1-Butene

Formula: C₄H₈
Molecular weight: 56.1063
IUPAC Standard InChI: InChI=1S/C4H8/c1-3-4-2/h3H,1,4H2,2H3
IUPAC Standard InChIKey: VXNZUUAINFGPBY-UHFFFAOYSA-N
CAS Registry Number: 106-98-9
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: α-Butene; α-Butylene; But-1-ene; Butene-1; Ethylethylene; 1-Butylene; 1-C4H8
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Gas phase thermochemistry data

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Data compiled as indicated in comments:
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
Δ_fH°_gas	-0.63 ± 0.79	kJ/mol	Cm	Prosen, Maron, et al., 1951	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_gas	-2716.8 ± 0.75	kJ/mol	Cm	Prosen, Maron, et al., 1951	Corresponding Δ_fHº_gas = -0.54 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of gas

C_p,gas (J/mol*K)	Temperature (K)	Reference	Comment
41.05	50.	Thermodynamics Research Center, 1997	p=1 bar. Calculated values of the thermodynamic functions [ Aston J.D., 1946, Kilpatrick J.E., 1946, Durig J.R., 1980, Thermodynamics Research Center, 1997] show some disagreement between authors as well as with experimental data [ Aston J.D., 1946, 2, Wacker P.F., 1947] (up to 3-4 J/mol*K). More reliable experimental data are required to solve available inconsistency.; GT
48.05	100.
56.41	150.
65.19	200.
80.03	273.15
85.56	298.15
85.98	300.
108.48	400.
129.06	500.
146.75	600.
161.88	700.
174.91	800.
186.21	900.
196.02	1000.
204.55	1100.
211.96	1200.
218.41	1300.
224.02	1400.
228.91	1500.
238.64	1750.
245.70	2000.
250.92	2250.
254.85	2500.
257.85	2750.
260.16	3000.

Constant pressure heat capacity of gas

C_p,gas (J/mol*K)	Temperature (K)	Reference	Comment
89.58 ± 0.06	313.55	Wacker P.F., 1947	GT
101.21 ± 0.07	363.25	Wacker P.F., 1947	GT

Condensed phase thermochemistry data

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Data compiled by: Eugene S. Domalski and Elizabeth D. Hearing

Quantity	Value	Units	Method	Reference
S°_liquid	229.06	J/mol*K	N/A	Takeda, Yamamuro, et al., 1991
S°_liquid	227.0	J/mol*K	N/A	Chao, Hall, et al., 1983
S°_liquid	213.84	J/mol*K	N/A	Aston, Fink, et al., 1946

Constant pressure heat capacity of liquid

C_p,liquid (J/mol*K)	Temperature (K)	Reference	Comment
128.96	298.15	Takeda, Yamamuro, et al., 1991	T = 5 to 300 K.
118.	298.15	Chao, Hall, et al., 1983	T = 12 to 360 K.
128.6	294.	Schlinger and Sage, 1949	T = 294 to 378 K. Cp given as 0.548 Btu/lb*R at 70°F at bubble point.
119.45	260.	Aston, Fink, et al., 1946	T = 11.5 to 260 K.
119.16	253.4	Todd and Parks, 1936	T = 81 to 253 K. Value is unsmoothed experimental datum.

Reaction thermochemistry data

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Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
B - John E. Bartmess

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Individual Reactions

1-Butene =

By formula: C₄H₈ = C₄H₈

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-12.6 ± 0.84	kJ/mol	Eqk	Meyer and Stroz, 1972	gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -11.0 kJ/mol; At 300 K; ALS
Δ_rH°	-12.4 ± 1.7	kJ/mol	Eqk	Happel, Hnatow, et al., 1971	gas phase; ALS
Δ_rH°	-12.7	kJ/mol	Eqk	Maccoll and Ross, 1965	gas phase; GC; ALS
Δ_rH°	-11.7 ± 0.84	kJ/mol	Eqk	Golden, Egger, et al., 1964	gas phase; ALS
Δ_rH°	-11.5	kJ/mol	Ciso	Levanova and Andreevskii, 1964	gas phase; At 420.3 K; ALS

C₄H₇^- + = 1-Butene

By formula: C₄H₇^- + H⁺ = C₄H₈

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1724. ± 8.4	kJ/mol	Bran	DePuy, Gronert, et al., 1989	gas phase; B
Δ_rH°	1729. ± 20.	kJ/mol	Bran	Peerboom, Rademaker, et al., 1992	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	1690. ± 8.8	kJ/mol	H-TS	DePuy, Gronert, et al., 1989	gas phase; B
Δ_rG°	1695. ± 21.	kJ/mol	H-TS	Peerboom, Rademaker, et al., 1992	gas phase; B

