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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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change 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, Phase change 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 |
Phase change 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:
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 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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]
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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, References
- Symbols used in this document:
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) Tfus Fusion (melting) point Ttriple Triple point temperature 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 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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