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Benzene, 1,4-dichloro-

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafgas5.88kcal/molCcrPlatonov and Simulin, 1984 

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
Deltacliquid-702. ± 1.kcal/molCcbSmith, Bjellerup, et al., 1953ALS
Quantity Value Units Method Reference Comment
Deltafsolid-10.12 ± 0.25kcal/molCcbHubbard, Knowlton, et al., 1954ALS
Quantity Value Units Method Reference Comment
Deltacsolid-702.65kcal/molCcrPlatonov and Simulin, 1984ALS
Deltacsolid-701.27 ± 0.25kcal/molCcbHubbard, Knowlton, et al., 1954ALS
Quantity Value Units Method Reference Comment
solid,1 bar41.924cal/mol*KN/ADworkin, Figuiere, et al., 1976crystaline, II phase; DH

Constant pressure heat capacity of solid

Cp,solid (cal/mol*K) Temperature (K) Reference Comment
23.180.Martin and Monti, 1988T = 30 to 180 K. Data given graphically, and estimated from graph.; DH
35.315298.15Dworkin, Figuiere, et al., 1976crystaline, II phase; T = 20 to 330 K.; DH
34.11298.15Ueberreiter and Orthmann, 1950T = 293 to 368 K. Equation only.; DH
41.11299.8Andrews and Haworth, 1928T = 101 to 336 K. Value is unsmoothed experimental datum.; DH
35.28298.Narbutt, 1918T = 194 to 372 K. Average specific heat over the temperature range 2.6 to 51.6 °C is 0.2400 cal/g*K.; 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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil447.3 ± 0.6KAVGN/AAverage of 6 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus326.1 ± 0.8KAVGN/AAverage of 26 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple326.150KN/ADworkin, Figuiere, et al., 1976, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.01 K; TRC
Quantity Value Units Method Reference Comment
Deltavap13.1kcal/molGCSpieksma, Luijk, et al., 1994Based on data from 413. - 453. K.; AC
Deltavap11.4kcal/molN/ABoublik, Fried, et al., 1984Based on data from 370. - 450. K. See also Basarová and Svoboda, 1991.; AC
Quantity Value Units Method Reference Comment
Deltasub15.48 ± 0.036kcal/molDMOonk, van Genderen, et al., 2000AC
Deltasub15.6 ± 0.48kcal/molCAn and Zheng, 1989AC

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
11.1326.N/ARohác, Ruzicka, et al., 1999AC
10.6373.EBRohác, Ruzicka, et al., 1998Based on data from 358. - 448. K.; AC
10.8356.AStephenson and Malanowski, 1987Based on data from 341. - 448. K.; 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
341.12 - 447.214.1171575.11-64.637McDonald, Shrader, et al., 1959

Enthalpy of sublimation

DeltasubH (kcal/mol) Temperature (K) Method Reference Comment
12.7258. - 313.N/ALiu and Dickhut, 1994AC
15.6313.GSShaub, 1985Based on data from 303. - 423. K.; AC
15.5 ± 0.1303.VWalsh and Smith, 1961ALS
15.5 ± 0.2303.N/AWalsh and Smith, 1961, 2Based on data from 293. - 311. K. See also Cox and Pilcher, 1970.; AC
15. ± 0.1318.N/AWalsh and Smith, 1961, 2Based on data from 311. - 325. K.; AC
13.6275.MEDarkis, Vermillion, et al., 1940Based on data from 248. - 303. K. See also Jones, 1960.; AC

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Method Reference Comment
4.348326.2DSCWei and Jin, 2009See also Wei, 2008.; AC
4.281326.2ACvan der Linde, van Miltenburg, et al., 2005Based on data from 5. - 380. K.; AC
4.340326.N/AAcree, 1991AC
4.3141326.15N/ABooss and Hauschildt, 1972DH
4.3403326.N/AUeberreiter and Orthmann, 1950DH
4.3365326.05N/ANarbutt, 1918DH

Entropy of fusion

DeltafusS (cal/mol*K) Temperature (K) Reference Comment
13.2326.15Booss and Hauschildt, 1972DH
13.3326.Ueberreiter and Orthmann, 1950DH
13.3326.05Narbutt, 1918DH

