Benzene, n-butyl-

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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
Δfgas-12.8kJ/molN/AGood, 1975Value computed using ΔfHliquid° value of -62.9±1.2 kj/mol from Good, 1975 and ΔvapH° value of 50.1 kj/mol from Prosen, Johnson, et al., 1946.; DRB
Δfgas-13.8 ± 1.3kJ/molCcbProsen, Johnson, et al., 1946Heat of combustion for gas phase =-1415.44 kcal/mol; ALS
Quantity Value Units Method Reference Comment
gas437.86J/mol*KN/AMesserly J.F., 1965S(298.15 K) estimated by the method of increments [ Thermodynamics Research Center, 1997, Taylor W.J., 1946] is 1-2 J/mol*K larger than experimental one.; GT

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
Δfliquid-62.9 ± 1.2kJ/molCcbGood, 1975see Good, 1973; ALS
Δfliquid-63.9 ± 1.3kJ/molCcbProsen, Johnson, et al., 1946Heat of combustion for gas phase =-1415.44 kcal/mol; ALS
Quantity Value Units Method Reference Comment
Δcliquid-5873.0 ± 1.1kJ/molCcbGood, 1975see Good, 1973; Corresponding Δfliquid = -62.93 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Δcliquid-5872.1 ± 1.1kJ/molCcbProsen, Johnson, et al., 1946Heat of combustion for gas phase =-1415.44 kcal/mol; Corresponding Δfliquid = -63.85 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid321.21J/mol*KN/AMesserly, Todd, et al., 1965DH
liquid321.3J/mol*KN/AHuffman, Parks, et al., 1931Extrapolation below 90 K, 78.95 J/mol*K.; DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
241.298.15Good, 1973DH
243.34298.15Messerly, Todd, et al., 1965T = 10 to 380 K.; DH
203.293.Tschamler, 1948DH
240.2298.2Huffman, Parks, et al., 1931T = 94 to 298 K. Value is unsmoothed experimental datum.; 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
Tboil456. ± 2.KAVGN/AAverage of 40 out of 43 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus185.1 ± 0.6KAVGN/AAverage of 11 out of 12 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple185.30KN/AMesserly, Todd, et al., 1965, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.01 K; TRC
Ttriple185.14KN/AMesserly, Todd, et al., 1965, 2Metastable crystal phase; Uncertainty assigned by TRC = 0.01 K; TRC
Ttriple184.6KN/AHuffman, Parks, et al., 1931, 2Uncertainty assigned by TRC = 0.25 K; TRC
Quantity Value Units Method Reference Comment
Tc660.5 ± 0.5KN/ATsonopoulos and Ambrose, 1995 
Tc660.5KN/AMajer and Svoboda, 1985 
Tc660.05KN/AAmbrose, Broderick, et al., 1967Uncertainty assigned by TRC = 0.5 K; TRC
Tc660.45KN/AAmbrose, Cox, et al., 1960Uncertainty assigned by TRC = 0.1 K; Visual, PRT, IPTS-48, with decomp.; TRC
Tc661.0KN/ASimon, 1957Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Pc28.9 ± 0.4barN/ATsonopoulos and Ambrose, 1995 
Pc28.87barN/AAmbrose, Broderick, et al., 1967Uncertainty assigned by TRC = 0.07 bar; TRC
Quantity Value Units Method Reference Comment
Vc0.497l/molN/ATsonopoulos and Ambrose, 1995 
Quantity Value Units Method Reference Comment
ρc2.01 ± 0.04mol/lN/ATsonopoulos and Ambrose, 1995 
ρc2.009mol/lN/ASimon, 1957Uncertainty assigned by TRC = 0.075 mol/l; TRC
Quantity Value Units Method Reference Comment
Δvap51.37kJ/molN/AMajer and Svoboda, 1985 
Δvap50.8kJ/molN/ARu«7825»icka, Zábranský, et al., 1994AC
Δvap50.1kJ/molN/AReid, 1972AC
Δvap51.0 ± 2.9kJ/molVMesserly, Todd, et al., 1965, 3ALS
Δvap50.1kJ/molN/AProsen, Johnson, et al., 1946DRB