1-Butene + =

By formula: C₄H₈ + Br₂ = C₄H₈Br₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-120.9	kJ/mol	Cm	Lister, 1941	gas phase; Heat of bromination at 300 K; ALS
Δ_rH°	-123.2 ± 0.84	kJ/mol	Cm	Conn, Kistiakowsky, et al., 1938	gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -123.8 ± 0.84 kJ/mol; At 355 °K; ALS

+ 1-Butene =

By formula: HBr + C₄H₈ = C₄H₉Br

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-83.85 ± 0.50	kJ/mol	Cm	Lacher, Billings, et al., 1952	gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -84.3 ± 7.5 kJ/mol; Heat of hydrobromination at 367 K; ALS

C₄H₇^- + = 1-Butene

By formula: C₄H₇^- + H⁺ = C₄H₈

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1707. ± 15.	kJ/mol	CIDT	Graul and Squires, 1990	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	1674. ± 15.	kJ/mol	H-TS	Graul and Squires, 1990	gas phase; B

1-Butene =

By formula: C₄H₈ = C₄H₈

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-10.6 ± 2.1	kJ/mol	Eqk	Happel, Hnatow, et al., 1971	gas phase; ALS
Δ_rH°	-8.16	kJ/mol	Ciso	Levanova and Andreevskii, 1964	gas phase; At 420.3 K; ALS

= 1-Butene +

By formula: C₄H₈I₂ = C₄H₈ + I₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	50.2 ± 6.3	kJ/mol	Cm	Cline and Kistiakowsky, 1937	gas phase; Heat of formation derived by Cox and Pilcher, 1970; ALS

1-Butene + =

By formula: C₄H₈ + H₂ = C₄H₁₀

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-125.9 ± 0.42	kJ/mol	Chyd	Kistiakowsky, Ruhoff, et al., 1935	gas phase; At 355 °K; ALS

= 1-Butene +

By formula: C₄H₉Cl = C₄H₈ + HCl

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	75.31	kJ/mol	Eqk	Levanova and Andreevskii, 1964	gas phase; At 420 K; ALS

1-Butene + =

By formula: C₄H₈ + I₂ = C₄H₈I₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-50.2 ± 6.3	kJ/mol	Cm	Cline and Kistiakowsky, 1937	gas phase; ALS

= 1-Butene +

By formula: C₁₀H₁₄O = C₄H₈ + C₆H₆O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	77.8	kJ/mol	Cm	Kukui, Potolovskii, et al., 1973	liquid phase; ALS

= 1-Butene +

By formula: C₁₀H₁₄O = C₄H₈ + C₆H₆O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	82.8	kJ/mol	Cm	Kukui, Potolovskii, et al., 1973	liquid phase; ALS

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Notes

Prosen, Maron, et al., 1951
Prosen, E.J.; Maron, F.W.; Rossini, F.D., Heats of combustion, formation, and insomerization of ten C₄ hydrocarbons, J. Res. NBS, 1951, 46, 106-112. [all data]

Thermodynamics Research Center, 1997
Thermodynamics Research Center, Selected Values of Properties of Chemical Compounds., Thermodynamics Research Center, Texas A&M University, College Station, Texas, 1997. [all data]

Aston J.D., 1946
Aston J.D., Thermodynamic properties of gaseous 1,3-butadiene and normal butenes above 25 C. Equilibria in the system 1,3-butadiene, n-butenes, and n-butane, J. Chem. Phys., 1946, 14, 67-79. [all data]

Kilpatrick J.E., 1946
Kilpatrick J.E., Heat content, free energy function, entropy, and heat capacity of ethylene, propylene, and the four butenes to 1500 K, J. Res. Nat. Bur. Stand, 1946, 37, 163-171. [all data]

Durig J.R., 1980
Durig J.R., Spectroscopic and thermodynamic study of conformational properties and torsional potential functions of 1-butene, J. Phys. Chem., 1980, 84, 773-781. [all data]

Aston J.D., 1946, 2
Aston J.D., The heat capacity and entropy, heats of fusion and vaporization and the vapor pressure of butene-1. The zero point entropy of the glass. The entropy of the gas from molecular data, J. Am. Chem. Soc., 1946, 68, 52-57. [all data]

Wacker P.F., 1947
Wacker P.F., Heat capacities of gaseous oxygen, isobutane, and 1-butene from -30 to +90 C, J. Res. Nat. Bur. Stand., 1947, 38, 651-659. [all data]

Takeda, Yamamuro, et al., 1991
Takeda, K.; Yamamuro, O.; Suga, H., Thermodynamic study of 1-butene. Exothermic and endothermic enthalpy relaxations near the glass transition, J. Phys. Chem. Solids, 1991, 22, 607-615. [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]

