2-Hexanol
- Formula: C6H14O
- Molecular weight: 102.1748
- IUPAC Standard InChIKey: QNVRIHYSUZMSGM-UHFFFAOYSA-N
- CAS Registry Number: 626-93-7
- 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. - Species with the same structure:
- Stereoisomers:
- Other names: n-C4H9CH(OH)CH3; n-Butylmethylcarbinol; Hexanol-(2); sec-Hexyl alcohol; n-Hexan-2-ol; 2-Hexyl alcohol; Hexan-2-ol
- Information on this page:
- Other data available:
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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 by: Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -333.5 ± 2.2 | kJ/mol | N/A | Wiberg, Wasserman, et al., 1984 | Value computed using ΔfHliquid° value of -392±0.88 kj/mol from Wiberg, Wasserman, et al., 1984 and ΔvapH° value of 58.47±2 kj/mol from missing citation. |
ΔfH°gas | -335.6 ± 2.2 | kJ/mol | N/A | Wiberg and Wasserman, 1981 | Value computed using ΔfHliquid° value of -394.1±0.88 kj/mol from Wiberg and Wasserman, 1981 and ΔvapH° value of 58.47±2 kj/mol from missing citation. |
ΔfH°gas | -329.9 ± 2.1 | kJ/mol | N/A | Sachek, Peshchenko, et al., 1974 | Value computed using ΔfHliquid° value of -388.4±0.75 kj/mol from Sachek, Peshchenko, et al., 1974 and ΔvapH° value of 58.47±2 kj/mol from missing citation. |
Condensed 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -392.0 ± 0.88 | kJ/mol | Cm | Wiberg, Wasserman, et al., 1984 | Heat of hydration, see Wiberg and Wasserman, 1981; ALS |
ΔfH°liquid | -394.1 ± 0.88 | kJ/mol | Cm | Wiberg and Wasserman, 1981 | ALS |
ΔfH°liquid | -388.4 ± 0.75 | kJ/mol | Ccb | Sachek, Peshchenko, et al., 1974 | Heat of combustion not reported; ALS |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
256.31 | 298.15 | Tanaka, Luo, et al., 1988 | DH |
260.34 | 298.15 | Ortega, 1986 | 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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 411. ± 3. | K | AVG | N/A | Average of 24 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 583. ± 10. | K | AVG | N/A | Average of 7 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 33.1 ± 0.2 | bar | N/A | Gude and Teja, 1995 | |
Pc | 33.10 | bar | N/A | Rosenthal and Teja, 1990 | Uncertainty assigned by TRC = 0.20 bar; TRC |
Pc | 33.10 | bar | N/A | Rosenthal and Teja, 1989 | Uncertainty assigned by TRC = 0.20 bar; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Vc | 0.384 | l/mol | N/A | Gude and Teja, 1995 | |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 2.60 ± 0.02 | mol/l | N/A | Gude and Teja, 1995 | |
ρc | 2.60 | mol/l | N/A | Anselme and Teja, 1988 | Uncertainty assigned by TRC = 0.06 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 58.47 | kJ/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 57.0 ± 0.2 | kJ/mol | GS | Roganov, Pisarev, et al., 2005 | Based on data from 274. to 309. K.; AC |
ΔvapH° | 58.3 ± 0.3 | kJ/mol | GS | Kulikov, Verevkin, et al., 2001 | Based on data from 274. to 309. K.; AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
41.01 | 413. | N/A | Majer and Svoboda, 1985 | |
61.8 | 239. | N/A | N'Guimbi, Berro, et al., 1999 | Based on data from 224. to 323. K.; AC |
48.7 | 375. | A | Stephenson and Malanowski, 1987 | Based on data from 360. to 415. K.; AC |
47.8 | 366. | A | Stephenson and Malanowski, 1987 | Based on data from 351. to 412. K. See also Brazhnikov, Andreevskii, et al., 1975.; AC |
