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2-Butene, (E)-

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
Deltafgas-2.58 ± 0.24kcal/molCmProsen, Maron, et al., 1951ALS
Quantity Value Units Method Reference Comment
Deltacgas-646.90 ± 0.23kcal/molCmProsen, Maron, et al., 1951Corresponding «DELTA»fgas = -2.56 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
8.63350.Thermodynamics Research Center, 1997p=1 bar. Recommended entropies and heat capacities are in good agreement with those obtained from other statistical thermodynamics calculations [ Aston J.D., 1946, Kilpatrick J.E., 1946].; GT
11.77100.
14.43150.
16.59200.
19.78273.15
20.95298.15
21.04300.
25.939400.
30.612500.
34.759600.
38.375700.
41.527800.
44.273900.
46.6631000.
48.7401100.
50.5431200.
52.1081300.
53.4681400.
54.6531500.
57.0051750.
58.7092000.
59.9692250.
60.9182500.
61.6442750.
62.2083000.

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
20.98298.60Kistiakowsky G.B., 1940GT
22.69332.90
24.529371.50

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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 by: Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
liquid39.08cal/mol*KN/AChao, Hall, et al., 1983 
liquid49.070cal/mol*KN/AGuttman and Pitzer, 1945 
liquid48.989cal/mol*KN/ATodd and Parks, 1936Extrapolation below 90 K, 42.80 J/mol*K.

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
29.73280.Chao, Hall, et al., 1983T = 14 to 271 K.
29.240270280.Guttman and Pitzer, 1945T = 15 to 274 K.
29.171259.6Todd and Parks, 1936T = 93 to 260 K. Value is unsmoothed experimental datum.

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:
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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Tboil274.2 ± 0.5KAVGN/AAverage of 10 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus167.35KN/AKistiakowsky, Ruhoff, et al., 1935Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Ttriple167.62KN/AChao, Hall, et al., 1983, 2Uncertainty assigned by TRC = 0.02 K; TRC
Ttriple167.61KN/AGuttman and Pitzer, 1945, 2Uncertainty assigned by TRC = 0.02 K; by extrapolation of 1/f to 0; TRC
Ttriple167.3KN/ATodd and Parks, 1936, 2Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Tc428.6 ± 0.1KN/ATsonopoulos and Ambrose, 1996 
Tc428.6KN/AMajer and Svoboda, 1985 
Tc428.61KN/AAmbrose, Cox, et al., 1960Uncertainty assigned by TRC = 0.3 K; Visual, PRT, IPTS-48; TRC
Quantity Value Units Method Reference Comment
Pc40.5 ± 0.2atmN/ATsonopoulos and Ambrose, 1996 
Quantity Value Units Method Reference Comment
Vc0.2377l/molN/ATsonopoulos and Ambrose, 1996 
Quantity Value Units Method Reference Comment
rhoc4.21 ± 0.02mol/lN/ATsonopoulos and Ambrose, 1996 
Quantity Value Units Method Reference Comment
Deltavap5.251kcal/molN/AMajer and Svoboda, 1985 
Deltavap5.09kcal/molN/AReid, 1972AC

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
5.4391274.04N/AGuttman and Pitzer, 1945P = 101.325 kPa; DH
5.430274.N/AMajer and Svoboda, 1985 
5.71272.AStephenson and Malanowski, 1987Based on data from 205. - 287. K.; AC
5.64288.AStephenson and Malanowski, 1987Based on data from 273. - 315. K.; AC
5.57328.AStephenson and Malanowski, 1987Based on data from 313. - 385. K.; AC
5.54397.AStephenson and Malanowski, 1987Based on data from 382. - 428. K.; AC
5.44 ± 0.15274.CGuttman and Pitzer, 1945ALS
5.45 ± 0.02274.CGuttman and Pitzer, 1945AC
5.78259.N/AGuttman and Pitzer, 1945Based on data from 203. - 274. K. See also Boublik, Fried, et al., 1984.; AC
5.71268.N/ALamb and Roper, 1940Based on data from 205. - 283. K. See also Boublik, Fried, et al., 1984.; AC
5.695273.4VKistiakowsky, Ruhoff, et al., 1935, 2At 355 °K; ALS

Enthalpy of vaporization

ΔvapH = A exp(-αTr) (1 − Tr)β
    ΔvapH = Enthalpy of vaporization (at saturation pressure) (kcal/mol)
    Tr = reduced temperature (T / Tc)

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Temperature (K) 274. - 394.
A (kcal/mol) 7.335
alpha -0.1948
beta 0.417
Tc (K) 428.6
ReferenceMajer and Svoboda, 1985

Entropy of vaporization

DeltavapS (cal/mol*K) Temperature (K) Reference Comment
19.85274.04Guttman and Pitzer, 1945P; DH

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (atm)
    T = temperature (K)

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Temperature (K) A B C Reference Comment
201.70 - 274.134.0379982.166-30.775Guttman and Pitzer, 1945Coefficents calculated by NIST from author's data.

