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
- 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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Gas phase thermochemistry 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:
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 |
|---|---|---|---|---|---|
| ΔfH°gas | -465.76 ± 0.50 | kJ/mol | Ccr | Mansson, Morawetz, et al., 1969 | ALS |
| ΔfH°gas | -489.5 | kJ/mol | N/A | Walker and Carlisle, 1943 | Value 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 |
| ΔfH°gas | -464.0 | kJ/mol | N/A | Delepine and Badoche, 1942 | Value 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 |
| S°gas | 284.9 ± 3.4 | J/mol*K | N/A | Clegg G.A., 1968 | GT |
Constant pressure heat capacity of gas
| Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 33.50 | 50. | Dorofeeva O.V., 1992 | p=1 bar. Selected values are in close agreement with those calculated by [ Melia T.P., 1967].; GT |
| 38.63 | 100. | ||
| 47.52 | 150. | ||
| 57.69 | 200. | ||
| 75.24 | 273.15 | ||
| 81.9 ± 3.5 | 298.15 | ||
| 82.38 | 300. | ||
| 109.75 | 400. | ||
| 134.80 | 500. | ||
| 155.90 | 600. | ||
| 173.34 | 700. | ||
| 187.80 | 800. | ||
| 199.87 | 900. | ||
| 210.02 | 1000. | ||
| 218.60 | 1100. | ||
| 225.89 | 1200. | ||
| 232.12 | 1300. | ||
| 237.45 | 1400. | ||
| 242.05 | 1500. |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry 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, Gas phase 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
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, Gas phase thermochemistry 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.
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]
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, Gas phase ion energetics data, Gas Chromatography, 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 ΔfH°gas Enthalpy of formation of gas at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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