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
The 3d structure may be viewed using Java or Javascript.
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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Information on this page:
Other data available:
- IR Spectrum
- Mass spectrum (electron ionization)
Data at other public NIST sites:
- Gas Phase Kinetics Database
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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	-68.40	kcal/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	-67.61	kcal/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	-67.61 ± 0.20	kcal/mol	Ccr	Borjesson, Nakase, et al., 1966	ALS

Constant pressure heat capacity of gas

C_p,gas (cal/mol*K)	Temperature (K)	Reference	Comment
9.281	100.	Kudchadker S.A., 1975	Selected values are in close agreement with results of statistical calculation by [ Joshi R.M., 1970].; GT
10.72	150.
12.53	200.
15.81	273.15
17.03	298.15
17.12	300.
21.89	400.
26.018	500.
29.402	600.
32.165	700.
34.448	800.
36.355	900.
37.961	1000.
39.326	1100.
40.488	1200.
41.482	1300.
42.337	1400.
43.076	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	-79.64 ± 0.29	kcal/mol	Ccb	Dmitriev, Kotovich, et al., 1988	ALS
Δ_fH°_liquid	-78.8 ± 0.2	kcal/mol	Cm	Yevstroprov, Lebedev, et al., 1979	Hfusion=9.41±0.01 kJ/mol at 239.86 K; ALS
Δ_fH°_liquid	-78.85 ± 0.20	kcal/mol	Ccr	Borjesson, Nakase, et al., 1966	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-339.15 ± 0.29	kcal/mol	Ccb	Dmitriev, Kotovich, et al., 1988	Corresponding Δ_fHº_liquid = -79.64 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-339.93 ± 0.20	kcal/mol	Ccr	Borjesson, Nakase, et al., 1966	Corresponding Δ_fHº_liquid = -78.85 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_liquid	41.90	cal/mol*K	N/A	Lebedev and Yevstropov, 1983	DH
S°_liquid	41.92	cal/mol*K	N/A	Evstropov, Lebedev, et al., 1979	DH

Constant pressure heat capacity of liquid

C_p,liquid (cal/mol*K)	Temperature (K)	Reference	Comment
29.18	298.15	Lebedev and Yevstropov, 1983	T = 13.8 to 340 K.; DH
29.21	298.15	Evstropov, Lebedev, et al., 1979	T = 5 to 400 K.; DH

Phase change data

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Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity	Value	Units	Method	Reference	Comment
T_boil	435.2	K	N/A	Aldrich Chemical Company Inc., 1990	BS
Quantity	Value	Units	Method	Reference	Comment
T_triple	239.86	K	N/A	Lebedev and Yevstropov, 1983, 2	Uncertainty assigned by TRC = 0.02 K; TRC
T_triple	239.86	K	N/A	Evstropov, Lebedev, et al., 1979	Uncertainty assigned by TRC = 0.01 K; TRC
Quantity	Value	Units	Method	Reference	Comment
Δ_vapH°	11.24 ± 0.01	kcal/mol	C	Borjesson, Nakase, et al., 1966	ALS
Δ_vapH°	11.2	kcal/mol	N/A	Borjesson, Nakase, et al., 1966	DRB
Δ_vapH°	11.2 ± 0.02	kcal/mol	C	Borjesson, Nakase, et al., 1966	AC

Enthalpy of vaporization

Δ_vapH (kcal/mol)	Temperature (K)	Method	Reference	Comment
11.1	339.	A	Stephenson and Malanowski, 1987	Based on data from 324. to 435. K.; AC

Enthalpy of fusion

Δ_fusH (kcal/mol)	Temperature (K)	Reference	Comment
2.249	239.86	Lebedev and Yevstropov, 1983	DH
2.249	239.86	Evstropov, Lebedev, et al., 1979	DH
2.25	239.9	Domalski and Hearing, 1996	AC

Entropy of fusion

Δ_fusS (cal/mol*K)	Temperature (K)	Reference	Comment
9.376	239.86	Lebedev and Yevstropov, 1983	DH
9.376	239.86	Evstropov, Lebedev, et al., 1979	DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:

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

Propiolactone = C₃H₄O₂

By formula: C₃H₄O₂ = C₃H₄O₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	17.9 ± 0.91	kcal/mol	Cm	Yevstroprov, Lebedev, et al., 1979	liquid phase; Hfusion=9.41±0.01 kJ/mol at 239.86 K

Gas phase ion energetics data

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Data compiled by: Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Ionization energy determinations

IE (eV)	Method	Reference
9.70 ± 0.01	PI	Watanabe, Nakayama, et al., 1962

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Notes

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]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Lebedev and Yevstropov, 1983, 2
Lebedev, B.V.; Yevstropov, A.A. (see evstro aa), Thermodynamics of β-propiolactone, γ-butyrolactone, δ- valerolactone, and ε-caprolactone from 13.8 to 340 K, J. Chem. Thermodyn., 1983, 15, 115. [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]

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]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [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
T_boil	Boiling point
T_triple	Triple point temperature
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_fusH	Enthalpy of fusion
Δ_fusS	Entropy of fusion
Δ_rH°	Enthalpy of reaction at standard conditions
Δ_vapH	Enthalpy of vaporization
Δ_vapH°	Enthalpy of vaporization at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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