Ethanedioic acid, diethyl ester

• Formula: C₆H₁₀O₄
• Molecular weight: 146.1412
• IUPAC Standard InChI: InChI=1S/C6H10O4/c1-3-9-5(7)6(8)10-4-2/h3-4H2,1-2H3 Copy

  
• IUPAC Standard InChIKey: WYACBZDAHNBPPB-UHFFFAOYSA-N Copy
• CAS Registry Number: 95-92-1
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Other names: Oxalic acid, diethyl ester; Diethyl ethanedioate; Diethyl oxalate; Ethyl oxalate; C2H5OCOCOOC2H5; Diethylester kyseliny stavelove; UN 2525; Diethyl ester of oxalic acid; Oxalic ether; Ethanedioic acid, 1,2-diethyl ester; NSC 8851
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• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • IR Spectrum
  • 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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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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

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

Reduced pressure boiling point

Enthalpy of vaporization

Antoine Equation Parameters

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

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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

 + 6 +  = 10 + 2 + 3 + 6

By formula: C₄H₄F₂N₆O₁₀ + 6O₂ + C₆H₁₀O₄ = 10CO₂ + 2HF + 3N₂ + 6H₂O

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

IR Spectrum

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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

Gas Phase Spectrum

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Additional Data

References

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

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

Baroody and Carpenter, 1972
Baroody, E.E.; Carpenter, G.A., Heats of formation of propellant compounds (U), Rpt. Naval Ordnance Systems Command Task No. 331-003/067-1/UR2402-001 for Naval Ordance Station, Indian Head, MD, 1972, 1-9. [all data]

Zimmer, Baroody, et al., 1968
Zimmer, M.F.; Baroody, E.E.; Carpenter, G.A.; Robb, R.A., Heat of formation of hydroxylammonium perchlorate by combustion calorimetry, J. Chem. Eng. Data, 1968, 13, 212-214. [all data]

Zimmer, Robb, et al., 1966
Zimmer, M.F.; Robb, R.A.; Baroody, E.E.; Carpenter, G.A., Heat of formation and other properties of trinitrofluoromethane, J. Chem. Eng. Data, 1966, 11, 577-579. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

von Reis, 1881
von Reis, M.A., Die specifische Wärme flüssiger organischer Verbindungen und ihre Beziehung zu deren Moleculargewicht, Ann. Physik [3], 1881, 13, 447-464. [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, 1943
Lecat, M., Negative and other Azeotropes, C. R. Hebd. Seances Acad. Sci., 1943, 217, 242. [all data]

Lecat, 1943, 2
Lecat, M., Azeotropes of Ethyl Urethane and other Azeotropes, C. R. Hebd. Seances Acad. Sci., 1943, 217, 273. [all data]

Timmermans, 1911
Timmermans, J., Researches on the freezing point of organic liquid compounds, Bull. Soc. Chim. Belg., 1911, 25, 300. [all data]

Kahlbaum, 1884
Kahlbaum, G.W.A., The dependence of Boiling Temperature on Air Pressure, Ber. Dtsch. Chem. Ges., 1884, 17, 1245. [all data]

Timmermans, 1952
Timmermans, J., Freezing points of organic compounds. VVI New determinations., Bull. Soc. Chim. Belg., 1952, 61, 393. [all data]

Steele, Chirico, et al., 1994
Steele, W.V.; Chirico, R.D.; Hossenlopp, I.A.; Knipmeyer, S.E.; Nguyen, A.; Smith, N.K., DIPPR project 871. Determination of ideal-gas enthalpies of formation for key compounds. The 1990 project results, Experimental Results for DIPPR 1990-91 Projects on Phase Equilibria and Pure Component Properties, 1994, 1994, DIPPR Data Ser. No. 2, p. 188-215. [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]

Baroody and Carpenter, 1973
Baroody, E.E.; Carpenter, G.A., Enthalpies of formation of some fluorodinitroethyl derivatives and 2,2',4,4',6,6'-hexanitroazobenzene, J. Chem. Eng. Data, 1973, 18, 28-36. [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:
  

  Cp,liquid	Constant pressure heat capacity of liquid
  Pc	Critical pressure
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔvapH	Enthalpy of vaporization
  ρc	Critical density

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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