TATB
Encyclopedia
TATB, or triaminotrinitrobenzene, is an aromatic
explosive, based on the basic six-carbon benzene
ring structure with three nitro functional groups (NO2) and three amine
(NH2) groups attached, alternating around the ring.
TATB is a powerful explosive (somewhat less powerful than RDX
, but more than TNT), but it is extremely insensitive to shock
, vibration
, fire
, or impact. Because it is so difficult to detonate by accident, even under severe conditions, it has become preferred for applications where extreme safety
is required, such as the explosives used in nuclear weapon
s, where accidental detonation during an airplane crash or rocket misfiring would present extreme dangers. All British
and almost all US nuclear warheads, except those where weight is factor, are believed to use TATB based explosives for main explosive charges. 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 compositions, such as PBX-9502, LX-17-0, and PBX-9503 (with 15% HMX
). These formulations are described as Insensitive High Explosives or IHE 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.
TATB's chemical structure is somewhat similar to the powerful experimental insensitive high explosive FOX-7
.
of 7,350 meters per second.
TATB has a crystal density of 1.93 grams/cm3, though most use forms have no higher density than 1.80. TATB melts at 350 °C. The chemical formula for TATB is C6(NO2)3(NH2)3.
TATB is 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.
of 1,3,5-trichlorobenzene
to 1,3,5-trichloro-2,4,6-trinitrobenzene, then the chlorine atoms are substituted
with amine groups.
However, it is likely that the production of TATB will be switched over to a process involving the nitration and transamination
of phloroglucinol
, 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 uns-dimethylhydrazine (UDMH
) and methyl iodide, 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 had to have been destroyed when no longer needed are converted into a high value explosive.
Aromaticity
In organic chemistry, Aromaticity is a chemical property in which a conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibit a stabilization stronger than would be expected by the stabilization of conjugation alone. The earliest use of the term was in an article by August...
explosive, based on the basic six-carbon benzene
Benzene
Benzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....
ring structure with three nitro functional groups (NO2) and three amine
Amine
Amines are organic compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines,...
(NH2) groups attached, alternating around the ring.
TATB is a powerful explosive (somewhat less powerful than RDX
RDX
RDX, an initialism for Research Department Explosive, is an explosive nitroamine widely used in military and industrial applications. It was developed as an explosive which was more powerful than TNT, and it saw wide use in WWII. RDX is also known as cyclonite, hexogen , and T4...
, but more than TNT), but it is extremely insensitive to shock
Shock (mechanics)
A mechanical or physical shock is a sudden acceleration or deceleration caused, for example, by impact, drop, kick, earthquake, or explosion. Shock is a transient physical excitation....
, vibration
Vibration
Vibration refers to mechanical oscillations about an equilibrium point. The oscillations may be periodic such as the motion of a pendulum or random such as the movement of a tire on a gravel road.Vibration is occasionally "desirable"...
, fire
Fire
Fire is the rapid oxidation of a material in the chemical process of combustion, releasing heat, light, and various reaction products. Slower oxidative processes like rusting or digestion are not included by this definition....
, or impact. Because it is so difficult to detonate by accident, even under severe conditions, it has become preferred for applications where extreme safety
Explosives safety
Explosives safety originated as a formal program in the US in the aftermath of World War I when several ammunition storage areas were destroyed in a series of mishaps. The most serious occurred at Lake Denmark Naval Ammunition Storage Depot, New Jersey, in July, 1926 when an electrical storm led to...
is required, such as the explosives used in nuclear weapon
Nuclear weapon
A nuclear weapon is an explosive device that derives its destructive force from nuclear reactions, either fission or a combination of fission and fusion. Both reactions release vast quantities of energy from relatively small amounts of matter. The first fission bomb test released the same amount...
s, where accidental detonation during an airplane crash or rocket misfiring would present extreme dangers. All British
and almost all US nuclear warheads, except those where weight is factor, are believed to use TATB based explosives for main explosive charges. According to David Albright
David Albright
David Albright, M.S., is the founder of the non-governmental Institute for Science and International Security , its current president, and author of several books on proliferation of atomic weapons. Albright holds a Master of Science in physics from Indiana University and a M.Sc. in mathematics...
