Propylene Carbonate

Formula: C₄H₆O₃
Molecular weight: 102.0886
IUPAC Standard InChI: InChI=1S/C4H6O3/c1-3-2-6-4(5)7-3/h3H,2H2,1H3
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:
- 1,3-Dioxolan-2-one, 4-methyl-, (4R)-
- 1,3-Dioxolan-2-one, 4-methyl-, (4S)-
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 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	-563.7	kJ/mol	N/A	Vasil'eva, Zhil'tosova, et al., 1972	Value computed using Δ_fH_liquid° value of -613.0±1.0 kj/mol from Vasil'eva, Zhil'tosova, et al., 1972 and Δ_vapH° value of 49.3 kj/mol from Choi and Joncich, 1971.; DRB
Δ_fH°_gas	-582.5 ± 2.5	kJ/mol	Ccb	Choi and Joncich, 1971	Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -601.16 kJ/mol; Pedley's value is off by 4.46kcal/mol; ALS

Constant pressure heat capacity of gas

C_p,gas (J/mol*K)	Temperature (K)	Reference	Comment
107.6	298.15	Vasilev I.A., 1984	GT
108.4	300.
136.1	400.
160.5	500.
180.7	600.
197.4	700.
211.2	800.
222.8	900.
232.5	1000.

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	-613. ± 1.	kJ/mol	Ccb	Vasil'eva, Zhil'tosova, et al., 1972	ALS
Δ_fH°_liquid	-631.8 ± 2.1	kJ/mol	Ccb	Choi and Joncich, 1971	Pedley's value is off by 4.46kcal/mol; ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-1818. ± 1.	kJ/mol	Ccb	Vasil'eva, Zhil'tosova, et al., 1972	Corresponding Δ_fHº_liquid = -613.0 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_liquid	-1799.7 ± 2.1	kJ/mol	Ccb	Choi and Joncich, 1971	Pedley's value is off by 4.46kcal/mol; Corresponding Δ_fHº_liquid = -631.83 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_liquid	218.6	J/mol*K	N/A	Vasil'ev, Korkhov, et al., 1976	DH
S°_liquid	219.17	J/mol*K	N/A	Vasil'ev and Korkhov, 1974	DH

Constant pressure heat capacity of liquid

C_p,liquid (J/mol*K)	Temperature (K)	Reference	Comment
175.	298.	Masood, Pethrick, et al., 1976	T = 200 to 325 K. Data graphically only. Value estimated from graph.; DH
167.4	298.15	Vasil'ev, Korkhov, et al., 1976	T = 5 to 415 K.; DH
167.60	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
184.1	323.15	Peppel, 1958	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
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
T_boil	513.2	K	N/A	Aldrich Chemical Company Inc., 1990	BS
T_boil	515.05	K	N/A	Rajapakse, Finston, et al., 1986	Uncertainty assigned by TRC = 0.7 K; TRC
Quantity	Value	Units	Method	Reference	Comment
T_fus	222.95	K	N/A	Rajapakse, Finston, et al., 1986	Uncertainty assigned by TRC = 1. K; TRC
T_fus	222.95	K	N/A	Hong, Waksiak, et al., 1982	Uncertainty assigned by TRC = 0.3 K; TRC
T_fus	218.62	K	N/A	Jones and Aikens, 1982	Uncertainty assigned by TRC = 0.06 K; TRC
Quantity	Value	Units	Method	Reference	Comment
T_triple	218.66	K	N/A	Fujimori and Oguni, 1994	Uncertainty assigned by TRC = 0.02 K; TRC
T_triple	224.85	K	N/A	Vasil'ev and Petrov, 1984	Uncertainty assigned by TRC = 0.02 K; TRC
T_triple	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
Δ_vapH°	60. ± 30.	kJ/mol	AVG	N/A	Average of 6 values; Individual data points

Enthalpy of vaporization

Δ_vapH (kJ/mol)	Temperature (K)	Method	Reference	Comment
54.4	427.	A	Stephenson and Malanowski, 1987	Based on data from 412. to 466. K.; AC
33.8	338.	A,MM	Stephenson and Malanowski, 1987	Based on data from 323. to 370. K. See also Choi and Joncich, 1971.; AC
57.8	383.	EB	Hong, Wakslak, et al., 1982	Based on data from 368. to 462. K.; AC
55.2	423.	EB	Hong, Wakslak, et al., 1982	Based on data from 368. to 462. K.; AC
53.0	443.	EB	Hong, Wakslak, et al., 1982	Based on data from 368. to 462. K.; AC
55.2	323.	N/A	Granzhan and Salganikova, 1972	Based on data from 293. to 353. K.; AC
55.229	423.	V	Peppel, 1958	ALS

Enthalpy of fusion

Δ_fusH (kJ/mol)	Temperature (K)	Method	Reference	Comment
9.617	224.85	N/A	Vasil'ev, Korkhov, et al., 1976	DH
9.617	224.85	N/A	Vasil'ev and Korkhov, 1974	DH
8.96	220.3	DSC	Ding, 2004	AC
8.01	218.7	AC	Fujimori and Oguni, 1994, 2	Based on data from 13. to 300. K.; AC
9.62	218.2	N/A	Vasil'ev and Korkhov, 1974, 2	AC

Entropy of fusion

Δ_fusS (J/mol*K)	Temperature (K)	Reference	Comment
42.8	224.85	Vasil'ev, Korkhov, et al., 1976	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

Propylene Carbonate + 2 = +

By formula: C₄H₆O₃ + 2CH₄O = C₃H₈O₂ + C₃H₆O₃

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-6.93	kJ/mol	Kin	Zhang and Luo, 1991	liquid phase

Gas phase ion energetics data

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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

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Data compiled by: Coblentz Society, Inc.

LIQUID (NEAT); DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm^-1 resolution

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Gas Chromatography

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Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Normal alkane RI, non-polar column, temperature ramp

View large format table.

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; T_start: 50. C; T_end: 250. C

Normal alkane RI, non-polar column, custom temperature program

View large format table.

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, Gas Chromatography, Notes

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

Symbols used in this document:

AE	Appearance energy
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_fus	Fusion (melting) 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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