Cyclonite
- Formula: C3H6N6O6
- Molecular weight: 222.1163
- IUPAC Standard InChIKey: XTFIVUDBNACUBN-UHFFFAOYSA-N
- CAS Registry Number: 121-82-4
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: 1,3,5-Triazine, hexahydro-1,3,5-trinitro-; RDX; s-Triazine, hexahydro-1,3,5-trinitro-; Cyclonit; Cyclotrimethylenenitramine; Cyclotrimethylenetrinitramine; Geksogen; Hexahydro-1,3,5-trinitro-s-triazine; Hexahydro-1,3,5-trinitro-1,3,5-triazine; Hexogen; Hexogen 5W; PBX(AF) 108; Trimethylenetrinitramine; T4; 1,3,5-Triaza-1,3,5-Trinitrocyclohexane; 1,3,5-Trinitro-1,3,5-triazacyclohexane; 1,3,5-Trinitrohexahydro-s-triazine; 1,3,5-Trinitrohexahydro-1,3,5-triazine; 1,3,5-Trinitroperhydro-1,3,5-triazine; sym-Trimethylenetrinitramine; Esaidro-1,3,5-trinitro-1,3,5-triazina; Heksogen; Hexahydro-1,3,5-trinitro-1,3,5-triazin; Hexogeen; Hexogen (explosive); Hexolite; Trimethyleentrinitramine; Trinitrocyclotrimethylene triamine; Cyklonit; PBXW 108(E); UN 0072; 1,3,5-Triazacyclohexane 1,3,5-trinitro-; CX 84A; NSC 312447; PE 4; perhydro-1,3,5-trinitro-1,3,5-triazine
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 192. | kJ/mol | Ccb | Pepekin, Matyushin, et al., 1974 |
Condensed phase thermochemistry data
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°solid | 79.1 ± 5.0 | kJ/mol | Ccb | Krien, Licht, et al., 1973 | Author's hf298_condensed=17. kcal/mol; ALS |
ΔfH°solid | 61.5 | kJ/mol | Ccb | Handrick, 1956 | Naval Ordnance Laboratory, 1951; ALS |
ΔfH°solid | 66.5 ± 2.1 | kJ/mol | Ccb | Delepine and Badoche, 1942 | Reanalyzed by Cox and Pilcher, 1970, Original value = 70.3 kJ/mol; Author's hf298_condensed=15.7 kcal/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -2120. ± 5.0 | kJ/mol | Ccb | Krien, Licht, et al., 1973 | Author's hf298_condensed=17. kcal/mol; ALS |
ΔcH°solid | -2100. | kJ/mol | Ccb | Handrick, 1956 | Naval Ordnance Laboratory, 1951; ALS |
ΔcH°solid | -2092.0 ± 2.1 | kJ/mol | Ccb | Young, Keith, et al., 1956 | Reanalyzed by Cox and Pilcher, 1970, Original value = -2106. kJ/mol; ALS |
ΔcH°solid | -2104.6 ± 2.1 | kJ/mol | Ccb | Delepine and Badoche, 1942 | Reanalyzed by Cox and Pilcher, 1970, Original value = -2108. kJ/mol; Author's hf298_condensed=15.7 kcal/mol; ALS |
Constant pressure heat capacity of solid
Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
248.9 | 298. | Krien, Licht, et al., 1973 | T = 200 to 475 K. Equation only.; DH |
Phase change data
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tfus | 478.5 | K | N/A | Hall, 1971 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 134.3 | kJ/mol | N/A | Cundall, Frank Palmer, et al., 1978 | AC |
ΔsubH° | 112. ± 2. | kJ/mol | V | Edwards, 1953 | ALS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
84.4 | 513. | A | Stephenson and Malanowski, 1987 | Based on data from 503. to 523. K.; AC |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
112.5 ± 0.8 | 325. to 360. | ME | Pepekin, Matyushin, et al., 1974 | AC |
130.1 | 350. | N/A | Rosen and Dickinson, 1969 | Based on data from 329. to 371. K.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
37.66 | 478.2 | Domalski and Hearing, 1996 | AC |
35.648 | 478.5 | Hall, 1971, 2 | DH |
Mass spectrum (electron ionization)
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | N.D.Kagramanov, Moscow, Russia |
NIST MS number | 389281 |
Gas Chromatography
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | DB-5 | 140. | 1859.01 | Hobbs and Conde, 1992 | 30. m/0.25 mm/0.25 μm |
Capillary | DB-5 | 140. | 1891.47 | Hobbs and Conde, 1992 | 30. m/0.25 mm/0.25 μm |
