Urethane
- Formula: C3H7NO2
- Molecular weight: 89.0932
- IUPAC Standard InChIKey: JOYRKODLDBILNP-UHFFFAOYSA-N
- CAS Registry Number: 51-79-6
- 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: Carbamic acid, ethyl ester; Ethyl carbamate; Ethyl urethane; O-Ethylurethane; Leucethane; NSC 746; Pracarbamine; Urethan; NH2COOC2H5; A 11032; Aethylcarbamat; Aethylurethan; Carbamidsaeure-aethylester; Estane 5703; Ethyl urethan; Leucothane; Pracarbamin; U-Compound; Uretan; X 41; Ethylester kyseliny karbaminove; Rcra waste number U238; Uretan etylowy; Ethyl ester of carbamic acid
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -106.7 | kcal/mol | Cm | Bernard, Boukari, et al., 1976 | hfusion=20.9±0.8 kJ/mol |
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -118.9 | kcal/mol | Cm | Bernard, Boukari, et al., 1976 | hfusion=20.9±0.8 kJ/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔfH°solid | -123.6 | kcal/mol | Ccb | Schmidt and Becker, 1933 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -397.65 | kcal/mol | Ccb | Schmidt and Becker, 1933 | ALS |
Constant pressure heat capacity of solid
Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
37.388 | 300. | DeWit, DeKruif, et al., 1983 | T = 90 to 330 K.; DH |
Phase change data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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 as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 456.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 458.40 | K | N/A | Lecat, 1947 | Uncertainty assigned by TRC = 0.6 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 322. ± 4. | K | AVG | N/A | Average of 6 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 321.41 | K | N/A | De Wit, De Kruif, et al., 1983 | Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 12. ± 0.60 | kcal/mol | V | Bernard, Boukari, et al., 1976 | hfusion=20.9±0.8 kJ/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 18.2 | kcal/mol | N/A | De Wit, Van Miltenburg, et al., 1983 | AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
13.5 | 353. | A | Stephenson and Malanowski, 1987 | Based on data from 338. to 457. K. See also Stull, 1947.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
339.0 to 457. | 5.48347 | 2278.15 | -41.707 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
18.6 | 265. | TE,ME | De Wit, Van Miltenburg, et al., 1983 | Based on data from 256. to 273. K.; AC |
17.2 | 322. | N/A | Bernard, Boukari, et al., 1976 | AC |
21.3 ± 0.2 | 299. | GS | Davies and Jones, 1959 | Based on data from 292. to 307. K.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
4.0139 | 321.41 | DeWit, DeKruif, et al., 1983 | DH |
4.9952 | 321.7 | Bernard, Boukari, et al., 1976 | DH |
3.640 | 321.9 | Acree, 1991 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
12.49 | 321.41 | DeWit, DeKruif, et al., 1983 | DH |
15.5 | 321.7 | Bernard, Boukari, et al., 1976 | DH |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Bernard, Boukari, et al., 1976
Bernard, M.A.; Boukari, Y.; Busnot, F.,
Thermodynamic study of methyl and ethyl carbamates and their eutectic,
Thermochim. Acta, 1976, 16, 267-275. [all data]
Schmidt and Becker, 1933
Schmidt, V.A.; Becker, F.,
Die Bildungswarme von Nitrocellulofen, Nitroglycerin und anderen widuigen Beltandteilen von Treibmitteln,
Z. Gesamte Schiess Sprengstoffwes., 1933, 33, 280-282. [all data]
DeWit, DeKruif, et al., 1983
DeWit, H.G.M.; DeKruif, C.G.; Van Miltenburg, J.C.,
Thermodynamic properties of molecular organic crystals containing organic crystals containing nitrogen, oxygen, and sulfur. II. Molar heat capacities of eight compounds by adiabatic calorimetry,
J. Chem. Thermodynam., 1983, 15, 891-902. [all data]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Lecat, 1947
Lecat, M.,
Orthobaric Azeotropes of Sulfides,
Bull. Cl. Sci., Acad. R. Belg., 1947, 33, 160-82. [all data]
De Wit, De Kruif, et al., 1983
De Wit, H.G.M.; De Kruif, C.G.; Van Miltenburg, J.C.,
Thermodynamic properties of molecular organic crystals containing nitrogen, oxygen, and sulfur II. Molar heat capacities of eight compounds by adiabatic calorimetry,
J. Chem. Thermodyn., 1983, 15, 9, 891, https://doi.org/10.1016/0021-9614(83)90095-2
. [all data]
De Wit, Van Miltenburg, et al., 1983
De Wit, H.G.M.; Van Miltenburg, J.C.; De Kruif, C.G.,
Thermodynamic properties of molecular organic crystals containing nitrogen, oxygen, and sulphur 1. Vapour pressures and enthalpies of sublimation,
The Journal of Chemical Thermodynamics, 1983, 15, 7, 651-663, https://doi.org/10.1016/0021-9614(83)90079-4
. [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]
Davies and Jones, 1959
Davies, Mansel; Jones, A. Hamilton,
Lattice energies of some n-methyl amides and of some carbamates,
Trans. Faraday Soc., 1959, 55, 1329, https://doi.org/10.1039/tf9595501329
. [all data]
Acree, 1991
Acree, William E.,
Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation,
Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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