2-Butene, 2,3-dimethyl-

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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 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
Δfgas-70.3 ± 1.5kJ/molEqkWiberg and Hao, 1991Heat of hydration; ALS
Δfgas-68.4 ± 1.5kJ/molEqkRodgers and Wu, 1971Heat of isomerization; ALS

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
135.31 ± 0.27334.20Scott D.W., 1955GT
142.00 ± 0.28355.25
154.64 ± 0.31393.20
167.65 ± 0.34433.20
180.33 ± 0.36473.20

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
115.94273.15Scott D.W., 1955Recommended results of statistical thermodynamics calculation are in good agreement with experimental data.; GT
123.60298.15
124.18300.
156.82400.
188.45500.
216.65600.
241.29700.
262.67800.
281.37900.
297.651000.
311.921100.
324.301200.
335.051300.
344.471400.
352.751500.

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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil346.3 ± 0.4KAVGN/AAverage of 28 out of 30 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus198.8 ± 0.3KAVGN/AAverage of 13 out of 15 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple198.92KN/AScott, Finke, et al., 1955Crystal phase 1 phase; Uncertainty assigned by TRC = 0.01 K; TRC
Ttriple198.900KN/AWaddington, 1951Crystal phase 1 phase; Uncertainty assigned by TRC = 0.05 K; TRC
Ttriple198.920KN/AWaddington, 1951Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC
Ttriple198.5KN/AParks, Todd, et al., 1936Crystal phase 1 phase; Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Tc524.KN/AMajer and Svoboda, 1985 
Quantity Value Units Method Reference Comment
Δvap32.67kJ/molN/AMajer and Svoboda, 1985 
Δvap32.5kJ/molN/AReid, 1972AC
Δvap32.6kJ/molVCamin and Rossini, 1956ALS
Δvap32.6kJ/molN/ACamin and Rossini, 1956, 2Based on data from 289. to 347. K.; AC

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
29.64346.4N/AMajer and Svoboda, 1985 
32.1328.N/AUusi-Kyyny, Pokki, et al., 2004Based on data from 313. to 346. K.; AC
33.1297.AStephenson and Malanowski, 1987Based on data from 282. to 348. K. See also Bevan, Malkin, et al., 1955.; AC
32.7304.N/AFried, Baghdoyan, et al., 1971Based on data from 289. to 347. K.; AC
32.9 ± 0.1292.CScott, Finke, et al., 1955, 2AC
32.0 ± 0.1308.CScott, Finke, et al., 1955, 2AC
30.9 ± 0.1326.CScott, Finke, et al., 1955, 2AC
29.7 ± 0.1346.CScott, Finke, et al., 1955, 2AC

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
292. to 346.48.290.2801524.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
289.48 to 347.003.704681021.564-70.242Baghdoyan, Malik, et al., 1971Coefficents calculated by NIST from author's data.
302.18 to 346.364.095871224.926-46.812Scott, Finke, et al., 1955, 2Coefficents calculated by NIST from author's data.

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
6.44198.9Domalski and Hearing, 1996AC

Entropy of fusion

ΔfusS (J/mol*K) Temperature (K) Reference Comment
17.94196.8Domalski and Hearing, 1996CAL
32.39198.9

Enthalpy of phase transition

ΔHtrs (kJ/mol) Temperature (K) Initial Phase Final Phase Reference Comment
3.531196.82crystaline, IIcrystaline, IScott, Finke, et al., 1955, 2DH
6.452198.92crystaline, IliquidScott, Finke, et al., 1955, 2Enthalpies of transition and fusion calculated from total enthalpy change 196.82 to 198.92 K and assumed Cp of 150 J/mol*K for c,I.; DH
4.577196.6crystaline, IIcrystaline, IParks, Todd, et al., 1936, 2DH
5.460198.5crystaline, IliquidParks, Todd, et al., 1936, 2DH

Entropy of phase transition

ΔStrs (J/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
17.94196.82crystaline, IIcrystaline, IScott, Finke, et al., 1955, 2DH
32.44198.92crystaline, IliquidScott, Finke, et al., 1955, 2Enthalpies; DH
23.28196.6crystaline, IIcrystaline, IParks, Todd, et al., 1936, 2DH
27.51198.5crystaline, IliquidParks, Todd, et al., 1936, 2DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


Reaction thermochemistry data

Go To: Top, Gas 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

Hydrogen + 2-Butene, 2,3-dimethyl- = Butane, 2,3-dimethyl-

By formula: H2 + C6H12 = C6H14

Quantity Value Units Method Reference Comment
Δr-108.7 ± 0.45kJ/molChydRogers, Crooks, et al., 1987liquid phase
Δr-110.4 ± 0.42kJ/molChydKistiakowsky, Ruhoff, et al., 1936gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -111.4 ± 0.42 kJ/mol; At 355 K

2-Butene, 2,3-dimethyl- = 1-Butene, 2,3-dimethyl-

By formula: C6H12 = C6H12

Quantity Value Units Method Reference Comment
Δr7.61 ± 0.50kJ/molEqkRadyuk, Kabo, et al., 1972gas phase; At 562 K
Δr7.1 ± 0.8kJ/molEqkRodgers and Wu, 1971gas phase; Heat of isomerization

1-Butene, 2,3-dimethyl- = 2-Butene, 2,3-dimethyl-

By formula: C6H12 = C6H12

Quantity Value Units Method Reference Comment
Δr-7.1 ± 0.8kJ/molEqkRodgers and Wu, 1971gas phase; Heat of isomerization
Δr-7.5kJ/molEqkAbell, 1966gas phase

