Propiolactone
- Formula: C3H4O2
- Molecular weight: 72.0627
- 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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Gas phase thermochemistry data
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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:
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 |
---|---|---|---|---|---|
ΔfH°gas | -286.2 | kJ/mol | N/A | Dmitriev, Kotovich, et al., 1988 | Value computed using ΔfHliquid° value of -333.2±1.2 kj/mol from Dmitriev, Kotovich, et al., 1988 and ΔvapH° value of 47.0 kj/mol from Borjesson, Nakase, et al., 1966.; DRB |
ΔfH°gas | -282.9 | kJ/mol | N/A | Yevstroprov, Lebedev, et al., 1979 | Value computed using ΔfHliquid° value of -329.9±0.8 kj/mol from Yevstroprov, Lebedev, et al., 1979 and ΔvapH° value of 47.0 kj/mol from Borjesson, Nakase, et al., 1966.; DRB |
ΔfH°gas | -282.9 ± 0.84 | kJ/mol | Ccr | Borjesson, Nakase, et al., 1966 | ALS |
Constant pressure heat capacity of gas
Cp,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 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°liquid | -333.2 ± 1.2 | kJ/mol | Ccb | Dmitriev, Kotovich, et al., 1988 | ALS |
ΔfH°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 |
ΔfH°liquid | -329.9 ± 0.84 | kJ/mol | Ccr | Borjesson, Nakase, et al., 1966 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -1419.0 ± 1.2 | kJ/mol | Ccb | Dmitriev, Kotovich, et al., 1988 | Corresponding ΔfHºliquid = -333.2 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -1422.3 ± 0.84 | kJ/mol | Ccr | Borjesson, Nakase, et al., 1966 | Corresponding ΔfHºliquid = -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
Cp,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 |
Phase change data
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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:
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 |
---|---|---|---|---|---|
Tboil | 435.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 239.86 | K | N/A | Lebedev and Yevstropov, 1983, 2 | Uncertainty assigned by TRC = 0.02 K; TRC |
Ttriple | 239.86 | K | N/A | Evstropov, Lebedev, et al., 1979 | Uncertainty assigned by TRC = 0.01 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 47.03 ± 0.04 | kJ/mol | C | Borjesson, Nakase, et al., 1966 | ALS |
ΔvapH° | 47.0 | kJ/mol | N/A | Borjesson, Nakase, et al., 1966 | DRB |
ΔvapH° | 47.0 ± 0.1 | kJ/mol | C | Borjesson, Nakase, et al., 1966 | AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
46.4 | 339. | A | Stephenson and Malanowski, 1987 | Based on data from 324. to 435. K.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
9.410 | 239.86 | Lebedev and Yevstropov, 1983 | DH |
9.410 | 239.86 | Evstropov, Lebedev, et al., 1979 | DH |
9.41 | 239.9 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
39.23 | 239.86 | Lebedev and Yevstropov, 1983 | DH |
39.23 | 239.86 | Evstropov, Lebedev, et al., 1979 | DH |
Reaction thermochemistry data
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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
= C3H4O2
By formula: C3H4O2 = C3H4O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 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 |
Gas phase ion energetics data
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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 |
IR Spectrum
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: Coblentz Society, Inc.
Condensed Phase Spectrum
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Notice: Except where noted, spectra from this collection were measured on dispersive instruments, often in carefully selected solvents, and hence may differ in detail from measurements on FTIR instruments or in other chemical environments. More information on the manner in which spectra in this collection were collected can be found here.
Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
Additional Data
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Owner | COBLENTZ SOC. Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | DOW CHEMICAL COMPANY |
Source reference | COBLENTZ NO. 05634 |
Date | 1951/10/19 |
Name(s) | 2-oxetanone |
State | SOLUTION (10% CCl4 FOR 2-7.6, SATURATED-LESS THAN 10% -NaCl ADDED CS2 FOR 7.4-16) |
Instrument | BAIRD (PRISM) |
Instrument parameters | NaCl PRISM |
Path length | 0.0114 CM, 0.0112 CM |
Resolution | 2 |
Sampling procedure | TRANSMISSION |
Data processing | DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY |
Mass spectrum (electron ionization)
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
NIST MS number | 19145 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), NIST Free Links, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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:
Cp,gas Constant pressure heat capacity of gas Cp,liquid Constant pressure heat capacity of liquid S°liquid Entropy of liquid at standard conditions Tboil Boiling point Ttriple Triple point temperature ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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