Butane, 2-methoxy-2-methyl-
- Formula: C6H14O
- Molecular weight: 102.1748
- IUPAC Standard InChI: InChI=1S/C6H14O/c1-5-6(2,3)7-4/h5H2,1-4H3
- IUPAC Standard InChIKey: HVZJRWJGKQPSFL-UHFFFAOYSA-N
- CAS Registry Number: 994-05-8
- 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, methyl tert-pentyl; tert-Amyl Methyl ether; Methyl tert-pentyl ether; 1,1-Dimethylpropyl methyl ether; 2-Methyl-2-methoxybutane; Methyl 2-methyl-2-butyl ether; 2-Methoxy-2-methylbutane
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Gas 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -306.5 ± 1.1 | kJ/mol | Ccb | Rozhnov, Safronov, et al., 1991 | Unpublished Hv |
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| ΔfH°liquid | -341.79 ± 0.79 | kJ/mol | Ccb | Rozhnov, Safronov, et al., 1991 | Unpublished Hv; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -4020.07 ± 0.73 | kJ/mol | Ccb | Rozhnov, Safronov, et al., 1991 | Unpublished Hv; Corresponding ΔfHºliquid = -341.80 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |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 |
|---|---|---|---|
| 222. | 298. | Evans and Edlund, 1936 | DH |
Phase change 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:
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 | 359.3 | K | N/A | Loras, Aucejo, et al., 1999 | Uncertainty assigned by TRC = 0.3 K; TRC |
| Tboil | 359.2 | K | N/A | Monton, Torre, et al., 1999 | Uncertainty assigned by TRC = 0.3 K; TRC |
| Tboil | 359.5 | K | N/A | Weast and Grasselli, 1989 | BS |
| Tboil | 359.57 | K | N/A | Cervenkova and Boublik, 1984 | Uncertainty assigned by TRC = 0.1 K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔvapH° | 35. ± 1. | kJ/mol | AVG | N/A | Average of 7 values; Individual data points |
Enthalpy of vaporization
| ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 36.6 ± 0.1 | 320. | EB | Steele, Chirico, et al., 2002 | Based on data from 309. to 396. K.; AC |
| 34.5 ± 0.2 | 360. | EB | Steele, Chirico, et al., 2002 | Based on data from 309. to 396. K.; AC |
| 32.1 ± 0.5 | 400. | EB | Steele, Chirico, et al., 2002 | Based on data from 309. to 396. K.; AC |
| 33.4 | 329. | N/A | Aucejo, Loras, et al., 1998 | Based on data from 314. to 362. K.; AC |
| 35.7 ± 1.0 | 295. | GS | Verevkin and Welle, 1998 | Based on data from 283. to 308. K.; AC |
| 33.8 | 321. | EB | Kraehenbuehl and Gmehling, 1994 | Based on data from 306. to 359. K.; AC |
| 34.3 | 309. | EB | Cervenkova and Boublik, 1984, 2 | Based on data from 294. to 359. K.; AC |
| 33.7 | 324. | EB | Palczewska-Tulinska, Cholinski, et al., 1984 | Based on data from 309. to 358. 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: C5H10 + CH4O = C6H14O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -35.8 | kJ/mol | Eqk | Serda, Izquierdo, et al., 1995 | liquid phase |
| ΔrH° | -20.4 ± 0.8 | kJ/mol | Eqk | Hwang and Wu, 1994 | liquid phase |
| ΔrH° | -33.6 ± 5.1 | kJ/mol | Eqk | Rihko, Linnekoski, et al., 1994 | liquid phase; solvent: Alcohol/alkane mixture |
+
=
By formula: C5H10 + CH4O = C6H14O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -32.8 | kJ/mol | Eqk | Serda, Izquierdo, et al., 1995 | liquid phase |
| ΔrH° | -26.8 ± 2.3 | kJ/mol | Eqk | Rihko, Linnekoski, et al., 1994 | liquid phase; solvent: Alcohol/alkane mixture |
=
+
By formula: C6H14O = C5H10 + CH4O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 67.96 ± 0.39 | kJ/mol | Eqk | Rozhnov, Safronov, et al., 1991 | liquid phase |
Mass spectrum (electron ionization)
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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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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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 | D.HENNEBERG, MAX-PLANCK INSTITUTE, MULHEIM, WEST GERMANY |
| NIST MS number | 61443 |
Gas Chromatography
