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)

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