1,3,5-Trioxane

• Formula: C₃H₆O₃
• Molecular weight: 90.0779
• IUPAC Standard InChI: InChI=1S/C3H6O3/c1-4-2-6-3-5-1/h1-3H2 Copy

  
• IUPAC Standard InChIKey: BGJSXRVXTHVRSN-UHFFFAOYSA-N Copy
• CAS Registry Number: 110-88-3
• 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: s-Trioxane; Formaldehyde, trimer; Triformol; Trioxan; Trioxane; Trioxymethylene; Metaformaldehyde; sym-Trioxane; Trioxin; 1,3,5-Trioxan; s-Trioxan; s-Trixane; Aldeform; Formagene; Marvosan; Paraformaldehyde; Triossimetilene; Trioxymethyleen; Trioxymethylen; 1,3,5-Trioxacyclohexane; NSC 26347
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• Information on this page:
  • Gas phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Computational Chemistry Comparison and Benchmark Database
  • Gas Phase Kinetics Database
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Gas 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
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

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
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing

Enthalpy of vaporization

Enthalpy of sublimation

Enthalpy of fusion

Gas phase ion energetics 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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Ionization energy determinations

Appearance energy determinations

References

Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Mansson, Morawetz, et al., 1969
Mansson, M.; Morawetz, E.; Nakase, Y.; Sunner, S., The enthalpies of formation of trioxane and tetroxane, Acta Chem. Scand., 1969, 23, 56-60. [all data]

Walker and Carlisle, 1943
Walker, J.F.; Carlisle, P.J., Trioxane, Chem. Eng. News, 1943, 21, 1250-1251. [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]

Clegg G.A., 1968
Clegg G.A., Thermodynamics of polymerization of heterocyclic compounds. I. The heat capacity, entropy, and enthalpy of trioxane, Polymer, 1968, 9, 75-79. [all data]

Dorofeeva O.V., 1992
Dorofeeva O.V., Ideal gas thermodynamic properties of oxygen heterocyclic compounds. Part 2. Six-membered, seven-membered and eight-membered rings, Thermochim. Acta, 1992, 200, 121-150. [all data]

Melia T.P., 1967
Melia T.P., Thermodynamics of addition polymerization. I. The system trioxane-polyoxymethylene, J. Appl. Chem., 1967, 17, 15-17. [all data]

Le Fevre, Sundaram, et al., 1963
Le Fevre, R.J.W.; Sundaram, A.; Pierens, R.K., Molecular Polarisability: the Anisotropy of the Carbon-Oxygen Link, J. Chem. Soc., 1963, 1963, 479-488. [all data]

Van Bommel, van Miltenburg, et al., 1988
Van Bommel, M.J.; van Miltenburg, J.C.; Schuijff, A., Heat Capacity Measurements and Thermodynamic Functions of 1,3,5- Triazine and 1,3,5-Trioxane, J. Chem. Thermodyn., 1988, 20, 397-403. [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]

Serebryannaya and Byk, 1965
Serebryannaya, I.I.; Byk, S.Sh., Khim. Prom., 1965, 23, 828. [all data]

De Wit, Van Miltenburg, et al., 1983
De Wit, H.G.M.; Van Miltenburg, J.C.; De Kruif, C.G., Thermodynamic properties of molecular organic crystals containing nitrogen, oxygen, and sulphur 1. Vapour pressures and enthalpies of sublimation, The Journal of Chemical Thermodynamics, 1983, 15, 7, 651-663, https://doi.org/10.1016/0021-9614(83)90079-4 . [all data]

van Bommel, van Miltenburg, et al., 1988
van Bommel, M.J.; van Miltenburg, J.C.; Schuijff, A., Heat-capacity measurements and thermodynamic functions of 1,3,5-triazine and 1,3,5-trioxane, J. Chem. Thermodynam., 1988, 20, 397-403. [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]

Acree, 1991
Acree, William E., Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation, Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H . [all data]

Sweigart and Turner, 1972
Sweigart, D.A.; Turner, D.W., Lone pair orbitals and their interactions studied by photoelectron spectroscopy. II. Equivalent orbitals in saturated oxygen and sulfur J. Heterocycl. Chem., J. Am. Chem. Soc., 1972, 94, 5599. [all data]

Kumakura, Sugiura, et al., 1968
Kumakura, M.; Sugiura, T.; Okamura, S., Characteristics of RPD ion source of time-of-flight mass spectrometer, and measurement of the ionization potential and the appearance potentials of trioxymethylene, Mass Spectry. (Tokyo), 1968, 16, 16. [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, References

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,gas	Constant pressure heat capacity of gas
  S°gas	Entropy of gas at standard conditions
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔfH°gas	Enthalpy of formation of gas 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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