Phenol
- Formula: C6H6O
- Molecular weight: 94.1112
- IUPAC Standard InChIKey: ISWSIDIOOBJBQZ-UHFFFAOYSA-N
- CAS Registry Number: 108-95-2
- 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: Carbolic acid; Baker's P and S Liquid and Ointment; Benzenol; Hydroxybenzene; Izal; Monohydroxybenzene; Monophenol; Oxybenzene; Phenic acid; Phenyl alcohol; Phenyl hydrate; Phenyl hydroxide; Phenylic acid; Phenylic alcohol; PhOH; Benzene, hydroxy-; Acide carbolique; Baker's P & S liquid & Ointment; Fenol; Fenolo; NCI-C50124; Paoscle; Phenole; Carbolsaure; NA 2821; Phenol alcohol; Phenol, molten; Rcra waste number U188; UN 1671; UN 2312; UN 2821; Phenic alcohol; NSC 36808; Campho-Phenique Cold Sore Gel (Salt/Mix); Campho-Phenique Gel (Salt/Mix); Campho-Phenique Liquid (Salt/Mix)
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Gas phase thermochemistry data
Go To: Top, Phase change 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
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -96.36 ± 0.59 | kJ/mol | Ccb | Cox, 1961 | ALS |
ΔfH°gas | -96.44 ± 0.63 | kJ/mol | Ccb | Andon, Biddiscombe, et al., 1960 | ALS |
ΔfH°gas | -94.2 | kJ/mol | N/A | Parks, Manchester, et al., 1954 | Value computed using ΔfHsolid° value of -162.8±1.0 kj/mol from Parks, Manchester, et al., 1954 and ΔsubH° value of 68.6 kj/mol from Cox, 1961.; DRB |
ΔfH°gas | -95.3 | kJ/mol | N/A | Badoche, 1941 | Value computed using ΔfHsolid° value of -163.9 kj/mol from Badoche, 1941 and ΔsubH° value of 68.6 kj/mol from Cox, 1961.; DRB |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
33.91 | 50. | Kudchadker S.A., 1978 | Recommended S(T) and Cp(T) values are in close agreement with statistical values calculated by [ Evans J.C., 1960, Green J.H.S., 1961]. Entropy value calculated by [ Sarin V.N., 1973] agrees well with the third-law entropy at 298.15 K but not at 400 K. Statistical values calculated by [ Ramaswamy V., 1970] seem to be erroneous.; GT |
41.38 | 100. | ||
54.19 | 150. | ||
69.65 | 200. | ||
94.61 | 273.15 | ||
103.22 | 298.15 | ||
103.86 | 300. | ||
135.79 | 400. | ||
161.91 | 500. | ||
182.48 | 600. | ||
198.84 | 700. | ||
212.14 | 800. | ||
223.19 | 900. | ||
232.49 | 1000. | ||
240.41 | 1100. | ||
247.20 | 1200. | ||
253.06 | 1300. | ||
258.12 | 1400. | ||
262.52 | 1500. |
Phase change data
Go To: Top, Gas phase thermochemistry 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 455.0 ± 0.6 | K | AVG | N/A | Average of 25 out of 27 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 314. ± 1. | K | AVG | N/A | Average of 60 out of 61 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 314.06 | K | N/A | Andon, Counsell, et al., 1963 | Uncertainty assigned by TRC = 0.01 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 694.3 | K | N/A | Delaunois, 1968 | Uncertainty assigned by TRC = 0.4 K; TRC |
Tc | 694.25 | K | N/A | Ambrose, 1963 | Uncertainty assigned by TRC = 0.15 K; TRC |
Tc | 692.4 | K | N/A | Radice, 1899 | Uncertainty assigned by TRC = 2. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 59.30 | bar | N/A | Delaunois, 1968 | Uncertainty assigned by TRC = 0.7845 bar; TRC |
