Propane, 2-ethoxy-2-methyl-
- Formula: C6H14O
- Molecular weight: 102.1748
- IUPAC Standard InChIKey: NUMQCACRALPSHD-UHFFFAOYSA-N
- CAS Registry Number: 637-92-3
- 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: Ether, tert-butyl ethyl; tert-Butyl Ethyl ether; Ethyl tert-butyl ether; Ethyl tert-butyl oxide; tert-C4H9OC2H5; t-Butyl ethyl ether; 2-Ethoxy-2-methylpropane
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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 as indicated in comments:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -75.96 | kcal/mol | N/A | Sharonov, Rozhnov, et al., 1995 | Value computed using ΔfHliquid° value of -350.8±2.6 kj/mol from Sharonov, Rozhnov, et al., 1995 and ΔvapH° value of 32.97 kj/mol from missing citation.; DRB |
ΔfH°gas | -75.0 ± 0.5 | kcal/mol | Eqk | Iborra, Izquierdo, et al., 1989 | GC; ALS |
Constant pressure heat capacity of gas
Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
35.691 | 300. | Dunphy M.P., 1991 | These values were calculated using estimated structural parameters and vibrational frequencies. According to estimation by difference method [ Dorofeeva O.V., 1997] the uncertainty of S(298.15 K) is evaluated to be 5-8 J/mol*K.; GT |
46.135 | 400. | ||
55.514 | 500. | ||
63.255 | 600. | ||
69.613 | 700. | ||
74.945 | 800. | ||
79.477 | 900. | ||
83.399 | 1000. | ||
86.776 | 1100. | ||
89.725 | 1200. | ||
92.299 | 1300. | ||
94.555 | 1400. | ||
96.530 | 1500. | ||
98.260 | 1600. | ||
99.783 | 1700. | ||
101.12 | 1800. | ||
102.30 | 1900. | ||
103.36 | 2000. | ||
104.29 | 2100. | ||
105.12 | 2200. | ||
105.87 | 2300. | ||
106.53 | 2400. | ||
107.14 | 2500. |
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 | -83.84 ± 0.62 | kcal/mol | Eqk | Sharonov, Rozhnov, et al., 1995 | ALS |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
52.1 | 298. | Evans and Edlund, 1936 | DH |
Phase change data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry 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 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 | 346.1 | K | N/A | Fandary, Aljima, et al., 1999 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tboil | 346.3 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 345.6 | K | N/A | Majer and Svoboda, 1985 | |
Tboil | 345.9 | K | N/A | Olson, Hipsher, et al., 1947 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 179.15 | K | N/A | Olson, Hipsher, et al., 1947 | Uncertainty assigned by TRC = 0.2 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 7.880 | kcal/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 7.91 ± 0.1 | kcal/mol | EB | Efimova, Pashchenko, et al., 2007 | Based on data from 303. to 345. K.; AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
7.113 | 345.6 | N/A | Majer and Svoboda, 1985 | |
7.67 | 328. | N/A | Sapei, Zaytseva, et al., 2007 | Based on data from 313. to 346. K.; AC |
7.62 | 328. | N/A | Kim, Keskinen, et al., 2004 | Based on data from 313. to 345. K.; AC |
7.67 | 322. | N/A | Reich, Cartes, et al., 2000 | Based on data from 307. to 346. K.; AC |
7.70 | 321. | EB | Kraehenbuehl and Gmehling, 1994 | Based on data from 306. to 345. K.; AC |
8.01 | 299. | A | Stephenson and Malanowski, 1987 | Based on data from 284. to 346. K.; AC |
8.44 | 263. | A | Stephenson and Malanowski, 1987 | Based on data from 248. to 350. K.; AC |
7.46 | 355. | A | Stephenson and Malanowski, 1987 | Based on data from 340. to 407. K.; AC |
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
By formula: C4H8 + C2H6O = C6H14O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -7.65 | kcal/mol | Cm | Sola, Pericas, et al., 1995 | liquid phase |
ΔrH° | -7.65 | kcal/mol | Kin | Sola, Pericas, et al., 1995 | liquid phase |
ΔrH° | -14.9 ± 0.5 | kcal/mol | Eqk | Iborra, Izquierdo, et al., 1989 | gas phase; GC |
By formula: C6H14O = C4H8 + C2H6O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 8.47 ± 0.46 | kcal/mol | Eqk | Sharonov, Rozhnov, et al., 1995 | liquid phase |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction 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 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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 204.6 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 197.6 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.39 ± 0.015 | PE | Klessinger, Asmus, et al., 1975 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C5H11O+ | 9.24 | CH3 | EI | Lossing, 1977 | LLK |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Sharonov, Rozhnov, et al., 1995
