1-Hexadecanol

Formula: C₁₆H₃₄O
Molecular weight: 242.4406
IUPAC Standard InChI: InChI=1S/C16H34O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h17H,2-16H2,1H3
IUPAC Standard InChIKey: BXWNKGSJHAJOGX-UHFFFAOYSA-N
CAS Registry Number: 36653-82-4
Chemical structure:
This structure is also available as a 2d Mol file
Other names: n-Cetyl alcohol; n-Hexadecan-1-ol; n-Hexadecanol; n-1-Hexadecanol; Adol 52; Adol 52 NF; Adol 54; Aldol 54; Alfol 16; Atalco C; Cachalot C-51; Cachalot C-52; Cetaffine; Cetal; Cetalol CA; Cetanol; Cetylic alcohol; Cetylol; Crodacol C; Crodacol-CAS; Crodacol-CAT; Elfacos C; Ethal; Ethol; Hexadecanol; Hexadecyl alcohol; Hyfatol 16; Lanol C; Lorol 24; Loxanol K; Loxanol K extra; Loxanwachs SK; Palmityl alcohol; Product 308; Siponol wax-A; Siponol CC; 1-Hexadecyl alcohol; Alcohol c-16; Hexadecan-1-ol; n-Hexadecyl alcohol; 1-Hydroxyhexadecane; Adol 520; Cachalot C-50; CO-1670; CO-1695; Dytol F-11; Cachalot C-50 NF; Cetyl alcohol NF; Crodacol C70; Crodacol C95 NF; Epal 16NF; Fancol CA; Lanette 16; Lipocol C; Lorol C16; LorolL 24; Philcohol 1600; Rita CA; Cetyl alcohol; 1-Hexanedecanol; 1-Cetanol; Epal 16; Hyfatol 16-95; Laurex 16; Alfol 16RD; Kalcol 6098; Palmitic alcohol; 19141-82-3; SSD; SSD RP; 8023-37-8; 124-29-8; 8032-16-4; 8032-89-1; 8032-17-5; SSD (Salt/Mix); SSD RP (Salt/Mix)
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Condensed phase thermochemistry data

Go To: Top, Phase change data, References, Notes

Data compiled as indicated in comments:
DH - Eugene S. Domalski and Elizabeth D. Hearing
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_solid	-164.1 ± 0.1	kcal/mol	Ccb	Mosselman and Dekker, 1975	ALS
Δ_fH°_solid	-164.21 ± 0.48	kcal/mol	Ccb	Gundry, Harrop, et al., 1969	ALS
Δ_fH°_solid	-163.32 ± 0.91	kcal/mol	Ccb	Parks, Mosley, et al., 1950	Reanalyzed by Cox and Pilcher, 1970, Original value = -163.55 kcal/mol; see Richardson and Parks, 1939; ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_solid	-2512. ± 2.	kcal/mol	Ccb	Freeman and Bagby, 1989	Corresponding Δ_fHº_solid = -154. kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_solid	-2502.1 ± 0.2	kcal/mol	Ccb	Mosselman and Dekker, 1975	Corresponding Δ_fHº_solid = -164.1 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_solid	-2506.28 ± 0.41	kcal/mol	Ccb	Gundry, Harrop, et al., 1969	Corresponding Δ_fHº_solid = -159.90 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Δ_cH°_solid	-2502.85 ± 0.90	kcal/mol	Ccb	Parks, Mosley, et al., 1950	Reanalyzed by Cox and Pilcher, 1970, Original value = -2502.67 kcal/mol; see Richardson and Parks, 1939; Corresponding Δ_fHº_solid = -163.32 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity	Value	Units	Method	Reference	Comment
S°_{solid,1 bar}	108.0	cal/mol*K	N/A	Parks, Kennedy, et al., 1956	Extrapolation below 80 K, 115.3 J/mol*K.; DH

Constant pressure heat capacity of liquid

C_p,liquid (cal/mol*K)	Temperature (K)	Reference	Comment
147.8	333.15	Khasanshin and Zykova, 1989	T = 333 to 583 K.; DH
125.	323.	Mosselman, Mourik, et al., 1974	T = 323 to 346 K.; DH

Constant pressure heat capacity of solid

C_p,solid (cal/mol*K)	Temperature (K)	Reference	Comment
101.	298.15	Mosselman, Mourik, et al., 1974	T = 293 to 311 K.; DH
105.46	290.	Parks, Kennedy, et al., 1956	T = 80 to 290 K.; DH