Pc | 61.3016 | bar | N/A | Herz and Neukirch, 1923 | Uncertainty assigned by TRC = 0.8106 bar; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 58.8 | kJ/mol | CGC | Chickos, Hosseini, et al., 1995 | Based on data from 393. to 433. K.; AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 69.7 ± 0.9 | kJ/mol | ME | Parsons, Rochester, et al., 1971 | Based on data from 230. to 273. K.; AC |
ΔsubH° | 68.6 | kJ/mol | N/A | Cox, 1961 | DRB |
ΔsubH° | 68.66 ± 0.50 | kJ/mol | V | Andon, Biddiscombe, et al., 1960 | ALS |
ΔsubH° | 68.7 | kJ/mol | N/A | Andon, Biddiscombe, et al., 1960 | DRB |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
53.2 | 378. | EB | Chylinski, Fras, et al., 2001 | Based on data from 363. to 391. K.; AC |
49.5 | 470. | A | Stephenson and Malanowski, 1987 | Based on data from 455. to 655. K.; AC |
57.4 | 329. | A | Stephenson and Malanowski, 1987 | Based on data from 314. to 395. K.; AC |
50.9 | 402. | A | Stephenson and Malanowski, 1987 | Based on data from 387. to 456. K.; AC |
46.8 | 464. | A | Stephenson and Malanowski, 1987 | Based on data from 449. to 526. K.; AC |
43.8 | 535. | A | Stephenson and Malanowski, 1987 | Based on data from 520. to 625. K.; AC |
51.3 | 398. | EB,GS | Stephenson and Malanowski, 1987 | Based on data from 383. to 473. K. See also Andon, Biddiscombe, et al., 1960, 2 and Dykyj, 1972.; AC |
51.4 | 395. | N/A | Dreisbach and Shrader, 1949 | Based on data from 380. to 455. K. See also Dreisbach and Martin, 1949 and Boublik, Fried, et al., 1984.; AC |
48.1 | 434. | N/A | Goldblum, Martin, et al., 1947 | Based on data from 414. to 454. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
380.30 to 454.90 | 4.24688 | 1509.677 | -98.949 | Dreisbach and Shrader, 1949 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
65.3 ± 3.3 | 280. | HSA | Chickos, 1975 | Based on data from 263. to 298. K.; AC |
68.7 ± 0.5 | 282. to 313. | GS | Andon, Biddiscombe, et al., 1960, 2 | See also Cox and Pilcher, 1970.; AC |
68.2 | 293. | ME | Sklyarenko, Markin, et al., 1958 | Based on data from 283. to 303. K.; AC |
68.1 | 292. | N/A | Nitta and Seki, 1948 | Based on data from 270. to 313. K.; AC |
67.8 | 278. to 305. | TE | Balson, 1947 | See also Jones, 1960.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
11.514 | 314.06 | Andon, Counsell, et al., 1963, 2 | DH |
12.125 | 314.13 | Mastrangelo, 1957 | DH |
11.51 | 314. | Inozemtsev, Liakumovich, et al., 1972 | See also Domalski and Hearing, 1996.; AC |
10.581 | 312.7 | Eykman, 1889 | DH |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
36.66 | 314.06 | Andon, Counsell, et al., 1963, 2 | DH |
33.3 | 314. | Bret-Dibat and Lichanot, 1989 | CAL |
33.8 | 312.7 | Eykman, 1889 | DH |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
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 | NIST Mass Spectrometry Data Center, 1994 |
NIST MS number | 133909 |
References
Go To: Top, Gas phase thermochemistry data, Phase change 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.
