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Ethylbenzene

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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:
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
Deltafgas29.8 ± 0.84kJ/molCcbProsen, Gilmont, et al., 1945Hf by Prosen, Johnson, et al., 1946; ALS
Deltafgas49.0 ± 4.0kJ/molCcbN/AValue computed using «DELTA»fHliquid° from missing citation and «DELTA»vapH° value of 42.2 kJ/mol from missing citation. recalculated with modern CO2,H2O thermo; estimated uncertainty (NOTE all values in source also have wrong sign); DRB
Deltafgas69.3kJ/molN/AMoureu and Andre, 1914Value computed using «DELTA»fHliquid° value of 27.0 kj/mol from Moureu and Andre, 1914 and «DELTA»vapH° value of 42.3 kj/mol from Prosen, Gilmont, et al., 1945.; DRB
Quantity Value Units Method Reference Comment
gas360.6 ± 0.5J/mol*KN/AMiller A., 1978S(298.16 K)=361.5 J/mol*K was obtained from earlier experimental data [ Guttman L., 1943].; GT

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
44.3750.Thermodynamics Research Center, 1997Recommended values are in good agreement with other statistically calculated data [ Miller A., 1978, Taylor W.J., 1946].; GT
57.72100.
72.35150.
88.54200.
116.88273.15
127.40298.15
128.19300.
169.95400.
206.58500.
236.75600.
261.51700.
282.08800.
299.37900.
314.041000.
326.561100.
337.271200.
346.481300.
354.411400.
361.271500.

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
159.24 ± 0.80373.15Hossenlopp I.A., 1981Heat capacities determined from acoustical measurements [ Colgate S.O., 1990] (124.98, 138.21, 158.84, and 173.88 J/mol*K at 298.15, 323.15, 373.15, and 408.15 K, respectively) are slightly lower than calorimetric ones. Please also see Scott R.B., 1945.; GT
164.25 ± 0.33385.65
169.25 ± 0.34398.15
178.96 ± 0.36423.15
188.28 ± 0.38448.15
197.35 ± 0.39473.15
205.94 ± 0.41498.15
214.02 ± 0.43523.15

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Reaction 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:
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
Deltafliquid-12.5 ± 0.84kJ/molCcbProsen, Gilmont, et al., 1945Hf by Prosen, Johnson, et al., 1946; ALS
Deltafliquid6.8 ± 4.0kJ/molCcbN/Arecalculated with modern CO2,H2O thermo; estimated uncertainty (NOTE all values in source also have wrong sign); DRB
Deltafliquid27.kJ/molCcbMoureu and Andre, 1914ALS
Quantity Value Units Method Reference Comment
Deltacliquid-4567. ± 20.kJ/molAVGN/AAverage of 6 values; Individual data points
Quantity Value Units Method Reference Comment
liquid255.01J/mol*KN/AGuthrie, Spitzer, et al., 1944DH
liquid256.1J/mol*KN/AHuffman, Parks, et al., 1930Extrapolation below 90 K, 61.09 J/mol*K.; DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
184.8293.31Andolenko and Grigor'ev, 1979T = 293 to 393 K. Unsmoothed experimental datum given as 1.741 kJ/kg*K.; DH
185.572298.15Fortier and Benson, 1979DH
185.559298.15Fortier and Benson, 1977DH
185.78298.15Fortier, Benson, et al., 1976DH
161.295.Tschamler, 1948DH
185.8298.Kurbatov, 1947T = 15 to 18 C, mean Cp, four temperatures.; DH
186.04298.15Scott and Brickwedde, 1945T = 15 to 300 K.; DH
185.81298.15Guthrie, Spitzer, et al., 1944T = 13 to 305 K.; DH
178.7302.8de Kolossowsky and Udowenko, 1934DH
178.7302.7Kolosovskii and Udovenko, 1934DH
186.6298.15Blacet, Leighton, et al., 1931T = 286 to 368 K. Heat capacity reported as 0.420 cal g-1 K-1 at 25 C.; DH
183.7298.5Smith and Andrews, 1931T = 102 to 299 K. Value is unsmoothed experimental datum.; DH
181.6297.4Huffman, Parks, et al., 1930T = 93 to 305 K. Value is unsmoothed experimental datum.; DH
181.6303.Willams and Daniels, 1924T = 303 to 343 K. Equation only.; DH
184.5298.von Reis, 1881T = 292 to 425 K.; DH

