "safe", the condition of being protected from harm or other danger. Safety can also refer to risk management, the control of recognized hazards in order to achieve an acceptable level of risk. Meanings There are ...
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 bomb) or a combination of fission and fusion reactions ( thermonuclear bomb), producing a nuclear explosion. Both bom ...
s, where accidental detonation during an airplane crash or rocket misfiring would present extreme dangers. All British
nuclear warhead A nuclear weapon is an explosive device that derives its destructive force from nuclear reactions, either fission (fission bomb) or a combination of fission and fusion reactions (thermonuclear bomb), producing a nuclear explosion. Both bomb ...
s use TATB-based explosives in their primary stage.Memorandum from Prospect
UK MOD position statement, 23 January 2006 According to
David Albright David Albright, M.Sc., is an American physicist and a weapons expert who is the founder of the non-governmental Institute for Science and International Security (ISIS), its current president, and author of several books on proliferation of atom ...
, 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 In materials science, a refractory material or refractory is a material that is resistant to decomposition by heat, pressure, or chemical attack, and retains strength and form at high temperatures. Refractories are polycrystalline, polyphase, ...
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 alcohols and ...
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 ...
of
phloroglucinol Phloroglucinol is an organic compound with the formula C6H3(OH)3. It is a colorless solid. It is used in the synthesis of pharmaceuticals and explosives. Phloroglucinol is one of three isomeric benzenetriols. The other two isomers are hydroxyqu ...
, since this process is milder, cheaper, and reduces the amount of ammonium chloride 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 (UDMH; 1,1-dimethylhydrazine, НДМГ or codenamed Geptil) is a chemical compound with the formula H2NN(CH3)2 that is used as a rocket propellant. It is a colorless liquid, with a sharp, fishy, ammonia-like smell ...
) 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 In organic chemistry, the vicarious nucleophilic substitution is a special type of nucleophilic aromatic substitution in which a nucleophile replaces a hydrogen atom on the aromatic ring and not leaving groups such as halogen substituents which are ...
(VNS) amination reagent. When
Picramide 2,4,6-Trinitroaniline, C6H4N4O6, abbreviated as TNA and also known as picramide, a nitrated amine. Materials in this group range from slight to strong oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides, they ...
, which is easily produced from
Explosive D Dunnite, also known as Explosive D or systematically as ammonium picrate, is an explosive developed in 1906 by US Army Major Beverly W. Dunn, who later served as the chief inspector of the Bureau of Transportation Explosives. Ammonium picrate is ...
, 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.


See also

*
FOX-7 FOX-7 or 1,1-diamino-2,2-dinitroethylene (DADNE) is an insensitive high explosive compound. It was first synthesized in 1998 by the Swedish National Defence Research Institute (FOS).Bemm, U.; Östmark, H. (1998) "1,1-Diamino-2,2-dinitroethylene: a ...
*
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 ...
*
RE factor TNT equivalent is a convention for expressing energy, typically used to describe the energy released in an explosion. The is a unit of energy defined by that convention to be , which is the approximate energy released in the detonation of a m ...


Notes


References

* Cooper, Paul W., ''Explosives Engineering'', New York: Wiley-VCH, 1996. {{ISBN, 0-471-18636-8 * Michell, Alexander R., et al.; ''Conversion of the Rocket Propellant UDMH to a Reagent Useful in Vicarious Nucleophilic Substitution Reactions''; Lawrence Livermore National Laboratory; UCRL-JC-122489 Explosive chemicals Nitrobenzenes Anilines