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Reference Comment
2.332167.62Chao, Hall, et al., 1983DH
2.332167.61Guttman and Pitzer, 1945DH
2.33167.6Domalski and Hearing, 1996AC
2.357167.3Todd and Parks, 1936DH

Entropy of fusion

DeltafusS (cal/mol*K) Temperature (K) Reference Comment
13.9167.62Chao, Hall, et al., 1983DH
13.91167.61Guttman and Pitzer, 1945DH
14.09167.3Todd and Parks, 1936DH

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Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, IR Spectrum, 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
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

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

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

By formula: C4H8 = C4H8

Quantity Value Units Method Reference Comment
Deltar-0.9 ± 0.5kcal/molAVGN/AAverage of 7 values; Individual data points

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

By formula: C4H8 = C4H8

Quantity Value Units Method Reference Comment
Deltar-3.00 ± 0.20kcal/molEqkMeyer and Stroz, 1972gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -2.64 kcal/mol; At 300 K; ALS
Deltar-2.96 ± 0.40kcal/molEqkHappel, Hnatow, et al., 1971gas phase; ALS
Deltar-3.03kcal/molEqkMaccoll and Ross, 1965gas phase; GC; ALS
Deltar-2.80 ± 0.20kcal/molEqkGolden, Egger, et al., 1964gas phase; ALS
Deltar-2.75kcal/molCisoLevanova and Andreevskii, 1964gas phase; At 420.3 K; ALS

Hydrogen bromide + 2-Butene, (E)- = Butane, 2-bromo-

By formula: HBr + C4H8 = C4H9Br

Quantity Value Units Method Reference Comment
Deltar-17.26 ± 0.12kcal/molCmLacher, Billings, et al., 1952gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -17.3 ± 1.4 kcal/mol; Heat of hydrobromination at 373 K; ALS

C3H9Si+ + 2-Butene, (E)- = (C3H9Si+ bullet 2-Butene, (E)-)

By formula: C3H9Si+ + C4H8 = (C3H9Si+ bullet C4H8)

Quantity Value Units Method Reference Comment
Deltar30.9kcal/molPHPMSLi and Stone, 1989gas phase; condensation; M
Quantity Value Units Method Reference Comment
Deltar41.5cal/mol*KPHPMSLi and Stone, 1989gas phase; condensation; M

Hydrogen + 2-Butene, (E)- = Butane

By formula: H2 + C4H8 = C4H10

Quantity Value Units Method Reference Comment
Deltar-27.38 ± 0.10kcal/molChydKistiakowsky, Ruhoff, et al., 1935, 2gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -27.621 ± 0.021 kcal/mol; At 355 °K; ALS

2-Butene, (E)- + Bromine = erythro-2,3-Dibromobutane

By formula: C4H8 + Br2 = C4H8Br2

Quantity Value Units Method Reference Comment
Deltar-28.95 ± 0.20kcal/molCmConn, Kistiakowsky, et al., 1938gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -29.08 ± 0.20 kcal/mol; At 355 °K; ALS

Butane, 2-chloro- = 2-Butene, (E)- + Hydrogen chloride

By formula: C4H9Cl = C4H8 + HCl

Quantity Value Units Method Reference Comment
Deltar15.25kcal/molEqkLevanova and Andreevskii, 1964gas phase; At 420 K; ALS

2-Butene, (E)- + Ethylene = cyclobutane, 1,2-dimethyl-, trans-

By formula: C4H8 + C2H4 = C6H12

Quantity Value Units Method Reference Comment
Deltar-16.7kcal/molEqkScacchi and Back, 1977liquid phase; ALS

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), References, Notes

Data compiled by: Coblentz Society, Inc.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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

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Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
NIST MS number 18915

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References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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.

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]

Kistiakowsky G.B., 1940
Kistiakowsky G.B., Gaseous heat capacities. III, J. Chem. Phys., 1940, 8, 618-622. [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]

Guttman and Pitzer, 1945
Guttman, L.; Pitzer, K.S., trans-2-Butene. The heat capacity, heats of fusion and vaporization, and vapor pressure. The entropy and barrier to internal rotation, J. Am. Chem. Soc., 1945, 67, 324-327. [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]

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, 876-82. [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]

Guttman and Pitzer, 1945, 2
Guttman, L.; Pitzer, K.S., trans-2-Butene. The Heat Capacity, Heats of Fusion and Vaporization and Vapor Pressure. The Entropy and Barrier to Internal Rotation, J. Am. Chem. Soc., 1945, 67, 324-7. [all data]

Todd and Parks, 1936, 2
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. [all data]

Tsonopoulos and Ambrose, 1996
Tsonopoulos, C.; Ambrose, D., Vapor-Liquid Critical Properties of Elements and Compounds. 6. Unsaturated Aliphatic Hydrocarbons, J. Chem. Eng. Data, 1996, 41, 645-656. [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]

Ambrose, Cox, et al., 1960
Ambrose, D.; Cox, J.D.; Townsend, R., The critical temperatures of forty organic compounds, Trans. Faraday Soc., 1960, 56, 1452. [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]

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]

Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]

Lamb and Roper, 1940
Lamb, Arthur B.; Roper, Edwin E., The Vapor Pressures of Certain Unsaturated Hydrocarbons, J. Am. Chem. Soc., 1940, 62, 4, 806-814, https://doi.org/10.1021/ja01861a032 . [all data]

Kistiakowsky, Ruhoff, et al., 1935, 2
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]

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]

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]

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]

Li and Stone, 1989
Li, X.; Stone, J.A., Determination of the beta silicon effect from a mass spectrometric study of the association of trimethylsilylium ion with alkenes, J. Am. Chem. Soc., 1989, 111, 15, 5586, https://doi.org/10.1021/ja00197a013 . [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]

Scacchi and Back, 1977
Scacchi, G.; Back, M.H., The cycloaddition of ethylene to butene-2. II. Energy relations, Int. J. Chem. Kinet., 1977, 9, 525-534. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References