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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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Petrocol DH-100 | 672.5 | Haagen-Smit Laboratory, 1997 | He; Column length: 100. m; Column diameter: 0.2 mm; Program: 5C(10min) => 5C/min => 50C(48min) => 1.5C/min => 195C(91min) |
| Capillary | DB-1 | 674. | Hoekman, 1993 | 60. m/0.32 mm/1.0 μm, He; Program: -40 C for 12 min; -40 - 125 C at 3 deg.min; 125-185 C at 6 deg/min; 185 - 220 C at 20 deg/min; hold 220 C for 2 min |
Normal alkane RI, non-polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Capillary | DB-5 | 60. | 655. | Verevkin, Krasnykh, et al., 2003 | 60. m/0.32 mm/0.25 μm, Nitrogen |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Polydimethyl siloxane: CP-Sil 5 CB | 673. | Bramston-Cook, 2013 | 60. m/0.25 mm/1.0 μm, Helium, 45. C @ 1.45 min, 3.6 K/min, 210. C @ 2.72 min |
| Capillary | DB-5MS | 668.3 | Shoenmakers, Oomen, et al., 2000 | 30. m/0.25 mm/0.25 μm, He, 40. C @ 1. min, 3. K/min; Tend: 250. C |
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | HP-5 | 678. | Garcia-Estaban, Ansorena, et al., 2004 | 50. m/0.32 mm/1.05 μm; Program: 40C(10min) => 5C/min => 200C => 20C/min => 250C(5min) |
| Capillary | DB-1 | 666. | Ciccioli, Cecinato, et al., 1994 | 60. m/0.32 mm/0.25 μm; Program: not specified |
Normal alkane RI, polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | SOLGel-Wax | 790. | Johanningsmeier and McFeeters, 2011 | 30. m/0.25 mm/0.25 μm, Helium; Program: 40 0C (2 min) 5 0C/min -> 140 0C 10 0C/min -> 250 0C (3 min) |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, NIST Subscription Links, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Rozhnov, Safronov, et al., 1991
Rozhnov, A.M.; Safronov, V.V.; Verevkin, S.P.; Sharonov, K.G.; Alenin, V.I.,
Enthalpy of combustion and enthalpy of vaporization of 2-ethyl-2-methoxypropane and thermodynamics of its gas-phase synthesis from (methanol + a 2-methylbutene),
J. Chem. Thermodyn., 1991, 23, 629-635. [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]
Loras, Aucejo, et al., 1999
Loras, S.; Aucejo, A.; Munoz, R.; Ordonez, L.M.,
Phase Equilibria in the Systems 2-Methyl-2-propanol + Methyl 1,1-Dimethylpropyl Ether and 2-Methylpentane + 2-Methyl-2-propanol + Methyl 1,1-Dimethylpropyl Ether,
J. Chem. Eng. Data, 1999, 44, 1163-8. [all data]
Monton, Torre, et al., 1999
Monton, J.B.; Torre, J.d.l.; Burguet, M.C.; Munoz, R.; Loras, S.,
Isobaric Vapor-Liquid Equilibrium in the Systems 2,3-Dimethylpentane + Methyl 1,1-dimethylethyl Ether, + Diisopropyl Ether and + Methyl 1,1-Dimethylpropyl Ether,
J. Chem. Eng. Data, 1999, 44, 1158-62. [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]
Cervenkova and Boublik, 1984
Cervenkova, I.; Boublik, T.,
Vapor pressures, refractive indexes, and densities at 20.0 .degree.C, and vapor-liquid equilibrium at 101.325 kPa, in the tert-amyl methyl ether-methanol system,
J. Chem. Eng. Data, 1984, 29, 425. [all data]
Steele, Chirico, et al., 2002
Steele, W.V.; Chirico, R.D.; Cowell, A.B.; Knipmeyer, S.E.; Nguyen, A.,
Thermodynamic Properties and Ideal-Gas Enthalpies of Formation for Methyl Benzoate, Ethyl Benzoate, ( R )-(+)-Limonene, tert -Amyl Methyl Ether, trans -Crotonaldehyde, and Diethylene Glycol,
J. Chem. Eng. Data, 2002, 47, 4, 667-688, https://doi.org/10.1021/je0100847
. [all data]
Aucejo, Loras, et al., 1998
Aucejo, Antonio; Loras, Sonia; Muñoz, Rosa; Reich, Ricardo; Segura, Hugo,
Isobaric Vapor-Liquid Equilibrium in the Systems 2-Methylpentane + Methyl 1,1-Dimethylethyl Ether, + Ethyl 1,1-Dimethylethyl Ether, and + Methyl 1,1-Dimethylpropyl Ether,
J. Chem. Eng. Data, 1998, 43, 6, 973-977, https://doi.org/10.1021/je980090b
. [all data]
Verevkin and Welle, 1998
Verevkin, Sergey P.; Welle, Frank M.,
Structural Chemistry, 1998, 9, 3, 215-221, https://doi.org/10.1023/A:1022475115296
. [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]
Cervenkova and Boublik, 1984, 2
Cervenkova, Irena; Boublik, Tomas,
Vapor pressure, refractive indexes and densities at 20.0.degree.C, and vapor-liquid equilibrium at 101.325 kPa in the tert-amyl methyl ether-methanol system,