Reaction 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:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

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

C8H9- + Hydrogen cation = Ethylbenzene

By formula: C8H9- + H+ = C8H10

Quantity Value Units Method Reference Comment
Deltar1699. ± 19.kJ/molCIDTGraul and Squires, 1990gas phase; From decarboxylation threshold. Stable form probably the spiro[2.5]octadienide Maas and van Keelen, 1989; B
Quantity Value Units Method Reference Comment
Deltar1664. ± 20.kJ/molH-TSGraul and Squires, 1990gas phase; From decarboxylation threshold. Stable form probably the spiro[2.5]octadienide Maas and van Keelen, 1989; B

C8H9- + Hydrogen cation = Ethylbenzene

By formula: C8H9- + H+ = C8H10

Quantity Value Units Method Reference Comment
Deltar1589. ± 8.8kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar1562. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B

2Hydrogen + Phenylethyne = Ethylbenzene

By formula: 2H2 + C8H6 = C8H10

Quantity Value Units Method Reference Comment
Deltar-276.6 ± 0.3kJ/molChydDavis, Allinger, et al., 1985liquid phase; solvent: Hexane; ALS
Deltar-271. ± 4.kJ/molChydRogers and McLafferty, 1971liquid phase; solvent: Hydrocarbon; ALS
Deltar-296. ± 4.2kJ/molChydFlitcroft and Skinner, 1958liquid phase; ALS

Nitric oxide anion + Ethylbenzene = (Nitric oxide anion bullet Ethylbenzene)

By formula: NO- + C8H10 = (NO- bullet C8H10)

Quantity Value Units Method Reference Comment
Deltar186.kJ/molICRReents and Freiser, 1981gas phase; switching reaction,Thermochemical ladder(NO+)C2H5OH, Entropy change calculated or estimated; Farid and McMahon, 1978; M

Ethylbenzene + 3Hydrogen = Cyclohexane, ethyl-

By formula: C8H10 + 3H2 = C8H16

Quantity Value Units Method Reference Comment
Deltar-201.6 ± 0.42kJ/molChydDolliver, Gresham, et al., 1937gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -204.7 ± 0.4 kJ/mol; At 355 °K; ALS

Chlorine anion + Ethylbenzene = (Chlorine anion bullet Ethylbenzene)

By formula: Cl- + C8H10 = (Cl- bullet C8H10)

Quantity Value Units Method Reference Comment
Deltar20.9kJ/molTDEqFrench, Ikuta, et al., 1982gas phase; B

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
21.300.PHPMSFrench, Ikuta, et al., 1982gas phase; M

Ethylbenzene + Benzene, bromo- = C8H9Br + Benzene

By formula: C8H10 + C6H5Br = C8H9Br + C6H6

Quantity Value Units Method Reference Comment
Deltar-0.59 ± 0.021kJ/molCmMerdzhanov, Alenin, et al., 1982gas phase; Heat of isomerization at 349 K; ALS

Styrene + Hydrogen = Ethylbenzene

By formula: C8H8 + H2 = C8H10

Quantity Value Units Method Reference Comment
Deltar-117.2 ± 1.7kJ/molChydAbboud, Jimenez, et al., 1995liquid phase; solvent: Hydrocarbon; Like gas phase; ALS

Ethylbenzene = Styrene + Hydrogen

By formula: C8H10 = C8H8 + H2

Quantity Value Units Method Reference Comment
Deltar124.85kJ/molEqkGhosh, Ram Das Guha, et al., 1945gas phase; ALS

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Notes

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

Prosen, Gilmont, et al., 1945
Prosen, E.J.; Gilmont, R.; Rossini, F.D., Heats of combustion of benzene, toluene, ethyl-benzene, o-xylene, m-xylene, p-xylene, n-propylbenzene, and styrene, J. Res. NBS, 1945, 34, 65-70. [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]

Moureu and Andre, 1914
Moureu, C.; Andre, E., Thermochimie des composes acetyleniques, Ann. Chim. Phys., 1914, 1, 113-145. [all data]

