Ethanedioic acid, dimethyl 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.

Quantity Value Units Method Reference Comment
Δfgas-169.52 ± 0.13kcal/molCcbAnthoney, Carson, et al., 1976See Anthoney, Carson, et al., 1975; ALS
Δfgas-169.6kcal/molN/AAnthoney, Finch, et al., 1975Value computed using ΔfHsolid° value of -756.7±0.3 kj/mol from Anthoney, Finch, et al., 1975 and ΔsubH° value of 47.0 kj/mol from Anthoney, Carson, et al., 1976.; DRB

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
Δfsolid-180.76 ± 0.20kcal/molCcbAnthoney, Carson, et al., 1976See Anthoney, Carson, et al., 1975
Δfsolid-180.86 ± 0.074kcal/molCmAnthoney, Finch, et al., 1975Hydrolysis
Quantity Value Units Method Reference Comment
Δcsolid-400.39 ± 0.15kcal/molCcbAnthoney, Carson, et al., 1976See Anthoney, Carson, et al., 1975; Corresponding Δfsolid = -180.76 kcal/mol (simple calculation by NIST; no Washburn corrections)
Δcsolid-400.8kcal/molCcbVerkade, Coops, et al., 1926Heat of combustion at 15°C; Corresponding Δfsolid = -180.3 kcal/mol (simple calculation by NIST; no Washburn corrections)

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.

Quantity Value Units Method Reference Comment
Tboil437.7KN/AWeast and Grasselli, 1989BS
Tboil437.4KN/ALecat, 1927Uncertainty assigned by TRC = 0.5 K; TRC
Tboil437.4KN/ALecat, 1926Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Tfus327.95KN/AAnthoney, Carson, et al., 1976, 2Uncertainty assigned by TRC = 0.25 K; TRC
Tfus322.65KN/ABruner, 1894Uncertainty assigned by TRC = 0.6 K; TRC
Quantity Value Units Method Reference Comment
Tc628.KN/AStern and Kay, 1957Uncertainty assigned by TRC = 8. K; TRC
Tc533.KN/AWeger, 1883Uncertainty assigned by TRC = 40. K; TRC
Tc533.KN/ARegnault, 1862Uncertainty assigned by TRC = 40. K; TRC
Quantity Value Units Method Reference Comment
Pc39.28atmN/AStern and Kay, 1957Uncertainty assigned by TRC = 4.000 atm; TRC
Pc94.84atmN/ARegnault, 1862Uncertainty assigned by TRC = 20.000 atm; TRC
Quantity Value Units Method Reference Comment
Δvap13.1 ± 0.07kcal/molGSVerevkin, Kozlova, et al., 2006Based on data from 330. to 365. K.; AC
Δvap12.5kcal/molN/AMa, Liu, et al., 2004Based on data from 328. to 443. K. See also Verevkin, Kozlova, et al., 2006.; AC
Quantity Value Units Method Reference Comment
Δsub18.0 ± 0.1kcal/molCChickos, Sabbah, et al., 1996ALS
Δsub17.8 ± 0.2kcal/molCChickos, Sabbah, et al., 1996AC
Δsub18.0 ± 0.38kcal/molN/AChickos, Sabbah, et al., 1996AC
Δsub11.2kcal/molN/AAnthoney, Carson, et al., 1976DRB

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
10.7416.HG,EBAskonas and Daubert, 1988Based on data from 347. to 485. K.; AC
11.7308.AStephenson and Malanowski, 1987Based on data from 293. to 437. K. See also Stull, 1947.; AC

Antoine Equation Parameters

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

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Temperature (K) A B C Reference Comment
293. to 436.55.040141994.334-41.204Stull, 1947Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

ΔsubH (kcal/mol) Temperature (K) Method Reference Comment
18.1 ± 0.38283.HSAChickos, Sabbah, et al., 1996Based on data from 268. to 298. K.; AC
11.33 ± 0.11289.21VAnthoney, Carson, et al., 1976See Anthoney, Carson, et al., 1975; ALS

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
5.036327.6Acree, 1991AC

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, 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: 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

Ethanedioic acid, dimethyl ester + 2Water = Oxalic acid + 2Methyl Alcohol

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

Quantity Value Units Method Reference Comment
Δr4.165 ± 0.016kcal/molCmAnthoney, Finch, et al., 1975solid phase; solvent: Water; Hydrolysis

Mass spectrum (electron ionization)

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

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Mass spectrum
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Additional Data

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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-5045
NIST MS number 228095

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References

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

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]


Notes

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