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
38.87456.4N/AMajer and Svoboda, 1985 
47.4 ± 0.2350.EBSteele, Chirico, et al., 2002Based on data from 343. to 501. K. See also Verevkin, 2006.; AC
43.5 ± 0.2410.EBSteele, Chirico, et al., 2002Based on data from 343. to 501. K.; AC
40.6 ± 0.4450.EBSteele, Chirico, et al., 2002Based on data from 343. to 501. K.; AC
37.5 ± 0.7490.EBSteele, Chirico, et al., 2002Based on data from 343. to 501. K.; AC
53.5258.N/AKasehgari, Mokbel, et al., 1993Based on data from 243. to 403. K.; AC
45.7384.AStephenson and Malanowski, 1987Based on data from 369. to 463. K. See also Forziati, Norris, et al., 1949.; AC
48.0 ± 0.1343.CSvoboda, Charvátová, et al., 1982AC
46.8 ± 0.1358.CSvoboda, Charvátová, et al., 1982AC
46.0 ± 0.1368.CSvoboda, Charvátová, et al., 1982AC
45.2389.N/ALinek, Fried, et al., 1965Based on data from 374. to 454. K. See also Boublik, Fried, et al., 1984.; AC

Enthalpy of vaporization

ΔvapH = A exp(-βTr) (1 − Tr)β
    ΔvapH = Enthalpy of vaporization (at saturation pressure) (kJ/mol)
    Tr = reduced temperature (T / Tc)

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Temperature (K) A (kJ/mol) β Tc (K) Reference Comment
343. to 368.73.640.3425660.5Majer and Svoboda, 1985 

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
369.38 to 457.484.108081577.965-71.772Forziati, Norris, et al., 1949, 2

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
11.22185.3Domalski and Hearing, 1996AC
10.979184.6Huffman, Parks, et al., 1931DH

Entropy of fusion

ΔfusS (J/mol*K) Temperature (K) Reference Comment
59.5184.6Huffman, Parks, et al., 1931DH

Enthalpy of phase transition

ΔHtrs (kJ/mol) Temperature (K) Initial Phase Final Phase Reference Comment
11.259185.14crystaline, IIliquidMesserly, Todd, et al., 1965Metastable crystals.; DH
11.221185.30crystaline, IliquidMesserly, Todd, et al., 1965DH

Entropy of phase transition

ΔStrs (J/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
60.81185.14crystaline, IIliquidMesserly, Todd, et al., 1965Metastable; DH
60.56185.30crystaline, IliquidMesserly, Todd, et al., 1965DH

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:


Henry's Law data

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: Rolf Sander

Henry's Law constant (water solution)

kH(T) = H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(kH))/d(1/T) = Temperature dependence constant (K)

H (mol/(kg*bar)) d(ln(kH))/d(1/T) (K) Method Reference Comment
0.075 QN/A missing citation give several references for the Henry's law constants but don't assign them to specific species.
0.078 LN/A 
0.080 VN/A 

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Henry's Law data, References, Notes

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
L - Sharon G. Lias

Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
LL - Sharon G. Lias and Joel F. Liebman
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
IE (evaluated)8.69 ± 0.01eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)791.9kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity764.2kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.68EIMcLoughlin, Morrison, et al., 1979LLK
8.71 ± 0.01EQLias and Ausloos, 1978LLK
8.69PIPrice, Bralsford, et al., 1959RDSH
8.69 ± 0.01PIWatanabe, 1957RDSH
8.69 ± 0.05PENagy-Felsobuki and Peel, 1979Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C7H7+10.67 ± 0.35C3H7CADKatritzky, Watson, et al., 1990LL
C7H7+9.93C3H7EIMcLoughlin, Morrison, et al., 1979LLK
C7H8+9.78 ± 0.35C3H6CADKatritzky, Watson, et al., 1990LL
C7H8+10.3 ± 0.1C3H6EIBurgers, Terlouw, et al., 1982LBLHLM
C7H8+9.73 ± 0.04C3H6PIMcLoughlin, Morrison, et al., 1978LLK
C7H8+10.1 ± 0.1C3H6EILightner, Majeti, et al., 1972LLK
C8H9+9.98C2H5EIMcLoughlin, Morrison, et al., 1979LLK

