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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Comparative modeling of improved synthesis of energetic dinitrobenzofuroxan (DNBF) derivatives
Yung-Hsien Liu1, Yi-Huan Wu2, Jin-Shuh Li1,3
1Department of Chemical and Materials Engineering, Chung Cheng Institute of Technology, National Defense University, Daxi District, Taoyuan City, Taiwan, 335, Republic of China.
Abstract:
Quantum chemical theoretical computation was performed on gaseous molecular reaction systems to simulate parallel synthesis of energetic primary explosive precursor 4,6-dinitrobenzofuroxan (4,6-DNBF) and its isomeric derivatives. Related polarized continuum model (PCM) and Materials Studio (MS/forcite) energies were collected via kinetic rate and thermodynamic equilibrium analyses, enabling comparison of and suggestions as to suitable reaction conditions (reaction temperature, reagent concentration, mixed acid ratio) together with feasible pathways to obtain a high production yield of the research target. In summary, at a low reaction temperature of 278 K, 1.0 M 4-nitrobenzofuroxan (or 5,6-nitrobenzofuroxan) could be nitrated using concentrated nitric acid/sulfuric acid at a 1 to 2 volume ratio to efficiently and rapidly produce 4,6-dinitro-benzofuroxan (or 5,6-dinitrobenzofuroxan), in agreement with the experimental results reported in the literature. Graphical abstract.
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