2-Butene, 2,3-dimethyl-
- Formula: C6H12
- Molecular weight: 84.1595
- IUPAC Standard InChIKey: WGLLSSPDPJPLOR-UHFFFAOYSA-N
- CAS Registry Number: 563-79-1
- 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: Tetramethylethylene; 1,1,2,2-Tetramethylethylene; 2,3-Dimethyl-2-butene; 2,3-Dimethylbut-2-ene; 2,3-Dimethylbutene-2; (CH3)2C=C(CH3)2; Tetramethylethene
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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 |
---|---|---|---|---|---|
ΔfH°gas | -70.3 ± 1.5 | kJ/mol | Eqk | Wiberg and Hao, 1991 | Heat of hydration; ALS |
ΔfH°gas | -68.4 ± 1.5 | kJ/mol | Eqk | Rodgers and Wu, 1971 | Heat of isomerization; ALS |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
135.31 ± 0.27 | 334.20 | Scott D.W., 1955 | GT |
142.00 ± 0.28 | 355.25 | ||
154.64 ± 0.31 | 393.20 | ||
167.65 ± 0.34 | 433.20 | ||
180.33 ± 0.36 | 473.20 |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
115.94 | 273.15 | Scott D.W., 1955 | Recommended results of statistical thermodynamics calculation are in good agreement with experimental data.; GT |
123.60 | 298.15 | ||
124.18 | 300. | ||
156.82 | 400. | ||
188.45 | 500. | ||
216.65 | 600. | ||
241.29 | 700. | ||
262.67 | 800. | ||
281.37 | 900. | ||
297.65 | 1000. | ||
311.92 | 1100. | ||
324.30 | 1200. | ||
335.05 | 1300. | ||
344.47 | 1400. | ||
352.75 | 1500. |
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 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 | -102.9 ± 1.5 | kJ/mol | Eqk | Wiberg and Hao, 1991 | Heat of hydration; ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 270.20 | J/mol*K | N/A | Scott, Finke, et al., 1955 | DH |
S°liquid | 272.4 | J/mol*K | N/A | Parks, Todd, et al., 1936 | Extrapolation below 90 K, 58.45 J/mol*K.; DH |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
174.68 | 298.15 | Scott, Finke, et al., 1955 | T = 10 to 320 K.; DH |
175.73 | 295.5 | Parks, Todd, et al., 1936 | T = 83 to 296 K. Value is unsmoothed experimental datum.; DH |
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 |
---|---|---|---|---|---|
Tboil | 346.3 ± 0.4 | K | AVG | N/A | Average of 28 out of 30 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 198.8 ± 0.3 | K | AVG | N/A | Average of 13 out of 15 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 198.92 | K | N/A | Scott, Finke, et al., 1955, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.01 K; TRC |
Ttriple | 198.900 | K | N/A | Waddington, 1951 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.05 K; TRC |
Ttriple | 198.920 | K | N/A | Waddington, 1951 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC |
Ttriple | 198.5 | K | N/A | Parks, Todd, et al., 1936, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.2 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 524. | K | N/A | Majer and Svoboda, 1985 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 32.67 | kJ/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 32.5 | kJ/mol | N/A | Reid, 1972 | AC |
ΔvapH° | 32.6 | kJ/mol | V | Camin and Rossini, 1956 | ALS |
ΔvapH° | 32.6 | kJ/mol | N/A | Camin and Rossini, 1956, 2 | Based on data from 289. to 347. K.; AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
29.64 | 346.4 | N/A | Majer and Svoboda, 1985 | |
32.1 | 328. | N/A | Uusi-Kyyny, Pokki, et al., 2004 | Based on data from 313. to 346. K.; AC |
33.1 | 297. | A | Stephenson and Malanowski, 1987 | Based on data from 282. to 348. K. See also Bevan, Malkin, et al., 1955.; AC |
32.7 | 304. | N/A | Fried, Baghdoyan, et al., 1971 | Based on data from 289. to 347. K.; AC |
32.9 ± 0.1 | 292. | C | Scott, Finke, et al., 1955 | AC |
32.0 ± 0.1 | 308. | C | Scott, Finke, et al., 1955 | AC |
30.9 ± 0.1 | 326. | C | Scott, Finke, et al., 1955 | AC |
29.7 ± 0.1 | 346. | C | Scott, Finke, et al., 1955 | 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 |
---|---|---|---|---|---|
292. to 346. | 48.29 | 0.2801 | 524. | 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 347.00 | 3.70468 | 1021.564 | -70.242 | Baghdoyan, Malik, et al., 1971 | Coefficents calculated by NIST from author's data. |