Sharonov, K.G.; Rozhnov, A.M.; Korol'kov, A.V.; Karaseva, S.Y.,
Enthalpies of formation of 2-methyl-2-ethoxypropane and 2-ethyl-2-ethoxypropane from equilibrium measurements,
J. Chem. Thermodyn., 1995, 27, 751-753. [all data]
Iborra, Izquierdo, et al., 1989
Iborra, M.; Izquierdo, J.F.; Tejero, J.; Cunill, F.,
Equilibrium constant for ethyl tert-butyl ether vapor-phase synthesis,
J. Chem. Eng. Data, 1989, 34, 1-5. [all data]
Dunphy M.P., 1991
Dunphy M.P.,
Preliminary observations on the high temperature oxidation of ethyl tert-butyl ether,
Int. J. Chem. Kinet., 1991, 23, 553-558. [all data]
Dorofeeva O.V., 1997
Dorofeeva O.V.,
Unpublished results. Thermocenter of Russian Academy of Science, Moscow, 1997. [all data]
Evans and Edlund, 1936
Evans, T.W.; Edlund, K.R.,
Tertiary alkyl ethers preparation and properties,
Ind. Eng. Chem., 1936, 28, 1186-1188. [all data]
Fandary, Aljima, et al., 1999
Fandary, M.S.H.; Aljima, A.S.; Al-Kandary, J.A.,
Liquid-Liquid Equilibria for the System Water + Ethanol + Ethyl tert-Butyl Ether,
J. Chem. Eng. Data, 1999, 44, 1129-31. [all data]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [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]
Olson, Hipsher, et al., 1947
Olson, W.T.; Hipsher, H.F.; Buess, C.M.; Goodman, I.A.; Hart, I.; Lamneck, J.H.; Gibbons, L.C.,
The Synthesis and Purification of Ethers,
J. Am. Chem. Soc., 1947, 69, 2451-4. [all data]
Efimova, Pashchenko, et al., 2007
Efimova, A.A.; Pashchenko, L.L.; Varushchenko, R.M.; Krasnyh, E.; Levanova, S.V.,
The thermodynamics of vaporization of ethyl tert-butyl ether, isobutyl tert-butyl ether, and di-isopropyl ether,
The Journal of Chemical Thermodynamics, 2007, 39, 1, 142-147, https://doi.org/10.1016/j.jct.2006.05.007
. [all data]
Sapei, Zaytseva, et al., 2007
Sapei, Erlin; Zaytseva, Anna; Uusi-Kyyny, Petri; Keskinen, Kari I.; Aittamaa, Juhani,
Vapor--liquid equilibrium for binary system of diethyl sulfide+cyclohexane at 353.15 and 343.15K and diethyl sulfide+2-ethoxy-2-methylpropane at 343.15 and 333.15K,
Fluid Phase Equilibria, 2007, 252, 1-2, 130-136, https://doi.org/10.1016/j.fluid.2006.12.015
. [all data]
Kim, Keskinen, et al., 2004
Kim, Younghun; Keskinen, Kari I.; Aittamaa, Juhani,
Vapor-Liquid Equilibrium for Binary Systems 2-Propanol + 2-Ethoxy-2-methylpropane and Ethyl Ethanoate + 2-Ethoxy-2-methylpropane at 333 K and 2-Propanone + 2-Ethoxy-2-methylpropane at 323 K,
J. Chem. Eng. Data, 2004, 49, 5, 1273-1278, https://doi.org/10.1021/je0342421
. [all data]
Reich, Cartes, et al., 2000
Reich, Ricardo; Cartes, Marcela; Segura, Hugo; Wisniak, Jaime,
Isobaric Vapor-Liquid Equilibria in the Systems Ethyl 1,1-Dimethylethyl Ether + Hexane and + Heptane,
Physics and Chemistry of Liquids, 2000, 38, 2, 217-232, https://doi.org/10.1080/00319100008030271
. [all data]
Kraehenbuehl and Gmehling, 1994
Kraehenbuehl, M.A.; Gmehling, J.,
Vapor Pressures of Methyl tert-Butyl Ether, Ethyl tert-Butyl Ether, Isopropyl tert-Butyl Ether, tert-Amyl Methyl Ether, and tert-Amyl Ethyl Ether,
J. Chem. Eng. Data, 1994, 39, 4, 759-762, https://doi.org/10.1021/je00016a026
. [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]
Sola, Pericas, et al., 1995
Sola, L.; Pericas, M.A.; Cunill, F.; Tejero, J.,
Thermodynamic and kinetic studies of the liquid phase synthesis of tert-butyl ethyl ether using a reaction calorimeter,
Ind. Eng. Chem. Res., 1995, 34, 3718-3725. [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]
Klessinger, Asmus, et al., 1975
Klessinger, M.; Asmus, P.; Kraatz, U.,
Photoelektronenspektren organischer verbindungen-VII,
Tetrahedron, 1975, 31, 517. [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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas Cp,liquid Constant pressure heat capacity of liquid Tboil Boiling point Tfus Fusion (melting) point ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrH° Enthalpy of reaction 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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