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	-465.76 ± 0.50	kJ/mol	Ccr	Mansson, Morawetz, et al., 1969	ALS
Δ_fH°_gas	-489.5	kJ/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	-464.0	kJ/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	284.9 ± 3.4	J/mol*K	N/A	Clegg G.A., 1968	GT

Constant pressure heat capacity of gas

C_p,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.

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°	12. ± 0.8	kJ/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°	194.0 ± 2.5	kJ/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°	-139.2 ± 2.1	kJ/mol	Eqk	Busfield and Merigold, 1969	gas phase

Gas phase ion energetics data

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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, Reaction thermochemistry data, Gas phase ion energetics data, Notes

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]

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

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Symbols used in this document:

AE	Appearance energy
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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