2-Butene, 2,3-dimethyl- + Hydrogen chloride = Butane, 2-chloro-2,3-dimethyl-

By formula: C6H12 + HCl = C6H13Cl

Quantity Value Units Method Reference Comment
Δr-54.0 ± 1.4kJ/molCmArnett and Pienta, 1980liquid phase; solvent: Methylene chloride; Hydrochlorination

1-Hexene = 2-Butene, 2,3-dimethyl-

By formula: C6H12 = C6H12

Quantity Value Units Method Reference Comment
Δr-30.0 ± 1.1kJ/molCisoBartolo and Rossini, 1960liquid phase; Calculated from ΔHc

References

Go To: Top, Gas 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]

Rodgers and Wu, 1971
Rodgers, A.S.; Wu, M.-C.R., Thermochemistry of the gas-phase iodine catalyzed isomerization: 2,3-dimethyl-1-butene = 2,3-dimethyl-2-butene, J. Chem. Thermodyn., 1971, 3, 591-597. [all data]

Scott D.W., 1955
Scott D.W., 2,3-Dimethyl-2-butene: thermodynamic properties in the solid, liquid and vapor states, J. Am. Chem. Soc., 1955, 77, 4993-4998. [all data]

Scott, Finke, et al., 1955
Scott, D.W.; Finke, H.L.; McCullough, J.P.; Gross, M.E.; Messerly, J.F.; Pennington, R.E.; Waddington, G., 2,3-dimethyl-2-butene: thermodynamic properties in the solid, liquid, and vapor states., J. Am. Chem. Soc., 1955, 77, 4993. [all data]

Waddington, 1951
Waddington, G., Personal Commun., U. S. Bur. Mines, Bartlesville, OK, 1951. [all data]

Parks, Todd, et al., 1936
Parks, G.S.; Todd, S.S.; Shomate, C.H., Thermal data on organic compounds. XVII. Some heat capacity, entropy and free energy data for five higher olefins, J. Am. Chem. Soc., 1936, 58, 2505. [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]

Camin and Rossini, 1956
Camin, D.L.; Rossini, F.D., Physical properties of the 17 isomeric hexenes of the API research series, J. Phys. Chem., 1956, 60, 1446. [all data]

Camin and Rossini, 1956, 2
Camin, David L.; Rossini, Frederick D., Physical Properties of the 17 Isomeric Hexenes.of the API Research Series, J. Phys. Chem., 1956, 60, 10, 1446-1451, https://doi.org/10.1021/j150544a029 . [all data]

Uusi-Kyyny, Pokki, et al., 2004
Uusi-Kyyny, Petri; Pokki, Juha-Pekka; Kim, Younghun; Aittamaa, Juhani, Isobaric Vapor Liquid Equilibrium for 2,3-Dimethyl-2-butene + Methanol, + Ethanol, + 2-Propanol, or + 2-Butanol at Atmospheric Pressure, J. Chem. Eng. Data, 2004, 49, 2, 251-255, https://doi.org/10.1021/je034106w . [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]

Bevan, Malkin, et al., 1955
Bevan, T.H.; Malkin, T.; Smith, D.B.; Davey, W.; Gwilt, J.R.; Cooper, W.; Kertes, S.; Roberts, J.J.; Ross, W.C.J.; Wilson, Walter; Cummings, G.A.McD.; McLaughlin, E., Notes, J. Chem. Soc., 1955, 1383, https://doi.org/10.1039/jr9550001383 . [all data]

Fried, Baghdoyan, et al., 1971
Fried, Vojtech.; Baghdoyan, Armen.; Malik, Jana., Vapor pressures and densities of 2,3-dimethyl-2-butene and 3,3-dimethyl-1-butene, J. Chem. Eng. Data, 1971, 16, 1, 96-97, https://doi.org/10.1021/je60048a009 . [all data]

Scott, Finke, et al., 1955, 2
Scott, D.W.; Finke, H.L.; McCullough, J.P.; Gross, M.E.; Messerly, J.F.; Pennington, R.E.; Waddington, G., 2,3-Dimethyl-2-butene: Thermodynamic properties in the solid, liquid and vapor states, J. Am. Chem. Soc., 1955, 77, 4993-4998. [all data]

Baghdoyan, Malik, et al., 1971
Baghdoyan, A.; Malik, J.; Fried, V., Vapor Pressures and Densities of 2,3-Dimethyl-2-butene and 3,3-Dimethyl-1-butene, J. Chem. Eng. Data, 1971, 16, 1, 96-97, https://doi.org/10.1021/je60048a009 . [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]

Parks, Todd, et al., 1936, 2
Parks, G.S.; Todd, S.S.; Shomate, C.H., Thermal data on organic compounds. XVII. Some heat capacity, entropy and free energy data for five higher olefins, J. Am. Chem. Soc., 1936, 58, 2505-2508. [all data]

Rogers, Crooks, et al., 1987
Rogers, D.W.; Crooks, E.; Dejroongruang, K., Enthalpies of hydrogenation of the hexenes, J. Chem. Thermodyn., 1987, 19, 1209-1215. [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]

Radyuk, Kabo, et al., 1972
Radyuk, Z.A.; Kabo, G.Ya.; Andreevskii, D.N., Equilibrium and thermodynamics of the isomerization of hexene isomers, Neftekhimiya, 1972, 12, 679-686. [all data]

Abell, 1966
Abell, P.I., Bromine atom catalyzed isomerization of terminal olefins, J. Am. Chem. Soc., 1966, 88, 1346-1348. [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]

Bartolo and Rossini, 1960
Bartolo, H.F.; Rossini, F.D., Heats of isomerization of the seventeen isomeric hexenes, J. Phys. Chem., 1960, 64, 1685-1689. [all data]


Notes

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