Carbonic acid, dimethyl ester

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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

Quantity Value Units Method Reference Comment
Tboil363.5 ± 0.4KAVGN/AAverage of 9 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus267.55KN/ABiltz, Fischer, et al., 1930Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Tc557.KN/ASteele, Chirico, et al., 1997Uncertainty assigned by TRC = 2. K; TRC
Tc557.KN/ASteele, Chirico, et al., 1997, 2Uncertainty assigned by TRC = 2. K; same data as in 1997 stechi 0; TRC
Quantity Value Units Method Reference Comment
Pc48.00barN/ASteele, Chirico, et al., 1997Uncertainty assigned by TRC = 1.50 bar; derived from fit of obs. vapor pressure; TRC
Pc48.00barN/ASteele, Chirico, et al., 1997, 2Uncertainty assigned by TRC = 3.00 bar; same data as in 1997 stechi 0; TRC
Quantity Value Units Method Reference Comment
ρc3.97mol/lN/ASteele, Chirico, et al., 1997Uncertainty assigned by TRC = 0.11 mol/l; TRC
ρc3.80mol/lN/ASteele, Chirico, et al., 1997, 2Uncertainty assigned by TRC = 0.17 mol/l; same data as in 1997 stechi 0; TRC
Quantity Value Units Method Reference Comment
Δvap38.0 ± 0.2kJ/molGSKozlova, Emel'yanenko, et al., 2008Based on data from 274. to 304. K.; AC
Δvap37.7 ± 0.2kJ/molEBSteele, Chirico, et al., 1997, 3Based on data from 311. to 397. K. See also Steele, Chirico, et al., 1997, 4.; AC

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Reference Comment
36.4341.Rodriguez, Canosa, et al., 2002Based on data from 326. to 411. K.; AC

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
11.58278.2Ding, 2004AC

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

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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

Tetramethyl orthocarbonate + Water = Carbonic acid, dimethyl ester + 2Methyl Alcohol

By formula: C5H12O4 + H2O = C3H6O3 + 2CH4O

Quantity Value Units Method Reference Comment
Δr31.47 ± 0.046kJ/molCmWiberg, 1980liquid phase; solvent: Water; Hydroysis
Δr-31.466 ± 0.044kJ/molCmWiberg and Squires, 1979liquid phase; solvent: Water; Hydrolysis
Δr-31.1 ± 1.7kJ/molCmHine and Klueppet, 1974liquid phase

Propylene Carbonate + 2Methyl Alcohol = Propylene Glycol + Carbonic acid, dimethyl ester

By formula: C4H6O3 + 2CH4O = C3H8O2 + C3H6O3

Quantity Value Units Method Reference Comment
Δr-6.93kJ/molKinZhang and Luo, 1991liquid phase

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

Quantity Value Units Method Reference Comment
Proton affinity (review)830.2kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity799.2kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
11.00PEMcGlynn and Meeks, 1976Vertical value; LLK
11.2PEWittel, Astrup, et al., 1975Vertical value; LLK
11.00PEMeeks, Arnett, et al., 1975Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CH3O+10.96 ± 0.05C2H3O2EISuh, Kingsmill, et al., 1995Unpublished result of F.P.Lossing; LL
C2H3O2+11.50 ± 0.05CH3OEIBlanchette, Holmes, et al., 1986LBLHLM
C2H3O2+12.15 ± 0.08CH3OEIBriggs and Shannon, 1969RDSH
C2H4O2+11.56 ± 0.05CH2OEITerlouw, Wezenberg, et al., 1983LBLHLM
C2H4O2+11.5 ± 0.2CH2OEITerlouw, Wezenberg, et al., 1983LBLHLM

References

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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]


Notes

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