Kovats' RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Methyl Silicone | 1870. | Staples, 2005 | Column diameter: 0.25 mm; Program: not specified |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 1914.09 | Hobbs and Conde, 1992 | 30. m/0.25 mm/0.25 μm, 5. K/min; Tstart: 40. C; Tend: 300. C |
Capillary | DB-5 | 1914.76 | Hobbs and Conde, 1992 | 30. m/0.25 mm/0.25 μm, 5. K/min; Tstart: 40. C; Tend: 300. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 1870. | Staples, 2004 | He; Program: not specified |
Capillary | DB-5 | 1870. | Staples, 2004 | He; Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Pepekin, Matyushin, et al., 1974
Pepekin, V.I.; Matyushin, Yu.N.; Lebedev, Yu.A.,
Thermochemistry of N-nitro- and N-nitrosoamines of the alicyclic series,
Bull. Acad. Sci. USSR, Div. Chem. Sci., 1974, 1707-1710. [all data]
Krien, Licht, et al., 1973
Krien, G.; Licht, H.H.; Zierath, J.,
Thermochemical investigation of nitramines,
Thermochim. Acta, 1973, 6, 465-472. [all data]
Handrick, 1956
Handrick, G.R.,
Report of the study of pure explosive compounds. Part IV. Calculation of heat of combustion of organic compounds from structural features and calculation of power of high explosives, Rpt. C-58247 for the Office of the Chief of Ordnance, contract DA-19-020-ORD-47 by the Arthur D. Little, Inc., Cambridge, MA, 1956, 467-573. [all data]
Delepine and Badoche, 1942
Delepine, M.; Badoche, M.,
Thermochimie de l'aldehyde formique, de l'hexamethylene-tetramine et de ses derive,
C. R. Acad. Sci. Paris, 1942, 214, 777-780. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Young, Keith, et al., 1956
Young, J.A.; Keith, J.E.; Stehle, P.; Dzombak, W.C.; Hunt, H.,
Heats of combustion of some organic nitrogen compounds,
Ind. Eng. Chem., 1956, 48, 1375-1378. [all data]
Hall, 1971
Hall, P.G.,
Thermal decomposition and phase transition in solid nitramines,
Trans. Faraday Soc., 1971, 67, 556-62. [all data]
Cundall, Frank Palmer, et al., 1978
Cundall, Robert B.; Frank Palmer, T.; Wood, Colin E.C.,
Vapour pressure measurements on some organic high explosives,
J. Chem. Soc., Faraday Trans. 1, 1978, 74, 0, 1339, https://doi.org/10.1039/f19787401339
. [all data]
Edwards, 1953
Edwards, G.,
The vapour pressure of cyclo-trimethylenetrinitramine (cyclonite) and pentaerythritoltetranitrate,
Trans. Faraday Soc., 1953, 49, 152. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Rosen and Dickinson, 1969
Rosen, Jerome M.; Dickinson, Charles,
Vapor pressures and heats of sublimation of some high-melting organic explosives,
J. Chem. Eng. Data, 1969, 14, 1, 120-124, https://doi.org/10.1021/je60040a044
. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [all data]
Hall, 1971, 2
Hall, P.G.,
Thermal decomposition and phase transitions in solid nitramines,
Trans. Faraday Soc., 1971, 67(3), 556-562. [all data]
Hobbs and Conde, 1992
Hobbs, J.R.; Conde, E.P.,
Gas chromatographic retention indices of explosives and nitro-compounds
in Advances in Analysis and Detection of Explosives: Proceedings of the 4th International Symposium on Analysis of Detection of Explosives, September 7-10, 1992, Jerusalem Israel, J. Yinon, ed(s)., Kluwer Academic Publishers, Netherlands, 1992, 153-164. [all data]
Staples, 2005
Staples, E.J.,
Ultrahigh-speed chromatography and virtual chemical sensors for detecting explosives and chemical warfare agents,
IEEE Sens. J., 2005, 5, 4, 622-631, https://doi.org/10.1109/JSEN.2005.850990
. [all data]
Staples, 2004
Staples, E.J.,
Analysis of odors from explosives using an electronic nose, 2004, retrieved from http://www.estcal.com/TechPapers/OdorsofExplosives.doc. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid Tfus Fusion (melting) point ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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