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TATB (triamino-trinitrobenzene)

One of the most important accomplishments made by nuclear weapons laboratories' chemists in the past two decades has been the formulation of powerful conventional high explosives that are remarkably insensitive to high temperatures, shock, and impact. These insensitive high explosives (IHEs) significantly improve the safety and survivability of munitions, weapons, and personnel.

The Department of Energy's most important IHE for use in modern nuclear warheads is TATB (triamino-trinitrobenzene) because its resistance to heat and physical shock is greater than that of any other known material of comparable energy. The Department of Energy currently maintains an estimated five-year supply of TATB for its Stockpile Stewardship and Management Program, which is designed to ensure the safety, security, and reliability of the U.S. nuclear stockpile. The Department of Defense is also studying the possible use of TATB as an insensitive booster material, because even with its safety characteristics, a given amount of that explosive has more power than an equivalent volume of TNT.

The compound 1,3,5-triamino-2,4,6-trinitrobenzene (TATB) is a reasonably powerful high explosive (HE) whose thermal and shock stability is considerably greater than that of any other known material of comparable energy. The high stability of TATB favors its use in military2 and civilian applications3 when insensitive high explosives are required. In addition to its applications as a HE, TATB is used to produce the important intermediate benzenehexamine. Benzenehexamine has been used in the preparation of ferromagnetic organic salts and in the synthesis of new heteropolycyclic molecules such as 1,4,5,8,9,12-hexaazatriphenylene (HAT) that serve as strong electron acceptor ligands for low-valence transition metals.

In addition to its military uses, TATB has been proposed for use as a reagent in the manufacturing of components for liquid crystal computer displays. The use of TATB to prepare components of lyotropic liquid-crystal phases for use in display devices is the subject of a German patent. There is also interest in employing the explosive in the civilian sector for deep oil well explorations where heat-insensitive explosives are required. Despite its broad potential, the high cost of manufacturing TATB has limited its use. Several years ago, TATB produced on an industrial scale in the U.S. was priced at $90 to $250 per kilogram. Today it is available to customers outside DOE for about $200 per kilogram. In response to a need for a more economical product, chemists at Lawrence Livermore have developed a flexible and convenient means of synthesizing TATB as well as DATB (diamino-trinitrobenzene), a closely related but less well known IHE developed by the U.S. Navy. The initial phase of this work was funded by the Department of Defense (U.S. Navy) to explore the chemical conversion of surplus energetic materials to higher value products as an alternative to detonation.

The Lawrence Livermore process--also called the VNS (vicarious nucleophilic substitution) process--should be able to produce TATB for less than $90 a kilogram on an industrial scale in about 40% less manufacturing time. The process also offers significant advantages over the current method of synthesis in environmental friendliness, for example, by avoiding chlorinated starting materials.