Cox, 1961
Cox, J.D.,
The heats of combustion of phenol and the three cresols,
Pure Appl. Chem., 1961, 2, 125-128. [all data]
Andon, Biddiscombe, et al., 1960
Andon, R.J.L.; Biddiscombe, D.P.; Cox, J.D.; Handley, R.; Harrop, D.; Herington, E.F.G.; Martin, J.F.,
Thermodynamic properties of organic oxygen compounds. Part I. Preparation and physical properties of pure phenol, cresols, and xylenols,
J. Chem. Soc., 1960, 5246-5254. [all data]
Parks, Manchester, et al., 1954
Parks, G.S.; Manchester, K.E.; Vaughan, L.M.,
Heats of combustion and formation of some alcohols, phenols, and ketones,
J. Chem. Phys., 1954, 22, 2089-2090. [all data]
Badoche, 1941
Badoche, M.,
No 19. - Chaleurs de combustion du phenol, du-m-cresol et del leurs ethers; par M. Marius BADOCHE.,
Bull. Soc. Chim. Fr., 1941, 8, 212-220. [all data]
Kudchadker S.A., 1978
Kudchadker S.A.,
Ideal gas thermodynamic properties of phenol and cresols,
J. Phys. Chem. Ref. Data, 1978, 7, 417-423. [all data]
Evans J.C., 1960
Evans J.C.,
The vibrational spectra phenol and phenol-OD,
Spectrochim. Acta, 1960, 16, 1382-1392. [all data]
Green J.H.S., 1961
Green J.H.S.,
The thermodynamic properties of organic oxygen compounds. II. Vibrational assignment and calculated thermodynamic properties of phenol,
J. Chem. Soc., 1961, 2236-2241. [all data]
Sarin V.N., 1973
Sarin V.N.,
Thermodynamic properties in the gaseous state of certain monosubstituted benzenes,
Thermochim. Acta, 1973, 6, 39-46. [all data]
Ramaswamy V., 1970
Ramaswamy V.,
Thermo data for n-alkyl phenols,
Hydrocarbon Process., 1970, 49, 217-218. [all data]
Andon, Counsell, et al., 1963
Andon, R.J.L.; Counsell, J.F.; Herington, E.F.G.; Martin, J.F.,
Thermodyn. prop. of organic oxygen compds., part 7- calorimetric study of phenol from 12 to330o K,
Trans. Faraday Soc., 1963, 59, 830. [all data]
Delaunois, 1968
Delaunois, C.,
Effect of the Filling Rate of a Reactor on the Vapor Tension and the Temperature at the Beginning of Cracking of Phenols at High Pressures,
Ann. Mines Belg., 1968, No. 1, 9-16. [all data]
Ambrose, 1963
Ambrose, D.,
Critical Temperatures of Some Phenols and Other Organic Compounds,
Trans. Faraday Soc., 1963, 59, 1988. [all data]
Radice, 1899
Radice, G.,
, Ph. D. Thesis, Univ. of Geneve, 1899. [all data]
Herz and Neukirch, 1923
Herz, W.; Neukirch, E.,
On Knowldge of the Critical State,
Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1923, 104, 433-50. [all data]
Chickos, Hosseini, et al., 1995
Chickos, James S.; Hosseini, Sarah; Hesse, Donald G.,
Determination of vaporization enthalpies of simple organic molecules by correlations of changes in gas chromatographic net retention times,
Thermochimica Acta, 1995, 249, 41-62, https://doi.org/10.1016/0040-6031(95)90670-3
. [all data]
Parsons, Rochester, et al., 1971
Parsons, G.H.; Rochester, C.H.; Wood, C.E.C.,
Effect of 4-substitution on the thermodynamics of hydration of phenol and the phenoxide anion,
J. Chem. Soc., B:, 1971, 533, https://doi.org/10.1039/j29710000533
. [all data]
Chylinski, Fras, et al., 2001
Chylinski, K.; Fras, Z.; Malanowski, S.K.,
Vapor-Liquid Equilibrium in Phenol + 2-Ethoxyethanol at 363.15 to 383.15 K,
J. Chem. Eng. Data, 2001, 46, 1, 29-33, https://doi.org/10.1021/je0001072
