- Production of hexanitrostilbene (HNS)
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A process for the manufacture of 2,2', 4,4', 6,6-hexanitrostilbene (HNS) from dipicrylethane (DPE) or trinitrotoluene (TNT) which consists of oxidizing DPE or TNE substrate in the presence of an aprotic solvent and a basic salt of a carboxylic acid. The acid preferably consists of an ammonium or an alkali metal salt of a monocarboxylic or a dicarboxylic acid. The reaction step consists of heating the substrate and salt dissolved in the solvent to between 15° and 50° C., and contacting the reaction mixture with dry air or oxygen for up to 2 hours. The HNS product is precipitated out by quenching the reaction mixture in acidified water, and is optionally purified by washing first in methanol and then in acetone.
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- The Stabilities of Meisenheimer Complexes. Part 38. Kinetic and Equilibrium Studies of the Reaction of 2,2',4,4',6,6'-Hexanitrostilbene with Aliphatic Amines in Dimethyl Sulphoxide
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Kinetic and equilibrium data are reported for the reactions of 2,2',4,4',6,6'-hexanitrostilbene (HNS) with four aliphatic amines in dimethyl sulphoxide, and are compared with those for related aromatic nitro-compounds.With each amine the most rapid reaction involves ?-adduct formation by attack at the 3(3')-positions.With the primary amines, n-butylamine and benzylamine, isomerisation to the thermodynamically more stable 1(1')-adducts occurs.However, with the secondary amines piperidine and pyrrolidine, attack at the 1(1')-positions is not observed, and this is attributed to their high steric requirements.It is shown that the formation of ?-adducts may involve rate-limiting proton transfer from zwitterionic intermediates to amine.A slow reaction is observed between HNS and each amine and is likely to involve amine attack at the olefinic bond.
- Crampton, Michael R.,Routledge, Paul J.,Golding, Peter
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p. 1785 - 1792
(2007/10/02)
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- The Stabilities of Meisenheimer Complexes. Part 31. The Reactions of 2,2'4,4'6,6'-Hexanitrostilbene with Alkoxides
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1H N.m.r. and visible spectral measurements indicate three types of 1 : 1 interaction of 2,2'4,4'6,6'-hexanitrostilbene with alkoxides. ?-Adducts are formed by attack at the 3- or 1-ring position, while the third interaction may involve attack at the olefinic double bond.A 1 : 2 adduct is produced by attack at the 1- and 1'-ring position.Kinetic and equilibrium results for reactions with methoxide ions in methanol and ethoxide ions in ethanol have been obtained and are compared with those for related compounds.
- Crampton, Michael R.,Routledge, Paul J.,Golding, Peter
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p. 1621 - 1624
(2007/10/02)
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- Method for preparing hexanitrostilbene
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2,2',4,4',6,6'-hexanitrostilbene, a thermally stable explosive material, isrepared by reacting 2,2',4,4',6,6'-hexanitrobibenzyl with a quinone in a suitable reaction solvent such as hexamethyl phosphoric triamide, dimethyl sulfoxide and N-methyl-pyrrolidi
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