2-Methyl-1-butene
- Formula: C5H10
- Molecular weight: 70.1329
- IUPAC Standard InChIKey: MHNNAWXXUZQSNM-UHFFFAOYSA-N
- CAS Registry Number: 563-46-2
- 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: 1-Butene, 2-methyl-; γ-Isoamylene; 1-Isoamylene; C2H5C(CH3)=CH2; 2-Methylbutene-1; Isopentene; UN 2371; UN 2459; 2-methylbut-1-ene
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Gas phase thermochemistry data
Go To: Top, 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 compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -35.1 ± 0.84 | kJ/mol | Eqk | Wiberg and Hao, 1991 | Heat of hydration; ALS |
ΔfH°gas | -34.8 | kJ/mol | N/A | Good and Smith, 1979 | Value computed using ΔfHliquid° value of -60.96±0.84 kj/mol from Good and Smith, 1979 and ΔvapH° value of 26.19 kj/mol from missing citation.; DRB |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
102.97 | 273.15 | McCullough J.P., 1959 | Results of more recent statistical calculation [ Durig J.R., 1980] are different from recommended and experimental values up to 3 J/mol*K for S(T) and Cp(T).; GT |
109.96 | 298.15 | ||
110.50 | 300. | ||
138.91 | 400. | ||
164.85 | 500. | ||
187.11 | 600. | ||
206.10 | 700. | ||
222.38 | 800. | ||
236.48 | 900. | ||
248.66 | 1000. | ||
259.24 | 1100. | ||
268.40 | 1200. | ||
276.35 | 1300. | ||
283.30 | 1400. | ||
289.32 | 1500. |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
116.15 ± 0.35 | 320.66 | Scott D.W., 1949 | GT |
128.37 ± 0.39 | 362.51 | ||
140.62 ± 0.42 | 407.11 | ||
153.13 ± 0.46 | 453.41 | ||
165.35 ± 0.50 | 502.21 |
Condensed phase thermochemistry data
Go To: Top, Gas 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 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 | -60.96 ± 0.84 | kJ/mol | Ccb | Good and Smith, 1979 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -3335.74 ± 0.80 | kJ/mol | Ccb | Good and Smith, 1979 | Corresponding ΔfHºliquid = -60.96 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 254.0 | J/mol*K | N/A | Chao, Hall, et al., 1983 | DH |
S°liquid | 253.97 | J/mol*K | N/A | Todd, Oliver, et al., 1947 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
157.3 | 298.15 | Chao, Hall, et al., 1983 | T = 12 to 293 K.; DH |
157.19 | 298.15 | Todd, Oliver, et al., 1947 | T = 12 to 300 K.; DH |
Phase change data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 304.3 ± 0.7 | K | AVG | N/A | Average of 35 out of 38 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 136. ± 3. | K | AVG | N/A | Average of 6 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 135.60 | K | N/A | Chao, Hall, et al., 1983, 2 | Uncertainty assigned by TRC = 0.02 K; TRC |
Ttriple | 135.62 | K | N/A | Todd, Oliver, et al., 1947, 2 | Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 470. | K | N/A | Majer and Svoboda, 1985 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 26.19 | kJ/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 25.9 | kJ/mol | N/A | Reid, 1972 | AC |
ΔvapH° | 25.9 ± 0.1 | kJ/mol | C | Scott, Waddington, et al., 1949 | AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
25.5 | 304.3 | N/A | Majer and Svoboda, 1985 | |
28.5 | 255. | A | Stephenson and Malanowski, 1987 | Based on data from 240. to 336. K.; AC |
27.3 | 289. | N/A | Scott, Waddington, et al., 1949 | Based on data from 274. to 336. K.; AC |
25.5 ± 0.1 | 304. | C | Scott, Waddington, et al., 1949 | AC |
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 |
---|---|---|---|---|---|
278. to 304. | 41.2 | 0.2839 | 470. | 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 | Comment |
---|---|---|---|---|---|
274.30 to 335.82 | 3.98652 | 1047.811 | -41.089 | Scott, Waddington, et al., 1949 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
7.911 | 135.60 | Chao, Hall, et al., 1983 | DH |
7.9103 | 135.62 | Todd, Oliver, et al., 1947 | DH |
5.36 | 104.7 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
58.34 | 135.60 | Chao, Hall, et al., 1983 | DH |
58.33 | 135.62 | Todd, Oliver, et al., 1947 | DH |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, 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
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: H2 + C5H10 = C5H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -126.95 | kJ/mol | Chyd | Dolliver, Gresham, et al., 1937 | gas phase; At 355 °K |
ΔrH° | -118.2 ± 0.42 | kJ/mol | Chyd | Kistiakowsky, Ruhoff, et al., 1936 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -119.2 ± 1.5 kJ/mol; At 355 K |
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 = C5H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -6.7 ± 3.0 | kJ/mol | Eqk | Rihko, Linnekoski, et al., 1994 | liquid phase; solvent: Methanol/H+ |
ΔrH° | -8.0 ± 1.4 | kJ/mol | Eqk | Rihko, Linnekoski, et al., 1994 | liquid phase; solvent: Ethanol/H+ |
