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:
  • Phase change data
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
• Options:
  • Switch to calorie-based units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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.

Phase change data

Go To: Top, 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
DRB - Donald R. Burgess, Jr.

Enthalpy of vaporization

Antoine Equation Parameters

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

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

Enthalpy of sublimation

Enthalpy of fusion

Mass spectrum (electron ionization)

Go To: Top, Phase change data, 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.

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

References

Go To: Top, Phase change data, 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.

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
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]

Anthoney, Carson, et al., 1976, 2
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]

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]

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]

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]

Notes

Go To: Top, Phase change data, Mass spectrum (electron ionization), References

• Symbols used in this document:
  

  Pc	Critical pressure
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  ΔfusH	Enthalpy 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
• The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
• Customer support for NIST Standard Reference Data products.