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, Condensed phase thermochemistry data, Reaction 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:
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, Reaction 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:
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 |
Reaction thermochemistry 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 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
4 = 3
By formula: 4C3H6O3 = 3C4H8O4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 2.9 ± 0.2 | kcal/mol | Cm | Bogdanova, Bonetskaya, et al., 1971 | crystal phase |
= 3
By formula: C3H6O3 = 3CH2O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 46.37 ± 0.60 | kcal/mol | Eqk | Busfield and Merigold, 1969 | solid phase |
3 =
By formula: 3CH2O = C3H6O3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -33.27 ± 0.50 | kcal/mol | Eqk | Busfield and Merigold, 1969 | gas phase |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry 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]
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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry 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) 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 ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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