Acetic acid, chloro-, methyl ester

Data at NIST subscription sites:

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.


Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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
Δfgas-106.1 ± 2.4kcal/molEqkGuthrie and Cullimore, 1980Using Hf(s,ClCH2COOH)=-122.0±2.0 kcal/mol

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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
Δfliquid-116.4 ± 2.1kcal/molEqkGuthrie and Cullimore, 1980Using Hf(s,ClCH2COOH)=-122.0±2.0 kcal/mol
Quantity Value Units Method Reference Comment
Δcliquid-346.8kcal/molCcbSchjanberg, 1935 

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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:
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
Δvap11.17kcal/molN/AMajer and Svoboda, 1985 
Δvap10.4 ± 1.0kcal/molEGuthrie and Cullimore, 1980Using Hf(s,ClCH2COOH)=-122.0±2.0 kcal/mol; ALS
Δvap11.17 ± 0.01kcal/molCLaynez and Wadso, 1972ALS
Δvap11.2 ± 0.02kcal/molCLaynez, Wadsö, et al., 1972AC

Reduced pressure boiling point

Tboil (K) Pressure (atm) Reference Comment
403.20.974Aldrich Chemical Company Inc., 1990BS

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
9.376402.6N/AMajer and Svoboda, 1985 
10.9333.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
11.2313.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 (atm)
    T = temperature (K)

View plot Requires a JavaScript / HTML 5 canvas capable browser.

Temperature (K) A B C Reference Comment
318.17 to 403.014.275471390.083-77.51Goevel, 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

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

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-7.80 ± 0.26kcal/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-13.70 ± 0.70kcal/molEqkGuthrie and Cullimore, 1980liquid phase; Using Hf(s,ClCH2COOH)=-122.0±2.0 kcal/mol

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Ionization energy determinations

IE (eV) Method Reference Comment
10.3PECannington and Ham, 1985LBLHLM
10.53 ± 0.05EIPignataro, Foffani, et al., 1966RDSH
10.7PECannington and Ham, 1985Vertical value; LBLHLM

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C2H3O2+11.10 ± 0.05CH2ClEIBlanchette, Holmes, et al., 1986LBLHLM
C2H3O2+11.50 ± 0.05?EIBriggs and Shannon, 1969RDSH
C2H5Cl+10.7 ± 0.2CO2EIBlanchette, Holmes, et al., 1987LBLHLM

IR Spectrum

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

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

Mass spectrum
For Zoom
1.) Enter the desired X axis range (e.g., 100, 200)
2.) Check here for automatic Y scaling
3.) Press here to zoom

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 Japan AIST/NIMC Database- Spectrum MS-NW-2175
NIST MS number 228208

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.


Gas Chromatography

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

View large format table.

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

View large format table.

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

View large format table.

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 phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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]

Cannington and Ham, 1985
Cannington, P.H.; Ham, N.S., He(II) photoelectron spectra of esters, J. Electron Spectrosc. Relat. Phenom., 1985, 36, 203. [all data]

Pignataro, Foffani, et al., 1966
Pignataro, S.; Foffani, A.; Innorta, G.; Distefano, G., Molecular structural effects on the ionization potentials for metasubstituted aromatic compounds and for compounds of the type X-CH2-R, Z. Physik. Chem. (Frankfurt), 1966, 49, 291. [all data]

Blanchette, Holmes, et al., 1986
Blanchette, M.C.; Holmes, J.L.; Hop, C.E.C.A.; Lossing, F.P.; Postma, R.; Ruttink, P.J.A.; Terlouw, J.K., Theory and experiment in concert; the CH3O-C=O+ ion and its isomers, J. Am. Chem. Soc., 1986, 108, 7589. [all data]

Briggs and Shannon, 1969
Briggs, P.R.; Shannon, T.W., The heat of formation of the methoxycarbonyl ion, J. Am. Chem. Soc., 1969, 91, 4307. [all data]

Blanchette, Holmes, et al., 1987
Blanchette, M.C.; Holmes, J.L.; Lossing, F.P., The ethyl halides: Stable neutral and radical cation isomers [C2, H5, X] where X = F, Cl, Br, I, Org. Mass Spectrom., 1987, 22, 701. [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

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