2-Pentene, 2,4,4-trimethyl-
- Formula: C8H16
- Molecular weight: 112.2126
- IUPAC Standard InChIKey: LAAVYEUJEMRIGF-UHFFFAOYSA-N
- CAS Registry Number: 107-40-4
- 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: Diisobutylene; 2,2,4-Trimethyl-3-pentene; 2,4,4-Trimethyl-2-pentene; (CH3)3CCH=C(CH3)2; 2,4,4-Trimethylpent-2-ene
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Condensed phase thermochemistry data
Go To: Top, Phase change data, Gas Chromatography, 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 |
---|---|---|---|---|---|
ΔcH°liquid | -1264.89 ± 0.43 | kcal/mol | Ccb | Rockenfeller and Rossini, 1961 | Derived from the ratio of Heat of combustion; Corresponding ΔfHºliquid = -34.04 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 71.39 | cal/mol*K | N/A | Parks and Huffman, 1930 | Extrapolation below 90 K, 63.76 J/mol*K.; DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
55.81 | 296.0 | Parks and Huffman, 1930 | T = 92 to 296 K. Value is unsmoothed experimental datum.; DH |
Phase change data
Go To: Top, Condensed phase thermochemistry data, Gas Chromatography, 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:
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 378. ± 1. | K | AVG | N/A | Average of 6 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 166.790 | K | N/A | Streiff, Zimmerman, et al., 1948 | Uncertainty assigned by TRC = 0.05 K; TRC |
Tfus | 166.820 | K | N/A | Streiff, Zimmerman, et al., 1948 | Uncertainty assigned by TRC = 0.02 K; TRC |
Tfus | 166.64 | K | N/A | Howard, Mears, et al., 1947 | Uncertainty assigned by TRC = 0.1 K; TRC |
Tfus | 166.65 | K | N/A | Tongberg, Pickens, et al., 1932 | Uncertainty assigned by TRC = 0.2 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 166. | K | N/A | Parks, Todd, et al., 1936 | Uncertainty assigned by TRC = 2. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 9.39 | kcal/mol | N/A | Reid, 1972 | AC |
ΔvapH° | 8.94 | kcal/mol | V | Camin and Rossini, 1960 | ALS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
8.53 | 334. | A | Stephenson and Malanowski, 1987 | Based on data from 319. to 380. K.; AC |
8.89 | 320. | MM | Camin and Rossini, 1960, 2 | Based on data from 305. to 378. K.; AC |
8.42 | 374.6 | V | Holmes and Tyrrall, 1956 | ALS |
7.62 | 374.3 | V | Mathews and Fehlandt, 1931 | ALS |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
1.62 | 166. | Domalski and Hearing, 1996 | AC |
Gas Chromatography
Go To: Top, Condensed 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | Petrocol DH | 30. | 726.7 | Soják, Addová, et al., 2004 | 150. m/0.25 mm/1. μm, H2 |
Capillary | Squalane | 30. | 714.5 | Soják, Addová, et al., 2004 | He; Column length: 93. m; Column diameter: 0.25 mm |
Capillary | Squalane | 25. | 714. | Hilal, Carreira, et al., 1994 | |
Capillary | OV-101 | 30. | 724. | Chien, Furio, et al., 1983 | |
Capillary | OV-101 | 40. | 725. | Chien, Furio, et al., 1983 | |
Capillary | OV-101 | 50. | 726. | Chien, Furio, et al., 1983 | |
Capillary | OV-101 | 60. | 726. | Chien, Furio, et al., 1983 | |
Capillary | OV-101 | 70. | 727. | Chien, Furio, et al., 1983 | |
Capillary | OV-101 | 80. | 728. | Chien, Furio, et al., 1983 | |
Capillary | OV-3 | 30. | 729.5 | Chien, Furio, et al., 1983, 2 | |
Capillary | OV-3 | 40. | 729.8 | Chien, Furio, et al., 1983, 2 | |
Capillary | OV-3 | 50. | 730.1 | Chien, Furio, et al., 1983, 2 | |
Capillary | OV-3 | 60. | 730.5 | Chien, Furio, et al., 1983, 2 | |
Capillary | OV-3 | 70. | 730.9 | Chien, Furio, et al., 1983, 2 | |
Capillary | OV-3 | 80. | 731.3 | Chien, Furio, et al., 1983, 2 | |
Capillary | OV-1 | 30. | 727.5 | Chien, Kopecni, et al., 1981 | H2 |
