1,3,5-Trinitro-1,3,5-triazacyclohexane

The nitrolysis of hexamine is a direct route to the military high explosives 1,3,5-trinitro-1,3,5-triazacyclohexane (RDX) and l,3,5,7-tetranitro-13,5,7-tetraazacyclooctane (HMX). " The direct nitrolysis of hexamine with dinitrogen pentoxide in absolute ifitric acid provides RDX in 57 % yield. RDX prepared by this process is exceptionally pure, but other reagents, like ammonium nitrate-nitric acid-acetic anhydride, give much higher yields, partly because they use ammonium nitrate to supplement for ammonium nitrogen deficiency in the reaction. 

Eminger S, Vejrostova M. 1984. Photometric determination of microgram quantities of 1,3,5-trinitro-1,3,5-triazacyclohexane in air. Collection of Czechoslovak Chem Commun 49 1464-1467. 

Trinitro-1,3,5-triazacyclohexane. Same as RDX or Cyclonltp. See in Vol 3, C611-L to C630-L under Cyclotrimethylenetrinitramine, Cyclonite or RDX , and an updated article under RDX in this Vol... 

Bulusu, S., Weinstein, D.I., Autera, J.R. and Velicky, R.W. (1986) Deuterium Kinetic Isotope Effect in the Thermal Decomposition of 1,3,5-Trinitro-1,3,5-triazacyclohexane and 1,3,5,7-Tetranitro-1,3,5,7-tetrazacyclooctane It s Use as an Experimental Probe for Their Shock-Induced Chemistry Journal of Physical Chemistry 90, 4121-4126. 

All reagents and solvents were used as received (Sigma-Aldrich) if not stated otherwise. NOL-130 stab initiation mix and preformed, 19 mg graphite-blended l,3,5-trinitro-l,3,5-triazacyclohexane (RDX) pellets were purchased from Day Zimmerman (DZI). Samples prepared for LC-MS analysis were dissolved in ammonium hydroxide and run utilizing a Phenomenex Gemini C6-Phenyl column (4.6 mm X 150 mm) and a mobile phase of 20 mM ammonium acetate in water pH 7.02 at 0.75 ml,-min The HPLC analysis is done using... 

Investigated explosives included 2,4,6-trinitrotoluene (TNT), 2,4,6,N-tetranitro-N-methylaniline (tetryl), l,3,5-trinitro-l,3,5-triazacyclohexane (RDX), 1,3,5,7-tetranitro-l,3,5,7-tetrazacyclooctane (HMX) and pentaerythritol tetranitrate (PETN). The temperature of the injector, cooled with liquid CO2, was —5°C for 0.3 min, programmed from —5 to 250° C, at a rate of 200°C/min, with a final hold time of 8.4 min. The column temperature was 80° C for 2 min, programmed to 250° C at 25°C/min, with a final hold of 2 min. Electron ionization (El) in the positive-ion mode was used. Figure 4 shows the mass chromatograms of a mixture of explosives (lOppb each), extracted from water by Hquid—liquid extraction and X 100 concentration. Identification was based on typical fragment ions for each one of the explosives. 

The choice of reagent determines whether a nitrosamine undergoes conversion to a nitramine by either nitrolysis or oxidation. An example is given for the conversion of 1,3,5-trinitroso-1,3,5-triazacyclohexane (109) to l,3,5-trinitro-l,3,5-triazacyclohexane (3) (RDX) - the use of 30 % hydrogen peroxide in 99 % nitric acid at subambient temperature goes via oxidation of the nitrosamine functionality, whereas dinitrogen pentoxide in pure nitric acid makes use of a nitrolysis pathway via C-N bond cleavage. 

Krimmel and co-workers ° have reported the synthesis of 2,4,6-tris(trifluoromethyl)-l,3,5-trinitro-l,3,5-triazacyclohexane (123) from the nitrolysis of the nitrosamine (122). 

Trinitro-l 3 5-triazacyclohexane (I) has been synthesised from (V), acetic anhydride, and formaldehyde... 

Cyclonite or cyclo-trimethylenetrinitramine (1,3,5-trinitrohexahydro-sym-triazine. l,3r5-trinitro-l,3>5-triazacyclohexane) is a very... 

There is an alternative view(e.g. expressed by Wright et al. [59]) that hexamethylenetetramine is first formed and then nitrolysed. This assumption is said to be supported by the separation from the reaction products of both methods 4 and 5 of the cyclic products (XXIX) l-aceto-3,5-dinitro-l,3,5-triazacyclohexane and (XXX) 1-aceto-3,5,7-trinitro-l,3,5,7-tetrazacyclo-octane which may also be obtained from hexamine by treating it with nitric acid and acetic anhydride ... 

The same MEKC system was also used for the separation of a test mixture of 15 compounds of interest in high explosive analysis, including nitroguanidine, ethylene glycol dinitrate, diethylene glycol dinitrate, l,3,5-trinitro-l,3,5-triazacyclohexane (RDX), nitroglycerin, 2,4,6-trinitrotoluene (TNT), penta-erythritol tetranitrate, and picric acid, with excellent resolution except for the overlapping of 1,5- and 1,8-isomers of dinitronaphthalene. Also, separation of all the components (26) of the two sets of standards was attempted with extremely limited coelutions. 

Me t hoxy me thy 1-3 5 -d in itro -1 3 5 -tri azacy clo -hexane (IV R = Me) has been synthesized from (II), methyl alcohol, and formaldehyde. l 3 5-Trinitro-I 3 5-triazacyclohexane (I) has been synthesised from (V), acetic anhydride, and formaldehyde... 

Cyclonite (RDX in Anglo-Saxon literature, that is. Research Department Explosive) l,3,5-trinitro l,3,5-triazacyclohexane is a present one of the most important explosives. Over the last two decades extensive literature has been dedicated mainly to its analysis and application. 

Synonyms/Trade Names Cyclotrimethylenetrinitramine Hexahydro-1,3,5-trinitro-s-triazine RDX T rimethylenetrinitramine 1,3,5-T rinitro-1,3,5-triazacyclohexane... 

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