Phase change data

Go To: Top, Condensed phase thermochemistry data, References, Notes

Data compiled as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
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
T_boil	613.15	K	N/A	Senderens, 1925	Uncertainty assigned by TRC = 5. K; TRC
Quantity	Value	Units	Method	Reference	Comment
T_fus	322. ± 3.	K	AVG	N/A	Average of 16 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
T_triple	321. ± 3.	K	AVG	N/A	Average of 7 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
Δ_vapH°	25.74 ± 0.29	kcal/mol	CGC	Nichols, Kweskin, et al., 2006	AC
Δ_vapH°	26.00	kcal/mol	GS	Kulikov, Verevkin, et al., 2001	Based on data from 328. to 362. K.; AC
Δ_vapH°	26.89	kcal/mol	CGC	Ova, Koultek, et al., 2000	AC
Quantity	Value	Units	Method	Reference	Comment
Δ_subH°	40.51 ± 0.60	kcal/mol	C	Gundry, Harrop, et al., 1969	ALS
Δ_subH°	40.54	kcal/mol	N/A	Gundry, Harrop, et al., 1969	DRB
Δ_subH°	40.0 ± 0.5	kcal/mol	V	Davies and Kybett, 1965	ALS
Δ_subH°	40.51 ± 0.50	kcal/mol	N/A	Davies and Kybett, 1965	AC

Reduced pressure boiling point

T_boil (K)	Pressure (atm)	Reference	Comment
453.2	0.013	Aldrich Chemical Company Inc., 1990	BS

Enthalpy of vaporization

Δ_vapH (kcal/mol)	Temperature (K)	Method	Reference	Comment
24.00	347.	GS	Kulikov, Verevkin, et al., 2001	Based on data from 328. to 362. K.; AC
21.1	403.	N/A	N'Guimbi, Kasehgari, et al., 1992	Based on data from 343. to 463. K.; AC
16.5	524.	A	Stephenson and Malanowski, 1987	Based on data from 509. to 569. K.; AC
19.9	430.	A	Stephenson and Malanowski, 1987	Based on data from 415. to 487. K. See also Ambrose, Ellender, et al., 1974.; AC
26.15	329.	N/A	Stephenson and Malanowski, 1987	Based on data from 323. to 335. K.; AC
26.84	338.	N/A	Wilhoit and Zwolinski, 1973	Based on data from 323. to 376. K.; AC
18.8	423.	N/A	Wilhoit and Zwolinski, 1973	Based on data from 418. to 463. K.; AC
18.5	460.	DTA	Kemme and Kreps, 1969	Based on data from 445. to 598. K.; AC
26.17	329.	ME	Davies and Kybett, 1965	Based on data from 323. to 335. K.; AC

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)

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Temperature (K)	A	B	C	Reference	Comment
415.44 to 487.32	4.05181	1803.451	-152.831	Ambrose, Ellender, et al., 1974	Coefficents calculated by NIST from author's data.
498.46 to 569.1	4.10957	1845.188	-148.524	Ambrose and Sprake, 1970	Coefficents calculated by NIST from author's data.
445.3 to 598.3	4.16102	1880.126	-146.027	Kemme and Kreps, 1969

Enthalpy of sublimation

Δ_subH (kcal/mol)	Temperature (K)	Method	Reference	Comment
40.01 ± 0.50	314.	ME	Davies and Kybett, 1965	Based on data from 308. to 320. K. See also Stephenson and Malanowski, 1987.; AC

Enthalpy of fusion

Δ_fusH (kcal/mol)	Temperature (K)	Method	Reference	Comment
13.8	322.2	AC	Xing, Tan, et al., 2008	Based on data from 80. to 370. K.; AC
7.91	321.6	DSC	Ventol«65533», Calvet, et al., 2004	AC
8.119	322.9	N/A	Kuchhal, Shukla, et al., 1979	AC
8.3000	320.	N/A	Eykman, 1889	DH

Entropy of fusion

Δ_fusS (cal/mol*K)	Temperature (K)	Reference	Comment
25.93	320.	Eykman, 1889	DH

Enthalpy of phase transition

ΔH_trs (kcal/mol)	Temperature (K)	Initial Phase	Final Phase	Reference	Comment
2.9876	308.9	crystaline, III	crystaline, II	Petropavlov, Tsygankova, et al., 1988	DH
1.243	310.4	crystaline, II	crystaline, I	Petropavlov, Tsygankova, et al., 1988	DH
8.0306	322.3	crystaline, α	liquid	Mosselman, Mourik, et al., 1974	DH