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Good, 1975
Good, W.D., The standard enthalpies of combustion and formation of n-butylbenzene, the dimethylethylbenzenes, and the tetramethylbenzenes in the condensed state, J. Chem. Thermodyn., 1975, 7, 49-59. [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]

Messerly J.F., 1965
Messerly J.F., Low-temperature thermodynamic properties of n-propyl- and n-butyl-benzene, J. Phys. Chem., 1965, 69, 4304-4310. [all data]

Thermodynamics Research Center, 1997
Thermodynamics Research Center, Selected Values of Properties of Chemical Compounds., Thermodynamics Research Center, Texas A&M University, College Station, Texas, 1997. [all data]

Taylor W.J., 1946
Taylor W.J., Heats, equilibrium constants, and free energies of formation of the alkylbenzenes, J. Res. Nat. Bur. Stand., 1946, 37, 95-122. [all data]

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]

Messerly, Todd, et al., 1965
Messerly, J.F.; Todd, S.S.; Finke, H.L., Low-temperature thermodynamic properties of n-propyl- and n-butylbenzene, J. Phys. Chem., 1965, 69, 4304-4311. [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]

Tschamler, 1948
Tschamler, H., Uber binare flussige Mischungen I. Mischungswarment, Volumseffekte und Zustandsdiagramme von chlorex mit benzol und n-alkylbenzolen, Monatsh. Chem., 1948, 79, 162-177. [all data]

Messerly, Todd, et al., 1965, 2
Messerly, J.F.; Todd, S.S.; Finke, H.L., Low-Temperature Thermodynamic Prop. of n-Propyl and n-Butylbenzenes, J. Phys. Chem., 1965, 69, 4304-11. [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]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Ambrose, Broderick, et al., 1967
Ambrose, D.; Broderick, B.E.; Townsend, R., The Vapour Pressures above the Normal Boiling Point and the Critical Pressures of Some Aromatic Hydrocarbons, J. Chem. Soc. , 1967, 1967, 1967, 633-41. [all data]

Ambrose, Cox, et al., 1960
Ambrose, D.; Cox, J.D.; Townsend, R., The critical temperatures of forty organic compounds, Trans. Faraday Soc., 1960, 56, 1452. [all data]

Simon, 1957
Simon, M., Methods and Apparatus Used at the Bureau of Physicochemical Standards XV. Critical Constants and Straight-Line Diameters of Ten Hydrocarbons, Bull. Soc. Chim. Belg., 1957, 66, 375-81. [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]

Messerly, Todd, et al., 1965, 3
Messerly, J.F.; Todd, S.S.; Finke, H.L., Low-Temperature thermodynamic properties of n-Propyl- and n-Butylbenzene, J. Phys. Chem., 1965, 69, 4304. [all data]

Steele, Chirico, et al., 2002
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A., Vapor Pressure, Heat Capacity, and Density along the Saturation Line: Measurements for Benzenamine, Butylbenzene, sec -Butylbenzene, tert -Butylbenzene, 2,2-Dimethylbutanoic Acid, Tridecafluoroheptanoic Acid, 2-Butyl-2-ethyl-1,3-propanediol, 2,2,4-Trimethyl-1,3-pentanediol, and 1-Chloro-2-propanol, J. Chem. Eng. Data, 2002, 47, 4, 648-666, https://doi.org/10.1021/je010083e . [all data]

Verevkin, 2006
Verevkin, Sergey P., Vapour pressures and enthalpies of vaporization of a series of the linear n-alkyl-benzenes, The Journal of Chemical Thermodynamics, 2006, 38, 9, 1111-1123, https://doi.org/10.1016/j.jct.2005.11.009 . [all data]

Kasehgari, Mokbel, et al., 1993
Kasehgari, H.; Mokbel, I.; Viton, C.; Jose, J., Vapor pressure of 11 alkylbenzenes in the range 10-3 -- 280 torr, correlation by equation of state, Fluid Phase Equilibria, 1993, 87, 1, 133-152, https://doi.org/10.1016/0378-3812(93)85022-E . [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]

