1,3-Dioxolan-2-one
- Formula: C3H4O3
- Molecular weight: 88.0621
- IUPAC Standard InChIKey: KMTRUDSVKNLOMY-UHFFFAOYSA-N
- CAS Registry Number: 96-49-1
- Chemical structure:
This structure is also available as a 2d Mol file - Other names: Carbonic acid, cyclic ethylene ester; Cyclic ethylene carbonate; Ethylene carbonate; Ethylene glycol carbonate; Glycol carbonate; 2-Dioxolone; Dioxolone-2; Ethylene glycol, cyclic carbonate; 1,3-Dioxacyclopentan-2-one; Ethylenester kyseliny uhlicite; Texacar EC; NSC 11801
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References, Notes
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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -120.2 ± 1.0 | kcal/mol | Ccb | Choi and Joncich, 1971 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -144.43 kcal/mol; Pedley's value is off by 24.20kcal/mol; ALS |
Constant pressure heat capacity of gas
Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
19.5 | 298.15 | Vasilev I.A., 1984 | GT |
19.6 | 300. | ||
25.07 | 400. | ||
29.76 | 500. | ||
33.58 | 600. | ||
36.69 | 700. | ||
39.22 | 800. | ||
41.35 | 900. | ||
43.12 | 1000. |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References, Notes
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 | -163.20 ± 0.50 | kcal/mol | Ccb | Choi and Joncich, 1971 | Pedley's value is off by 24.20kcal/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -255.58 ± 0.50 | kcal/mol | Ccb | Choi and Joncich, 1971 | Pedley's value is off by 24.20kcal/mol; Corresponding ΔfHºliquid = -163.20 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔfH°solid | -141.2 | kcal/mol | Ccb | Vogdanis, Martens, et al., 1990 | ALS |
ΔfH°solid | -140.1 ± 0.90 | kcal/mol | Ccb | Calhoun, 1983 | ALS |
ΔfH°solid | -139.00 ± 0.09 | kcal/mol | Ccb | Vasil'eva, Zhil'tosova, et al., 1972 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -277.58 | kcal/mol | Ccb | Vogdanis, Martens, et al., 1990 | Corresponding ΔfHºsolid = -141.2 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -278.65 ± 0.89 | kcal/mol | Ccb | Calhoun, 1983 | Corresponding ΔfHºsolid = -140.13 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -279.78 ± 0.09 | kcal/mol | Ccb | Vasil'eva, Zhil'tosova, et al., 1972 | Corresponding ΔfHºsolid = -139.00 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -279.9516 | kcal/mol | Ccb | Silvestro and Lenchitz, 1961 | Corresponding ΔfHºsolid = -138.8319 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 31.678 | cal/mol*K | N/A | Vasil'ev and Korkhov, 1974 | DH |
S°solid,1 bar | 31.678 | cal/mol*K | N/A | Vasil'ev and Korkhov, 1973 | Extrapolation below 52 K.; DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
32.00 | 323.15 | Peppel, 1958 | DH |
Constant pressure heat capacity of solid
Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
28.069 | 298.15 | Vasil'ev and Korkhov, 1974 | T = 52 to 340 K. Cp(liq) = 88.977 + 0.1586T J/mol*K (309 to 340 K).; DH |
28.069 | 298.15 | Vasil'ev and Korkhov, 1973 | T = 52 to 310 K. Full data deposited in VINITI, No. 326-73, 21 June 1973.; 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
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tfus | 310. ± 3. | K | AVG | N/A | Average of 7 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 309.47 | K | N/A | Marsh, 1987 | Uncertainty assigned by TRC = 0.004 K; recommended as calibration standard; TRC |
Ttriple | 309.49 | K | N/A | Vasil'ev and Korkhov, 1973 | Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 20. ± 20. | kcal/mol | AVG | N/A | Average of 6 values; Individual data points |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
516.7 | 0.974 | Aldrich Chemical Company Inc., 1990 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
14.2 | 396. | A | Stephenson and Malanowski, 1987 | Based on data from 381. to 437. K.; AC |
14.4 | 383. | EB | Hong, Wakslak, et al., 1982 | Based on data from 368. to 449. K.; AC |
13.5 | 423. | EB | Hong, Wakslak, et al., 1982 | Based on data from 368. to 449. K.; AC |
13.1 | 433. | EB | Hong, Wakslak, et al., 1982 | Based on data from 368. to 433. K.; AC |
13.500 | 423. | V | Peppel, 1958 | ALS |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
16.4 | 285. | A | Stephenson and Malanowski, 1987 | Based on data from 273. to 297. K.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
3.1776 | 309.49 | N/A | Vasil'ev and Korkhov, 1974 | DH |
3.1776 | 309.49 | N/A | Vasil'ev and Korkhov, 1973 | DH |
3.112 | 311.2 | DSC | Ding, 2004 | AC |
3.18 | 309.5 | N/A | Vasil'ev and Korkhov, 1973 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
10.27 | 309.49 | Vasil'ev and Korkhov, 1974 | DH |
10.27 | 309.49 | Vasil'ev and Korkhov, 1973 | DH |
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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 194.6 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 187.5 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.40 | PE | McGlynn and Meeks, 1976 | LLK |
