n-Butyl ether
- Formula: C8H18O
- Molecular weight: 130.2279
- IUPAC Standard InChIKey: DURPTKYDGMDSBL-UHFFFAOYSA-N
- CAS Registry Number: 142-96-1
- 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: Butane, 1,1'-oxybis-; Butyl ether; n-Dibutyl ether; Di-n-butyl ether; Dibutyl ether; Dibutyl oxide; 1,1'-Oxybis(butane); (n-C4H9)2O; 1-Butoxybutane; Butyl oxide; Ether butylique; UN 1149; NSC 8459
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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 | -378.0 ± 1.0 | kJ/mol | Ccb | Colomina, Pell, et al., 1965 | ALS |
ΔfH°liquid | -377.6 ± 2.8 | kJ/mol | Ccb | Murrin and Goldhagen, 1957 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -5342.63 ± 0.92 | kJ/mol | Ccb | Colomina, Pell, et al., 1965 | Corresponding ΔfHºliquid = -377.9 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -5343.1 ± 2.8 | kJ/mol | Ccb | Murrin and Goldhagen, 1957 | Corresponding ΔfHºliquid = -377.4 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -5343.4 ± 3.3 | kJ/mol | Ccb | Skuratov, Strepikheev, et al., 1957 | Reanalyzed by Cox and Pilcher, 1970, Original value = -5345. ± 3. kJ/mol; Combustion at 293 K; Corresponding ΔfHºliquid = -377.1 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
278.16 | 298.15 | Cobos, Casanova, et al., 1987 | Average of two measurements.; 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
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 | 415. ± 1. | K | AVG | N/A | Average of 8 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 175.25 | K | N/A | Timmermans, 1952 | Uncertainty assigned by TRC = 0.4 K; TRC |
Tfus | 177.78 | K | N/A | Dreisbach and Martin, 1949 | Uncertainty assigned by TRC = 0.05 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 588.1 | K | N/A | Majer and Svoboda, 1985 | |
Tc | 584.1 | K | N/A | Toczylkin. L.S. and Young, 1980 | Uncertainty assigned by TRC = 0.58 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 30.10 | bar | N/A | Toczylkin. L.S. and Young, 1980 | Uncertainty assigned by TRC = 0.3007 bar; Visual; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 45. | kJ/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 44.7 ± 0.1 | kJ/mol | C | Fuchs, Peacock, et al., 1982 | AC |
ΔvapH° | 44.99 | kJ/mol | C | Majer, Wagner, et al., 1980 | ALS |
ΔvapH° | 45.0 ± 0.1 | kJ/mol | C | Majer, Wagner, et al., 1980 | AC |
ΔvapH° | 44.4 | kJ/mol | N/A | Ambrose, Ellender, et al., 1976 | Based on data from 362. to 414. K.; AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
36.49 | 413.5 | N/A | Majer and Svoboda, 1985 | |
40.9 | 354. | A | Stephenson and Malanowski, 1987 | Based on data from 339. to 415. K.; AC |
41.7 | 351. | A | Stephenson and Malanowski, 1987 | Based on data from 336. to 415. K.; AC |
36.4 | 413. | N/A | Ambrose, Ellender, et al., 1976 | Based on data from 362. to 414. K.; AC |
40.6 | 377. | EB | Cidlinský and Polák, 1969 | Based on data from 362. to 413. K.; AC |
39.4 | 413. | N/A | Nisel'son and Lapivus, 1965 | Based on data from 386. to 440. K.; AC |
46.9 | 293. | V | Skuratov, Strepikheev, et al., 1957 | Combustion at 293 K; ALS |
43.93 ± 0.42 | 414.3 | V | Mathews and Fehlandt, 1931 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = 36.9 kJ/mol; ALS |
Enthalpy of vaporization
ΔvapH =
A exp(-βTr) (1 − Tr)β
ΔvapH =
Enthalpy of vaporization (at saturation pressure)
(kJ/mol)
Tr = reduced temperature (T / Tc)
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Temperature (K) | A (kJ/mol) | β | Tc (K) | Reference | Comment |
---|---|---|---|---|---|
298. to 358. | 64.53 | 0.2974 | 588.1 | Majer and Svoboda, 1985 |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference |
---|---|---|---|---|
362.29 to 413.21 | 3.93018 | 1302.768 | -81.481 | Cidlinský and Polák, 1969 |
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:
MM - Michael M. Meot-Ner (Mautner)
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 845.7 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 818.3 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Gas basicity at 298K
Gas basicity (review) (kJ/mol) | Reference | Comment |
---|---|---|
815.5 ± 0.5 | Decouzon, Gal, et al., 1996 | T = 338K; MM |
815.5 ± 0.5 | Decouzon, Gal, et al., 1996 | T = 338K; MM |
816.5 | Decouzon, Gal, et al., 1996 | T = T(eff) = 430K; MM |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.28 ± 0.05 | EI | Williams and Hamill, 1968 | RDSH |
9.44 | PE | Aue and Bowers, 1979 | Vertical value; LLK |
9.40 | PE | Benoit and Harrison, 1977 | Vertical value; LLK |
9.51 ± 0.015 | PE | Klessinger, Asmus, et al., 1975 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C4H9+ | 11.8 ± 0.1 | ? | EI | Williams and Hamill, 1968 | RDSH |
C4H9O+ | 13.0 ± 0.1 | C4H9 | EI | Williams and Hamill, 1968 | RDSH |
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
Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.