Forziati, Norris, et al., 1949
Forziati, Alphonse F.; Norris, William R.; Rossini, Frederick D., Vapor pressures and boiling points of sixty API-NBS hydrocarbons, J. RES. NATL. BUR. STAN., 1949, 43, 6, 555-17, https://doi.org/10.6028/jres.043.050 . [all data]

Svoboda, Charvátová, et al., 1982
Svoboda, Václav; Charvátová, Vladimíra; Majer, Vladimír; Hynek, Vladimír, Determination of heats of vaporization and some other thermodynamic properties for four substituted hydrocarbons, Collect. Czech. Chem. Commun., 1982, 47, 2, 543-549, https://doi.org/10.1135/cccc19820543 . [all data]

Linek, Fried, et al., 1965
Linek, J.; Fried, V.; Pick, J., Gleichgewicht flüssigkeit-dampf XXXIV. System äthylbenzol-cumol-butylbenzol unter atmosphärischem druck, Collect. Czech. Chem. Commun., 1965, 30, 5, 1358-1365, https://doi.org/10.1135/cccc19651358 . [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]

Forziati, Norris, et al., 1949, 2
Forziati, A.F.; Norris, W.R.; Rossini, F.D., Vapor Pressures and Boiling Points of Sixty API-NBS Hydrocarbons, J. Res. Natl. Bur. Stand. (U.S.), 1949, 43, 6, 555-563, https://doi.org/10.6028/jres.043.050 . [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]

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]

McLoughlin, Morrison, et al., 1979
McLoughlin, R.G.; Morrison, J.D.; Traeger, J.C., Photoionization of the C-1 - C-4 monosubstituted alkyl benzenes: Thermochemistry of [C7H7]+ and [C8H9]+ formation, Org. Mass Spectrom., 1979, 14, 104. [all data]

Lias and Ausloos, 1978
Lias, S.G.; Ausloos, P.J., eIonization energies of organic compounds by equilibrium measurements, J. Am. Chem. Soc., 1978, 100, 6027. [all data]

Price, Bralsford, et al., 1959
Price, W.C.; Bralsford, R.; Harris, P.V.; Ridley, R.G., Ultra-violet spectra and ionization potentials of hydrocarbon molecules, Spectrochim. Acta, 1959, 14, 45. [all data]

Watanabe, 1957
Watanabe, K., Ionization potentials of some molecules, J. Chem. Phys., 1957, 26, 542. [all data]

Nagy-Felsobuki and Peel, 1979
Nagy-Felsobuki, E.; Peel, J.B., Photoelectron spectroscopic studies of the butylbenzenes, J. Electron Spectrosc. Relat. Phenom., 1979, 16, 397. [all data]

Katritzky, Watson, et al., 1990
Katritzky, A.R.; Watson, C.H.; Dega-Szafran, Z.; Eyler, J.R., Collisionally activated dissociation of N-alkylpyridinium cations to pyridine and alkyl cations in the gas phase, J. Am. Chem. Soc., 1990, 112, 2471. [all data]

Burgers, Terlouw, et al., 1982
Burgers, P.C.; Terlouw, J.K.; Levsen, K., Gaseous [C7H8+] ions: [Methylene cyclohexadiene]+, a stable species in the gas phase, Org. Mass Spectrom., 1982, 17, 295. [all data]

McLoughlin, Morrison, et al., 1978
McLoughlin, R.G.; Morrison, J.D.; Traeger, J.C., A photoionization study of the [C7H8]+ ion formed from some monosubstituted alkyl benzenes, Org. Mass Spectrom., 1978, 13, 483. [all data]

Lightner, Majeti, et al., 1972
Lightner, D.A.; Majeti, S.; Nicoletti, R.; Thommen, E., Benzyl vs. tropylium ions in the electron impact induced decomposition of n- butylbenzenes, Intra-Sci. Chem. Rep., 1972, 6, 113. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, References