Entropy of phase transition

ΔS_trs (cal/mol*K)	Temperature (K)	Initial Phase	Final Phase	Reference	Comment
9.66	308.9	crystaline, III	crystaline, II	Petropavlov, Tsygankova, et al., 1988	DH
4.02	310.4	crystaline, II	crystaline, I	Petropavlov, Tsygankova, et al., 1988	DH
24.93	322.3	crystaline, α	liquid	Mosselman, Mourik, et al., 1974	DH

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:

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Notes

Mosselman and Dekker, 1975
Mosselman, C.; Dekker, H., Enthalpies of formation of n-alkan-1-ols, J. Chem. Soc. Faraday Trans. 1, 1975, 417-424. [all data]

Gundry, Harrop, et al., 1969
Gundry, H.A.; Harrop, D.; Head, A.J.; Lewis, G.B., Thermodynamic properties of organic oxygen compounds. 21. Enthalpies of combustion of benzoic acid, pentan-1-ol, octan-1-ol, and hexadecan-1-ol, J. Chem. Thermodyn., 1969, 1, 321-332. [all data]

Parks, Mosley, et al., 1950
Parks, G.S.; Mosley, J.R.; Peterson, P.V., Jr., Heats of combustion and formation of some organic compounds containing oxygen, J. Chem. Phys., 1950, 18, 152. [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]

Richardson and Parks, 1939
Richardson, J.W.; Parks, G.S., Thermal data on organic compounds. XIX. Modern combustion data for some non-volatile compounds containing carbon, hydrogen and oxygen, J. Am. Chem. Soc., 1939, 61, 3543-3546. [all data]

Freeman and Bagby, 1989
Freeman, B.; Bagby, M.O., Heats of combustion of fatty esters and triglycerides, J. Am. Oil Chem. Soc., 1989, 66, 1601-1605. [all data]

Parks, Kennedy, et al., 1956
Parks, G.S.; Kennedy, W.D.; Gates, R.R.; Mosley, J.R.; Moore, G.E.; Renquist, M.L., Thermal data on organic compounds. XXVI. Some heat capacity, entropy and free energy data for seven compounds containing oxygen., Not In System, 1956, 78, 56-59. [all data]

Khasanshin and Zykova, 1989
Khasanshin, T.S.; Zykova, T.B., Specific heat of saturated monatomic alcohols, Inzh. -Fiz. Zhur., 1989, 56(6), 991-994. [all data]

Mosselman, Mourik, et al., 1974
Mosselman, C.; Mourik, J.; Dekker, H., Enthalpies of phase change and heat capacities of some long-chain alcohols. Adiabatic semi-microcalorimeter for studies of polymorphism, J. Chem. Thermodynam., 1974, 6, 477-487. [all data]

Senderens, 1925
Senderens, J.B., C. R. Hebd. Seances Acad. Sci., 1925, 181, 698. [all data]

Nichols, Kweskin, et al., 2006
Nichols, Gary; Kweskin, Sasha; Frericks, Margaret; Reiter, Sarah; Wang, Gin; Orf, Jennifer; Carvallo, Brett; Hillesheim, Dorothea; Chickos, James, Evaluation of the Vaporization, Fusion, and Sublimation Enthalpies of the 1-Alkanols: The Vaporization Enthalpy of 1-, 6-, 7-, and 9-Heptadecanol, 1-Octadecanol, 1-Eicosanol, 1-Docosanol, 1-Hexacosanol, and Cholesterol at T = 298.15 K by Correlation Gas Chromatography, J. Chem. Eng. Data, 2006, 51, 2, 475-482, https://doi.org/10.1021/je0503857 . [all data]

Kulikov, Verevkin, et al., 2001
Kulikov, Dmitry; Verevkin, Sergey P.; Heintz, Andreas, Enthalpies of vaporization of a series of aliphatic alcohols, Fluid Phase Equilibria, 2001, 192, 1-2, 187-207, https://doi.org/10.1016/S0378-3812(01)00633-1 . [all data]

