An Investigation of the Shipp Hexanitrostilbene (HNS) Process

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.