Enthalpy of phase transition

DeltaHtrs (kcal/mol) Temperature (K) Initial Phase Final Phase Reference Comment
0.0478304.0crystaline, IIcrystaline, IPetropavlov, Tsygankova, et al., 1988DH
0.3002271.77crystaline, IIIcrystaline, IIDworkin, Figuiere, et al., 1976DH
0.05127304.35crystaline, IIcrystaline, IDworkin, Figuiere, et al., 1976DH
4.3468326.14crystaline, IliquidDworkin, Figuiere, et al., 1976DH
0.3002271.77crystaline, IIIcrystaline, IIDworkin, Figuiere, et al., 1975DH
0.05127304.35crystaline, IIcrystaline, IDworkin, Figuiere, et al., 1975DH
4.3468326.14crystaline, IliquidDworkin, Figuiere, et al., 1975DH

Entropy of phase transition

DeltaStrs (cal/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
0.1304.0crystaline, IIcrystaline, IPetropavlov, Tsygankova, et al., 1988DH
1.10271.77crystaline, IIIcrystaline, IIDworkin, Figuiere, et al., 1976DH
0.168304.35crystaline, IIcrystaline, IDworkin, Figuiere, et al., 1976DH
13.33326.14crystaline, IliquidDworkin, Figuiere, et al., 1976DH
1.10271.77crystaline, IIIcrystaline, IIDworkin, Figuiere, et al., 1975DH
0.168304.35crystaline, IIcrystaline, IDworkin, Figuiere, et al., 1975DH
13.33326.14crystaline, IliquidDworkin, Figuiere, et al., 1975DH

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

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, IR Spectrum, 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:
B - John E. Bartmess
ALS - 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

C6H3Cl2- + Hydrogen cation = Benzene, 1,4-dichloro-

By formula: C6H3Cl2- + H+ = C6H4Cl2

Quantity Value Units Method Reference Comment
Deltar377.0 ± 2.1kcal/molG+TSSchlosser, Marzi, et al., 2001gas phase; Acid: p-dichlorobenzene.; B
Quantity Value Units Method Reference Comment
Deltar368.8 ± 2.0kcal/molIMRESchlosser, Marzi, et al., 2001gas phase; Acid: p-dichlorobenzene.; B

Benzene, 1,4-dichloro- = Benzene, 1,3-dichloro-

By formula: C6H4Cl2 = C6H4Cl2

Quantity Value Units Method Reference Comment
Deltar0.96kcal/molEqkGodnev and Sverdlin, 1961gas phase; Correction of 56GOD/SVE; ALS

Benzene, 1,4-dichloro- = Benzene, 1,2-dichloro-

By formula: C6H4Cl2 = C6H4Cl2

Quantity Value Units Method Reference Comment
Deltar2.104kcal/molEqkGodnev and Sverdlin, 1961gas phase; Correction of 56GOD/SVE; ALS

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), References, Notes

Data compiled by: Coblentz Society, Inc.

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


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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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Mass spectrum
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Additional Data

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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 Chuck Anderson, Aldrich Chemical Co.
NIST MS number 107698

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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.

Platonov and Simulin, 1984
Platonov, V.A.; Simulin, Yu.N., Experimental determination of the standard enthalpies of formation of polychlorobenzenes. II. Standard enthalpies of formation of dichlorobenzenes, Russ. J. Phys. Chem. (Engl. Transl.), 1984, 58, 1630-1632. [all data]

Smith, Bjellerup, et al., 1953
Smith, L.; Bjellerup, L.; Krook, S.; Westermark, H., Heats of combustion of organic chloro compounds determined by the "quartz wool" method, Acta Chem. Scand., 1953, 7, 65. [all data]

Hubbard, Knowlton, et al., 1954
Hubbard, W.N.; Knowlton, J.W.; Huffman, H.M., Combustion calorimetry of organic chlorine compounds. Heats of combustion of chlorobenzene, the dichlorobenzenes and o- and p-chloroethylbenzene, J. Phys. Chem., 1954, 58, 396. [all data]

