Synthesis of RDX

Preparation of  1,3,5-trinitro-1,3,5-triazine (RDX, Cyclonit, Hexogen)

Alternative Names: Hexogen; CYCLONITE; Hexolite; Geksogen; Trimethylenetrinitramine; Hexahydro-1,3,5-trinitro-1,3,5-triazine;

Preparation of 1,3,5-trinitro-1,3,5-triazine (RDX, Cyclonit, Hexogen)

Preparation of 1,3,5-trinitro-1,3,5-triazine (RDX, Cyclonit, Hexogen)

50 g of well-dried hexamethylenetetramine are added during 15 minutes to 362 ml of 100% nitric acid (d=1.52 g/ml) while the temperature was not allowed to rise above 30°C. During the process of hexamethylenetetramine addition the solution is stirred continuously but only slowly. The mixture is then cooled to 0° C, held there for 20 minutes. After the nitration is completed the reaction solution is poured into four times its volume of cold water and the liquid filtered through glass wool. The product is then washed with cold water until free from acid and dried at 100° C to constant weight. 1,3,5-trinitro-1,3,5-triazine is purified by recrystallization from acetone. 1,3,5-trinitro-1,3,5-triazine is a white crystalline solid, m.p. 202° C. It is insoluble in water, alcohol, ether, ethyl acetate, petroleum ether, and carbon tetrachloride, very slightly soluble in hot benzene, and soluble 1 part in about 135 parts of boiling xylene. It is readily soluble in hot aniline, phenol, ethyl benzoate, and nitrobenzene, from all of which it crystallizes in needles. It is moderately soluble in hot acetone, about 1 part in 8, and is conveniently recrystallized from this solvent from which it is deposited in beautiful, transparent, sparkling prisms. It dissolves very slowly in cold concentrated sulfuric acid, and the solution decomposes on standing. It dissolves readily in warm nitric acid (d=1.42 g/ml or stronger) and separates only partially again when the liquid is cooled.

J. Am. Chem. Soc., 47 (11), 2754–2763, 1925.

IUPAC Name

1,3,5-trinitro-1,3,5-triazinane

InChI

InChI=1S/C3H6N6O6/c10-7(11)4-1-5(8(12)13)3-6(2-4)9(14)15/h1-3H2

InChI Key

XTFIVUDBNACUBN-UHFFFAOYSA-N

Canonical SMILES

C1N(CN(CN1[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-]

MeSH Synonyms

1,3,5-trinitro-1,3,5-triazacyclohexane, 1,3,5-trinitro-1,3,5-triazine, cyclonite, cyclotrimethylene trinitramine, hexahydro-1,3,5-trinitro-1,3,5-triazine, hexahydro-1,3,5-trinitro-s-triazine, Hexogen, RDX