, South Africa's nuclear weapons
South Africa and weapons of mass destruction
From the 1960s to the 1980s, South Africa pursued research into weapons of mass destruction, including nuclear, biological, and chemical weapons. Six nuclear weapons were assembled...
used TATB to increase their safety.
TATB is normally used as the explosive ingredient in plastic bonded explosive compositions, such as PBX-9502, LX-17-0, and PBX-9503 (with 15% HMX
HMX
HMX, also called octogen, is a powerful and relatively insensitive nitroamine high explosive, chemically related to RDX. Like RDX, the name has been variously listed as High Melting eXplosive, Her Majesty's eXplosive, High-velocity Military eXplosive, or High-Molecular-weight rdX.The molecular...
). These formulations are described as Insensitive High Explosives or IHE 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.
TATB's chemical structure is somewhat similar to the powerful experimental insensitive high explosive FOX-7
FOX-7
FOX-7 or 1,1-diamino-2,2-dinitroethene ' is an insensitive high power explosive compound. It was first synthesized in 1998 by the FOA Defence Research Establishment ....
.
Properties
At a pressed density of 1.80, TATB has a velocity of detonationDetonation
Detonation involves a supersonic exothermic front accelerating through a medium that eventually drives a shock front propagating directly in front of it. Detonations are observed in both conventional solid and liquid explosives, as well as in reactive gases...
of 7,350 meters per second.
TATB has a crystal density of 1.93 grams/cm3, though most use forms have no higher density than 1.80. TATB melts at 350 °C. The chemical formula for TATB is C6(NO2)3(NH2)3.
TATB is 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 nitrationNitration
Nitration is a general chemical process for the introduction of a nitro group into a chemical compound. The dominant application of nitration is for the production of nitrobenzene, the precursor to methylene diphenyl diisocyanate...
of 1,3,5-trichlorobenzene
1,3,5-Trichlorobenzene
1,3,5-Trichlorobenzene is a chlorinated derivative of benzene. It is a good solvent for fullerenes....
to 1,3,5-trichloro-2,4,6-trinitrobenzene, then the chlorine atoms are substituted
Substitution reaction
In a substitution reaction, a functional group in a particular chemical compound is replaced by another group. In organic chemistry, the electrophilic and nucleophilic substitution reactions are of prime importance...
with amine groups.
However, it is likely that the production of TATB will be switched over to a process involving the nitration and transamination
Transamination
There are two chemical reactions known as transamination . The first is the reaction between an amino acid and an alpha-keto acid...
of phloroglucinol
Phloroglucinol
Phloroglucinol is a benzenetriol. It is an organic compound that is used in the synthesis of pharmaceuticals and explosives. This molecule exists in two forms, or tautomers, 1,3,5-trihydroxybenzene, which has phenol-like, and 1,3,5-cyclohexanetrione , which has ketone-like character. These two...
, since this process is milder, cheaper, and reduces the amount of ammonium chloride
Ammonium chloride
Ammonium chloride NH4Cl is an inorganic compound with the formula NH4Cl. It is a white crystalline salt that is highly soluble in water. Solutions of ammonium chloride are mildly acidic. Sal ammoniac is a name of natural, mineralogical form 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 uns-dimethylhydrazine (UDMH
UDMH
Unsymmetrical dimethylhydrazine is a toxic volatile hygroscopic clear liquid, with a sharp, fishy, ammoniacal smell typical for organic amines. It turns yellowish on exposure to air and absorbs oxygen and carbon dioxide. It mixes completely with water, ethanol, and kerosene. In concentration...
) and methyl iodide, and acts as a vicarious nucleophilic substitution
Vicarious nucleophilic substitution
Vicarious nucleophilic substitution in organic chemistry is a special type of nucleophilic aromatic substitution in which a nucleophile replaces hydrogen and not an aromatic substituent like a halogen that is ordinarily encountered in this reaction type...
(VNS) amination
Amination
Amination is the process by which an amine group is introduced into an organic molecule. Enzymes which catalyse this reaction, are termed aminases. This can occur in a number of ways including reaction with ammonia or another amine such as an alkylation, reductive amination and the Mannich reaction...
reagent. When Picramide, which is easily produced from Explosive D, is reacted with TMHI it is aminated to TATB. Thus, materials that would have had to have been destroyed when no longer needed are converted into a high value explosive.