Dworkin, Figuiere, et al., 1976
Dworkin, A.; Figuiere, P.; Ghelfenstein, M.; Szwarc, H., Heat capacities, enthalpies of transition, and thermodynamic properties of the three solid phases of p-dichlorobenzene from 20 to 330 K, J. Chem. Thermodynam., 1976, 8, 835-844. [all data]

Martin and Monti, 1988
Martin, C.A.; Monti, G.A., Dynamical analysis of the specific heat in p-dichlorobenzene, Thermochim. Acta, 1988, 134, 35-39. [all data]

Ueberreiter and Orthmann, 1950
Ueberreiter, K.; Orthmann, H.-J., Specifische Wärme, spezifisches Volumen, Temperatur- und Wärme-leittähigkeit einiger disubstituierter Benzole und polycyclischer Systeme, Z. Natursforsch. 5a, 1950, 101-108. [all data]

Andrews and Haworth, 1928
Andrews, D.H.; Haworth, E., An application of the rule of Dulong and Petit to molecules, J. Am. Chem. Soc., 1928, 50, 2998-3002. [all data]

Narbutt, 1918
Narbutt, J., Die Spezifischen Warmen und Schmelzwarmen der dichloro-, chlorbrom-, dibrom-, bromjod-, und dijodbenzole. I, Z. Elektrochem., 1918, 24, 339-342. [all data]

Dworkin, Figuiere, et al., 1976, 2
Dworkin, A.; Figuiere, P.; Ghelfenstein, M.; Szwarc, H., Heat Capacities, Enthalpies of Transition, and Thermodynamic Properties of the Three Solid Phases of p-Dichlorobenzene from 20 to 330 K, J. Chem. Thermodyn., 1976, 8, 835-44. [all data]

Spieksma, Luijk, et al., 1994
Spieksma, Walter; Luijk, Ronald; Govers, Harrie A.J., Determination of the liquid vapour pressure of low-volatility compounds from the Kováts retention index, Journal of Chromatography A, 1994, 672, 1-2, 141-148, https://doi.org/10.1016/0021-9673(94)80602-0 . [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]

Basarová and Svoboda, 1991
Basarová, Pavlína; Svoboda, Václav, Calculation of heats of vaporization of halogenated hydrocarbons from saturated vapour pressure data, Fluid Phase Equilibria, 1991, 68, 13-34, https://doi.org/10.1016/0378-3812(91)85008-I . [all data]

Oonk, van Genderen, et al., 2000
Oonk, Harry A.J.; van Genderen, Aad C.G.; Blok, Jacobus G.; van der Linde, Peter R., Vapour pressures of crystalline and liquid 1,4-dibromo- and 1,4-dichlorobenzene; lattice energies of 1,4-dihalobenzenes, Phys. Chem. Chem. Phys., 2000, 2, 24, 5614-5618, https://doi.org/10.1039/b005324o . [all data]

An and Zheng, 1989
An, Xuwu; Zheng, Xiaolin, Determination of Standard Enthalpies of Vaporization and Sublimation of Three Dichlorobenzenes, Acta Phys. Chim. Sin., 1989, 5, 4, 487-491, https://doi.org/10.3866/PKU.WHXB19890421 . [all data]

Rohác, Ruzicka, et al., 1999
Rohác, Vladislav; Ruzicka, Vlastimil; Ruzicka, Kvetoslav; Polednicek, Milos; Aim, Karel; Jose, Jacques; Zábranský, Milan, Recommended vapour and sublimation pressures and related thermal data for chlorobenzenes, Fluid Phase Equilibria, 1999, 157, 1, 121-142, https://doi.org/10.1016/S0378-3812(99)00003-5 . [all data]

Rohác, Ruzicka, et al., 1998
Rohác, Vladislav; Ruzicka, Vlastimil; Ruzicka, Kvetoslav; Aim, Karel, Measurements of Saturated Vapor Pressure above the Liquid Phase for Isomeric Dichlorobenzenes and 1,2,4-Trichlorobenzene, J. Chem. Eng. Data, 1998, 43, 5, 770-775, https://doi.org/10.1021/je9701442 . [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]

Liu and Dickhut, 1994
Liu, Kewen; Dickhut, Rebecca M., Saturation vapor pressures and thermodynamic properties of benzene and selected chlorinated benzenes at environmental temperatures, Chemosphere, 1994, 29, 3, 581-589, https://doi.org/10.1016/0045-6535(94)90445-6 . [all data]

