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A Parametric Study of the Synthesis of 2,2′,4,4′,6,6′‐Hexanitrostilbene from trinitrotoluene and sodium hypochlorite
Author(s) -
Golding P.,
Hayes G. F.
Publication year - 1983
Publication title -
propellants, explosives, pyrotechnics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.56
H-Index - 65
eISSN - 1521-4087
pISSN - 0721-3115
DOI - 10.1002/prep.19830080202
Subject(s) - trinitrotoluene , sodium hypochlorite , sodium , chemistry , yield (engineering) , base (topology) , organic chemistry , materials science , mathematics , mathematical analysis , metallurgy , explosive material
The synthesis of 2,2′,4,4′,6,6′‐hexanitrostilbene by the action of alkaline sodium hypochlorite on 2,4,6‐trinitrotoluene has been studied. The effects of time, temperature, pH, solvent composition and mode of TNT addition on the yield of HNS are discussed. The reaction, usually referred to as the Shipp synthesis, is shown to be highly susceptible to variations in process conditions, particularly base and water concentrations. The conversion of 2,4,6‐trinitrobenzyl chloride, an intermediate in the Shipp reaction, to HNS has also been examined.