1-Hexanol
- Formula: C6H14O
- Molecular weight: 102.1748
- IUPAC Standard InChIKey: ZSIAUFGUXNUGDI-UHFFFAOYSA-N
- CAS Registry Number: 111-27-3
- 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. - Isotopologues:
- Other names: Hexyl alcohol; n-Hexan-1-ol; n-Hexanol; n-Hexyl alcohol; Amylcarbinol; Caproyl alcohol; Hexanol; Pentylcarbinol; 1-Hexyl alcohol; 1-Hydroxyhexane; n-C6H13OH; Hexan-1-ol; Hexanol-(1); Epal 6; NSC 9254
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Gas phase thermochemistry data
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 as indicated in comments:
DRB - Donald R. Burgess, Jr.
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 | -75. ± 2. | kcal/mol | AVG | N/A | Average of 7 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
S°gas | 105.10 ± 0.50 | cal/mol*K | N/A | Green J.H.S., 1961 | Other third-law value of entropy at 298.15 K is 441.41(4.18) J/mol*K [ Chermin H.A.G., 1961].; GT |
Condensed phase 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 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 | -90.22 ± 0.11 | kcal/mol | Ccb | Mosselman and Dekker, 1975 | ALS |
ΔfH°liquid | -90.67 ± 0.24 | kcal/mol | Ccb | Chao and Rossini, 1965 | see Rossini, 1934; ALS |
ΔfH°liquid | -91.75 ± 0.48 | kcal/mol | Ccb | Green, 1960 | ALS |
ΔfH°liquid | -92.66 | kcal/mol | Cm | Kelley, 1929 | hfusion=3.68 kcal/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -952.29 ± 0.11 | kcal/mol | Ccb | Mosselman and Dekker, 1975 | Corresponding ΔfHºliquid = -90.225 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -951.86 ± 0.22 | kcal/mol | Ccb | Chao and Rossini, 1965 | see Rossini, 1934; Corresponding ΔfHºliquid = -90.65 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -950.78 ± 0.48 | kcal/mol | Ccb | Green, 1960 | Corresponding ΔfHºliquid = -91.73 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -950.78 | kcal/mol | Ccb | Verkade and Coops, 1927 | Corrected for 298 and 1 atm.; Corresponding ΔfHºliquid = -91.73 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 68.69 | cal/mol*K | N/A | Kelley, 1929, 2 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
58.13 | 298.15 | Atrashenok, Nesterov, et al., 1991 | T = 227 to 363 K. Cp(liq) = 2.37095 - 0.0851173(T/100) - 0.195794(T/100)2 - 0.00639224(T/100)3 + 0.0530459(T/100)4 - 0.00859433(T/100)5 kJ/kg*K.; DH |
57.96 | 298.15 | Vesely, Barcal, et al., 1989 | T = 298.15 to 318.15 K.; DH |
57.677 | 298.15 | Andreoli-Ball, Patterson, et al., 1988 | DH |
56.848 | 298.15 | Ortega, 1986 | DH |
57.498 | 298.15 | Tanaka, Toyama, et al., 1986 | DH |
57.285 | 298.15 | Costas and Patterson, 1985 | T = 283.15, 298.15, 313.15 K.; DH |
57.271 | 298.15 | Bravo, Pintos, et al., 1984 | DH |
59.548 | 300.607 | Kalinowska and Woycicki, 1984 | T = 230 to 300 K. Value is unsmoothed experimental datum.; DH |
57.677 | 298.15 | Zegers and Somsen, 1984 | DH |
57.517 | 298.15 | Benson, D'Arcy, et al., 1983 | DH |
56.52 | 293.15 | Arutyunyan, 1981 | T = 273 to 533 K. p = 0.1 MPa. Unsmoothed experimental datum at 293.15 K, Cp = 2.315 kJ/kg*K.; DH |
56.52 | 293.15 | Arutyunyan, 1981 | T = 293 to 393 K. p = 0.1 MPa. Unsmoothed experimental datum given as 2.315 kJ/kg*K. Cp given from 293.15 to 533.15 K for pressure range 10 to 60 MPa.; DH |
59.20 | 303.74 | Griigo'ev, Yanin, et al., 1979 | T = 303 to 462 K. p = 0.98 bar.; DH |
58.51 | 298. | Hutchinson and Bailey, 1959 | DH |
55.559 | 290.01 | Kelley, 1929, 2 | T = 16 to 298 K. Value is unsmoothed experimental datum.; DH |
Phase change data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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 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
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 430. ± 2. | K | AVG | N/A | Average of 54 out of 59 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 225. ± 5. | K | AVG | N/A | Average of 6 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 225.8 | K | N/A | Kelley, 1929, 3 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 610.5 ± 0.9 | K | AVG | N/A | Average of 8 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 33.7 ± 0.2 | atm | N/A | Gude and Teja, 1995 | |
Pc | 33.75 | atm | N/A | Quadri, Khilar, et al., 1991 | Uncertainty assigned by TRC = 0.49 atm; TRC |
Pc | 33.68 | atm | N/A | Rosenthal and Teja, 1990 | Uncertainty assigned by TRC = 0.06 atm; TRC |
Pc | 33.68 | atm | N/A | Rosenthal and Teja, 1989 | Uncertainty assigned by TRC = 0.20 atm; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Vc | 0.387 | l/mol | N/A | Gude and Teja, 1995 | |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 2.58 ± 0.02 | mol/l | N/A | Gude and Teja, 1995 | |