Capillary | OV-1 | 40. | 728.2 | Chien, Kopecni, et al., 1981 | H2 |
Capillary | OV-1 | 50. | 728.8 | Chien, Kopecni, et al., 1981 | H2 |
Capillary | OV-1 | 60. | 729.5 | Chien, Kopecni, et al., 1981 | H2 |
Capillary | OV-1 | 70. | 730.2 | Chien, Kopecni, et al., 1981 | H2 |
Capillary | OV-1 | 80. | 730.9 | Chien, Kopecni, et al., 1981 | H2 |
Capillary | SE-30 | 30. | 730.3 | Chien, Kopecni, et al., 1981 | H2 |
Capillary | SE-30 | 40. | 729.5 | Chien, Kopecni, et al., 1981 | H2 |
Capillary | SE-30 | 50. | 728.7 | Chien, Kopecni, et al., 1981 | H2 |
Capillary | SE-30 | 60. | 727.8 | Chien, Kopecni, et al., 1981 | H2 |
Capillary | SE-30 | 70. | 726.8 | Chien, Kopecni, et al., 1981 | H2 |
Capillary | SE-30 | 80. | 725.8 | Chien, Kopecni, et al., 1981 | H2 |
Packed | Squalane | 80. | 717. | Chrétien and Dubois, 1977 | |
Capillary | Squalane | 50. | 715. | Chretien and Dubois, 1976 | |
Capillary | Squalane | 50. | 715. | Rijks and Cramers, 1974 | N2; Column length: 100. m; Column diameter: 0.25 mm |
Capillary | Squalane | 70. | 716. | Rijks and Cramers, 1974 | N2; Column length: 100. m; Column diameter: 0.25 mm |
Packed | Squalane | 50. | 715.0 | Takács, Tálas, et al., 1972 | N2, Chromosorb W; Column length: 3. m |
Capillary | Squalane | 40. | 715. | Matukuma, 1969 | N2; Column length: 91.4 m; Column diameter: 0.25 mm |
Packed | Squalane | 27. | 701. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 49. | 704. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 67. | 707. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 86. | 709. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 30. | 714.5 | Tourres, 1967 | H2; Column length: 10. m |
Packed | Squalane | 50. | 715. | Tourres, 1967 | H2; Column length: 10. m |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Petrocol DH | 724. | White, Hackett, et al., 1992 | 100. m/0.25 mm/0.5 μm, He, 1. K/min; Tstart: 30. C; Tend: 220. C |
Normal alkane RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | Methyl Silicone | 50. | 715. | N/A | N2; Column length: 74.6 m; Column diameter: 0.28 mm |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Polydimethyl siloxane: CP-Sil 5 CB | 727. | Bramston-Cook, 2013 | 60. m/0.25 mm/1.0 μm, Helium, 45. C @ 1.45 min, 3.6 K/min, 210. C @ 2.72 min |
Capillary | Petrocol DH | 728. | Supelco, 2012 | 100. m/0.25 mm/0.50 μm, Helium, 20. C @ 15. min, 15. K/min, 220. C @ 30. min |
Capillary | PONA | 729. | Zhang, Ding, et al., 2009 | 50. m/0.20 mm/0.50 μm, Nitrogen, 35. C @ 15. min, 2. K/min, 200. C @ 10. min |
Capillary | OV-101 | 727. | Orav, Kailas, et al., 1999 | 50. m/0.20 mm/0.50 μm, Helium, 30. C @ 6. min, 1. K/min; Tend: 100. C |
Capillary | SE-54 | 727. | Guan, Li, et al., 1995 | 60. C @ 2. min, 4. K/min; Column length: 50. m; Column diameter: 0.32 mm; Tend: 200. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | RTX-5 | 730. | Ádámová, Orinák, et al., 2005 | 30. m/0.25 mm/0.25 μm, N2; Program: not specified |
Capillary | RTX-5 | 730. | Ádámová, Orinák, et al., 2005 | 30. m/0.25 mm/0.25 μm, N2; Program: not specified |
Capillary | Polydimethyl siloxane | 718. | Junkes, Castanho, et al., 2003 | Program: not specified |
Capillary | Methyl Silicone | 722. | Zenkevich, 2000 | Program: not specified |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Rockenfeller and Rossini, 1961
Rockenfeller, J.D.; Rossini, F.D.,
Heats of combustion, isomerization, and formation of selected C7, C8, and C10 monoolefin hydrocarbons,
J. Phys. Chem., 1961, 65, 267-272. [all data]
Parks and Huffman, 1930
Parks, G.S.; Huffman, H.M.,