Miller A., 1978
Miller A., Chemical thermodynamic properties of ethylbenzene, J. Chem. Phys., 1978, 68, 1317-1319. [all data]

Guttman L., 1943
Guttman L., Jr., The thermodynamics of styrene (phenylethylene), including equilibrium of formation from ethylbenzene, J. Am. Chem. Soc., 1943, 65, 1246-1247. [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]

Hossenlopp I.A., 1981
Hossenlopp I.A., Vapor heat capacities and enthalpies of vaporization of four aromatic and/or cycloalkane hydrocarbons, J. Chem. Thermodyn., 1981, 13, 423-428. [all data]

Colgate S.O., 1990
Colgate S.O., Acoustical determination of ideal gas heat capacities of three C-8 compounds, Fluid Phase Equilib., 1990, 60, 191-203. [all data]

Scott R.B., 1945
Scott R.B., Specific heats of gaseous 1,3-butadiene, isobutene, styrene, and ethylbenzene, J. Res. Nat. Bur. Stand., 1945, 34, 243-254. [all data]

Guthrie, Spitzer, et al., 1944
Guthrie, G.B., Jr.; Spitzer, R.W.; Huffman, H.M., Thermal data. XVIII. The heat capacity, heat of fusion, entropy and free energy of ethylbenzene, J. Am. Chem. Soc., 1944, 66, 2120-2121. [all data]

Huffman, Parks, et al., 1930
Huffman, H.M.; Parks, G.S.; Daniels, A.C., Thermal data on organic compounds. VII. The heat capacities, entropies and free energies of twelve aromatic hydrocarbons, J. Am. Chem. Soc., 1930, 52, 1547-1558. [all data]

Andolenko and Grigor'ev, 1979
Andolenko, R.A.; Grigor'ev, B.A., Investigation of isobaric heat capacity of aromatic hydrocarbons at atmospheric pressure, Iaz. Vyssh. Ucheb. Zaved., Neft i Gaz (11), 1979, 78, 90. [all data]

Fortier and Benson, 1979
Fortier, J.-L.; Benson, G.C., Heat capacities of some binary aromatic hydrocarbon mixtures containing benzene or toluene, J. Chem. Eng. Data, 1979, 24(1), 34-37. [all data]

Fortier and Benson, 1977
Fortier, J.-L.; Benson, G.C., Excess heat capacities of binary mixtures of tetrachloromethane witlh some aromatic liquids at 298.15 K, J. Chem. Thermodynam., 1977, 9, 1181-1188. [all data]

Fortier, Benson, et al., 1976
Fortier, J.-L.; Benson, G.C.; Picker, P., Heat capacities of some organic liquids determined with the Picker flow calorimeter, J. Chem. Thermodynam., 1976, 8, 289-299. [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]

Kurbatov, 1947
Kurbatov, V.Ya., Specific heat of liquids. I. Specific heat of benzenoid hydrocarbons, Zhur. Obshch. Khim., 1947, 17, 1999-2003. [all data]

Scott and Brickwedde, 1945
Scott, R.B.; Brickwedde, F.G., Thermodynamic properties of solid and liquid ethylbenzene from 0 to 300K, J. Res., 1945, NBS 35, 501-512. [all data]

de Kolossowsky and Udowenko, 1934
de Kolossowsky, N.; Udowenko, W.W., Determination des chaleurs specifiques des liquides, Compt. rend., 1934, 198, 1394-1395. [all data]

Kolosovskii and Udovenko, 1934
Kolosovskii, N.A.; Udovenko, W.W., Specific heat of liquids. II., Zhur. Obshchei Khim., 1934, 4, 1027-1033. [all data]

Blacet, Leighton, et al., 1931
Blacet, F.E.; Leighton, P.A.; Bartlett, E.P., The specific heats of five pure organic liquids and of ethyl alcohol-water mixtures, J. Phys. Chem., 1931, 35, 1935-1943. [all data]

Smith and Andrews, 1931
Smith, R.H.; Andrews, D.H., Thermal energy studies. I. Phenyl derivatives of methane, ethane and some related compounds. J. Am. Chem. Soc., 1931, 53, 3644-3660. [all data]

