Trinitrobenzyl chloride

Trinitrobenzyl chloride is isolated in 85 % yield if a reaction mixture composed of TNT and 5 % aqueous sodium hypochlorite in methanol at 0 °C is quenched into dilute acid after 1 minute longer reaction times at ambient temperature lead to the isolation of the heat resistant explosive 2,2, 4,4, 6,6 -hexanitrostilbene (HNS) in 42 % yield. HNS (16) is also formed in 50 % yield from the reaction of 2,4,6-trinitrobenzyl chloride (145) with sodium hydroxide in THF-methanol. Sollot ° later found that the yield of 2,2, 4,4, 6,6 -hexanitrostilbene (16) could be increased to 70 % by treating the same substrate with 2.4 mole equivalents of triethylamine in the same solvent mixture. 

N 18.67% yel ndls (from Nitrobenz), mp 316° (dec), mp — explodes sol in dimethyl form-amide si sol in hot acet, methyl ethyl ketone glac acet acid. This compd was prepd by Shipp (Ref 5) from 2,4,6-Trinitrobenzyl chloride in methanol by heating on a steam bath with methanol contg KOH. Since this product melts at 105° higher than that.reported by Reich,et al (Refs 1 2), its identity was confirmed by mw detn, elemental analysis, and by an unambiguous independent synthesis. Its X-ray diffraction measurements were also made its unit cell dimensions reported. The product of Reich et al [mp 211°(dec), correct value 218—20°] is probably 2,4,6,2, 4, 6 -Hexanitrobibenzil... 

Trinitrobenzyl chloride, Triethylbenzyl ammonium chloride, Methylene chloride. Sodium hydroxide. Methanol... 

Benzyl chloride and derivs 2 B95 mononitrobenzyl chloride 2 B95 trinitrobenzyl chloride 2 B95... 

Summary HNS is prepared by treating the high explosive, trinitrobenzyl chloride, with sodium hydroxide in the presence of triethylbenzyl ammonium chloride. Commercial Industrial note For related, or similar information, see Application No. 966,674, December 5, 1978, by The United Sates Navy, to Isaac Angres, Gaithersburg, MD. Part or parts of this laboratory process may be protected by international, and/or commercial/industrial processes. Before using this process to legally manufacture the mentioned explosive, with intent to sell, consult any protected commercial or industrial processes related to, similar to, or additional to, the process discussed in this procedure. This process may be used to legally prepare the mentioned explosive for laboratory, educational, or research purposes. 

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