Aston, Fink, et al., 1946
Aston, J.G.; Fink, H.L.; Bestul, A.B.; Pace, E.L.; Szasz, G.J., The heat capacity and entropy, heats of fusion and vaporization and the vapor pressure of butene-1. The zero point entropy of the glass. The entropy of the gas from molecular data, J. Am. Chem. Soc., 1946, 68, 52-57. [all data]

Schlinger and Sage, 1949
Schlinger, W.G.; Sage, B.H., Isobaric heat capacity of 1-butene and 1-pentene at bubble point, Ind. Eng. Chem., 1949, 41, 1779-1782. [all data]

Todd and Parks, 1936
Todd, S.S.; Parks, G.S., Thermal data on organic compounds. XV. Some heat capacity, entropy and free energy data for the isomeric butenes, J. Am. Chem. Soc., 1936, 58, 134-137. [all data]

Meyer and Stroz, 1972
Meyer, E.F.; Stroz, D.G., Thermodynamics of n-butene isomerization, J. Am. Chem. Soc., 1972, 94, 6344-6347. [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]

Happel, Hnatow, et al., 1971
Happel, J.; Hnatow, M.A.; Mezaki, R., Isomerization equilibrium constants of n-butenes, J. Chem. Eng. Data, 1971, 16, 206-209. [all data]

Maccoll and Ross, 1965
Maccoll, A.; Ross, R.A., The hydrogen bromide catalyzed isomerization of n-butenes. I. equilibrium values, J. Am. Chem. Soc., 1965, 87, 1169-1170. [all data]

Golden, Egger, et al., 1964
Golden, D.M.; Egger, K.W.; Benson, S.W., Iodine-catalyzed isomerization of olefins. I. Thermodynamics data from equilibrium studies of positional and geometrical isomerization of 1-butene and 2-butene, J. Am. Chem. Soc., 1964, 86, 5416-5420. [all data]

Levanova and Andreevskii, 1964
Levanova, S.V.; Andreevskii, D.N., The equilibrium of 2-chlorobutane dehydrochlorination, Neftekhimiya, 1964, 4, 329-336. [all data]

DePuy, Gronert, et al., 1989
DePuy, C.H.; Gronert, S.; Barlow, S.E.; Bierbaum, V.M.; Damrauer, R., The Gas Phase Acidities of the Alkanes, J. Am. Chem. Soc., 1989, 111, 6, 1968, https://doi.org/10.1021/ja00188a003 . [all data]

Peerboom, Rademaker, et al., 1992
Peerboom, R.A.L.; Rademaker, G.J.; Dekoning, L.J.; Nibbering, N.M.M., Stabilization of Cycloalkyl Carbanions in the Gas Phase, Rapid Commun. Mass Spectrom., 1992, 6, 6, 394, https://doi.org/10.1002/rcm.1290060608 . [all data]

Lister, 1941
Lister, M.W., Heats of organic reactions. X. Heats of bromination of cyclic olefins, J. Am. Chem. Soc., 1941, 63, 143-149. [all data]

Conn, Kistiakowsky, et al., 1938
Conn, J.B.; Kistiakowsky, G.B.; Smith, E.A., Heats of organic reactions. VII. Addition of halogens to olefins, J. Am. Chem. Soc., 1938, 60, 2764-2771. [all data]

Lacher, Billings, et al., 1952
Lacher, J.R.; Billings, T.J.; Campion, D.E., Vapor phase heats of hydrobromination of the isomeric butenes, J. Am. Chem. Soc., 1952, 74, 5291-52. [all data]

Graul and Squires, 1990
Graul, S.T.; Squires, R.R., Gas-Phase Acidities Derived from Threshold Energies for Activated Reactions, J. Am. Chem. Soc., 1990, 112, 7, 2517, https://doi.org/10.1021/ja00163a007 . [all data]

Cline and Kistiakowsky, 1937
Cline, J.E.; Kistiakowsky, G.B., The gaseous equilibrium of 1,2-diiodobutane, butene-1 and iodine, J. Chem. Phys., 1937, 5, 990. [all data]

Kistiakowsky, Ruhoff, et al., 1935
Kistiakowsky, G.B.; Ruhoff, J.R.; Smith, H.A.; Vaughan, W.E., Heats of organic reactions. II. Hydrogenation of some simpler olefinic hydrocarbons, J. Am. Chem. Soc., 1935, 57, 876-882. [all data]

Kukui, Potolovskii, et al., 1973
Kukui, N.M.; Potolovskii, L.A.; Vasileva, V.N., Thermochemical and thermodynamic calculation of the alkylation of phenol by normal α-olefins, Khim. Tekhnol. Topl. Masel, 1973, 18, 10-13. [all data]

Notes

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Symbols used in this document:

C_p,gas	Constant pressure heat capacity of gas
C_p,liquid	Constant pressure heat capacity of liquid
S°_liquid	Entropy of liquid at standard conditions
Δ_cH°_gas	Enthalpy of combustion of gas at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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