. [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]
Andon, Biddiscombe, et al., 1960, 2
Andon, R.J.L.; Biddiscombe, D.P.; Cox, J.D.; Handley, R.; Harrop, D.; Herington, E.F.G.; Martin, J.F.,
1009. Thermodynamic properties of organic oxygen compounds. Part I. Preparation and physical properties of pure phenol, cresols, and xylenols,
J. Chem. Soc., 1960, 5246, https://doi.org/10.1039/jr9600005246
. [all data]
Dykyj, 1972
Dykyj, J.,
Petrochemia, 1972, 12, 1, 13. [all data]
Dreisbach and Shrader, 1949
Dreisbach, R.R.; Shrader, S.A.,
Vapor Pressure--Temperature Data on Some Organic Compounds,
Ind. Eng. Chem., 1949, 41, 12, 2879-2880, https://doi.org/10.1021/ie50480a054
. [all data]
Dreisbach and Martin, 1949
Dreisbach, R.R.; Martin, R.A.,
Physical Data on Some Organic Compounds,
Ind. Eng. Chem., 1949, 41, 12, 2875-2878, https://doi.org/10.1021/ie50480a053
. [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]
Goldblum, Martin, et al., 1947
Goldblum, K.B.; Martin, R.W.; Young, R.B.,
Vapor Pressure Data for Phenols,
Ind. Eng. Chem., 1947, 39, 11, 1474-1476, https://doi.org/10.1021/ie50455a017
. [all data]
Chickos, 1975
Chickos, James Speros,
A simple equilibrium method for determining heats of sublimation,
J. Chem. Educ., 1975, 52, 2, 134-39, https://doi.org/10.1021/ed052p134
. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [all data]
Sklyarenko, Markin, et al., 1958
Sklyarenko, S.I.; Markin, B.I.; Belyaeva, L.B.,
Zh. Fiz. Khim., 1958, 32, 1916. [all data]
Nitta and Seki, 1948
Nitta, I.; Seki, S.,
J. Chem. Soc. Jpn. Pure Chem. Sect., 1948, 69, 141. [all data]
Balson, 1947
Balson, E.W.,
Studies in vapour pressure measurement, Part III.?An effusion manometer sensitive to 5 «65533» 10?6 millimetres of mercury: vapour pressure of D.D.T. and other slightly volatile substances,
Trans. Faraday Soc., 1947, 43, 54, https://doi.org/10.1039/tf9474300054
. [all data]
Jones, 1960
Jones, A.H.,
Sublimation Pressure Data for Organic Compounds.,
J. Chem. Eng. Data, 1960, 5, 2, 196-200, https://doi.org/10.1021/je60006a019
. [all data]
Andon, Counsell, et al., 1963, 2
Andon, R.J.L.; Counsell, J.F.; Herington, E.F.G.; Martin, J.F.,
Thermodynamic properties of organic oxygen compounds,
Trans. Faraday Soc., 1963, 59, 830-835. [all data]
Mastrangelo, 1957
Mastrangelo, S.V.R.,
Adiabatic calorimeter for determination of cryoscopic data,
Anal. Chem., 1957, 29(5), 841-845. [all data]
Inozemtsev, Liakumovich, et al., 1972
Inozemtsev, P.P.; Liakumovich, A.G.; Gracheva, Z.D.,
Russ. J. Phys. Chem., 1972, 46, 6, 914. [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]
Eykman, 1889
Eykman, J.F.,
Zur kryoskopischen Molekulargewichtsbestimmung,
Z. Physik. Chem., 1889, 4, 497-519. [all data]
Bret-Dibat and Lichanot, 1989
Bret-Dibat, P.; Lichanot, A.,
Proprietes thermodynamiques des isomeres de position de benzenes disubstitues en phase condensee,
Thermochim. Acta, 1989, 147, 2, 261, https://doi.org/10.1016/0040-6031(89)85181-0
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas Pc Critical pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation 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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