56.8 ± 0.2 | 313. | C | Majer, Svoboda, et al., 1985 | AC |
55.0 ± 0.2 | 328. | C | Majer, Svoboda, et al., 1985 | AC |
53.0 ± 0.2 | 343. | C | Majer, Svoboda, et al., 1985 | AC |
50.7 ± 0.2 | 358. | C | Majer, Svoboda, et al., 1985 | AC |
49.2 ± 0.2 | 368. | C | Majer, Svoboda, et al., 1985 | AC |
52.4 | 352. | N/A | Sachek, Markovnik, et al., 1984 | Based on data from 337. to 413. K.; AC |
53.1 | 316. | N/A | Wilhoit and Zwolinski, 1973 | Based on data from 301. to 415. K.; AC |
49.7 | 356. | I | Hovorka, Lankelma, et al., 1938 | Based on data from 298. to 413. K.; AC |
Enthalpy of vaporization
ΔvapH = A exp(-αTr)
(1 − Tr)β
ΔvapH =
Enthalpy of vaporization (at saturation pressure)
(kJ/mol)
Tr = reduced temperature (T / Tc)
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Temperature (K) | 313. to 368. |
---|---|
A (kJ/mol) | 65.48 |
α | -1.4306 |
β | 1.1616 |
Tc (K) | 568.2 |
Reference | Majer and Svoboda, 1985 |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
298. to 415. | 5.51932 | 2076.433 | -36.261 | Hovorka, Lankelma, et al., 1938 | Coefficents calculated by NIST from author's data. |
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:
B - John E. Bartmess
ALS - 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
C6H13O- + =
By formula: C6H13O- + H+ = C6H14O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1560. ± 8.4 | kJ/mol | CIDC | Haas and Harrison, 1993 | gas phase; Both metastable and 50 eV collision energy.; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1532. ± 8.8 | kJ/mol | H-TS | Haas and Harrison, 1993 | gas phase; Both metastable and 50 eV collision energy.; B |
By formula: C6H14O = C6H12 + H2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 33.8 ± 0.3 | kJ/mol | Cm | Wiberg, Wasserman, et al., 1984 | liquid phase; Heat of hydration, see Wiberg and Wasserman, 1981; ALS |
By formula: C6H12 + H2O = C6H14O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -34.5 ± 0.3 | kJ/mol | Cm | Wiberg and Wasserman, 1981 | liquid phase; solvent: Water; Hydration; ALS |
By formula: C4F6O3 + C6H14O = C2HF3O2 + C8H13F3O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -89.33 ± 0.04 | kJ/mol | Cm | Wiberg and Wasserman, 1981 | liquid phase; ALS |
References
Go To: Top, Gas phase thermochemistry data, Condensed 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, Wasserman, et al., 1984
Wiberg, K.B.; Wasserman, D.J.; Martin, E.,
Enthalpies of hydration of alkenes. 2. The n-heptenes and n-pentenes,
J. Phys. Chem., 1984, 88, 3684-3688. [all data]
Wiberg and Wasserman, 1981
Wiberg, K.B.; Wasserman, D.J.,
Enthalpies of hydration of alkenes. 1. The n-hexenes,
J. Am. Chem. Soc., 1981, 103, 6563-6566. [all data]
Sachek, Peshchenko, et al., 1974
Sachek, A.I.; Peshchenko, A.D.; Andreevskii, D.N.,
Heats of formation of secondary pentanols and hexanols,
Russ. J. Phys. Chem. (Engl. Transl.), 1974, 48, 617. [all data]
Tanaka, Luo, et al., 1988
Tanaka, R.; Luo, B.; Benson, G.C.; Lu, B.C.-Y.,
Excess isobaric heat capacities and excess volumes of some hexanol + n-heptane mixtures,
Thermochim. Acta, 1988, 127, 15-23. [all data]
Ortega, 1986
Ortega, J.,
Excess molar heat capacities of the binary mixtures of cyclohexane with isomers of hexanol at 298.15 K,
Rev. Latinoam. Ing. Quim. Quim. Apl., 1986, 16, 307-315. [all data]
Gude and Teja, 1995