By formula: C5H10 + HCl = C5H11Cl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -63.7 ± 1.4 | kJ/mol | Cm | Arnett and Pienta, 1980 | liquid phase; solvent: Methylene chloride; Hydrochlorination |
By formula: C5H10 + C2H6O = C7H16O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -35.2 ± 5.8 | kJ/mol | Eqk | Rihko, Linnekoski, et al., 1994 | liquid phase; solvent: Alcohol/alkane mixture |
By formula: C5H10 + C2HF3O2 = C7H11F3O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -45.7 ± 0.2 | kJ/mol | Cm | Wiberg and Hao, 1991 | liquid phase; Trifuoroacetolysis |
By formula: C5H10 = C5H10
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 8.08 ± 0.50 | kJ/mol | Eqk | Radyuk, Kabo, et al., 1973 | gas phase; Heat of isomerization at 562 K |
By formula: C5H10 + CH4O = C6H14O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -35.8 ± 1.3 | kJ/mol | Eqk | Serda, Izquierdo, et al., 1995 | liquid phase |
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 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Wiberg and Hao, 1991
Wiberg, K.B.; Hao, S.,
Enthalpies of hydration of alkenes. 4. Formation of acyclic tert-alcohols,
J. Org. Chem., 1991, 56, 5108-5110. [all data]
Good and Smith, 1979
Good, W.D.; Smith, N.K.,
The enthalpies of combustion of the isomeric pentenes in the liquid state. A warning to combustion calorimetrists about sample drying,
J. Chem. Thermodyn., 1979, 11, 111-118. [all data]
McCullough J.P., 1959
McCullough J.P.,
Thermodynamic properties, vibrational assignment and rotational conformations of 2-methyl-1-butene,
J. Am. Chem. Soc., 1959, 81, 1331-1334. [all data]
Durig J.R., 1980
Durig J.R.,
Torsional spectra of molecules with two internal C3v rotors. 19. Vibrational spectra, torsional potential functions, and conformational and thermodynamic properties of 2-methyl-1-butene,
J. Phys. Chem., 1980, 84, 3554-3561. [all data]
Scott D.W., 1949
Scott D.W.,
Thermodynamic properties of three isomeric pentenes,
J. Am. Chem. Soc., 1949, 71, 2767-2773. [all data]
Chao, Hall, et al., 1983
Chao, J.; Hall, K.R.; Yao, J.M.,
Thermodynamic properties of simple alkenes,
Thermochim. Acta, 1983, 64(3), 285-303. [all data]
Todd, Oliver, et al., 1947
Todd, S.S.; Oliver, G.D.; Huffman, H.M.,
The heat capacities, heats of fusion and entropies of the six pentenes,
J. Am. Chem. Soc., 1947, 69, 1519-1525. [all data]
Chao, Hall, et al., 1983, 2
Chao, J.; Hall, K.R.; Yao, J.M.,
Thermodynamic Properties of Simple Alkenes,
Thermochim. Acta, 1983, 64, 285. [all data]
Todd, Oliver, et al., 1947, 2
Todd, S.S.; Oliver, G.D.; Huffman, H.M.,
The heat capacities, heats of fusion and entropies of the six pentenes.,
J. Am. Chem. Soc., 1947, 69, 1519. [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]
Reid, 1972
Reid, Robert C.,
Handbook on vapor pressure and heats of vaporization of hydrocarbons and related compounds, R. C. Wilhort and B. J. Zwolinski, Texas A Research Foundation. College Station, Texas(1971). 329 pages.$10.00,
AIChE J., 1972, 18, 6, 1278-1278, https://doi.org/10.1002/aic.690180637
. [all data]
Scott, Waddington, et al., 1949
Scott, D.W.; Waddington, G.; Smith, J.C.; Huffman, H.M.,
Thermodynamic properties of three isomeric pentenes,
J. Am. Chem. Soc., 1949, 71, 2767-2773. [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]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [all data]
Dolliver, Gresham, et al., 1937
Dolliver, M.a.; Gresham, T.L.; Kistiakowsky, G.B.; Vaughan, W.E.,
Heats of organic reactions. V. Heats of hydrogenation of various hydrocarbons,
J. Am. Chem. Soc., 1937, 59, 831-841. [all data]
Kistiakowsky, Ruhoff, et al., 1936
Kistiakowsky, G.B.; Ruhoff, J.R.; Smith, H.A.; Vaughan, W.E.,
Heats of organic reactions. III. Hydrogenation of some higher olefins,
J. Am. Chem. Soc., 1936, 58, 137-145. [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]
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]
Arnett and Pienta, 1980
Arnett, E.M.; Pienta, N.J.,
Stabilities of carbonium ions in solution. 12. Heats of formation of alkyl chlorides as an entree to heats of solvation of aliphatic carbonium ions,
J. Am. Chem. Soc., 1980, 102, 3329-3334. [all data]
Radyuk, Kabo, et al., 1973
Radyuk, Z.A.; Kabo, G.Ya.; Andreevskii, D.N.,
Isomerization equilibrium and thermodynamic properties of methylbutenes,
Neftekhimiya, 1973, 13, 356-360. [all data]
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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas Cp,liquid Constant pressure heat capacity of liquid S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature 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 ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion 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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