10.40 | PE | Meeks, Arnett, et al., 1975 | LLK |
10.70 | PE | Yokoyama, Jinno, et al., 1974 | LLK |
11.1 | PE | Wittel, Astrup, et al., 1975 | Vertical value; LLK |
11.47 | PE | Bain and Frost, 1973 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C2H4O+[c-C2H4O+] | 11.34 ± 0.05 | CH2O2 | EI | Buschek, Holmes, et al., 1987 | LBLHLM |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, References, Notes
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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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. |
---|---|
Origin | Japan AIST/NIMC Database- Spectrum MS-NW-4916 |
NIST MS number | 229208 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Choi and Joncich, 1971
Choi, J.K.; Joncich, M.J.,
Heats of combustion, heats of formation and vapor pressures of some organic carbonates. Estimation of carbonate group contribution to heat of formation,
J. Chem. Eng. Data, 1971, 16, 87-90. [all data]
Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P.,
Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]
Vasilev I.A., 1984
Vasilev I.A.,
Thermodynamic Properties of Oxygen-Containing Organic Compounds. Khimiya, Leningrad, 1984. [all data]
Vogdanis, Martens, et al., 1990
Vogdanis, L.; Martens, B.; Uchtmann, H.; Hensel, F.; Heitz, W.,
Synthetic and thermodynamic investigations in the polymerization of ethylene carbonate,
Makromol. Chem., 1990, 191, 456-472. [all data]
Calhoun, 1983
Calhoun, W.L.,
Enthalpies of combustion and formation of ethylene carbonate,
J. Chem. Eng. Data, 1983, 28, 146-148. [all data]
Vasil'eva, Zhil'tosova, et al., 1972
Vasil'eva, T.F.; Zhil'tosova, E.N.; Vvedenski, A.A.,
Enthalpies of combustion of alkylene carbonates,
Russ. J. Phys. Chem. (Engl. Transl.), 1972, 46, 316. [all data]
Silvestro and Lenchitz, 1961
Silvestro, G.; Lenchitz, C.,
Heat of combustion of ethylene carbonate,
J. Phys. Chem., 1961, 65, 694-695. [all data]
Vasil'ev and Korkhov, 1974
Vasil'ev, I.A.; Korkhov, A.D.,
Thermodynamic properties of alkylene carbonates at low temperatures, Tr. Khim. Khim. Tekhnol.,
Gor'kii, 1974, 36, 103-105. [all data]
Vasil'ev and Korkhov, 1973
Vasil'ev, I.A.; Korkhov, A.D.,
The heat capacities and enthalpies of fusion and the thermodynamic properties of solid and liquid ethylene carbonate,
Zhur. Fiz. Khim., 1973, 47, 2710. [all data]
Peppel, 1958
Peppel, W.J.,
Preparation and properties of the alkylene carbonates,
Ind. Eng. Chem., 1958, 50, 767-770. [all data]
Marsh, 1987
Marsh, K.N.,
Recommended Reference Materials for the Realization of Physicochemical Properties, Blackwell Sci. Pub., Oxford, 1987. [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]
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]
Hong, Wakslak, et al., 1982
Hong, C.S.; Wakslak, R.; Finston, H.; Fried, V.,
Some thermodynamic properties of systems containing propylene carbonate and ethylene carbonate,
J. Chem. Eng. Data, 1982, 27, 2, 146-148, https://doi.org/10.1021/je00028a012
. [all data]
Ding, 2004
Ding, Michael S.,
Liquid-Solid Phase Equilibria and Thermodynamic Modeling for Binary Organic Carbonates,
J. Chem. Eng. Data, 2004, 49, 2, 276-282, https://doi.org/10.1021/je034134e
. [all data]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [all data]
McGlynn and Meeks, 1976
McGlynn, S.P.; Meeks, J.L.,
Photoelectron spectra of carbonyls, carbonates, oxalates and esterification effects,
J. Electron Spectrosc. Relat. Phenom., 1976, 8, 85. [all data]
Meeks, Arnett, et al., 1975
Meeks, J.L.; Arnett, J.F.; Larson, D.; McGlynn, S.P.,
Photoelectron spectroscopy of carbonyls. Ionization assignments,
Chem. Phys. Lett., 1975, 30, 190. [all data]
Yokoyama, Jinno, et al., 1974
Yokoyama, Y.; Jinno, M.; Watanabe, I.; Ikeda, S.,
Identification of accidentally degenerate bands in UV photoelectron spectra of ethylene carbonate and propylene carbonate,
J. Electron Spectrosc. Relat. Phenom., 1974, 5, 1095. [all data]
Wittel, Astrup, et al., 1975
Wittel, K.; Astrup, E.E.; Bock, H.; Graeffe, G.; Juslen, H.,
Photoelectron spectra and molecular properties, XLVIII Carbonates thio- carbonates,
Z. Naturforsch. B:, 1975, 30, 862. [all data]
Bain and Frost, 1973
Bain, A.D.; Frost, D.C.,
Studies of the carbonyl group in some five-membered ring compounds by photoelectron spectroscopy,
Can. J. Chem., 1973, 51, 1245. [all data]
Buschek, Holmes, et al., 1987
Buschek, J.M.; Holmes, J.L.; Terlouw, J.K.,
CH3OCH+, a new stable C2H4O+ isomer, and a reassessment of the oxirane+ potential surface,
J. Am. Chem. Soc., 1987, 109, 7321. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas Cp,liquid Constant pressure heat capacity of liquid Cp,solid Constant pressure heat capacity of solid S°solid,1 bar Entropy of solid at standard conditions (1 bar) Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔsubH Enthalpy of sublimation 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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