Carbonic acid, dimethyl ester

• Formula: C₃H₆O₃
• Molecular weight: 90.0779
• IUPAC Standard InChI: InChI=1S/C3H6O3/c1-5-3(4)6-2/h1-2H3 Copy

  
• IUPAC Standard InChIKey: IEJIGPNLZYLLBP-UHFFFAOYSA-N Copy
• CAS Registry Number: 616-38-6
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Other names: Dimethyl carbonate; Methyl carbonate; Methyl carbonate ((MeO)2CO); CH3OCOOCH3; UN 1161; Dimethyl ester of carbonic acid
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• Information on this page:
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
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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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Enthalpy of vaporization

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

By formula: C₅H₁₂O₄ + H₂O = C₃H₆O₃ + 2CH₄O

 + 2 =  + 

By formula: C₄H₆O₃ + 2CH₄O = C₃H₈O₂ + C₃H₆O₃

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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
LL - Sharon G. Lias and Joel F. Liebman
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

Appearance energy determinations

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• SOLUTION (10% CCl4 FOR 3800-1333, 10% CS2 FOR 1333-430 CM^-1); Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

• gas

Mass spectrum (electron ionization)

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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

Spectrum

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Additional Data

Gas Chromatography

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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

Normal alkane RI, non-polar column, custom temperature program

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References

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, NIST Subscription Links, Notes

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

Biltz, Fischer, et al., 1930
Biltz, W.; Fischer, W.; Wunnenberg, E., Molecular and Atomic Volumes. The Volume Requirements of Crystalline Organic Compounds and Low Temperatures, Z. Phys. Chem., Abt. A, 1930, 151, 13-55. [all data]

Steele, Chirico, et al., 1997
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A., Vapor Pressure, Heat Capacity, and Density along the Saturated Line, Measurements for Dimethyl Isophthalate, Dimethyl Carbonate, 1,3,5-Trimethyl benzene, Pentafluorophenol, 4-tert-Butylcatechol, .alp, J. Chem. Eng. Data, 1997, 42, 1008-20. [all data]

Steele, Chirico, et al., 1997, 2
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.; Smith, N.K., Thermocynamic Properties and Ideal-Gas Enthalpies of Formation for Carbonate, Piperazine, Hexachloroprop-1-ene, Tetrakis(dimethylamino) ethylene, N,N'-Bis(2-hydroxyethyl)ethylenediamine, and 1,2,4-Tr, J. Chem. Eng. Data, 1997, 42, 1037-52. [all data]

Kozlova, Emel'yanenko, et al., 2008
Kozlova, Svetlana A.; Emel'yanenko, Vladimir N.; Georgieva, Miglena; Verevkin, Sergey P.; Chernyak, Yury; Schäffner, Benjamin; Börner, Armin, Vapour pressure and enthalpy of vaporization of aliphatic dialkyl carbonates, The Journal of Chemical Thermodynamics, 2008, 40, 7, 1136-1140, https://doi.org/10.1016/j.jct.2008.02.012 . [all data]

Steele, Chirico, et al., 1997, 3
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.; Smith, N.K., Thermodynamic Properties and Ideal-Gas Enthalpies of Formation for Dicyclohexyl Sulfide, Diethylenetriamine, Di- n -octyl Sulfide, Dimethyl Carbonate, Piperazine, Hexachloroprop-1-ene, Tetrakis(dimethylamino)ethylene, N , N '-Bis-(2-hydroxyethyl)ethylenediamine, and 1,2,4-Triazolo[1,5- a ]pyrimidine, J. Chem. Eng. Data, 1997, 42, 6, 1037-1052, https://doi.org/10.1021/je9700986 . [all data]

Steele, Chirico, et al., 1997, 4
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A., Vapor Pressure, Heat Capacity, and Density along the Saturation Line, Measurements for Dimethyl Isophthalate, Dimethyl Carbonate, 1,3,5-Triethylbenzene, Pentafluorophenol, 4- tert -Butylcatechol, α-Methylstyrene, and N , N '-Bis(2-hydroxyethyl)ethylenediamine, J. Chem. Eng. Data, 1997, 42, 6, 1008-1020, https://doi.org/10.1021/je970102d . [all data]

Rodriguez, Canosa, et al., 2002
Rodriguez, A.; Canosa, J.; Dominguez, A.; Tojo, J., Isobaric vapour--liquid equilibria of dimethyl carbonate with alkanes and cyclohexane at 101.3 kPa, Fluid Phase Equilibria, 2002, 198, 1, 95-109, https://doi.org/10.1016/S0378-3812(01)00761-0 . [all data]

Ding, 2004
Ding, Michael S., Liquid-Solid Phase Equilibria and Thermodynamic Modeling for Binary Organic Carbonates, J. Chem. Eng. Data, 2004, 49, 2, 276-282, https://doi.org/10.1021/je034134e . [all data]

Wiberg, 1980
Wiberg, K.B., Energies of organic compounds, Rept. DOE-E(11-1)4060 Prepared for US Dept. of Energy by Yale Univ., New Haven, CT. Avail. NTIS, 1980, 1-24. [all data]

Wiberg and Squires, 1979
Wiberg, K.B.; Squires, R.R., A microprocessor-controlled system for precise measurement of temperature changes. Determination of the enthalpies of hydrolysis of some polyoxygenated hydrocarbons, J. Chem. Thermodyn., 1979, 11, 773-786. [all data]

Hine and Klueppet, 1974
Hine, J.; Klueppet, A.W., Structural effects on rates and equilibria. XVIII. Thermodynamic stability of ortho esters, J. Am. Chem. Soc., 1974, 96, 2924-2929. [all data]

Zhang and Luo, 1991
Zhang, S.; Luo, Y., Kinetics and technological conditions for the synthesis of dimethyl carbonate, Chem. React. Eng. Tech., 1991, 7, 10-19. [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [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]

Wittel, Astrup, et al., 1975
Wittel, K.; Astrup, E.E.; Bock, H.; Graeffe, G.; Juslen, H., Photoelectron spectra and molecular properties, XLVIII Carbonates thio- carbonates, Z. Naturforsch. B:, 1975, 30, 862. [all data]

Meeks, Arnett, et al., 1975
Meeks, J.L.; Arnett, J.F.; Larson, D.; McGlynn, S.P., Photoelectron spectroscopy of carbonyls. Ionization assignments, Chem. Phys. Lett., 1975, 30, 190. [all data]

Suh, Kingsmill, et al., 1995
Suh, D.; Kingsmill, C.A.; Ruttink, P.J.A.; Burgers, P.C.; Terlouw, J.K., C-H...O and O...H...O bonded intermediates in the dissociation of low energy methyl glycolate radical cations, Int. J. Mass Spectrom. Ion Processes, 1995, 146/147, 305. [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]

Terlouw, Wezenberg, et al., 1983
Terlouw, J.K.; Wezenberg, J.; Burgers, P.C.; Holmes, J.L., New stable isomers of [C₂H₄O]⁺ and [C₂H₄O₂]⁺, the radical cations [CH₂COH]⁺ and [CH₃OCOH]⁺, J. Chem. Soc., Chem. Commun., 1983, 1121. [all data]

Rotsatschakul, Visesanguan, et al., 2009
Rotsatschakul, P.; Visesanguan, W.; Smitinont, T.; Chaiseri, S., Changes in volatile compounds during fermentation of nham (Thai fermented sausage), Int. Food Res. J., 2009, 16, 391-414. [all data]

Notes

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• Symbols used in this document:
  

  AE	Appearance energy
  Pc	Critical pressure
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  ΔfusH	Enthalpy of fusion
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions
  ρc	Critical density

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