Shaub, 1985
Shaub, W.M., Containment of dioxin emissions from refuse fired thermal processing units - prospects and technical issues, Thermochimica Acta, 1985, 85, 435-438, https://doi.org/10.1016/0040-6031(85)85614-8 . [all data]

Walsh and Smith, 1961
Walsh, P.N.; Smith, N.O., Sublimation pressure of a-p-dichloro-,«beta»-p-dichloro-, p-dibromo-, and p-bromochlorobenzene, J. Chem. Eng. Data, 1961, 6, 33. [all data]

Walsh and Smith, 1961, 2
Walsh, P.N.; Smith, N.O., Sublimation Pressure of «alpha»-p-Dichloro-«beta»-p-Dichloro, and p-Dibromo-, and p-Bromochlorobenzene., J. Chem. Eng. Data, 1961, 6, 1, 33-35, https://doi.org/10.1021/je60009a010 . [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]

Darkis, Vermillion, et al., 1940
Darkis, F.R.; Vermillion, H.E.; Gross, P.M., p--Dichlorobenzene as a Vapor Fumigant Physical and Chemical Studies, Ind. Eng. Chem., 1940, 32, 7, 946-949, https://doi.org/10.1021/ie50367a018 . [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]

Wei and Jin, 2009
Wei, Dongwei; Jin, Kexin, (Solid+liquid) equilibria of (naphthalene+isomeric dichlorobenzenes), The Journal of Chemical Thermodynamics, 2009, 41, 2, 145-149, https://doi.org/10.1016/j.jct.2008.10.005 . [all data]

Wei, 2008
Wei, Dongwei, (Solid+liquid) equilibria of (phenanthrene+dichlorobenzenes), Thermochimica Acta, 2008, 479, 1-2, 32-36, https://doi.org/10.1016/j.tca.2008.09.010 . [all data]

van der Linde, van Miltenburg, et al., 2005
van der Linde, Peter R.; van Miltenburg, J. Cees; van den Berg, Gerrit J.K.; Oonk, Harry A.J., Low-Temperature Heat Capacities and Derived Thermodynamic Functions of 1,4-Dichlorobenzene, 1,4-Dibromobenzene, 1,3,5-Trichlorobenzene, and 1,3,5-Tribromobenzene, J. Chem. Eng. Data, 2005, 50, 1, 164-172, https://doi.org/10.1021/je049762q . [all data]

Acree, 1991
Acree, William E., Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation, Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H . [all data]

Booss and Hauschildt, 1972
Booss, H.J.; Hauschildt, K.R., Die Schmelzenthalpie des Benzils und 4-Nitrophenols, Z. Anal. Chem., 1972, 261(1), 32. [all data]

Petropavlov, Tsygankova, et al., 1988
Petropavlov, N.N.; Tsygankova, I.G.; Teslenko, L.A., Microcalorimetric investigation of polymorphic transitions in organic crystals, Sov. Phys. Crystallogr., 1988, 33(6), 853-855. [all data]

Dworkin, Figuiere, et al., 1975
Dworkin, A.; Figuiere, P.; Ghelfenstein, M.; Szwarc, H., Thermodynamic properties of the three solid phases of p-dichlorobenzene, Quatrieme Conference International de Thermodynamique Chimique, 1975, II, Thermophysique (capacites thermiques) pp. [all data]

Schlosser, Marzi, et al., 2001
Schlosser, M.; Marzi, E.; Cottet, F.; Buker, H.H.; Nibbering, N.M.M., The acidity of chloro-substituted benzenes: A comparison of gas phase, ab initio, and kinetic data, Chem. Eur. J., 2001, 7, 16, 3511-3516, https://doi.org/10.1002/1521-3765(20010817)7:16<3511::AID-CHEM3511>3.0.CO;2-U . [all data]

Godnev and Sverdlin, 1961
Godnev, I.N.; Sverdlin, A.S., Equilibrium and dichlorobenzene isomer (Corrections), Russ. J. Phys. Chem. (Engl. Transl.), 1961, 35, 231-232. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References