Gude, M.; Teja, A.S.,
Vapor-Liquid Critical Properties of Elements and Compounds. 4. Aliphatic Alkanols,
J. Chem. Eng. Data, 1995, 40, 1025-1036. [all data]
Rosenthal and Teja, 1990
Rosenthal, D.J.; Teja, A.S.,
The Critical Pressures and temperatures of Isomeric Alkanols,
Ind. Eng. Chem. to be published 1990 1990, 1990. [all data]
Rosenthal and Teja, 1989
Rosenthal, D.J.; Teja, A.S.,
Critical pressures and temperatures of isomeric alkanols,
Ind. Eng. Chem. Res., 1989, 28, 1693. [all data]
Anselme and Teja, 1988
Anselme, M.J.; Teja, A.S.,
Critical Temperatures and Densities of Isomeric Alkanols with Six to Ten Carbon Atoms,
Fluid Phase Equilib., 1988, 40, 127-34. [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]
Roganov, Pisarev, et al., 2005
Roganov, Gennady N.; Pisarev, Pavel N.; Emel'yanenko, Vladimir N.; Verevkin, Sergey P.,
Measurement and Prediction of Thermochemical Properties. Improved Benson-Type Increments for the Estimation of Enthalpies of Vaporization and Standard Enthalpies of Formation of Aliphatic Alcohols,
J. Chem. Eng. Data, 2005, 50, 4, 1114-1124, https://doi.org/10.1021/je049561m
. [all data]
Kulikov, Verevkin, et al., 2001
Kulikov, Dmitry; Verevkin, Sergey P.; Heintz, Andreas,
Determination of Vapor Pressures and Vaporization Enthalpies of the Aliphatic Branched C 5 and C 6 Alcohols,
J. Chem. Eng. Data, 2001, 46, 6, 1593-1600, https://doi.org/10.1021/je010187p
. [all data]
N'Guimbi, Berro, et al., 1999
N'Guimbi, J.; Berro, C.; Mokbel, I.; Rauzy, E.; Jose, J.,
Experimental vapour pressures of 13 secondary and tertiary alcohols---correlation and prediction by a group contribution method,
Fluid Phase Equilibria, 1999, 162, 1-2, 143-158, https://doi.org/10.1016/S0378-3812(99)00168-5
. [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]
Brazhnikov, Andreevskii, et al., 1975
Brazhnikov, M.M.; Andreevskii, D.N.; Sachek, A.I.; Peshchenko, A.D.,
Zh. Prikl. Khim. (Leningrad), 1975, 48, 10, 2181. [all data]
Majer, Svoboda, et al., 1985
Majer, V.; Svoboda, V.; Lencka, M.,
Enthalpies of vaporization and cohesive energies of dimethylpyridines and trimethylpyridines,
The Journal of Chemical Thermodynamics, 1985, 17, 4, 365-370, https://doi.org/10.1016/0021-9614(85)90133-8
. [all data]
Sachek, Markovnik, et al., 1984
Sachek, A.I.; Markovnik, V.S.; Peshchenko, A.D.; Shvaro, A.V.; Andreevskii, D.N.,
Khim. Prom-st. (Moscow), 1984, 337. [all data]
Wilhoit and Zwolinski, 1973
Wilhoit, R.C.; Zwolinski, B.J.,
Physical and thermodynamic properties of aliphatic alcohols,
J. Phys. Chem. Ref. Data Suppl., 1973, 1, 2, 1. [all data]
Hovorka, Lankelma, et al., 1938
Hovorka, Frank; Lankelma, Herman P.; Stanford, Spencer C.,
Thermodynamic Properties of the Hexyl Alcohols. II. Hexanols-1, -2, -3 and 2-Methylpentanol-1 and -4,
J. Am. Chem. Soc., 1938, 60, 4, 820-827, https://doi.org/10.1021/ja01271a018
. [all data]
Haas and Harrison, 1993
Haas, M.J.; Harrison, A.G.,
The Fragmentation of Proton-Bound Cluster Ions and the Gas-Phase Acidities of Alcohols,
Int. J. Mass Spectrom. Ion Proc., 1993, 124, 2, 115, https://doi.org/10.1016/0168-1176(93)80003-W
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid Pc Critical pressure Tboil Boiling point Tc Critical temperature Vc Critical volume ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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