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 Hydrogen is the chemical element wi ...

(NH₂) groups attached, alternating around the ring. TATB is a very powerful explosive (somewhat less powerful than RDX, 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, such as the motion of a pendulum—or random, su ...

fire Fire is the rapid oxidation of a material (the fuel) in the exothermic chemical process of combustion, releasing heat, light, and various reaction products. At a certain point in the combustion reaction, called the ignition point, flames a ...

, or impact. 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 the control of recognized hazards in order to achieve an acceptable level of risk. Meanings There are two slightly dif ...

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 bom ...

s use TATB-based explosives in their primary stage.Memorandum from Prospect
UK MOD position statement, 23 January 2006 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 (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 s ...

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 an ...

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 ...

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, 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.

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

Properties

Production

See also

Notes

References