1,3,5-Trioxane
- Formula: C3H6O3
- Molecular weight: 90.0779
- IUPAC Standard InChIKey: BGJSXRVXTHVRSN-UHFFFAOYSA-N
- 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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Phase change data
Go To: Top, Gas phase ion energetics data, Gas Chromatography, 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 |
---|---|---|---|---|---|
Tfus | 335.65 | K | N/A | Le Fevre, Sundaram, et al., 1963 | Uncertainty assigned by TRC = 1.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 333.44 | K | N/A | Van Bommel, van Miltenburg, et al., 1988 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 13. ± 1. | kcal/mol | AVG | N/A | Average of 6 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
9.56 | 344. | A | Stephenson and Malanowski, 1987 | Based 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 |
---|---|---|---|---|
13.8 | 223. | TE,ME | De Wit, Van Miltenburg, et al., 1983 | Based on data from 212. to 231. K.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
3.6102 | 333.44 | van Bommel, van Miltenburg, et al., 1988 | DH |
3.61 | 333.4 | Domalski and Hearing, 1996 | See also Acree, 1991.; AC |
Gas phase ion energetics data
Go To: Top, Phase change data, Gas Chromatography, 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 |
---|---|---|---|
10.3 | PE | Sweigart and Turner, 1972 | LLK |
10.59 ± 0.05 | EI | Kumakura, Sugiura, et al., 1968 | RDSH |
~10.8 | PE | Sweigart and Turner, 1972 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CHO+ | 13.59 ± 0.05 | ? | EI | Kumakura, Sugiura, et al., 1968 | RDSH |
CH3O+ | 11.49 ± 0.05 | ? | EI | Kumakura, Sugiura, et al., 1968 | RDSH |
C2H5O2+ | 10.79 ± 0.05 | CHO? | EI | Kumakura, Sugiura, et al., 1968 | RDSH |
C3H5O3+ | 10.59 ± 0.05 | H | EI | Kumakura, Sugiura, et al., 1968 | RDSH |
Gas Chromatography
Go To: Top, Phase change 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
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | Apiezon L | 120. | 650. | Bogoslovsky, Anvaer, et al., 1978 | Celite 545 |
Packed | Apiezon L | 160. | 660. | Bogoslovsky, Anvaer, et al., 1978 | Celite 545 |
Normal alkane RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | Apieson L | 120. | 658. | Kurdina, Markovich, et al., 1969 | not specified, not specified |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 1167. | Peng, Yang, et al., 1991 | Program: not specified |
References
Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
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, Phase change data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy Tfus Fusion (melting) point Ttriple Triple point temperature 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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