Ethanedioic acid, dimethyl ester

• Formula: C₄H₆O₄
• Molecular weight: 118.0880
• IUPAC Standard InChI: InChI=1S/C4H6O4/c1-7-3(5)4(6)8-2/h1-2H3 Copy

  
• IUPAC Standard InChIKey: LOMVENUNSWAXEN-UHFFFAOYSA-N Copy
• CAS Registry Number: 553-90-2
• Chemical structure:
  This structure is also available as a 2d Mol file
• Other names: Oxalic acid, dimethyl ester; Dimethyl oxalate; Methyl oxalate; CH3OCOCOOCH3; Dimethyl ester of oxalic acid; Ethanedioc acid dimethyl ester
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.

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

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
DRB - Donald R. Burgess, Jr.

Enthalpy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Enthalpy of sublimation

Enthalpy of fusion

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

 + 2 =  + 2

By formula: C₄H₆O₄ + 2H₂O = C₂H₂O₄ + 2CH₄O

Gas phase ion energetics 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: Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

References

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

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

Anthoney, Carson, et al., 1976
Anthoney, M.E.; Carson, A.S.; Laye, P.G.; Yrekli, M., The enthalpy of formation of dimethyl oxalate, J. Chem. Thermodyn., 1976, 8, 1009-1010. [all data]

Anthoney, Carson, et al., 1975
Anthoney, M.E.; Carson, A.S.; Laye, P.G., The thermochemistry of formates and oxalates, Conf. Int. Thermodyn. Chim. C.R. 4th, 1975, 1, 99-103. [all data]

Anthoney, Finch, et al., 1975
Anthoney, M.E.; Finch, A.; Stephens, M., The solution of dimethyl oxalate and oxalic acid in water and alkali. Standard enthalpy of formation of dimethyl oxalate, Thermochim. Acta, 1975, 12, 427-431. [all data]

Verkade, Coops, et al., 1926
Verkade, P.E.; Coops, J.; Hartman, H., Calorimetric researches. XIII. Heats of combustion of successive terms of homologous series: Dimethyl esters of the oxalic acid series. A general survey of the oscillation phenomena, Recl. Trav. Chim. Pays-Bas, 1926, 45, 585-606. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Lecat, 1927
Lecat, M., New binary azeotropes: 6th list, Ann. Soc. Sci. Bruxelles, Ser. B, 1927, 47, 63-71. [all data]

Lecat, 1926
Lecat, M., New binary azeotropes: 3rd list, Ann. Soc. Sci. Bruxelles, Ser. B, 1926, 45, 284-94. [all data]

Anthoney, Carson, et al., 1976, 2
Anthoney, M.E.; Carson, A.S.; Carson, P.G.; Laye, P.G.; Yurckli, M., J. Chem. Thermodyn., 1976, 8, 1009. [all data]

Bruner, 1894
Bruner, L., The heats of fusion of some organic compounds, Ber. Dtsch. Chem. Ges., 1894, 27, 2102. [all data]

Stern and Kay, 1957
Stern, S.A.; Kay, W.B., The Critical Pressure and Temperature of Dimethyl Oxalate, J. Phys. Chem., 1957, 61, 374. [all data]

Weger, 1883
Weger, F., Justus Liebigs Ann. Chem., 1883, 221, 61. [all data]

Regnault, 1862
Regnault, V., Mem. Acad. Sci. Inst. Fr., 1862, 26, 335. [all data]

Verevkin, Kozlova, et al., 2006
Verevkin, Sergey P.; Kozlova, Svetlana A.; Emel'yanenko, Vladimir N.; Nikitin, Eugene D.; Popov, Alexander P.; Krasnykh, Eugen L., Vapor Pressures, Enthalpies of Vaporization, and Critical Parameters of a Series of Linear Aliphatic Dimethyl Esters of Dicarboxylic Acids, J. Chem. Eng. Data, 2006, 51, 5, 1896-1905, https://doi.org/10.1021/je0602418 . [all data]

Ma, Liu, et al., 2004
Ma, Xin-Bin; Liu, Xin-Gang; Li, Zhen-Hua; Xu, Gen-Hui, Vapor--liquid equilibria for the ternary system methanol + dimethyl carbonate + dimethyl oxalate and constituent binary systems at different temperatures, Fluid Phase Equilibria, 2004, 221, 1-2, 51-56, https://doi.org/10.1016/j.fluid.2004.04.018 . [all data]

Chickos, Sabbah, et al., 1996
Chickos, J.S.; Sabbah, R.; Hosseini, S.; Liebman, J.F., The sublimation enthalpy of dimethyl oxalate, Struct. Chem., 1996, 7, 391-395. [all data]

Askonas and Daubert, 1988
Askonas, Charles F.; Daubert, Thomas E., Vapor pressure determination of eight oxygenated compounds, J. Chem. Eng. Data, 1988, 33, 3, 225-229, https://doi.org/10.1021/je00053a001 . [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]

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]

McGlynn and Meeks, 1976
McGlynn, S.P.; Meeks, J.L., Photoelectron spectra of carbonyls, carbonates, oxalates and esterification effects, J. Electron Spectrosc. Relat. Phenom., 1976, 8, 85. [all data]

Notes

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• Symbols used in this document:
  

  Pc	Critical pressure
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔrH°	Enthalpy of reaction at standard conditions
  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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