Ethanol, 2-methoxy-
- Formula: C3H8O2
- Molecular weight: 76.0944
- IUPAC Standard InChIKey: XNWFRZJHXBZDAG-UHFFFAOYSA-N
- CAS Registry Number: 109-86-4
- 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. - Species with the same structure:
- Other names: β-Methoxyethanol; Dowanol EM; Ethylene glycol monomethyl ether; Methoxyethanol; Methyl cellosolve; Monomethyl glycol; MECS; Poly-Solv EM; 1-Hydroxy-2-methoxyethane; 2-Methoxy-1-ethanol; 2-Methoxyethanol; HOCH2CH2OCH3; 2-Hydroxyethyl methyl ether; Aethylenglykol-monomethylaether; Ether monomethylique de l'ethylene-glycol; Ethylene glycol methyl ether; Glycol monomethyl ether; Glycolmethyl ether; Methoxyhydroxyethane; Methyl glycol; Methyl oxitol; Methylglykol; Metil cellosolve; Metoksyetylowy alkohol; Monomethyl ether of ethylene glycol; 2-Methoxy-aethanol; 2-Metossietanolo; EGME; Glycol ether EM; Jeffersol EM; Methylcelosolv; Methyl ethoxol; Prist; UN 1188; Methoxyethylene glycol; Ektasolve EM; 2-Methoxyethyl alcohol; Methyl icinol; 3-Oxa-1-butanol; Amsco-Solv EE; Monoethylene glycol methyl ether; NSC 1258; EGM; 2-methoxyethanol (methyl cellosolve)
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Condensed phase thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -100.9 ± 1.8 | kcal/mol | Cm | Guthrie, 1977 | Hydrolysis; ALS |
ΔfH°liquid | -105.4 | kcal/mol | Ccb | Simonetta, 1947 | Author value for hf298-condensed=-123 kcal/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -450. | kcal/mol | Ccb | Simonetta, 1947 | Author value for hf298-condensed=-123 kcal/mol; Corresponding ΔfHºliquid = -105. kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
41.917 | 298.15 | Svoboda, Zabransky, et al., 1991 | T = 298 to 330 K. Cp(liq) = 84.235 + 0.3057(T/K) J/mol*K. Cp value calculated from equation.; DH |
42.21 | 298.15 | Roux, Perron, et al., 1978 | DH |
41.80 | 298.15 | Kusano, Suurkuusk, et al., 1973 | DH |
Phase change data
Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics 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 as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 397.5 ± 0.3 | K | AVG | N/A | Average of 8 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 597.6 | K | N/A | Wilson, Wilson, et al., 1996 | Uncertainty assigned by TRC = 0.2 K; by a static method; TRC |
Tc | 571. | K | N/A | Steele, Chirico, et al., 1994 | Uncertainty assigned by TRC = 2. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 52.16 | atm | N/A | Wilson, Wilson, et al., 1996 | Uncertainty assigned by TRC = 0.20 atm; by a static method; TRC |
Pc | 35.53 | atm | N/A | Steele, Chirico, et al., 1994 | Uncertainty assigned by TRC = 0.05 atm; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 3.80 | mol/l | N/A | Wilson, Wilson, et al., 1996 | Uncertainty assigned by TRC = 0.09 mol/l; TRC |
ρc | 4.03 | mol/l | N/A | Steele, Chirico, et al., 1994 | Uncertainty assigned by TRC = 0.04 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 10.8 | kcal/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 10.8 | kcal/mol | N/A | Guthrie, 1977 | DRB |
ΔvapH° | 10.8 ± 0.05 | kcal/mol | C | Kusano, Wadsö, et al., 1971 | AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
8.972 | 397.3 | N/A | Majer and Svoboda, 1985 | |
10.3 | 361. | N/A | Marrufo, Loras, et al., 2010 | Based on data from 346. to 397. K.; AC |
10.2 | 348. | A | Stephenson and Malanowski, 1987 | Based on data from 333. to 423. K.; AC |
10.3 | 344. | N/A | Pick, Fried, et al., 1956 | Based on data from 329. to 396. K.; AC |
9.88 | 273. | V | Gallaugher and Hibbert, 1937 | ALS |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
329.3 to 396.7 | 5.05815 | 1853.556 | -30.838 | Pick, Fried, et al., 1956, 2 | Coefficents calculated by NIST from author's data. |
Gas phase ion energetics data
Go To: Top, 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 183.7 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 174.4 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.13 | PE | Kimura, Katsumata, et al., 1981 | LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C2H5O+ | 10.36 | CH2OH | EI | Lossing, 1977 | LLK |
C2H6O+ | 10.3 ± 0.2 | CH3O | EI | Burgers, Holmes, et al., 1983 | LBLHLM |
C2H6O+ | 10.45 ± 0.05 | CH2O | EI | Holmes, Lossing, et al., 1982 | LBLHLM |
C2H7O+ | 9.96 ± 0.05 | HCO | EI | Holmes and Lossing, 1984 | LBLHLM |
De-protonation reactions
C3H7O2- + =
By formula: C3H7O2- + H+ = C3H8O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 373.7 ± 2.1 | kcal/mol | G+TS | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 366.8 ± 2.0 | kcal/mol | IMRE | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics 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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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
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 | NIST Mass Spectrometry Data Center, 1998. |
NIST MS number | 290807 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics 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.
