Abstract
Abstract This report describes the separation, characterization, and analysis of products formed during the Shipp hexanitrostilbene (HNS) process. In this process, trinitrotoluene (TNT), dissolved in a mixture of tetrahydrofuran (THF) and methanol (MeOH), reacts with commercial bleach (NaOCl) to form HNS. The identified products include: hexanitrostilbene (HNS), hexanitrobibenzyl (HNBiB), trinitrobenzene (TNB), trinitrobenzoic acid (PiCOOH), trinitrobenzaldehyde (PiCHO), trinitrobenzyl chloride (PiCH2Cl), picryl chloride (PiCl), picric acid (PiOH), trinitrobenzyl alcohol (PiCH2OH), 4,6-dinitro [2,1] benzisoxazole (Anil), and trichloronitromethane (chloropicrin) as well as unreacted TNT. An additional study was made of the PiCH2Cl → HNS reaction which was the source of the red tar components. Approximately 5–10% of the red tar fraction could not be identified. Solvent effects on the yield of several of the above cited by-products are also discussed.
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