ρc | 2.62 | mol/l | N/A | Teja, Lee, et al., 1989 | TRC |
ρc | 2.54 | mol/l | N/A | Anselme and Teja, 1988 | Uncertainty assigned by TRC = 0.06 mol/l; TRC |
ρc | 2.62 | mol/l | N/A | Efremov, 1966 | Uncertainty assigned by TRC = 0.03 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 14.7 ± 0.4 | kcal/mol | AVG | N/A | Average of 13 out of 14 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
10.6 | 430.5 | N/A | Majer and Svoboda, 1985 | |
14.3 | 359. | EB | Gierycz, Kosowski, et al., 2009 | Based on data from 344. to 384. K.; AC |
12.3 | 385. | EB | Tan, Li, et al., 2004 | Based on data from 370. to 416. K.; AC |
14.8 | 288. | GS | Kulikov, Verevkin, et al., 2001 | Based on data from 265. to 328. K.; AC |
14.8 ± 0.05 | 301. | GS | Verevkin, 1998 | Based on data from 268. to 333. K.; AC |
14.6 | 296. | N/A | N'Guimbi, Kasehgari, et al., 1992 | Based on data from 253. to 338. K.; AC |
13.8 | 313. | A | Stephenson and Malanowski, 1987 | Based on data from 298. to 343. K.; AC |
14.0 | 340. | DTA | Stephenson and Malanowski, 1987 | Based on data from 325. to 431. K. See also Kemme and Kreps, 1969.; AC |
14.0 ± 0.05 | 328. | C | Majer, Svoboda, et al., 1985 | AC |
13.8 ± 0.05 | 343. | C | Majer, Svoboda, et al., 1985 | AC |
13.2 ± 0.05 | 358. | C | Majer, Svoboda, et al., 1985 | AC |
12.9 ± 0.05 | 368. | C | Majer, Svoboda, et al., 1985 | AC |
11.4 | 395. | EB | Reddy, Rao, et al., 1985 | Based on data from 380. to 417. K.; AC |
13.8 | 323. | N/A | Wilhoit and Zwolinski, 1973 | Based on data from 308. to 430. K.; AC |
13.4 | 349. | N/A | Rose and Supina, 1961 | Based on data from 334. to 381. K.; AC |
13.8 | 348. | N/A | Butler, Ramchandani, et al., 1935 | Based on data from 333. to 425. K. See also Boublik, Fried, et al., 1984.; AC |
Enthalpy of vaporization
ΔvapH = A exp(-αTr)
(1 − Tr)β
ΔvapH =
Enthalpy of vaporization (at saturation pressure)
(kcal/mol)
Tr = reduced temperature (T / Tc)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | 298. to 368. |
---|---|
A (kcal/mol) | 17.22 |
α | -1.059 |
β | 1.0052 |
Tc (K) | 610. |
Reference | Majer and Svoboda, 1985 |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
325.4 to 430.5 | 4.40700 | 1422.031 | -107.706 | Kemme and Kreps, 1969 | |
334.1 to 381.7 | 5.63785 | 2117.967 | -51.988 | Rose and Supina, 1961 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
3.6759 | 225.8 | Kelley, 1929, 2 | DH |
3.700 | 225.8 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
16.28 | 225.8 | Kelley, 1929, 2 | DH |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Green J.H.S., 1961
Green J.H.S.,
Thermodynamic properties of the normal alcohols C1-C12,
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Mosselman and Dekker, 1975
Mosselman, C.; Dekker, H.,
Enthalpies of formation of n-alkan-1-ols,
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Chao and Rossini, 1965
Chao, J.; Rossini, F.D.,
Heats of combustion, formation, and isomerization of nineteen alkanols,
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Rossini, 1934
Rossini, F.D.,
Heats of combustion and of formation of the normal aliphatic alcohols in the gaseous and liquid states, and the energies of their atomic linkages,
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Green, 1960
Green, J.H.S.,
Revision of the values of the heats of formation of normal alcohols,
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Kelley, 1929
Kelley, K.K.,
The heat capacities of ethyl and hexyl alcohols from 16°K. to 298°K. and the corresponding entropies and free energies and free energies,
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Verkade and Coops, 1927
Verkade, P.E.; Coops, J., Jr.,
Calorimetric researches XIV. Heats of combustion of successive members of homologous series: the normal primary aliphatic alcohols,
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Kelley, 1929, 2
Kelley, K.K.,
The heat capacities of ethyl and hexyl alcohols from 16°K to 298°K and the corresponding entropies and free energies,
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Atrashenok, Nesterov, et al., 1991
Atrashenok, T.R.; Nesterov, N.A.; Zhuk, I.P.; Peshchenko, A.D.,
Measured specific heats of hexan-1-ol and 3-methyl-2-butanol over wide temperature ranges,
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Vesely, F.; Barcal, P.; Zabransky, M.; Svoboda, V.,
Heat capacities of 4-methyl-2-pentanone, 2,6-dimethyl-4-heptanone, 1-hexanol, 1-heptanol, and 1-octanol in the temperature range 298-318 K,
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Andreoli-Ball, Patterson, et al., 1988