Willams and Daniels, 1924
Willams, J.W.; Daniels, F., The specific heats of certain organic liquids at elevated temperatures, J. Am. Chem. Soc., 1924, 46, 903-917. [all data]

von Reis, 1881
von Reis, M.A., Die specifische Wärme flüssiger organischer Verbindungen und ihre Beziehung zu deren Moleculargewicht, Ann. Physik [3], 1881, 13, 447-464. [all data]

Graul and Squires, 1990
Graul, S.T.; Squires, R.R., Gas-Phase Acidities Derived from Threshold Energies for Activated Reactions, J. Am. Chem. Soc., 1990, 112, 7, 2517, https://doi.org/10.1021/ja00163a007 . [all data]

Maas and van Keelen, 1989
Maas, W.P.M.; van Keelen, P.A., On the Generation and Characterization of the Spiro[2,5]Octadienyl Anion in the Gas Phase, Org. Mass Spectrom., 1989, 24, 8, 546, https://doi.org/10.1002/oms.1210240807 . [all data]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]

Davis, Allinger, et al., 1985
Davis, H.E.; Allinger, N.L.; Rogers, D.W., Enthalpies of hydrogenation of phenylalkynes: indirect determination of the enthalpy of formation of diphenylcyclopropenone, J. Org. Chem., 1985, 50, 3601-3604. [all data]

Rogers and McLafferty, 1971
Rogers, D.W.; McLafferty, F.J., A new hydrogen calorimeter. Heats of hydrogenation of allyl and vinyl unsaturation adjacent to a ring, Tetrahedron, 1971, 27, 3765-3775. [all data]

Flitcroft and Skinner, 1958
Flitcroft, T.L.; Skinner, H.A., Heats of hydrogenation Part 2.-Acetylene derivatives, Trans. Faraday Soc., 1958, 54, 47-53. [all data]

Reents and Freiser, 1981
Reents, W.D.; Freiser, B.S., Gas-Phase Binding Energies and Spectroscopic Properties of NO+ Charge-Transfer Complexes, J. Am. Chem. Soc., 1981, 103, 2791. [all data]

Farid and McMahon, 1978
Farid, R.; McMahon, T.B., Gas-Phase Ion-Molecule Reactions of Alkyl Nitrites by Ion Cyclotron Resonance Spectroscopy, Int. J. Mass Spectrom. Ion Phys., 1978, 27, 2, 163, https://doi.org/10.1016/0020-7381(78)80037-0 . [all data]

Dolliver, Gresham, et al., 1937
Dolliver, M.a.; Gresham, T.L.; Kistiakowsky, G.B.; Vaughan, W.E., Heats of organic reactions. V. Heats of hydrogenation of various hydrocarbons, J. Am. Chem. Soc., 1937, 59, 831-841. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

French, Ikuta, et al., 1982
French, M.A.; Ikuta, S.; Kebarle, P., Hydrogen bonding of O-H and C-H hydrogen donors to Cl-. Results from mass spectrometric measurement of the ion-molecule equilibria RH + Cl- = RHCl-, Can. J. Chem., 1982, 60, 1907. [all data]

Merdzhanov, Alenin, et al., 1982
Merdzhanov, V.R.; Alenin, V.I.; Nesterova, T.N.; Rozhnov, A.M., Study of equilibrium transformation of ethylbromobenzenes, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 1982, 25, 1047-1049. [all data]

Abboud, Jimenez, et al., 1995
Abboud, J.-L.M.; Jimenez, P.; Roux, M.V.; Turrion, C.; Lopez-Mardomingo, C.; Podosenin, A.; Rogers, D.W.; Liebman, J.F., Interrelations of the energetics of amides and alkenes: enthalpies of formation of N,N-dimethyl dertivatives of pivalamide, 1-adamantylcarboxamide and benzamide, and of styrene and its a-, trans-«beta»- and «beta»,«beta»-methylated derivates, J. Phys. Org. Chem., 1995, 8, 15-25. [all data]

Ghosh, Ram Das Guha, et al., 1945
Ghosh, J.C.; Ram Das Guha, S.; Roy, A.N., Chemical equilibrium in styrene formation from ethyl-benzene at low pressures, Curr. Sci., 1945, 14, 269. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References