Propylene Carbonate
- Formula: C4H6O3
- Molecular weight: 102.0886
- IUPAC Standard InChIKey: RUOJZAUFBMNUDX-UHFFFAOYSA-N
- CAS Registry Number: 108-32-7
- 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. - Stereoisomers:
- Other names: 1,3-Dioxolan-2-one, 4-methyl-; Carbonic acid, cyclic propylene ester; Cyclic methylethylene carbonate; Cyclic propylene carbonate; Cyclic 1,2-propylene carbonate; Propylene glycol cyclic carbonate; 1-Methylethylene carbonate; 1,2-Propanediol carbonate; 1,2-Propanediol cyclic carbonate; 1,2-Propanediyl carbonate; 1,2-Propylene carbonate; 4-Methyl-1,3-dioxolan-2-one; 1,2-Propylene glycol carbonate; 4-Methyl-1,3-dioxol-2-one; Dipropylene carbonate; 4-Methyldioxalone-2; 4-Methyl-2-oxo-1,3-dioxolane; 1,2-PDC; Propylenester kyseliny uhlicite; Arconate propylene carbonate; PC-HP; Solvenon PC; Texacar PC; Arconate 5000; Carbonic acid cyclic methylethylene ester; Carbonic acid, propylene ester; NSC 11784
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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 | -134.7 | kcal/mol | N/A | Vasil'eva, Zhil'tosova, et al., 1972 | Value computed using ΔfHliquid° value of -613.0±1.0 kj/mol from Vasil'eva, Zhil'tosova, et al., 1972 and ΔvapH° value of 49.3 kj/mol from Choi and Joncich, 1971.; DRB |
ΔfH°gas | -139.22 ± 0.59 | kcal/mol | Ccb | Choi and Joncich, 1971 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -143.68 kcal/mol; Pedley's value is off by 4.46kcal/mol; ALS |
Constant pressure heat capacity of gas
Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
25.72 | 298.15 | Vasilev I.A., 1984 | GT |
25.91 | 300. | ||
32.53 | 400. | ||
38.36 | 500. | ||
43.19 | 600. | ||
47.18 | 700. | ||
50.48 | 800. | ||
53.25 | 900. | ||
55.57 | 1000. |
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 | -146.6 ± 0.3 | kcal/mol | Ccb | Vasil'eva, Zhil'tosova, et al., 1972 | ALS |
ΔfH°liquid | -151.01 ± 0.50 | kcal/mol | Ccb | Choi and Joncich, 1971 | Pedley's value is off by 4.46kcal/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -434.6 ± 0.3 | kcal/mol | Ccb | Vasil'eva, Zhil'tosova, et al., 1972 | Corresponding ΔfHºliquid = -146.5 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -430.14 ± 0.50 | kcal/mol | Ccb | Choi and Joncich, 1971 | Pedley's value is off by 4.46kcal/mol; Corresponding ΔfHºliquid = -151.01 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 52.25 | cal/mol*K | N/A | Vasil'ev, Korkhov, et al., 1976 | DH |
S°liquid | 52.383 | cal/mol*K | N/A | Vasil'ev and Korkhov, 1974 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
41.8 | 298. | Masood, Pethrick, et al., 1976 | T = 200 to 325 K. Data graphically only. Value estimated from graph.; DH |
40.01 | 298.15 | Vasil'ev, Korkhov, et al., 1976 | T = 5 to 415 K.; DH |
40.057 | 298.15 | Vasil'ev and Korkhov, 1974 | T = 80 to 310 K. Cp(c) = 2.9899 + 91.0386(T/100) - 35.8262(T/100)2 + 7.2335(T/100)3 J/mol*K (55 to 224.5 K).; DH |
44.00 | 323.15 | Peppel, 1958 | 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 |
---|---|---|---|---|---|
Tboil | 513.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 515.05 | K | N/A | Rajapakse, Finston, et al., 1986 | Uncertainty assigned by TRC = 0.7 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 222.95 | K | N/A | Rajapakse, Finston, et al., 1986 | Uncertainty assigned by TRC = 1. K; TRC |
Tfus | 222.95 | K | N/A | Hong, Waksiak, et al., 1982 | Uncertainty assigned by TRC = 0.3 K; TRC |
Tfus | 218.62 | K | N/A | Jones and Aikens, 1982 | Uncertainty assigned by TRC = 0.06 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 218.66 | K | N/A | Fujimori and Oguni, 1994 | Uncertainty assigned by TRC = 0.02 K; TRC |
Ttriple | 224.85 | K | N/A | Vasil'ev and Petrov, 1984 | Uncertainty assigned by TRC = 0.02 K; TRC |
Ttriple | 224.85 | K | N/A | Vasil'ev, Korkhov, et al., 1976, 2 | Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 14. ± 7. | kcal/mol | AVG | N/A | Average of 6 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
13.0 | 427. | A | Stephenson and Malanowski, 1987 | Based on data from 412. to 466. K.; AC |
8.08 | 338. | A,MM | Stephenson and Malanowski, 1987 | Based on data from 323. to 370. K. See also Choi and Joncich, 1971.; AC |
13.8 | 383. | EB | Hong, Wakslak, et al., 1982 | Based on data from 368. to 462. K.; AC |
13.2 | 423. | EB | Hong, Wakslak, et al., 1982 | Based on data from 368. to 462. K.; AC |
12.7 | 443. | EB | Hong, Wakslak, et al., 1982 | Based on data from 368. to 462. K.; AC |
13.2 | 323. | N/A | Granzhan and Salganikova, 1972 | Based on data from 293. to 353. K.; AC |
13.200 | 423. | V | Peppel, 1958 | ALS |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
2.299 | 224.85 | N/A | Vasil'ev, Korkhov, et al., 1976 | DH |
2.299 | 224.85 | N/A | Vasil'ev and Korkhov, 1974 | DH |
2.14 | 220.3 | DSC | Ding, 2004 | AC |
1.91 | 218.7 | AC | Fujimori and Oguni, 1994, 2 | Based on data from 13. to 300. K.; AC |
2.30 | 218.2 | N/A | Vasil'ev and Korkhov, 1974, 2 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
