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
View 3d structure (requires JavaScript / HTML 5) - 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
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Data at other public NIST sites:
- Options:
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, 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 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 | -111.32 ± 0.12 | kcal/mol | Ccr | Mansson, Morawetz, et al., 1969 | ALS |
| ΔfH°gas | -117.0 | kcal/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 | -110.9 | kcal/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 | 68.09 ± 0.82 | cal/mol*K | N/A | Clegg G.A., 1968 | GT |
Constant pressure heat capacity of gas
| Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 8.007 | 50. | Dorofeeva O.V., 1992 | p=1 bar. Selected values are in close agreement with those calculated by [ Melia T.P., 1967].; GT |
| 9.233 | 100. | ||
| 11.36 | 150. | ||
| 13.79 | 200. | ||
| 17.98 | 273.15 | ||
| 19.57 ± 0.84 | 298.15 | ||
| 19.69 | 300. | ||
| 26.231 | 400. | ||
| 32.218 | 500. | ||
| 37.261 | 600. | ||
| 41.429 | 700. | ||
| 44.885 | 800. | ||
| 47.770 | 900. | ||
| 50.196 | 1000. | ||
| 52.247 | 1100. | ||
| 53.989 | 1200. | ||
| 55.478 | 1300. | ||
| 56.752 | 1400. | ||
| 57.851 | 1500. |
Condensed phase thermochemistry data
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 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 |
|---|---|---|---|---|---|
| ΔfH°solid | -124.84 ± 0.09 | kcal/mol | Ccr | Mansson, Morawetz, et al., 1969 | ALS |
| ΔfH°solid | -130.4 ± 2.6 | kcal/mol | Ccb | Walker and Carlisle, 1943 | ALS |
| ΔfH°solid | -124.40 | kcal/mol | Ccb | Delepine and Badoche, 1942 | Author's hf298_condensed=-125.55 kcal/mol; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -362.17 | kcal/mol | Ccb | Hayes, 1971 | Corresponding ΔfHºsolid = -124.93 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°solid | -362.26 ± 0.07 | kcal/mol | Ccr | Mansson, Morawetz, et al., 1969 | Corresponding ΔfHºsolid = -124.84 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°solid | -356.7 ± 0.3 | kcal/mol | Ccb | Walker and Carlisle, 1943 | Corresponding ΔfHºsolid = -130.4 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°solid | -362.7 | kcal/mol | Ccb | Delepine and Badoche, 1942 | Author's hf298_condensed=-125.55 kcal/mol; Corresponding ΔfHºsolid = -124.4 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°solid,1 bar | 34.152 | cal/mol*K | N/A | van Bommel, van Miltenburg, et al., 1988 | DH |
| S°solid,1 bar | 31.79 | cal/mol*K | N/A | Clegg, Melia, et al., 1968 | DH |
Constant pressure heat capacity of solid
| Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 27.027 | 298.15 | van Bommel, van Miltenburg, et al., 1988 | T = 10 to 350 K.; DH |
| 26.63 | 298.15 | Clegg, Melia, et al., 1968 | T = 80 to 310 K.; DH |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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 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 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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]
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]
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, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas Cp,solid Constant pressure heat capacity of solid S°gas Entropy of gas at standard conditions S°solid,1 bar Entropy of solid at standard conditions (1 bar) ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.