Formation of the Sensitive Impurity 1,3,5-Triamino-2-chloro-4,6-dinitrobenzene in Pilot Plant TATB Production

Abstract

A thermally stable, insensitive, high-explosive 1,3,5-triamino-2,4,6-trinitrobenzene (TATB) is manufactured by amination of 1,3,5-trichloro-2,4,6-trinitrobenzene in toluene with NH3 gas. An orange–red, sensitive impurity, 1,3,5-triamino-2-chloro-4,6-dinitrobenzene (TACDNB), was found forming with product TATB in the pilot-plant process. This impurity was isolated and characterized by single-crystal XRD, NMR, FTIR, DSC, and sensitivity test. The chemical reactivity of this impurity with aqueous sodium hydroxide solution was also studied. The process anomalies which led to the formation of this impurity with product TATB were investigated. This TACDNB impurity was formed due to amination of 1,3,5,6-tetrachloro-2,4-dinitrobenzene (T4) when excess NH3 gas was fed into the reactor.

Solubility and Dissolution Thermodynamics for 1,3,5-Trichlorobenzene in Organic Solvents

“…1,3,5-Trichlorobenzene is a very useful chemical in plant protection, for instance in synthesizing the plant protecting agent trichloro-trinitrobenzene. − It is also an important raw material in the preparation of 1,3,5-triamino-2,4,6-trinitrobenzene (TATB) . Many synthetic methods of 1,3,5-trichlorobenzene have been reported in the publications.…”

“…The aim of the present paper is to (1) measure the solubility data of 1,3,5-trichlorobenzene in eight pure organic solvents, (2) which was determined by means of a gas chromatography (Agilent 7890A Infinity GC, Agilent Technologies). The solvents with analytical grade, including n-propanol, isopropyl alcohol, n-butanol, isobutyl alcohol, cyclohexane, toluene, ethyl acetate and acetone were all provided from Sinopharm Chemical Reagent Co., Ltd., China, and used in experiment with no further purification.…”

Nitrogen-rich salts based on polyamino substituted N,N′-azo-1,2,4-triazole: a new family of high-performance energetic materials

“…Detonation velocity D (m s À1 ) and detonation pressure P (GPa), as the characterization of a high explosive's performance, as well as specic impulse (I sp ), were calculated by EXPLO5 v6.01 computer program [37][38][39][40][41] based on the measured densities and the calculated heat of formation. Meanwhile, the detonation data of TNT, 42 TATB, 43 and HMX 44 were also calculated using EXPLO5 v6.01 according to the reported densities and heat of formation for comparison. As shown in Table 1, the detonation pressures of salts 2-7 ranged from 26.3 GPa (2) to 45.7 GPa (4).…”

Trace Compound Analysis in TATB by Liquid Chromatography coupled with Spectroscopic and Spectrometric Detection

“…Nandi et al. (2012) [18] characterized T4A because it was a persistent impurity in the larger‐scale production of TATB. Tan et al.…”

“…Others have developed techniques for specific applications, narrowing the analysis to specific materials. Nandi et al (2012) [18] characterized T4A because it was a persistent impurity in the larger-scale production of TATB. Tan et al (1991) [19] developed a supercritical extraction method to remove tri-chloro-trinitrobenzene (TCTNB), which avoided heating solvent solutions, perhaps for safety reasons.…”