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
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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

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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
Δ_fH°_gas	-111.32 ± 0.12	kcal/mol	Ccr	Mansson, Morawetz, et al., 1969	ALS
Δ_fH°_gas	-117.0	kcal/mol	N/A	Walker and Carlisle, 1943	Value computed using Δ_fH_solid° value of -546.0±11.0 kj/mol from Walker and Carlisle, 1943 and Δ_subH° value of 56.5 kj/mol from Mansson, Morawetz, et al., 1969.; DRB
Δ_fH°_gas	-110.9	kcal/mol	N/A	Delepine and Badoche, 1942	Value computed using Δ_fH_solid° value of -520.5 kj/mol from Delepine and Badoche, 1942 and Δ_subH° 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

C_p,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.

Reaction thermochemistry data

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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 1,3,5-Trioxane = 3

By formula: 4C₃H₆O₃ = 3C₄H₈O₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	2.9 ± 0.2	kcal/mol	Cm	Bogdanova, Bonetskaya, et al., 1971	crystal phase

1,3,5-Trioxane = 3

By formula: C₃H₆O₃ = 3CH₂O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	46.37 ± 0.60	kcal/mol	Eqk	Busfield and Merigold, 1969	solid phase

3 = 1,3,5-Trioxane

By formula: 3CH₂O = C₃H₆O₃

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-33.27 ± 0.50	kcal/mol	Eqk	Busfield and Merigold, 1969	gas phase

Gas Chromatography

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Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

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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

View large format table.

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

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Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	1167.	Peng, Yang, et al., 1991	Program: not specified

References

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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]

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]

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

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Symbols used in this document:

C_p,gas	Constant pressure heat capacity of gas
S°_gas	Entropy of gas at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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