Guthrie, 1977
Guthrie, J.P.,
Cyclization of glycol monoesters to give hemiorthoesters: a test of the thermochemical method for determining free energies of tetrahedral intermediates,
Can. J. Chem., 1977, 55, 3562-3574. [all data]
Simonetta, 1947
Simonetta, M.,
II problema termico nella catena di reazioni tra ossido di etilene ed alcool metilico,
Chimi. Ind. (Milan), 1947, 29, 37-39. [all data]
Svoboda, Zabransky, et al., 1991
Svoboda, V.; Zabransky, M.; Barta, M.,
Molar heat capacities of 2-methoxyethanol, 2-ethoxyethanol, and 2-propoxyethanol in the temperature range from 298K to 330K,
J. Chem. Thermodynam., 1991, 23, 711-712. [all data]
Roux, Perron, et al., 1978
Roux, G.; Perron, G.; Desnoyers, J.E.,
Model systems for hydrophobic interactions: volumes and heat capacities of n-alkoxyethanols in water,
J. Solution Chem., 1978, 7, 639-654. [all data]
Kusano, Suurkuusk, et al., 1973
Kusano, K.; Suurkuusk, J.; Wads, I.,
Thermochemistry of solutions of biochemical model compounds. 2. Alkoxyethanols and 1,2-dialkoxyethanes in water, J. Chem. Thermodynam. 5,757-767 (1973).73LEB/TSV Lebedev, B.V., Tsvetkova, L.Ya., and Rabinovich, I.B., Specific heat and thermodynamic functions of poly(vinyltrimethylsilane),
Tr. Khim. Khim. Tekhnol., 1973, (1), 17-18. [all data]
Wilson, Wilson, et al., 1996
Wilson, L.C.; Wilson, H.L.; Wilding, W.V.; Wilson, G.M.,
Critical Point Measurements for Fourteen Compounds by a Static Method and a Flow Method,
J. Chem. Eng. Data, 1996, 41, 1252-4. [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]
Majer and Svoboda, 1985
Majer, V.; Svoboda, V.,
Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]
Kusano, Wadsö, et al., 1971
Kusano, Kazuhito; Wadsö, Ingemar; Rømming, Chr.; Lindberg, Alf A.; Lagerlund, Inger; Ehrenberg, L.,
Enthalpies of Vaporization of Organic Compounds. VIII. Alkoxyethanols.,
Acta Chem. Scand., 1971, 25, 219-224, https://doi.org/10.3891/acta.chem.scand.25-0219
. [all data]
Marrufo, Loras, et al., 2010
Marrufo, Beatriz; Loras, Sonia; Sanchotello, Margarita,
Isobaric Vapor-Liquid Equilibria for Binary and Ternary Mixtures with Cyclohexane, Cyclohexene, and 2-Methoxyethanol at 100 kPa,
J. Chem. Eng. Data, 2010, 55, 1, 62-68, https://doi.org/10.1021/je900259b
. [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]
Pick, Fried, et al., 1956
Pick, J.; Fried, V.; Hala, E.; Vilim, O.,
Collect. Czech. Chem. Commun., 1956, 21, 260. [all data]
Gallaugher and Hibbert, 1937
Gallaugher, A.F.; Hibbert, H.,
Studies on reactions relating to carbohydrates and polysaccharides. LV. Vapor pressures of the polyethylene glycols and their derivatives,
J. Am. Chem. Soc., 1937, 59, 2521-2525. [all data]
Pick, Fried, et al., 1956, 2
Pick, J.; Fried, V.; Hala, E.; Vilim, O.,
Der Dampfdruck des Athylenglykolmonomethylathers und des Athylenglykolmonoathylathers,
Collect. Czech. Chem. Commun., 1956, 21, 1, 260-261, https://doi.org/10.1135/cccc19560260
. [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]
Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S.,
Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules
in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]
Lossing, 1977
Lossing, F.P.,
Heats of formation of some isomeric [CnH2n+1]+ ions. Substitutional effects on ion stability,
J. Am. Chem. Soc., 1977, 99, 7526. [all data]
Burgers, Holmes, et al., 1983
Burgers, P.C.; Holmes, J.L.; Szulejko, J.E.; Mommers, A.A.; Terlouw, J.K.,
The gas phase ion chemistry of the acetyl cation and isomeric [C2H3O]+ ions. On the structure of the [C2H3O]+ daughter ions generated from the enol of acetone radical cation,
Org. Mass Spectrom., 1983, 18, 254. [all data]
Holmes, Lossing, et al., 1982
Holmes, J.L.; Lossing, F.P.; Terlouw, J.K.; Burgers, P.C.,
The radical cation [CH2OH2]+ and related stable gas phase ion-dipole complexes,
J. Am. Chem. Soc., 1982, 104, 2931. [all data]
Holmes and Lossing, 1984
Holmes, J.L.; Lossing, F.P.,
Heats of formation of organic radicals from appearance energies,
Int. J. Mass Spectrom. Ion Processes, 1984, 58, 113. [all data]
Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr.,
The gas phase acidity scale from methanol to phenol,
J. Am. Chem. Soc., 1979, 101, 6047. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid Pc Critical pressure Tboil Boiling point Tc Critical temperature ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrG° Free energy of reaction at standard conditions 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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