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1-Butene

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

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

1-Butene = 2-Butene, (E)-

By formula: C4H8 = C4H8

Quantity Value Units Method Reference Comment
Deltar-12.6 ± 0.84kJ/molEqkMeyer and Stroz, 1972gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -11.0 kJ/mol; At 300 K; ALS
Deltar-12.4 ± 1.7kJ/molEqkHappel, Hnatow, et al., 1971gas phase; ALS
Deltar-12.7kJ/molEqkMaccoll and Ross, 1965gas phase; GC; ALS
Deltar-11.7 ± 0.84kJ/molEqkGolden, Egger, et al., 1964gas phase; ALS
Deltar-11.5kJ/molCisoLevanova and Andreevskii, 1964gas phase; At 420.3 K; ALS

C4H7- + Hydrogen cation = 1-Butene

By formula: C4H7- + H+ = C4H8

Quantity Value Units Method Reference Comment
Deltar1724. ± 8.4kJ/molBranDePuy, Gronert, et al., 1989gas phase; B
Deltar1729. ± 20.kJ/molBranPeerboom, Rademaker, et al., 1992gas phase; B
Quantity Value Units Method Reference Comment
Deltar1690. ± 8.8kJ/molH-TSDePuy, Gronert, et al., 1989gas phase; B
Deltar1695. ± 21.kJ/molH-TSPeerboom, Rademaker, et al., 1992gas phase; B

1-Butene + Bromine = Butane, 1,2-dibromo-

By formula: C4H8 + Br2 = C4H8Br2

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

Hydrogen bromide + 1-Butene = Butane, 2-bromo-

By formula: HBr + C4H8 = C4H9Br

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

C4H7- + Hydrogen cation = 1-Butene

By formula: C4H7- + H+ = C4H8

Quantity Value Units Method Reference Comment
Deltar1707. ± 15.kJ/molCIDTGraul and Squires, 1990gas phase; B
Quantity Value Units Method Reference Comment
Deltar1674. ± 15.kJ/molH-TSGraul and Squires, 1990gas phase; B

1-Butene = 2-Butene, (Z)-

By formula: C4H8 = C4H8

Quantity Value Units Method Reference Comment
Deltar-10.6 ± 2.1kJ/molEqkHappel, Hnatow, et al., 1971gas phase; ALS
Deltar-8.16kJ/molCisoLevanova and Andreevskii, 1964gas phase; At 420.3 K; ALS

1,2-Diiodobutane = 1-Butene + Iodine

By formula: C4H8I2 = C4H8 + I2

Quantity Value Units Method Reference Comment
Deltar50.2 ± 6.3kJ/molCmCline and Kistiakowsky, 1937gas phase; Heat of formation derived by Cox and Pilcher, 1970; ALS

1-Butene + Hydrogen = Butane

By formula: C4H8 + H2 = C4H10

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

Butane, 2-chloro- = 1-Butene + Hydrogen chloride

By formula: C4H9Cl = C4H8 + HCl

Quantity Value Units Method Reference Comment
Deltar75.31kJ/molEqkLevanova and Andreevskii, 1964gas phase; At 420 K; ALS

1-Butene + Iodine = 1,2-Diiodobutane

By formula: C4H8 + I2 = C4H8I2

Quantity Value Units Method Reference Comment
Deltar-50.2 ± 6.3kJ/molCmCline and Kistiakowsky, 1937gas phase; ALS

Phenol, 2-(1-methylpropyl)- = 1-Butene + Phenol

By formula: C10H14O = C4H8 + C6H6O

Quantity Value Units Method Reference Comment
Deltar77.8kJ/molCmKukui, Potolovskii, et al., 1973liquid phase; ALS

Phenol, 4-(1-methylpropyl)- = 1-Butene + Phenol

By formula: C10H14O = C4H8 + C6H6O

Quantity Value Units Method Reference Comment
Deltar82.8kJ/molCmKukui, Potolovskii, et al., 1973liquid phase; ALS

References

Go To: Top, Reaction thermochemistry data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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 «alpha»-olefins, Khim. Tekhnol. Topl. Masel, 1973, 18, 10-13. [all data]


Notes

Go To: Top, Reaction thermochemistry data, References