Thermal data on organic compounds. IX. A study of the effect of unsaturation on the heat capacities, entropies and free energies of some hydrocarbons and other compounds,
J. Am. Chem. Soc., 1930, 52, 4381-4391. [all data]
Streiff, Zimmerman, et al., 1948
Streiff, A.J.; Zimmerman, J.C.; Soule, L.F.; Butt, M.T.; Sedlak, V.A.; Willingham, C.B.; Rossini, F.D.,
Purification, Purity, and Freezing Points of 30 Hydrocarbons of the API-Standard and API-NBS Series,
J. Res. Natl. Bur. Stand. (U. S.), 1948, 41, 323. [all data]
Howard, Mears, et al., 1947
Howard, F.L.; Mears, T.W.; Fookson, A.; Pomerantz, P.; Brooks, D.B.,
Preparation and physical properties of several aliphatic hydrocarbons and intermediates,
J. Res. Natl. Bur. Stand. (U. S.), 1947, 38, 365. [all data]
Tongberg, Pickens, et al., 1932
Tongberg, C.O.; Pickens, J.D.; Fenske, M.R.; Whitmore, F.C.,
The Isomers in "Diisobutylene". II.,
J. Am. Chem. Soc., 1932, 54, 3706-10. [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]
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
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Camin and Rossini, 1960
Camin, D.L.; Rossini, F.D.,
Physical properties of to selected C7 and C8 alkene hydrocarbons,
J. Chem. Eng. Data, 1960, 5, 368. [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
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Camin and Rossini, 1960, 2
Camin, D.L.; Rossini, F.D.,
Physical Properties of 16 Selected C 7 and C 8 Alkene Hydrocarbons.,
J. Chem. Eng. Data, 1960, 5, 3, 368-372, https://doi.org/10.1021/je60007a037
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Holmes and Tyrrall, 1956
Holmes, W.S.; Tyrrall, E.,
Entropy of vaporization and molecular rotation in the liquid state,
Chem. Ind. (London), 1956, 662-663. [all data]
Mathews and Fehlandt, 1931
Mathews, J.H.; Fehlandt, P.R.,
The heats of vaporization of some organic compounds,
J. Am. Chem. Soc., 1931, 53, 3212-32. [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
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Soják, Addová, et al., 2004
Soják, L.; Addová, G.; Kubinec, R.; Kraus, A.; Bohác, A.,
Capillary gas chromatography-mass spectrometry of all 93 acyclic octenes and their identification in fluid catalytic cracked gasoline,
J. Chromatogr. A, 2004, 1025, 2, 237-253, https://doi.org/10.1016/j.chroma.2003.10.112
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Hilal, Carreira, et al., 1994
Hilal, S.H.; Carreira, L.A.; Karickhoff, S.W.; Melton, C.M.,
Estimation of Gas-Liquid Chromatographic Retention Times from Molecular Structure,
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Chien, Furio, et al., 1983
Chien, C.-F.; Furio, D.L.; Kopecni, M.M.; Laub, R.J.,
Specific Retention Volumes and Retention Indices of Selected Hydrocarbon Solutes with OV-101 and SP-2100 Polydimethylsiloxane Solvents,
J. Hi. Res. Chromatogr. Chromatogr. Comm., 1983, 6, 10, 577-580, https://doi.org/10.1002/jhrc.1240061013
. [all data]
Chien, Furio, et al., 1983, 2
Chien, C.-F.; Furio, D.L.; Kopecni, M.M.; Laub, R.J.,
Specific retention volumes and retention indices of selected hydrocarbon solutes with OV-3, OV-7, OV-11, OV-17, OV-22, and OV-25 polymethylphenylsiloxane solvents,
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Chien, Kopecni, et al., 1981
Chien, C.-F.; Kopecni, M.M.; Laub, R.J.,
Specific Retention Volumes and Retention Indices of Selected Hydrocarbon Solutes with OV-1 and SE-30 Polydimethylsiloxane Solvents,
J. Hi. Res. Chromatogr. Chromatogr. Comm., 1981, 4, 10, 539-543, https://doi.org/10.1002/jhrc.1240041017
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Chrétien and Dubois, 1977
Chrétien, J.R.; Dubois, J.E.,
Topological analysis of gas-liquid chromatographic behavior of alkenes,
