Propiolactone

Formula: C₃H₄O₂
Molecular weight: 72.0627
IUPAC Standard InChI: InChI=1S/C3H4O2/c4-3-1-2-5-3/h1-2H2
IUPAC Standard InChIKey: VEZXCJBBBCKRPI-UHFFFAOYSA-N
CAS Registry Number: 57-57-8
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: β-Propiolactone; 2-Oxetanone; β-Propanoic acid lactone; β-Propionolactone; Betaprone; BPL; Hydracrylic acid β-lactone; Propanoic acid, 3-hydroxy-, β-lactone; Propanolide; 1,3-Propiolactone; 3-Hydroxypropionic acid, lactone; 3-Propanolide; 3-Propiolactone; 2-Oxacyclobutanone; β-lactone hydracrylic acid; 2-Oxooxetane; β-Proprolactone; Propiolactone β-; Propionic acid, 3-hydroxy-, β-lactone; β-Propriolactone; β-Propiolakton; 3-Hydroxypropionic acid β-lactone; NSC-21626; Oxetan-2-one; Propionolactone; Beta-propiolactone
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Gas phase thermochemistry data

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Data compiled as indicated in comments:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	-286.2	kJ/mol	N/A	Dmitriev, Kotovich, et al., 1988	Value computed using Δ_fH_liquid° value of -333.2±1.2 kj/mol from Dmitriev, Kotovich, et al., 1988 and Δ_vapH° value of 47.0 kj/mol from Borjesson, Nakase, et al., 1966.; DRB
Δ_fH°_gas	-282.9	kJ/mol	N/A	Yevstroprov, Lebedev, et al., 1979	Value computed using Δ_fH_liquid° value of -329.9±0.8 kj/mol from Yevstroprov, Lebedev, et al., 1979 and Δ_vapH° value of 47.0 kj/mol from Borjesson, Nakase, et al., 1966.; DRB
Δ_fH°_gas	-282.9 ± 0.84	kJ/mol	Ccr	Borjesson, Nakase, et al., 1966	ALS

Constant pressure heat capacity of gas

C_p,gas (J/mol*K)	Temperature (K)	Reference	Comment
38.83	100.	Kudchadker S.A., 1975	Selected values are in close agreement with results of statistical calculation by [ Joshi R.M., 1970].; GT
44.84	150.
52.42	200.
66.15	273.15
71.24	298.15
71.62	300.
91.57	400.
108.86	500.
123.02	600.
134.58	700.
144.13	800.
152.11	900.
158.83	1000.
164.54	1100.
169.40	1200.
173.56	1300.
177.14	1400.
180.23	1500.

Condensed phase thermochemistry data

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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
Δ_fH°_liquid	-333.2 ± 1.2	kJ/mol	Ccb	Dmitriev, Kotovich, et al., 1988	ALS
Δ_fH°_liquid	-329.9 ± 0.8	kJ/mol	Cm	Yevstroprov, Lebedev, et al., 1979	Hfusion=9.41±0.01 kJ/mol at 239.86 K; ALS
Δ_fH°_liquid	-329.9 ± 0.84	kJ/mol	Ccr	Borjesson, Nakase, et al., 1966	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-1419.0 ± 1.2	kJ/mol	Ccb	Dmitriev, Kotovich, et al., 1988	Corresponding Δ_fHº_liquid = -333.2 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-1422.3 ± 0.84	kJ/mol	Ccr	Borjesson, Nakase, et al., 1966	Corresponding Δ_fHº_liquid = -329.9 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_liquid	175.3	J/mol*K	N/A	Lebedev and Yevstropov, 1983	DH
S°_liquid	175.4	J/mol*K	N/A	Evstropov, Lebedev, et al., 1979	DH

Constant pressure heat capacity of liquid

C_p,liquid (J/mol*K)	Temperature (K)	Reference	Comment
122.1	298.15	Lebedev and Yevstropov, 1983	T = 13.8 to 340 K.; DH
122.2	298.15	Evstropov, Lebedev, et al., 1979	T = 5 to 400 K.; DH

Reaction thermochemistry data

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Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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Individual Reactions

Propiolactone = C₃H₄O₂

By formula: C₃H₄O₂ = C₃H₄O₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	74.8 ± 3.8	kJ/mol	Cm	Yevstroprov, Lebedev, et al., 1979	liquid phase; Hfusion=9.41±0.01 kJ/mol at 239.86 K

References

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Dmitriev, Kotovich, et al., 1988
Dmitriev, Yu.G.; Kotovich, K.Z.; Kochubei, V.V.; Mineravina, L.O., Heats of combustion of alkyl derivatives of β-propiolactones, Vestn. L'vov. Politekhn. Inst., 1988, 221, 34-35. [all data]

Borjesson, Nakase, et al., 1966
Borjesson, B.; Nakase, Y.; Sunner, S., The heat of combustion and polymerization of β-propiolactone, Acta Chem. Scand., 1966, 20, 803-810. [all data]

Yevstroprov, Lebedev, et al., 1979
Yevstroprov, A.A.; Lebedev, B.V.; Kulagina, T.G.; Lyudvig, Ye.B.; Belenkaya, B.G., The thermodynamic proerties of β-propiolactone, its polymer, and its polymerization in the 0-400°K range, Polym. Sci. USSR, 1979, 21, 2249-2256. [all data]

Kudchadker S.A., 1975
Kudchadker S.A., Thermodynamic properties of oxygen compounds. II. beta-Propiolactone, gamma-butyrolactone, and gamma-butyrolactam (2-pyrrolidone), Thermochim. Acta, 1975, 12, 11-17. [all data]

Joshi R.M., 1970
Joshi R.M., Thermodynamic properties of some monomeric compounds in the standard ideal gas state, J. Polym. Sci., Part A-2, 1970, 8, 679-687. [all data]

Lebedev and Yevstropov, 1983
Lebedev, B.V.; Yevstropov, A.A., Thermodynamics of β-propiolactone, t-butyrolactone, d-valerolactone, and e-caprolactone from 13.8 to 340 K, J. Chem. Thermodynam., 1983, 15, 115-128. [all data]

Evstropov, Lebedev, et al., 1979
Evstropov, A.A.; Lebedev, B.V.; Kulagina, T.G.; Lyudvig, E.B., and Belen'kaya, B.G. Thermodynamic parameters of β-propiolactone, poly-β-propiolactone, and β-propiolactone polymerization at 0 to 400 K, Vysokomol. Soedin., Ser., 1979, A 21(9), 2038-2044. [all data]

Notes

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Symbols used in this document:

C_p,gas	Constant pressure heat capacity of gas
C_p,liquid	Constant pressure heat capacity of liquid
S°_liquid	Entropy of liquid at standard conditions
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid 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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