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 | Japan AIST/NIMC Database- Spectrum MS-NW- 563 |
NIST MS number | 228442 |
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.
Colomina, Pell, et al., 1965
Colomina, M.; Pell, A.S.; Skinner, H.A.; Coleman, D.J.,
Heats of combustion of four dialkylethers,
Trans. Faraday Soc., 1965, 61, 2641. [all data]
Murrin and Goldhagen, 1957
Murrin, J.W.; Goldhagen, S.,
Determination of the C-O bond energy from the heats of combustion of four aliphatic ethers,
NAVORD Report No. 5491, U.S. Naval Powder Factory Res. & Dev. Dept., 1957, 1-14. [all data]
Skuratov, Strepikheev, et al., 1957
Skuratov, S.M.; Strepikheev, A.A.; Kozina, M.P.,
About the reaction activity of five and six-membered heterocyclic compounds,
Dokl. Akad. Nauk SSSR, 1957, 117, 452-454. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Cobos, Casanova, et al., 1987
Cobos, J.C.; Casanova, C.; Roux-Desgranges, G.; Grolier, J.-P.E.,
Excess properties of mixtures of some n-alkoxyethanols with organic solvents. II. VEm and CEp,m with di-n-butylether at 298.15 K,
J. Chem. Thermodynam., 1987, 19, 791-796. [all data]
Timmermans, 1952
Timmermans, J.,
Freezing points of organic compounds. VVI New determinations.,
Bull. Soc. Chim. Belg., 1952, 61, 393. [all data]
Dreisbach and Martin, 1949
Dreisbach, R.R.; Martin, R.A.,
Physical Data on Some Organic Compounds,
Ind. Eng. Chem., 1949, 41, 2875-8. [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]
Toczylkin. L.S. and Young, 1980
Toczylkin. L.S.; Young, C.L.,
Gas-liquid critical temperatures of mixtures containing electron donors II. Ether mixtures,
J. Chem. Thermodyn., 1980, 12, 355-64. [all data]
Fuchs, Peacock, et al., 1982
Fuchs, Richard; Peacock, L. Alan; Stephenson, W. Kirk,
Enthalpies of interaction of polar and nonpolar molecules with aromatic solvents,
Can. J. Chem., 1982, 60, 15, 1953-1958, https://doi.org/10.1139/v82-273
. [all data]
Majer, Wagner, et al., 1980
Majer, V.; Wagner, Z.; Svoboda, V.; Cadek, V.,
Enthalpies of vaporization and cohesive energies for a group of aliphatic ethers,
J. Chem. Thermodyn., 1980, 12, 387-391. [all data]
Ambrose, Ellender, et al., 1976
Ambrose, D.; Ellender, J.H.; Sprake, C.H.S.; Townsend, R.,
Thermodynamic properties of organic oxygen compounds XLIII. Vapour pressures of some ethers,
The Journal of Chemical Thermodynamics, 1976, 8, 2, 165-178, https://doi.org/10.1016/0021-9614(76)90090-2
. [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]
Cidlinský and Polák, 1969
Cidlinský, J.; Polák, J.,
Saturated vapour pressures of some ethers,
Collect. Czech. Chem. Commun., 1969, 34, 4, 1317-1321, https://doi.org/10.1135/cccc19691317
. [all data]
Nisel'son and Lapivus, 1965
Nisel'son, L.A.; Lapivus, I.I.,
Russ. J. Phys. Chem., 1965, 39, 80. [all data]
Mathews and Fehlandt, 1931
Mathews, J.H.; Fehlandt, P.R.,
The heats of vaporization of some organic compounds,
J. Am. Chem. Soc., 1931, 53, 3212-32. [all data]
Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P.,
Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [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]
Decouzon, Gal, et al., 1996
Decouzon, M.; Gal, J.E.; Herreros, M.; Marai, P.C.; Murrell, J.; Todd, J.F.J.,
On the Use of the Kinetic Method for the Determination of Proton Affinities by Fourier-Transfrom Ion Cyclotron Resonance Mass Spectrometry,
Rapid. Comm. Mass Spectrom., 1996, 10, 242. [all data]
Williams and Hamill, 1968
Williams, J.M.; Hamill, W.H.,
Ionization potentials of molecules and free radicals and appearance potentials by electron impact in the mass spectrometer,
J. Chem. Phys., 1968, 49, 4467. [all data]
Aue and Bowers, 1979
Aue, D.H.; Bowers, M.T.,
Chapter 9. Stabilities of positive ions from equilibrium gas phase basicity measurements
in Ions Chemistry,, ed. M.T. Bowers, 1979. [all data]
Benoit and Harrison, 1977
Benoit, F.M.; Harrison, A.G.,
Predictive value of proton affinity. Ionization energy correlations involving oxygenated molecules,
J. Am. Chem. Soc., 1977, 99, 3980. [all data]
Klessinger, Asmus, et al., 1975
Klessinger, M.; Asmus, P.; Kraatz, U.,
Photoelektronenspektren organischer verbindungen-VII,
Tetrahedron, 1975, 31, 517. [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 Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid 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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