Carbonic acid, dimethyl ester
- Formula: C3H6O3
- Molecular weight: 90.0779
- IUPAC Standard InChIKey: IEJIGPNLZYLLBP-UHFFFAOYSA-N
- 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
The 3d structure may be viewed using Java or Javascript. - Other names: Dimethyl carbonate; Methyl carbonate; Methyl carbonate ((MeO)2CO); CH3OCOOCH3; UN 1161; Dimethyl ester of carbonic acid
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Phase change data
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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:
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 |
---|---|---|---|---|---|
Tboil | 363.5 ± 0.4 | K | AVG | N/A | Average of 9 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 267.55 | K | N/A | Biltz, Fischer, et al., 1930 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 557. | K | N/A | Steele, Chirico, et al., 1997 | Uncertainty assigned by TRC = 2. K; TRC |
Tc | 557. | K | N/A | Steele, Chirico, et al., 1997, 2 | Uncertainty assigned by TRC = 2. K; same data as in 1997 stechi 0; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 47.37 | atm | N/A | Steele, Chirico, et al., 1997 | Uncertainty assigned by TRC = 1.48 atm; derived from fit of obs. vapor pressure; TRC |
Pc | 47.37 | atm | N/A | Steele, Chirico, et al., 1997, 2 | Uncertainty assigned by TRC = 2.96 atm; same data as in 1997 stechi 0; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 3.97 | mol/l | N/A | Steele, Chirico, et al., 1997 | Uncertainty assigned by TRC = 0.11 mol/l; TRC |
ρc | 3.80 | mol/l | N/A | Steele, Chirico, et al., 1997, 2 | Uncertainty assigned by TRC = 0.17 mol/l; same data as in 1997 stechi 0; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 9.08 ± 0.05 | kcal/mol | GS | Kozlova, Emel'yanenko, et al., 2008 | Based on data from 274. to 304. K.; AC |
ΔvapH° | 9.01 ± 0.05 | kcal/mol | EB | Steele, Chirico, et al., 1997, 3 | Based on data from 311. to 397. K. See also Steele, Chirico, et al., 1997, 4.; AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
8.70 | 341. | Rodriguez, Canosa, et al., 2002 | Based on data from 326. to 411. K.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
2.768 | 278.2 | Ding, 2004 | AC |
Reaction thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics data, IR Spectrum, 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
By formula: C5H12O4 + H2O = C3H6O3 + 2CH4O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 7.521 ± 0.011 | kcal/mol | Cm | Wiberg, 1980 | liquid phase; solvent: Water; Hydroysis |
ΔrH° | -7.521 ± 0.011 | kcal/mol | Cm | Wiberg and Squires, 1979 | liquid phase; solvent: Water; Hydrolysis |
ΔrH° | -7.43 ± 0.41 | kcal/mol | Cm | Hine and Klueppet, 1974 | liquid phase |
By formula: C4H6O3 + 2CH4O = C3H8O2 + C3H6O3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -1.66 | kcal/mol | Kin | Zhang and Luo, 1991 | liquid phase |
Gas phase ion energetics data
Go To: Top, Phase change data, Reaction thermochemistry data, IR Spectrum, References, Notes
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) | 198.4 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 191.0 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
11.00 | PE | McGlynn and Meeks, 1976 | Vertical value; LLK |
11.2 | PE | Wittel, Astrup, et al., 1975 | Vertical value; LLK |
11.00 | PE | Meeks, Arnett, et al., 1975 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CH3O+ | 10.96 ± 0.05 | C2H3O2 | EI | Suh, Kingsmill, et al., 1995 | Unpublished result of F.P.Lossing; LL |
C2H3O2+ | 11.50 ± 0.05 | CH3O | EI | Blanchette, Holmes, et al., 1986 | LBLHLM |
C2H3O2+ | 12.15 ± 0.08 | CH3O | EI | Briggs and Shannon, 1969 | RDSH |
C2H4O2+ | 11.56 ± 0.05 | CH2O | EI | Terlouw, Wezenberg, et al., 1983 | LBLHLM |
C2H4O2+ | 11.5 ± 0.2 | CH2O | EI | Terlouw, Wezenberg, et al., 1983 | LBLHLM |
IR Spectrum
Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, References, Notes
Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
References
Go To: Top, 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.
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
Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, References
- 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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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