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Chretien and Dubois, 1976
Chretien, J.R.; Dubois, J.-E.,
New Perspectives in the Prediction of Kovats Indices,
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Rijks and Cramers, 1974
Rijks, J.A.; Cramers, C.A.,
High precision capillary gas chromatography of hydrocarbons,
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Takács, Tálas, et al., 1972
Takács, J.; Tálas, Zs.; Bernáth, I.; Czakó, Gy.; Fischer, A.,
Contribution to the theory of the retention index system. IV. Retention index and molecular structure. Calculation of retention indices of olefins, cyclic hydrocarbons and homologues of benzene hydrocarbons on the basis of their molecular structures,
J. Chromatogr., 1972, 67, 2, 203-212, https://doi.org/10.1016/S0021-9673(01)91222-1
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Matukuma, 1969
Matukuma, A.,
Retention indices of alkanes through C10 and alkenes through C8 and relation between boiling points and retention data,
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Hively and Hinton, 1968
Hively, R.A.; Hinton, R.E.,
Variation of the retention index with temperature on squalane substrates,
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Tourres, 1967
Tourres, D.A.,
Structural analysis of industrial butene dimers by gas chromatography,
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White, Hackett, et al., 1992
White, C.M.; Hackett, J.; Anderson, R.R.; Kail, S.; Spock, P.S.,
Linear temperature programmed retention indices of gasoline range hydrocarbons and chlorinated hydrocarbons on cross-linked polydimethylsiloxane,
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Bramston-Cook, 2013
Bramston-Cook, R.,
Kovats indices for C2-C13 hydrocarbons and selected oxygenated/halocarbons with 100 % dimethylpolysiloxane columns, 2013, retrieved from http://lotusinstruments.com/monographs/List .... [all data]
Supelco, 2012
Supelco, CatalogNo. 24160-U,
Petrocol DH Columns. Catalog No. 24160-U, 2012, retrieved from http://www.sigmaaldrich.com/etc/medialib/docs/Supelco/Datasheet/1/w97949.Par.0001.File.tmp/w97949.pdf. [all data]
Zhang, Ding, et al., 2009
Zhang, X.; Ding, L.; Sun, Z.; Song, L.; Sun, T.,
Study on quantitative structure-retention relationships for hydrocarbons in FCC gasoline,
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Orav, Kailas, et al., 1999
Orav, A.; Kailas, T.; Muurisepp, M.; Kann, J.,
Composition of the oil from waste tires. 1. Fraction boiling at yp to 160 0C,
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Guan, Li, et al., 1995
Guan, Y.; Li, L.; Zhou, L.,
Live retention database for compound identification in capillary gas chromatography,
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Ádámová, Orinák, et al., 2005
Ádámová, M.; Orinák, A.; Halás, L.,
Retention indices as identification tool in pyrolysis-capillary gas chromatography,
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Junkes, Castanho, et al., 2003
Junkes, B.S.; Castanho, R.D.M.; Amboni, C.; Yunes, R.A.; Heinzen, V.E.F.,
Semiempirical Topological Index: A Novel Molecular Descriptor for Quantitative Structure-Retention Relationship Studies,
Internet Electronic Journal of Molecular Design, 2003, 2, 1, 33-49. [all data]
Zenkevich, 2000
Zenkevich, I.G.,
Mutual Correlation between Gas Chromatographic Retention Indices of Unsaturated and Saturated Hydrocarbons found by Molecular Dynamics,
Z. Anal. Chem., 2000, 55, 10, 1091-1097. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfusH Enthalpy of fusion 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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