1,3,5-Trioxane

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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

Quantity Value Units Method Reference Comment
Δfgas-111.32 ± 0.12kcal/molCcrMansson, Morawetz, et al., 1969ALS
Δfgas-117.0kcal/molN/AWalker and Carlisle, 1943Value computed using ΔfHsolid° value of -546.0±11.0 kj/mol from Walker and Carlisle, 1943 and ΔsubH° value of 56.5 kj/mol from Mansson, Morawetz, et al., 1969.; DRB
Δfgas-110.9kcal/molN/ADelepine and Badoche, 1942Value computed using ΔfHsolid° value of -520.5 kj/mol from Delepine and Badoche, 1942 and ΔsubH° value of 56.5 kj/mol from Mansson, Morawetz, et al., 1969.; DRB
Quantity Value Units Method Reference Comment
gas68.09 ± 0.82cal/mol*KN/AClegg G.A., 1968GT

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
8.00750.Dorofeeva O.V., 1992p=1 bar. Selected values are in close agreement with those calculated by [ Melia T.P., 1967].; GT
9.233100.
11.36150.
13.79200.
17.98273.15
19.57 ± 0.84298.15
19.69300.
26.231400.
32.218500.
37.261600.
41.429700.
44.885800.
47.770900.
50.1961000.
52.2471100.
53.9891200.
55.4781300.
56.7521400.
57.8511500.

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
Δfsolid-124.84 ± 0.09kcal/molCcrMansson, Morawetz, et al., 1969ALS
Δfsolid-130.4 ± 2.6kcal/molCcbWalker and Carlisle, 1943ALS
Δfsolid-124.40kcal/molCcbDelepine and Badoche, 1942Author's hf298_condensed=-125.55 kcal/mol; ALS
Quantity Value Units Method Reference Comment
Δcsolid-362.17kcal/molCcbHayes, 1971Corresponding Δfsolid = -124.93 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcsolid-362.26 ± 0.07kcal/molCcrMansson, Morawetz, et al., 1969Corresponding Δfsolid = -124.84 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcsolid-356.7 ± 0.3kcal/molCcbWalker and Carlisle, 1943Corresponding Δfsolid = -130.4 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcsolid-362.7kcal/molCcbDelepine and Badoche, 1942Author's hf298_condensed=-125.55 kcal/mol; Corresponding Δfsolid = -124.4 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
solid,1 bar34.152cal/mol*KN/Avan Bommel, van Miltenburg, et al., 1988DH
solid,1 bar31.79cal/mol*KN/AClegg, Melia, et al., 1968DH

Constant pressure heat capacity of solid

Cp,solid (cal/mol*K) Temperature (K) Reference Comment
27.027298.15van Bommel, van Miltenburg, et al., 1988T = 10 to 350 K.; DH
26.63298.15Clegg, Melia, et al., 1968T = 80 to 310 K.; 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
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
Δsub13. ± 1.kcal/molAVGN/AAverage of 6 values; Individual data points

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
9.56344.AStephenson and Malanowski, 1987Based on data from 329. to 386. K. See also Serebryannaya and Byk, 1965.; AC

Enthalpy of sublimation

ΔsubH (kcal/mol) Temperature (K) Method Reference Comment
13.8223.TE,MEDe Wit, Van Miltenburg, et al., 1983Based on data from 212. to 231. K.; AC

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
3.6102333.44van Bommel, van Miltenburg, et al., 1988DH
3.61333.4Domalski 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

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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: 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
Δr2.9 ± 0.2kcal/molCmBogdanova, Bonetskaya, et al., 1971crystal phase

1,3,5-Trioxane = 3Formaldehyde

By formula: C3H6O3 = 3CH2O

Quantity Value Units Method Reference Comment
Δr46.37 ± 0.60kcal/molEqkBusfield and Merigold, 1969solid phase

3Formaldehyde = 1,3,5-Trioxane

By formula: 3CH2O = C3H6O3

Quantity Value Units Method Reference Comment
Δr-33.27 ± 0.50kcal/molEqkBusfield and Merigold, 1969gas phase

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

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)

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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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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

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Gas Chromatography

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, 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

Kovats' RI, non-polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
PackedApiezon L120.650.Bogoslovsky, Anvaer, et al., 1978Celite 545
PackedApiezon L160.660.Bogoslovsky, Anvaer, et al., 1978Celite 545

Normal alkane RI, non-polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
PackedApieson L120.658.Kurdina, Markovich, et al., 1969not specified, not specified

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-Wax1167.Peng, Yang, et al., 1991Program: not specified

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), Gas Chromatography, 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, α-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]

Bogoslovsky, Anvaer, et al., 1978
Bogoslovsky, Yu.N.; Anvaer, B.I.; Vigdergauz, M.S., Chromatographic constants in gas chromatography (in Russian), Standards Publ. House, Moscow, 1978, 192. [all data]

Kurdina, Markovich, et al., 1969
Kurdina, Z.G.; Markovich, V.E.; Sakharov, V.M., Gas chromatography of cyclic O-containing compounds in Gas chromatography, Issue # 10, NIITEKhim, Moscow, 1969, 128-133. [all data]

Peng, Yang, et al., 1991
Peng, C.T.; Yang, Z.C.; Ding, S.F., Prediction of rentention idexes. II. Structure-retention index relationship on polar columns, J. Chromatogr., 1991, 586, 1, 85-112, https://doi.org/10.1016/0021-9673(91)80028-F . [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), Gas Chromatography, References