p-Cymene
- Formula: C10H14
- Molecular weight: 134.2182
- IUPAC Standard InChIKey: HFPZCAJZSCWRBC-UHFFFAOYSA-N
- CAS Registry Number: 99-87-6
- 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. - Isotopologues:
- Other names: Benzene, 1-methyl-4-(1-methylethyl)-; p-Cimene; p-Cymol; p-Isopropyltoluene; p-Methylisopropylbenzene; Camphogen; Dolcymene; 1-Isopropyl-4-methylbenzene; 1-Methyl-4-isopropylbenzene; 2-p-Tolylpropane; 4-Isopropyl-1-methylbenzene; 1-Methyl-4-(1-methylethyl)-benzene; Benzene, 1-isopropyl-4-methyl-; Cumene, p-methyl-; p-Isopropylmethylbenzene; Paracymene; Paracymol; p-Methylcumene; 4-Isopropyltoluene; 4-Methylisopropylbenzene; 1-(1-methylethyl)-4-methylbenzene; benzene, 1-methyl-4-methylethyl-; p-Mentha-1,3,5-triene; NSC 4162; Cymene; Cymol
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Condensed phase thermochemistry data
Go To: Top, Phase change 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 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 | -18.65 ± 0.27 | kcal/mol | Ccb | Good, 1973 | ALS |
ΔfH°liquid | -18.73 ± 0.51 | kcal/mol | Ccb | Prosen, Johnson, et al., 1946 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -1400.07 ± 0.24 | kcal/mol | Ccb | Good, 1973 | Corresponding ΔfHºliquid = -18.65 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -1400.01 ± 0.53 | kcal/mol | Ccb | Prosen, Johnson, et al., 1946 | Corresponding ΔfHºliquid = -18.71 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 73.30 | cal/mol*K | N/A | Huffman, Parks, et al., 1931 | Extrapolation below 90 K, 80.00 J/mol*K.; DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
57.91 | 298. | Kurbatov, 1947 | T = 10 to 166°C, mean Cp, four temperatures.; DH |
56.50 | 297.1 | Huffman, Parks, et al., 1931 | T = 92 to 297 K. Value is unsmoothed experimental datum.; DH |
Phase change data
Go To: Top, Condensed phase thermochemistry 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 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 450. ± 1. | K | AVG | N/A | Average of 50 out of 52 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 204. ± 3. | K | AVG | N/A | Average of 12 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 204.2 | K | N/A | Huffman, Parks, et al., 1931, 2 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 652. | K | N/A | Tsonopoulos and Ambrose, 1995 | |
Tc | 658.30 | K | N/A | Brown, 1906 | Uncertainty assigned by TRC = 6. K; TRC |
Tc | 651.8 | K | N/A | Altschul, 1893 | Uncertainty assigned by TRC = 2. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 28. | atm | N/A | Tsonopoulos and Ambrose, 1995 | |
Pc | 27.63 | atm | N/A | Altschul, 1893 | Uncertainty assigned by TRC = 0.0580 atm; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 11.8 | kcal/mol | GC | Hoskovec, Grygarová, et al., 2005 | Based on data from 333. to 443. K.; AC |
ΔvapH° | 11.7 | kcal/mol | N/A | Ru«7825»icka, Zábranský, et al., 1994 | AC |
ΔvapH° | 12.0 | kcal/mol | N/A | Reid, 1972 | AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
10.5 | 395. | A | Stephenson and Malanowski, 1987 | Based on data from 380. to 452. K. See also McDonald, Shrader, et al., 1959 and Boublik, Fried, et al., 1984.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference |
---|---|---|---|---|
380.19 to 451.57 | 4.15643 | 1599.29 | -65.491 | McDonald, Shrader, et al., 1959 |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
2.31 | 204.2 | Domalski and Hearing, 1996 | AC |
2.309 | 204.2 | Huffman, Parks, et al., 1931 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
11.3 | 204.2 | Huffman, Parks, et al., 1931 | DH |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Good, 1973
Good, W.D.,
The enthalpies of combustion and formation of n-butylbenzene, the diethylbenzenes, the methyl-n-propylbenzenes, and the methyl-iso-propylbenzenes,
J. Chem. Thermodyn., 1973, 5, 707-714. [all data]
Prosen, Johnson, et al., 1946
Prosen, E.J.; Johnson, W.H.; Rossini, F.D.,
Heats of combustion and formation at 25°C of the alkylbenzenes through C10H14, and of the higher normal monoalkylbenzenes,
J. Res. NBS, 1946, 36, 455-461. [all data]
Huffman, Parks, et al., 1931
Huffman, H.M.; Parks, G.S.; Barmore, M.,
Thermal data on organic compounds. X. Further studies on the heat capacities, entropies and free energies of hydrocarbons,
J. Am. Chem. Soc., 1931, 53, 3876-3888. [all data]
Kurbatov, 1947
Kurbatov, V.Ya.,
Specific heat of liquids. I. Specific heat of benzenoid hydrocarbons,
Zhur. Obshch. Khim., 1947, 17, 1999-2003. [all data]
Huffman, Parks, et al., 1931, 2
Huffman, H.M.; Parks, G.S.; Barmore, M.,
Thermal Data on Organic Compounds X. Further Studies on the Heat Capacities, Entropies, and Free Energies of Hydrocarbons,
J. Am. Chem. Soc., 1931, 53, 3876-88. [all data]
Tsonopoulos and Ambrose, 1995
Tsonopoulos, C.; Ambrose, D.,
Vapor-Liquid Critical Properties of Elements and Compounds. 3. Aromatic Hydrocarbons,
J. Chem. Eng. Data, 1995, 40, 547-558. [all data]
Brown, 1906
Brown, J.C.,
The critical temperature and value of ml/theta of some carbon compounds,
J. Chem. Soc., Trans., 1906, 89, 311. [all data]
Altschul, 1893
Altschul, M.,
The critical values of some organic compounds,
Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1893, 11, 577. [all data]
Hoskovec, Grygarová, et al., 2005
Hoskovec, Michal; Grygarová, Dana; Cvacka, Josef; Streinz, Ludvík; Zima, Jirí; Verevkin, Sergey P.; Koutek, Bohumír,
Determining the vapour pressures of plant volatiles from gas chromatographic retention data,
Journal of Chromatography A, 2005, 1083, 1-2, 161-172, https://doi.org/10.1016/j.chroma.2005.06.006
. [all data]
Ru«7825»icka, Zábranský, et al., 1994
Ru«7825»icka, Vlastimil; Zábranský, Milan; Ru«7825»icka, Kvetoslav; Majer, Vladimír,
Vapor pressures for a group of high-boiling alkylbenzenes under environmental conditions,
Thermochimica Acta, 1994, 245, 121-144, https://doi.org/10.1016/0040-6031(94)85073-9
. [all data]
Reid, 1972
Reid, Robert C.,
Handbook on vapor pressure and heats of vaporization of hydrocarbons and related compounds, R. C. Wilhort and B. J. Zwolinski, Texas A Research Foundation. College Station, Texas(1971). 329 pages.$10.00,
AIChE J., 1972, 18, 6, 1278-1278, https://doi.org/10.1002/aic.690180637
. [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]
McDonald, Shrader, et al., 1959
McDonald, R.A.; Shrader, S.A.; Stull, D.R.,
Vapor Pressures and Freezing Points of Thirty Pure Organic Compounds.,
J. Chem. Eng. Data, 1959, 4, 4, 311-313, https://doi.org/10.1021/je60004a009
. [all data]
Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E.,
The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [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]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid Pc Critical pressure S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion 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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