Ova, Koultek, et al., 2000
Ova, P.V.; Koultek, B.; Hoskovec, M., Practice Oriented Results on Use and Production of Neem Ingredients and Pheromones VI, H. Kleeberg and C.P.W. Zebitz, ed(s)., Druck and Graphic, Giessen, 2000, 211-218. [all data]

Davies and Kybett, 1965
Davies, M.; Kybett, B., Sublimation and vaporization heats of long-chain alcohols, Trans. Faraday Soc., 1965, 61, 1608. [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

N'Guimbi, Kasehgari, et al., 1992
N'Guimbi, J.; Kasehgari, H.; Mokbel, I.; Jose, J., Tensions de vapeur d'alcools primaires dans le domaine 0,3 Pa à 1,5 kPa, Thermochimica Acta, 1992, 196, 2, 367-377, https://doi.org/10.1016/0040-6031(92)80100-B . [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]

Ambrose, Ellender, et al., 1974
Ambrose, D.; Ellender, J.H.; Sprake, C.H.S., Thermodynamic properties of organic oxygen compounds XXXV. Vapour pressures of aliphatic alcohols, The Journal of Chemical Thermodynamics, 1974, 6, 9, 909-914, https://doi.org/10.1016/0021-9614(74)90235-3 . [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]

Kemme and Kreps, 1969
Kemme, Herbert R.; Kreps, Saul I., Vapor pressure of primary n-alkyl chlorides and alcohols, J. Chem. Eng. Data, 1969, 14, 1, 98-102, https://doi.org/10.1021/je60040a011 . [all data]

Ambrose and Sprake, 1970
Ambrose, D.; Sprake, C.H.S., Thermodynamic properties of organic oxygen compounds XXV. Vapour pressures and normal boiling temperatures of aliphatic alcohols, The Journal of Chemical Thermodynamics, 1970, 2, 5, 631-645, https://doi.org/10.1016/0021-9614(70)90038-8 . [all data]

Xing, Tan, et al., 2008
Xing, J.; Tan, Z.-C.; Shi, Q.; Tong, B.; Wang, S.-X.; Li, Y.-S., Heat capacity and thermodynamic properties of 1-hexadecanol, J Therm Anal Calorim, 2008, 92, 2, 375-380, https://doi.org/10.1007/s10973-007-8955-1 . [all data]

Ventol«65533», Calvet, et al., 2004
Ventol«65533», L.; Calvet, T.; Cuevas-Diarte, M.A.; Ram«65533»rez, M.; Oonk, H.A.J.; Mondieig, D.; Negrier, Ph., Melting behaviour in the n-alkanol family. Enthalpy?entropy compensation, Phys. Chem. Chem. Phys., 2004, 6, 8, 1786, https://doi.org/10.1039/b313106h . [all data]

Kuchhal, Shukla, et al., 1979
Kuchhal, Y.K.; Shukla, R.N.; Biswas, A.B., Differential thermal analysis of n-long chain alcohols and corresponding alkoxy ethanols, Thermochimica Acta, 1979, 31, 1, 61-70, https://doi.org/10.1016/0040-6031(79)80008-8 . [all data]

Eykman, 1889
Eykman, J.F., Zur kryoskopischen Molekulargewichtsbestimmung, Z. Physik. Chem., 1889, 4, 497-519. [all data]

Petropavlov, Tsygankova, et al., 1988
Petropavlov, N.N.; Tsygankova, I.G.; Teslenko, L.A., Microcalorimetric investigation of polymorphic transitions in organic crystals, Sov. Phys. Crystallogr., 1988, 33(6), 853-855. [all data]

Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, References

Symbols used in this document:

C_p,liquid	Constant pressure heat capacity of liquid
C_p,solid	Constant pressure heat capacity of solid
S°_{solid,1 bar}	Entropy of solid at standard conditions (1 bar)
T_boil	Boiling point
T_fus	Fusion (melting) point
T_triple	Triple point temperature
ΔH_trs	Enthalpy of phase transition
ΔS_trs	Entropy of phase transition
Δ_cH°_solid	Enthalpy of combustion of solid at standard conditions
Δ_fH°_solid	Enthalpy of formation of solid at standard conditions
Δ_fusH	Enthalpy of fusion
Δ_fusS	Entropy of fusion
Δ_subH	Enthalpy of sublimation
Δ_subH°	Enthalpy of sublimation at standard conditions
Δ_vapH	Enthalpy of vaporization
Δ_vapH°	Enthalpy of vaporization at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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