Benzoyl chloride

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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Δfgas-109. ± 4.2kJ/molCmCarson, Pritchard, et al., 1950Heat of formation derived by Cox and Pilcher, 1970

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-157.3 ± 0.4kJ/molCmMoselhy and Pritchard, 1975see Carson, Pritchard, et al., 1950 and Davies, Dunning, et al., 1972; ALS
Δfliquid-160.3kJ/molCcrHu and Sinke, 1969ALS
Δfliquid-164.4kJ/molCmCarson, Pritchard, et al., 1950Heat of hydrolysis; ALS
Quantity Value Units Method Reference Comment
Δcliquid-3332.6kJ/molCcrHu and Sinke, 1969ALS

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
187.0298.von Reis, 1881T = 290 to 477 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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Quantity Value Units Method Reference Comment
Tboil471. ± 2.KAVGN/AAverage of 8 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus272.KN/ABuckingham and Donaghy, 1982BS
Tfus272.52KN/AWitschonke, 1954Uncertainty assigned by TRC = 0.35 K; TRC
Tfus272.75KN/AWitschonke, 1954Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Δvap54.8 ± 4.2kJ/molECarson, Pritchard, et al., 1950Heat of formation derived by Cox and Pilcher, 1970; ALS

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
49.6320.AStephenson and Malanowski, 1987Based on data from 305. to 470. K. See also Stull, 1947 and Dykyj, Svoboda, et al., 1999.; 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
305.3 to 470.44.612961978.427-41.011Stull, 1947Coefficents calculated by NIST from author's data.

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

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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 by: 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

Water + Benzoyl chloride = Benzoic acid + Hydrogen chloride

By formula: H2O + C7H5ClO = C7H6O2 + HCl

Quantity Value Units Method Reference Comment
Δr-34.04 ± 0.21kJ/molCmMoselhy and Pritchard, 1975liquid phase; solvent: Diphenyl-ether; see Carson, Pritchard, et al., 1950 and Davies, Dunning, et al., 1972
Δr-101.9kJ/molCmCarson, Pritchard, et al., 1950liquid phase; Heat of hydrolysis

Benzenamine, 4-methoxy- + Benzoyl chloride = p-Benzanisidide + Hydrogen chloride

By formula: C7H9NO + C7H5ClO = C14H13NO2 + HCl

Quantity Value Units Method Reference Comment
Δr-168. ± 0.8kJ/molCacKiselev, Khuzyasheva, et al., 1979liquid phase; solvent: Benzene

p-Aminotoluene + Benzoyl chloride = Benzamide, N-(4-methylphenyl)- + Hydrogen chloride

By formula: C7H9N + C7H5ClO = C14H13NO + HCl

Quantity Value Units Method Reference Comment
Δr-164. ± 1.kJ/molCacKiselev, Khuzyasheva, et al., 1979liquid phase; solvent: Benzene

Aniline + Benzoyl chloride = Hydrogen chloride + Benzamide, N-phenyl-

By formula: C6H7N + C7H5ClO = HCl + C13H11NO

Quantity Value Units Method Reference Comment
Δr-149. ± 0.8kJ/molCacKiselev, Khuzyasheva, et al., 1979liquid phase; solvent: Benzene

Gas Chromatography

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

Kovats' RI, non-polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
PackedSE-30150.1080.Tiess, 1984Ar, Gas Chrom Q (80-100 mesh); Column length: 3. m

Van Den Dool and Kratz RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-11036.5Sun and Stremple, 200330. m/0.25 mm/0.25 μm, He, 3. K/min; Tstart: 40. C; Tend: 325. C
CapillaryDB-11038.Gandhe, Malhotra, et al., 198930. m/0.32 mm/0.25 μm, N2, 60. C @ 2. min, 8. K/min; Tend: 200. C

Van Den Dool and Kratz RI, non-polar column, custom temperature program

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Column type Active phase I Reference Comment
CapillaryVF-5MS1095.1Tret'yakov, 200730. m/0.25 mm/0.25 μm, He; Program: Multi-step temperature program; T(initial)=60C; T(final)=270C

Normal alkane RI, non-polar column, custom temperature program

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Column type Active phase I Reference Comment
CapillaryPolydimethyl siloxanes1046.Zenkevich, 2001Program: not specified

References

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

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

Carson, Pritchard, et al., 1950
Carson, A.S.; Pritchard, H.O.; Skinner, H.A., The heats of hydrolysis of the benzoyl halides, J. Chem. Soc., 1950, 656-659. [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]

Moselhy and Pritchard, 1975
Moselhy, G.M.; Pritchard, H.O., The thermochemistry of the chloro-benzoyl chlorides, J. Chem. Thermodyn., 1975, 7, 977-982. [all data]

Davies, Dunning, et al., 1972
Davies, J.V.; Dunning, B.K.; Pritchard, H.O., The enthalpy of formation of benzoyl chloride, J. Chem. Thermodyn., 1972, 4, 731-737. [all data]

Hu and Sinke, 1969
Hu, A.T.; Sinke, G.C., Combustion calorimetry of some chlorinated organic compounds, J. Chem. Thermodyn., 1969, 1, 507-513. [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]

Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M., Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [all data]

Witschonke, 1954
Witschonke, C.R., Freezing point and purity data for some organic compounds, Anal. Chem., 1954, 26, 562-4. [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]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [all data]

Dykyj, Svoboda, et al., 1999
Dykyj, J.; Svoboda, J.; Wilhoit, R.C.; Frenkel, M.L.; Hall, K.R., Vapor Pressure of Chemicals: Part A. Vapor Pressure and Antoine Constants for Hydrocarbons and Sulfur, Selenium, Tellurium and Hydrogen Containing Organic Compounds, Springer, Berlin, 1999, 373. [all data]

Kiselev, Khuzyasheva, et al., 1979
Kiselev, V.D.; Khuzyasheva, d.G.; Konovalov, A.I., Thermochemical study of the acylation of para-substituted anilines, J. Gen. Chem. USSR, 1979, 49, 2273-2276. [all data]

Tiess, 1984
Tiess, D., Gaschromatographische Retentionsindices von 125 leicht- bis mittelflüchtigen organischen Substanzen toxikologisch-analytischer Relevanz auf SE-30, Wiss. Z. Wilhelm-Pieck-Univ. Rostock Math. Naturwiss. Reihe, 1984, 33, 6-9. [all data]

Sun and Stremple, 2003
Sun, G.; Stremple, P., Retention index characterization of flavor, fragrance, and many other compounds on DB-1 and DB-XLB, 2003, retrieved from http://www.chem.agilent.com/cag/cabu/pdf/b-0279.pdf. [all data]

Gandhe, Malhotra, et al., 1989
Gandhe, B.R.; Malhotra, R.C.; Gutch, P.K., Gas chromatographic retention indices of tear gases on capillary columns, J. Chromatogr., 1989, 479, 165-169, https://doi.org/10.1016/S0021-9673(01)83328-8 . [all data]

Tret'yakov, 2007
Tret'yakov, K.V., Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2007. [all data]

Zenkevich, 2001
Zenkevich, I.G., Encyclopedia of Chromatography. Derivatization of Amines, Amino Acids, Amides and Imides for GC Analysis, Marcel Dekker, Inc, New York - Basel, 2001, 224. [all data]


Notes

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