Acetic acid, chloro-, methyl ester

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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-444. ± 10.kJ/molEqkGuthrie and Cullimore, 1980Using Hf(s,ClCH2COOH)=-122.0±2.0 kcal/mol

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

Quantity Value Units Method Reference Comment
Δfliquid-487.0 ± 8.8kJ/molEqkGuthrie and Cullimore, 1980Using Hf(s,ClCH2COOH)=-122.0±2.0 kcal/mol
Quantity Value Units Method Reference Comment
Δcliquid-1451.kJ/molCcbSchjanberg, 1935 

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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
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
Tboil403. ± 3.KAVGN/AAverage of 7 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus241.0KN/ADreisbach, 1955Uncertainty assigned by TRC = 0.02 K; TRC
Tfus240.50KN/ATimmermans, 1922Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Δvap46.74kJ/molN/AMajer and Svoboda, 1985 
Δvap43.4 ± 4.2kJ/molEGuthrie and Cullimore, 1980Using Hf(s,ClCH2COOH)=-122.0±2.0 kcal/mol; ALS
Δvap46.73 ± 0.06kJ/molCLaynez and Wadso, 1972ALS
Δvap46.7 ± 0.1kJ/molCLaynez, Wadsö, et al., 1972AC

Reduced pressure boiling point

Tboil (K) Pressure (bar) Reference Comment
403.20.987Aldrich Chemical Company Inc., 1990BS

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
39.23402.6N/AMajer and Svoboda, 1985 
45.5333.AStephenson and Malanowski, 1987Based on data from 318. to 402. K. See also Goebel, Schaffenger, et al., 1967 and Boublik, Fried, et al., 1984.; AC
46.7313.N/ANelson, 1928Based on data from 298. to 403. K. See also Boublik, Fried, et al., 1984.; 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
318.17 to 403.014.281181390.083-77.51Goevel, Schaffenger, et al., 1967Coefficents 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

1,1,1-Trimethoxy-2-chloroethane + Water = 2Methyl Alcohol + Acetic acid, chloro-, methyl ester

By formula: C5H11ClO3 + H2O = 2CH4O + C3H5ClO2

Quantity Value Units Method Reference Comment
Δr-32.6 ± 1.1kJ/molEqkGuthrie and Cullimore, 1980liquid phase; Using Hf(s,ClCH2COOH)=-122.0±2.0 kcal/mol

Water + Acetic acid, chloro-, methyl ester = Methyl Alcohol + Acetic acid, chloro-

By formula: H2O + C3H5ClO2 = CH4O + C2H3ClO2

Quantity Value Units Method Reference Comment
Δr-57.3 ± 2.9kJ/molEqkGuthrie and Cullimore, 1980liquid phase; Using Hf(s,ClCH2COOH)=-122.0±2.0 kcal/mol

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
CapillarySE-30100.708.Haken and Korhonen, 1986N2; Column length: 25. m; Column diameter: 0.33 mm
CapillarySE-30120.691.Haken and Korhonen, 1986N2; Column length: 25. m; Column diameter: 0.33 mm
CapillarySE-30140.679.Haken and Korhonen, 1986N2; Column length: 25. m; Column diameter: 0.33 mm
CapillarySE-3080.705.Haken and Korhonen, 1986N2; Column length: 25. m; Column diameter: 0.33 mm
CapillaryOV-10180.729.4Komárek, Hornová, et al., 1982N2; Column length: 15. m; Column diameter: 0.22 mm

Kovats' RI, polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
CapillaryOV-351100.1270.Haken and Korhonen, 1986N2; Column length: 25. m; Column diameter: 0.32 mm
CapillaryOV-351140.1314.Haken and Korhonen, 1986N2; Column length: 25. m; Column diameter: 0.32 mm
CapillaryOV-351160.1345.Haken and Korhonen, 1986N2; Column length: 25. m; Column diameter: 0.32 mm
CapillaryOV-351180.1318.Haken and Korhonen, 1986N2; Column length: 25. m; Column diameter: 0.32 mm

Normal alkane RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryHP-1731.Peters, de Leer, et al., 199425. m/0.2 mm/0.33 μm, He, 50. C @ 5. min, 8. K/min, 300. C @ 10. min

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.

