Benzene, 1,4-dichloro-
- Formula: C6H4Cl2
- Molecular weight: 147.002
- IUPAC Standard InChIKey: OCJBOOLMMGQPQU-UHFFFAOYSA-N
- CAS Registry Number: 106-46-7
- 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, p-dichloro-; p-Chlorophenyl chloride; p-Dichlorobenzene; Di-chloricide; Evola; Paradi; Paradow; Paramoth; Persia-Perazol; PDB; Santochlor; 1,4-Dichlorobenzene; p-Dichlorobenzol; Paradichlorobenzol; para-Dichlorobenzene; p-Dichloorbenzeen; p-Dichlorbenzol; p-Diclorobenzene; Dichlorobenzene; Dichlorobenzene, p-; NCI-C54955; para crystals; Paracide; Paranuggets; Parazene; 1,4-Dichloorbenzeen; 1,4-Dichlor-benzol; 1,4-Diclorobenzene; Dichlorobenzene, para; Globol; Paradichlorbenzol; Rcra waste number U070; Rcra waste number U071; Rcra waste number U072; UN 1592; Dichlorocide; Kaydox; p-Dichlorbenzene; NSC 36935; 1,4-chlorobenzene
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Phase change data
Go To: Top, 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:
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 |
---|---|---|---|---|---|
Tboil | 447.3 ± 0.6 | K | AVG | N/A | Average of 6 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 326.1 ± 0.8 | K | AVG | N/A | Average of 26 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 326.150 | K | N/A | Dworkin, Figuiere, et al., 1976 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.01 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 13.1 | kcal/mol | GC | Spieksma, Luijk, et al., 1994 | Based on data from 413. to 453. K.; AC |
ΔvapH° | 11.4 | kcal/mol | N/A | Boublik, Fried, et al., 1984 | Based on data from 370. to 450. K. See also Basarová and Svoboda, 1991.; AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 15.48 ± 0.036 | kcal/mol | DM | Oonk, van Genderen, et al., 2000 | AC |
ΔsubH° | 15.6 ± 0.48 | kcal/mol | C | An and Zheng, 1989 | AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
11.1 | 326. | N/A | Rohác, Ruzicka, et al., 1999 | AC |
10.6 | 373. | EB | Rohác, Ruzicka, et al., 1998 | Based on data from 358. to 448. K.; AC |
10.8 | 356. | A | Stephenson and Malanowski, 1987 | Based on data from 341. to 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 to 447.21 | 4.117 | 1575.11 | -64.637 | McDonald, Shrader, et al., 1959 |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
12.7 | 258. to 313. | N/A | Liu and Dickhut, 1994 | AC |
15.6 | 313. | GS | Shaub, 1985 | Based on data from 303. to 423. K.; AC |
15.5 ± 0.1 | 303. | V | Walsh and Smith, 1961 | ALS |
15.5 ± 0.2 | 303. | N/A | Walsh and Smith, 1961, 2 | Based on data from 293. to 311. K. See also Cox and Pilcher, 1970.; AC |
15. ± 0.1 | 318. | N/A | Walsh and Smith, 1961, 2 | Based on data from 311. to 325. K.; AC |
13.6 | 275. | ME | Darkis, Vermillion, et al., 1940 | Based on data from 248. to 303. K. See also Jones, 1960.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
4.348 | 326.2 | DSC | Wei and Jin, 2009 | See also Wei, 2008.; AC |
4.281 | 326.2 | AC | van der Linde, van Miltenburg, et al., 2005 | Based on data from 5. to 380. K.; AC |
4.340 | 326. | N/A | Acree, 1991 | AC |
4.3141 | 326.15 | N/A | Booss and Hauschildt, 1972 | DH |
4.3403 | 326. | N/A | Ueberreiter and Orthmann, 1950 | DH |
4.3365 | 326.05 | N/A | Narbutt, 1918 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
13.2 | 326.15 | Booss and Hauschildt, 1972 | DH |
13.3 | 326. | Ueberreiter and Orthmann, 1950 | DH |
13.3 | 326.05 | Narbutt, 1918 | DH |
Enthalpy of phase transition
ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.0478 | 304.0 | crystaline, II | crystaline, I | Petropavlov, Tsygankova, et al., 1988 | DH |
0.3002 | 271.77 | crystaline, III | crystaline, II | Dworkin, Figuiere, et al., 1976, 2 | DH |
0.05127 | 304.35 | crystaline, II | crystaline, I | Dworkin, Figuiere, et al., 1976, 2 | DH |
4.3468 | 326.14 | crystaline, I | liquid | Dworkin, Figuiere, et al., 1976, 2 | DH |
0.3002 | 271.77 | crystaline, III | crystaline, II | Dworkin, Figuiere, et al., 1975 | DH |
0.05127 | 304.35 | crystaline, II | crystaline, I | Dworkin, Figuiere, et al., 1975 | DH |
4.3468 | 326.14 | crystaline, I | liquid | Dworkin, Figuiere, et al., 1975 | DH |
Entropy of phase transition
ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.1 | 304.0 | crystaline, II | crystaline, I | Petropavlov, Tsygankova, et al., 1988 | DH |
1.10 | 271.77 | crystaline, III | crystaline, II | Dworkin, Figuiere, et al., 1976, 2 | DH |
0.168 | 304.35 | crystaline, II | crystaline, I | Dworkin, Figuiere, et al., 1976, 2 | DH |
13.33 | 326.14 | crystaline, I | liquid | Dworkin, Figuiere, et al., 1976, 2 | DH |
1.10 | 271.77 | crystaline, III | crystaline, II | Dworkin, Figuiere, et al., 1975 | DH |
0.168 | 304.35 | crystaline, II | crystaline, I | Dworkin, Figuiere, et al., 1975 | DH |
13.33 | 326.14 | crystaline, I | liquid | Dworkin, Figuiere, et al., 1975 | DH |
IR Spectrum
Go To: Top, Phase change 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, Phase change 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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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 | Chuck Anderson, Aldrich Chemical Co. |
NIST MS number | 107698 |
References
Go To: Top, Phase change 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.
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. 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-,β-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 α-p-Dichloro-β-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]
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]
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]
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., 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. Thermodynam., 1976, 8, 835-844. [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]
Notes
Go To: Top, Phase change data, IR Spectrum, Mass spectrum (electron ionization), References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition 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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