Depositor-Supplied Synonyms

Hexogen, CYCLONITE, Hexolite, Geksogen, Trimethylenetrinitramine, Hexahydro-1,3,5-trinitro-1,3,5-triazine, Hexogen 5W, Hexogen (Explosive), Heksogen, Hexogeen, Cyclotrimethylenetrinitramine, Cyclotrimethylenenitramine, 1,3,5-Trinitro-1,3,5-triazinane, 1,3,5-Triazine, hexahydro-1,3,5-trinitro-, 1,3,5-Trinitro-1,3,5-triazacyclohexane, Trimethyleentrinitramine, Hexahydro-1,3,5-trinitro-s-triazine, Cyclonit, Cyklonit, 121-82-4, RDX, PBX(AF) 108, Trinitrocyclotrimethylene triamine, Cyklonit [Czech], Hexogeen [Dutch], Heksogen [Polish], PBX (af) 108, CX 84A, PE 4, PBXW 108(E), 1,3,5-Triaza-1,3,5-trinitrocyclohexane, 1,3,5-Trinitrohexahydro-s-triazine, Trinitrotrimethylenetriamine, sym-Trimethylenetrinitramine, NSC 312447, sym-Trimethylene trinitramine, s-Triazine, hexahydro-1,3,5-trinitro-, 1,3,5-Trinitroperhydro-1,3,5-triazine, 1,3,5-Trinitrohexahydro-1,3,5-triazine, Perhydro-1,3,5-trinitro-1,3,5-triazine, Trimethyleentrinitramine [Dutch], HSDB 2079, KHP 281, XTFIVUDBNACUBN-UHFFFAOYSA-N, Cyclotrimethylenetrinitramine (RDX), EINECS 204-500-1, UN0072, UN0391, UN0483, BRN 0288466, Esaidro-1,3,5-trinitro-1,3,5-triazina, Hexahydro-1,3,5-trinitro-1,3,5-triazin, Esaidro-1,3,5-trinitro-1,3,5-triazina [Italian], Hexahydro-1,3,5-trinitro-1,3,5-triazin [German], Hexolite, dry or wetted with < 15% water, by mass, Cyclotrimethylenetrinitramine, desensitized or cyclonite, desensitized or hexogen, desensitized or RDX, desensitized, Cyclotrimethylenetrinitramine, wetted or cyclonite, wetted or hexogen, wetted or RDX, wetted with not < 15% water, by mass, Trinitrohexahydrotriazine, C-4 (Salt/Mix), AC1L1R3Y, s-Triazine,3,5-trinitro-, SCHEMBL19770, UN 0118 (Salt/Mix), Ex143, Research Development Explosive, UNII-W91SSV5831, CCRIS 9287, STOCK3S-23557, CHEBI:24556, 1,5-Trinitrohexahydro-s-triazine, W91SSV5831, Hexahydro-1,5-trinitro-s-triazine, 1,3,5-trinitrohexahydro-p-triazine, c0639, NSC312447, STK366162, AKOS015914094, 1,5-Trinitroperhydro-1,3,5-triazine, MCULE-5928095574, NSC-312447, UN 0072, WLN: T6N CN ENTJ ANW CNW ENW, 1,5-Triaza-1,3,5-trinitrocyclohexane, 1,5-Trinitro-1,3,5-triazacyclohexane, 1,5-Trinitrohexahydro-1,3,5-triazine, Esaidro-1,5-trinitro-1,3,5-triazina, 1,3,5-Trinitro-1,3,5-triazinane #, Hexahydro-1,5-trinitro-1,3,5-triazin, Hexahydro-1,5-trinitro-1,3,5-triazine, AN-22855, HE301960, HE391744, OR005291, 1,3,5-Triazacyclohexane 1,3,5-trinitro-, 1,5-Triazine, hexahydro-1,3,5-trinitro-, LS-155436, 1,3,5-Triazine,hexahydro-1,3,5-trinitro-, hexahydro-1,3 ,5-trinitro-1,3 5-triazine, CYCLONITE (CYCLOTRIMETHYLENE TRINITRAMINE), 4-26-00-00022 (Beilstein Handbook Reference), W-109070, I14-45085, 3B1-000719, 3B3-066072, 204655-61-8, 50579-23-2, 53800-53-6, 57608-45-4, 82030-42-0, Cyclotrimethylenetrinitramine, desensitized or cyclonite, desensitized or hexogen, desensitized or RDX, desensitized [UN0483] [Explosive 1.1D], Cyclotrimethylenetrinitramine, desensitized or cyclonite, desensitized or hexogen, desensitized or RDX, desensitized [UN0483] [Explosive 1.1D], Cyclotrimethylenetrinitramine, wetted or cyclonite, wetted or hexogen, wetted or RDX, wetted with not <15% water by mass, Cyclotrimethylenetrinitramine, wetted or cyclonite, wetted or hexogen, wetted or RDX, wetted with not <15% water by mass [UN0072] [Explosive 1.1D], Cyclotrimethylenetrinitramine, wetted or cyclonite, wetted or hexogen, wetted or RDX, wetted with not <15% water by mass [UN0072] [Explosive 1.1D], RDX and HMX mixtures, wetted with not <15% water by mass or RDX and HMX mixtures, desensitized with not <10% phlegmatizer by mass [UN0391] [Explosive 1.1D]

Removed Synonyms

cyclotrimethylene trinitramine, CID8490, 1,3,5-trinitro-1,3,5-triazine, C009160, t4, C-4

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