Cyclonite

• Formula: C₃H₆N₆O₆
• Molecular weight: 222.1163
• IUPAC Standard InChI: InChI=1S/C3H6N6O6/c10-7(11)4-1-5(8(12)13)3-6(2-4)9(14)15/h1-3H2 Copy

  
• IUPAC Standard InChIKey: XTFIVUDBNACUBN-UHFFFAOYSA-N Copy
• 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
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
• Options:
  • Switch to calorie-based units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), 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

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), References, Notes

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

Constant pressure heat capacity of solid

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Mass spectrum (electron ionization), References, Notes

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

Enthalpy of vaporization

Enthalpy of sublimation

Enthalpy of fusion

Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

For Zoom

1.) Enter the desired X axis range (e.g., 100, 200)

2.) Check here for automatic Y scaling

3.) Press here to zoom

Additional Data

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), 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]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), 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
• The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
• Customer support for NIST Standard Reference Data products.