Home Symbol which looks like a small house Up Solid circle with an upward pointer in it

1,3,5-Trioxane

Data at NIST subscription sites:

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, Reaction thermochemistry data, Gas phase ion energetics 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
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
Deltafgas-465.76 ± 0.50kJ/molCcrMansson, Morawetz, et al., 1969ALS
Deltafgas-489.5kJ/molN/AWalker and Carlisle, 1943Value computed using «DELTA»fHsolid° value of -546.0±11.0 kj/mol from Walker and Carlisle, 1943 and «DELTA»subH° value of 56.5 kj/mol from Mansson, Morawetz, et al., 1969.; DRB
Deltafgas-464.0kJ/molN/ADelepine and Badoche, 1942Value computed using «DELTA»fHsolid° value of -520.5 kj/mol from Delepine and Badoche, 1942 and «DELTA»subH° value of 56.5 kj/mol from Mansson, Morawetz, et al., 1969.; DRB
Quantity Value Units Method Reference Comment
gas284.9 ± 3.4J/mol*KN/AClegg G.A., 1968GT

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
33.5050.Dorofeeva O.V., 1992p=1 bar. Selected values are in close agreement with those calculated by [ Melia T.P., 1967].; GT
38.63100.
47.52150.
57.69200.
75.24273.15
81.9 ± 3.5298.15
82.38300.
109.75400.
134.80500.
155.90600.
173.34700.
187.80800.
199.87900.
210.021000.
218.601100.
225.891200.
232.121300.
237.451400.
242.051500.

Condensed phase thermochemistry data

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

Quantity Value Units Method Reference Comment
Deltafsolid-522.3 ± 0.4kJ/molCcrMansson, Morawetz, et al., 1969ALS
Deltafsolid-546. ± 11.kJ/molCcbWalker and Carlisle, 1943ALS
Deltafsolid-520.49kJ/molCcbDelepine and Badoche, 1942Author's hf298_condensed=-125.55 kcal/mol; ALS
Quantity Value Units Method Reference Comment
Deltacsolid-1515.3kJ/molCcbHayes, 1971Corresponding «DELTA»fsolid = -522.71 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacsolid-1515.7 ± 0.3kJ/molCcrMansson, Morawetz, et al., 1969Corresponding «DELTA»fsolid = -522.33 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacsolid-1492. ± 1.kJ/molCcbWalker and Carlisle, 1943Corresponding «DELTA»fsolid = -545.6 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacsolid-1518.kJ/molCcbDelepine and Badoche, 1942Author's hf298_condensed=-125.55 kcal/mol; Corresponding «DELTA»fsolid = -520.5 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
solid,1 bar142.89J/mol*KN/Avan Bommel, van Miltenburg, et al., 1988DH
solid,1 bar133.0J/mol*KN/AClegg, Melia, et al., 1968DH

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
113.08298.15van Bommel, van Miltenburg, et al., 1988T = 10 to 350 K.; DH
111.4298.15Clegg, Melia, et al., 1968T = 80 to 310 K.; DH

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics 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
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tfus335.65KN/ALe Fevre, Sundaram, et al., 1963Uncertainty assigned by TRC = 1.5 K; TRC
Quantity Value Units Method Reference Comment
Ttriple333.44KN/AVan Bommel, van Miltenburg, et al., 1988Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC
Quantity Value Units Method Reference Comment
Deltasub55. ± 6.kJ/molAVGN/AAverage of 6 values; Individual data points

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
40.0344.AStephenson and Malanowski, 1987Based on data from 329. - 386. K. See also Serebryannaya and Byk, 1965.; AC

Enthalpy of sublimation

DeltasubH (kJ/mol) Temperature (K) Method Reference Comment
57.9223.TE,MEDe Wit, Van Miltenburg, et al., 1983Based on data from 212. - 231. K.; AC

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
15.105333.44van Bommel, van Miltenburg, et al., 1988DH
15.1333.4Domalski and Hearing, 1996See also Acree, 1991.; AC

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


Reaction thermochemistry data

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

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

41,3,5-Trioxane = 31,3,5,7-Tetroxane

By formula: 4C3H6O3 = 3C4H8O4

Quantity Value Units Method Reference Comment
Deltar12. ± 0.8kJ/molCmBogdanova, Bonetskaya, et al., 1971crystal phase

1,3,5-Trioxane = 3Formaldehyde

By formula: C3H6O3 = 3CH2O

Quantity Value Units Method Reference Comment
Deltar194.0 ± 2.5kJ/molEqkBusfield and Merigold, 1969solid phase

3Formaldehyde = 1,3,5-Trioxane

By formula: 3CH2O = C3H6O3

Quantity Value Units Method Reference Comment
Deltar-139.2 ± 2.1kJ/molEqkBusfield and Merigold, 1969gas phase

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction 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:
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

IE (eV) Method Reference Comment
10.3PESweigart and Turner, 1972LLK
10.59 ± 0.05EIKumakura, Sugiura, et al., 1968RDSH
~10.8PESweigart and Turner, 1972Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CHO+13.59 ± 0.05?EIKumakura, Sugiura, et al., 1968RDSH
CH3O+11.49 ± 0.05?EIKumakura, Sugiura, et al., 1968RDSH
C2H5O2+10.79 ± 0.05CHO?EIKumakura, Sugiura, et al., 1968RDSH
C3H5O3+10.59 ± 0.05HEIKumakura, Sugiura, et al., 1968RDSH

Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics 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.

Mass spectrum
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

View image of digitized spectrum (can be printed in landscape orientation).

View spectrum image in SVG format.

Download spectrum in JCAMP-DX format.

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 Japan AIST/NIMC Database- Spectrum MS-NW-1446
NIST MS number 229021

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics 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.

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]

Hayes, 1971
Hayes, C.W., Bomb calorimetric studies on normal alkan-1-ols, steroregular polymethylmethacrylates, «alpha»-olefinic polymers, trioxane and oxygenated polymers, Diss. Abs., 1971, 31, 5903-5904. [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]

Clegg, Melia, et al., 1968
Clegg, G.A.; Melia, T.P.; Tyson, A., Thermodynamics of polymerization of heterocyclic compounds. I. The heat capacity, entropy and enthalpy of trioxan, Polymer, 1968, 9(2), 75-79. [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]

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]

Bogdanova, Bonetskaya, et al., 1971
Bogdanova, K.A.; Bonetskaya, A.K.; Berlin, A.A.; Rakova, G.V.; Enikolopyan, N.S., Thermal effects of trioxane and tetraoxane polymerization, Dokl. Akad. Nauk SSSR, 1971, 197, 618-620. [all data]

Busfield and Merigold, 1969
Busfield, W.K.; Merigold, D., The gas-phase equilibrium between trioxan and formaldehyde: The standard enthalpy and entropy of the trimerisation of formaldehyde, J. Chem. Soc. A, 1969, 19, 2975-2977. [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, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), References