Andreoli-Ball, L.; Patterson, D.; Costas, M.; Caceres-Alonso, M.,
Heat capacity and corresponding states in alkan-1-ol-n-alkane systems, J. Chem. Soc.,
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Ortega, 1986
Ortega, J.,
Excess molar heat capacities of the binary mixtures of cyclohexane with isomers of hexanol at 298.15 K,
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Heat capacities of {xCnH2n+1OH+(1-x)C7H16} for n = 1 to 6 at 298.15 K,
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Excess volumes excess heat capacities of some mixtures: (an isomer of hexanol + an n-alkane) at 298.15 K,
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Heat capacities of liquids in the temperature interval between 90 and 300 K and at atmospheric pressure. III. Heat capacities and excess heat capacities of (n-hexanol-1-ol + n-hexane),
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Zegers, H.C.; Somsen, G.,
Partial molar volumes and heat capacities in (dimethylformamide + an n-alkanol),
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Benson, G.C.; D'Arcy, P.J.; Sugamori, M.E.,
Heat capacities of binary mixtures of 1-hexanol with hexane isomers at 298.15 K,
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Arutyunyan, 1981
Arutyunyan, G.S.,
Experimental investigaiton of the isobaric heat capacity of n-hexyl alcohol at different temperatures and pressures,
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Hutchinson and Bailey, 1959
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A thermodynamic study of colloidal electrolyte solutions. II. Heat capacities of solubilized systems, experimental,
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Kelley, K.K.,
The heat capacities of ethyl and hexyl alcohols from 16 to 298 K and the corresponding entropies and free energies,
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Gude and Teja, 1995
Gude, M.; Teja, A.S.,
Vapor-Liquid Critical Properties of Elements and Compounds. 4. Aliphatic Alkanols,
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Quadri, Khilar, et al., 1991
Quadri, S.K.; Khilar, K.C.; Kudchadker, A.P.; Patni, M.J.,
Measurement of the critical temperatures and critical pressures of some thermally stable or mildly unstable alkanols,
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The Critical Pressures and temperatures of Isomeric Alkanols,
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Critical pressures and temperatures of isomeric alkanols,
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Teja, A.S.; Lee, R.J.; Rosenthal, D.J.; Anselme, M.J.,
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Isothermal and isobaric vapor--liquid equilibria for the binary system trimethylbenzoquinone + n-hexanol,
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Enthalpies of vaporization of a series of aliphatic alcohols,
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Verevkin, Sergey P.,
Thermochemistry of phenols: experimental standard molar enthalpies of formation of 2-phenylphenol, 4-phenylphenol, 2,6-diphenylphenol, and 2,2´- and 4,4´-dihydroxybiphenyl,
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Vapor pressure of primary n-alkyl chlorides and alcohols,
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Enthalpies of vaporization of aliphatic C5 and C6 alcohols,
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Reddy, K. Dayananda; Rao, M.V. Prabhakara; Ramakrishna, M.,
Activity coefficients and excess Gibbs free energies for the systems isobutyl methyl ketone(1)-1-pentanol(2) and isobutyl methyl ketone(1)-1-hexanol (2),
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Physical and thermodynamic properties of aliphatic alcohols,
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Rose, Arthur; Supina, W.R.,
Vapor Pressure and Vapor-Liquid Equilibrium Data for Methyl Esters of the Common Saturated Normal Fatty Acids.,
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58. The solubility of non-electrolytes. Part I. The free energy of hydration of some aliphatic alcohols,
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Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E.,
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. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid Pc Critical pressure S°gas Entropy of gas at standard conditions S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature Vc Critical volume ΔcH°liquid Enthalpy of combustion of liquid at standard conditions 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 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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