J. Chem. Eng. Data, 1984, 29, 4, 425-427, https://doi.org/10.1021/je00038a017
. [all data]
Palczewska-Tulinska, Cholinski, et al., 1984
Palczewska-Tulinska, Marcela; Cholinski, Jacek; Szafranski, Andrzej M.; Wyrzykowska-Stankiewicz, Danuta,
Experimental vapor pressures and maximum-likelihood Antoine-equation constants for 1,1,1-methoxydimethylpropane, thiacyclopentane and 1,4-butanediol,
Fluid Phase Equilibria, 1984, 15, 3, 295-307, https://doi.org/10.1016/0378-3812(84)87014-4
. [all data]
Serda, Izquierdo, et al., 1995
Serda, J.A.; Izquierdo, J.F.; Tejero, J.; Cunill, F.; Iborra, M.,
Equilibrium and thermodynamics for 2-methyl-2-methoxybutane liquid-phase decomposition,
Thermochim. Acta, 1995, 259, 111-120. [all data]
Hwang and Wu, 1994
Hwang, W.-S.; Wu, J.-C.,
Kinetics and thermodynamics of synthesis of tertiary-amyl methyl ether catalyzed by ion-exchange resin,
J. Chin. Chem. Soc. (Taipei), 1994, 41, 181-186. [all data]
Rihko, Linnekoski, et al., 1994
Rihko, L.K.; Linnekoski, J.A.; Krause, A.O.,
Reaction equilibria in the synthesis of 2-methoxy-2-methylbutane and 2-ethyoxy-2-methylbutane in the liquid phase,
J. Chem. Eng. Data, 1994, 39, 700-704. [all data]
Haagen-Smit Laboratory, 1997
Haagen-Smit Laboratory,
Procedure for the detailed hydrocarbon analysis of gasolines by single column high efficiency (capillary) column gas chromatography, SOP NO. MLD 118, Revision No. 1.1, California Environmental Protection Agency, Air Resources Board, El Monte, California, 1997, 22. [all data]
Hoekman, 1993
Hoekman, S.K.,
Improved gas chromatography procedure for speciated hydrocarbon measurements of vehicle emissions,
J. Chromatogr., 1993, 639, 2, 239-253, https://doi.org/10.1016/0021-9673(93)80260-F
. [all data]
Verevkin, Krasnykh, et al., 2003
Verevkin, Sergey P.; Krasnykh, Eugen L.; Vasiltsova, Tatiana V.; Heintz, Andreas,
Determination of Ambient Temperature Vapor Pressures and Vaporization Enthalpies of Branched Ethers,
J. Chem. Eng. Data, 2003, 48, 3, 591-599, https://doi.org/10.1021/je0255980
. [all data]
Bramston-Cook, 2013
Bramston-Cook, R.,
Kovats indices for C2-C13 hydrocarbons and selected oxygenated/halocarbons with 100 % dimethylpolysiloxane columns, 2013, retrieved from http://lotusinstruments.com/monographs/List .... [all data]
Shoenmakers, Oomen, et al., 2000
Shoenmakers, P.J.; Oomen, J.L.M.M.; Blomberg, J.; Genuit, W.; van Velzen, G.,
Comparison of comprehensive two-dimensional gas chromatography and gas chromatography-mass spectrometry for the characterization of complex hydrocarbon mixtures,
J. Chromatogr. A, 2000, 892, 1-2, 29-46, https://doi.org/10.1016/S0021-9673(00)00744-5
. [all data]
Garcia-Estaban, Ansorena, et al., 2004
Garcia-Estaban, M.; Ansorena, D.; Astiasaran, I.; Martin, D.; Ruiz, J.,
Comparison of simultaneous distillation extraction (SDE) and solid-phase microextraction (SPME) for the analysis of volatile compounds in dry-cured ham,
J. Sci. Food Agric., 2004, 84, 11, 1364-1370, https://doi.org/10.1002/jsfa.1826
. [all data]
Ciccioli, Cecinato, et al., 1994
Ciccioli, P.; Cecinato, A.; Brancaleoni, E.; Brachetti, A.; Frattoni, M.; Sparapani, R.,
Composition and Distribution of Polar and Non-Polar VOCs in Urban, Rural, Forest and Remote Areas,
Eur Commission EUR, 1994, 549-568. [all data]
Johanningsmeier and McFeeters, 2011
Johanningsmeier, S.D.; McFeeters, R.F.,
Detection of volatile spoilage metabolites in fermented cucumbers using nontargeted, comprehensive 2-dimensional gas chromatography-time-of-flight mass spectrometry (GCxGCxTOFMS),
J. Food Sci., 2011, 76, 1, c168-c177, https://doi.org/10.1111/j.1750-3841.2010.01918.x
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, NIST Subscription Links, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid Tboil Boiling point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions 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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