302.18 to 346.36 | 4.09587 | 1224.926 | -46.812 | Scott, Finke, et al., 1955 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
6.44 | 198.9 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
17.94 | 196.8 | Domalski and Hearing, 1996 | CAL |
32.39 | 198.9 |
Enthalpy of phase transition
ΔHtrs (kJ/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
3.531 | 196.82 | crystaline, II | crystaline, I | Scott, Finke, et al., 1955 | DH |
6.452 | 198.92 | crystaline, I | liquid | Scott, Finke, et al., 1955 | Enthalpies 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 |
4.577 | 196.6 | crystaline, II | crystaline, I | Parks, Todd, et al., 1936 | DH |
5.460 | 198.5 | crystaline, I | liquid | Parks, Todd, et al., 1936 | DH |
Entropy of phase transition
ΔStrs (J/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
17.94 | 196.82 | crystaline, II | crystaline, I | Scott, Finke, et al., 1955 | DH |
32.44 | 198.92 | crystaline, I | liquid | Scott, Finke, et al., 1955 | Enthalpies; DH |
23.28 | 196.6 | crystaline, II | crystaline, I | Parks, Todd, et al., 1936 | DH |
27.51 | 198.5 | crystaline, I | liquid | Parks, Todd, et al., 1936 | DH |
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 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 + C6H12 = C6H14
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -108.7 ± 0.45 | kJ/mol | Chyd | Rogers, Crooks, et al., 1987 | liquid phase |
ΔrH° | -110.4 ± 0.42 | kJ/mol | Chyd | Kistiakowsky, Ruhoff, et al., 1936 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -111.4 ± 0.42 kJ/mol; At 355 K |
By formula: C6H12 = C6H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 7.61 ± 0.50 | kJ/mol | Eqk | Radyuk, Kabo, et al., 1972 | gas phase; At 562 K |
ΔrH° | 7.1 ± 0.8 | kJ/mol | Eqk | Rodgers and Wu, 1971 | gas phase; Heat of isomerization |
By formula: C6H12 = C6H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -7.1 ± 0.8 | kJ/mol | Eqk | Rodgers and Wu, 1971 | gas phase; Heat of isomerization |
ΔrH° | -7.5 | kJ/mol | Eqk | Abell, 1966 | gas phase |
By formula: C6H12 + HCl = C6H13Cl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -54.0 ± 1.4 | kJ/mol | Cm | Arnett and Pienta, 1980 | liquid phase; solvent: Methylene chloride; Hydrochlorination |
By formula: C6H12 = C6H12
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -30.0 ± 1.1 | kJ/mol | Ciso | Bartolo and Rossini, 1960 | liquid phase; Calculated from ΔHc |
IR Spectrum
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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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Gas Phase Spectrum
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Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
Additional Data
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Owner | NIST Standard Reference Data Program Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Sadtler Research Labs Under US-EPA Contract |
State | gas |
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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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Japan AIST/NIMC Database- Spectrum MS-NW-3539 |
NIST MS number | 230825 |
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.
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, 4993-4998. [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, 2505-2508. [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. [all data]
Waddington, 1951
Waddington, G.,
Personal Commun., U. S. Bur. Mines, Bartlesville, OK, 1951. [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. [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]
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]
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
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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 ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition 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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