Guthrie and Cullimore, 1980
Guthrie, J.P.; Cullimore, P.A., Effect of the acyl substituent on the equilibrium constant for hydration of esters, Can. J. Chem., 1980, 58, 1281-1294. [all data]

Schjanberg, 1935
Schjanberg, E., Die Verbrennungswarmen und die Refraktionsdaten einiger chlorsubstituierter Fettsauren und Ester., Z. Phys. Chem. Abt. A, 1935, 172, 197-233. [all data]

Dreisbach, 1955
Dreisbach, R.R., Physical Properties of Chemical Compounds, Advances in Chemistry Series No. 15, Am. Chem. Soc.: Washington, D. C., 1955. [all data]

Timmermans, 1922
Timmermans, J., Investigation of the Freezing Point of Organic Substances VII, Bull. Soc. Chim. Belg., 1922, 31, 389. [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]

Laynez and Wadso, 1972
Laynez, J.; Wadso, I., Enthalpies of vaporization of organic compounds. IX. Some halogen substituted hydrocarbons and esters, Acta Chem. Scand., 1972, 26, 3148. [all data]

Laynez, Wadsö, et al., 1972
Laynez, José; Wadsö, Ingemar; Haug, Arne; Songstad, J.; Pilotti, Åke, Enthalpies of Vaporization of Organic Compounds. IX. Some Halogen Substituted Hydrocarbons and Esters., Acta Chem. Scand., 1972, 26, 3148-3152, https://doi.org/10.3891/acta.chem.scand.26-3148 . [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [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]

Goebel, Schaffenger, et al., 1967
Goebel, K.H.; Schaffenger, J.; Opel, G., Chem. Tech. (Leipzig), 1967, 19, 307. [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]

Nelson, 1928
Nelson, O.A., Vapor Pressures of Fumigants: I---Methyl, Ethyl, Isopropyl, and Secondary Butyl Chloroacetates 1, Ind. Eng. Chem., 1928, 20, 12, 1380-1382, https://doi.org/10.1021/ie50228a034 . [all data]

Goevel, Schaffenger, et al., 1967
Goevel, K.-H.; Schaffenger, J.; Opel, G., Die Viskositat des Dampfes von Chloressigsauremthylester zwischen 80 und 150 °C und sein Sattigungsdruck 77 und 130 °C, Chem. Tech. (Leipzig), 1967, 19, 5, 307-308. [all data]

Haken and Korhonen, 1986
Haken, J.R.; Korhonen, I.O.O., Gas chromatography of homologous esters. XXXIII. Capillary chromatography of monochlorinated C1-C8 n-alkyl acetates, chloracetates, dichloroacetates and trichloroacetates, J. Chromatogr., 1986, 357, 253-271, https://doi.org/10.1016/S0021-9673(01)95828-5 . [all data]

Komárek, Hornová, et al., 1982
Komárek, K.; Hornová, L.; Churácek, J., Glass capillary gas chromatography of homologous series of esters. Separation of homologous series of esters of halogenated carboxylic acids on a glass capillary column with the non-polar stationary silicone phase OV-101, J. Chromatogr., 1982, 244, 1, 142-147, https://doi.org/10.1016/S0021-9673(00)80131-4 . [all data]

Peters, de Leer, et al., 1994
Peters, R.J.D.; de Leer, E.W.B.; Versteegh, J.F.M., Identification of Halogenated Compounds Produced by Chlorination of Humic Acid in the Presence of Bromide, J. Chromatogr. A, 1994, 686, 2, 253-261, https://doi.org/10.1016/0021-9673(94)00719-5 . [all data]


Notes

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