10.2 | 224.85 | Vasil'ev, Korkhov, et al., 1976 | DH |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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: 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
By formula: C4H6O3 + 2CH4O = C3H8O2 + C3H6O3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -1.66 | kcal/mol | Kin | Zhang and Luo, 1991 | liquid phase |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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: Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
View reactions leading to C4H6O3+ (ion structure unspecified)
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C4H6O3+ | 10.52 | ? | PE | Yokoyama, Jinno, et al., 1974 |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References, Notes
Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
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. |
---|---|
Origin | Japan AIST/NIMC Database- Spectrum MS-NW- 810 |
NIST MS number | 227715 |
Gas Chromatography
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), 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
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-101 | 929. | Zenkevich, 2005 | 25. m/0.20 mm/0.10 μm, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-101 | 932. | Zenkevich and Malamakhov, 1987 | He; Column length: 50. m; Column diameter: 0.24 mm; Program: not specified |
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), Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
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]
Vasil'ev, Korkhov, et al., 1976
Vasil'ev, I.A.; Korkhov, A.D.; Minkin, D.M.; Rabinovich, I.B.; Sheiman, M.S.; Nistratov, V.P.,
Heat capacity and thermodynamic functions for propylene carbonate. Termodin. Org. Soedin., 1976, 21-26. [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]
Masood, Pethrick, et al., 1976
Masood, A.K.M.; Pethrick, R.A.; Swinton, F.L.,
Physicochemical studies of super-cooled liquids. Cyclic carbonates and a-β-unsaturated aldehydes,
J. Chem. Soc. Faraday Trans. I, 1976, 72, 20-28. [all data]
Peppel, 1958
Peppel, W.J.,
Preparation and properties of the alkylene carbonates,
Ind. Eng. Chem., 1958, 50, 767-770. [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]
Rajapakse, Finston, et al., 1986
Rajapakse, N.; Finston, H.L.; Fried, V.,
J. Chem. Eng. Data, 1986, 31, 408. [all data]
Hong, Waksiak, et al., 1982
Hong, C.S.; Waksiak, R.; Finston, H.; Fried, V.,
Some Thermodynamic Properties of Systems Containing Propylene Carbonate and Ethylene Carbonate,
J. Chem. Eng. Data, 1982, 27, 146. [all data]
Jones and Aikens, 1982
Jones, A.R.; Aikens, D.A.,
Propylene carbonate cryoscopy.,
J. Chem. Eng. Data, 1982, 27, 24-5. [all data]
Fujimori and Oguni, 1994
Fujimori, H.; Oguni, M.,
Calorimetric study of D,L-propene carbonate: observation of the β- as well as α-glass transition in the supercooled liquid,
J. Chem. Thermodyn., 1994, 26, 367. [all data]
Vasil'ev and Petrov, 1984
Vasil'ev, I.A.; Petrov, V.M.,
Thermodynamic Properties of Oxygen-containing Organic Compounds, Handbook, Soedinenii: Khimya, Leningrad, p 240, 1984. [all data]
Vasil'ev, Korkhov, et al., 1976, 2
Vasil'ev, I.A.; Korkhov, A.D.; Minkin, D.M.; Rabinovich, I.B.; Sheiman, M.S.; Nistratov, V.P.,
Heat capacity and thermodynamic functions of propylene carbonate.,
Termodin. Org. Soedin., 1976, No. 5, 21. [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]
Granzhan and Salganikova, 1972
Granzhan, V.A.; Salganikova, E.A.,
Tr. Nauch. Issled. Proekt. Inst. Azotn. Prom. Prod. Org. Sin., 1972, 16, 85. [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]
Fujimori and Oguni, 1994, 2
Fujimori, Hiroki; Oguni, Masaharu,
Calorimetric study of l,d-propene carbonate: observation of the β- as well as α-glass transition in the supercooled liquid,
The Journal of Chemical Thermodynamics, 1994, 26, 4, 367-378, https://doi.org/10.1006/jcht.1994.1046
. [all data]
Vasil'ev and Korkhov, 1974, 2
Vasil'ev, I.A.; Korkhov, A.D.,
Tr. Khim. Khim. Tekhnol., 1974, 103. [all data]
Zhang and Luo, 1991
Zhang, S.; Luo, Y.,
Kinetics and technological conditions for the synthesis of dimethyl carbonate,
Chem. React. Eng. Tech., 1991, 7, 10-19. [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]
Zenkevich, 2005
Zenkevich, I.G.,
Experimentally measured retention indices., 2005. [all data]
Zenkevich and Malamakhov, 1987
Zenkevich, I.G.; Malamakhov, A.C.,
Evaluation of Molecular Weights of Organic Compounds based on Retention Parameters at Chromato-Spectral Analysys. Additional Criterion of Molecular Ions' Identification,
Vestn. St. Petersb. Univ. Ser. 4: Fiz. Khim, 1987, 2, 101-106. [all data]
Notes
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), Gas Chromatography, 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 S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tfus Fusion (melting) 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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