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Octadecanoic acid

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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
Deltafliquid-891. ± 2.kJ/molCcbLebedeva, 1964Hfusion =10.81±0.10 kcal/mol; ALS
Quantity Value Units Method Reference Comment
Deltacliquid-11280.1 ± 1.9kJ/molCcbAdriaanse, Dekker, et al., 1965Reanalyzed by Cox and Pilcher, 1970, Original value = -11279.4 ± 1.9 kJ/mol; Hfusion=63.0 kJ/mol; Corresponding «DELTA»fliquid = -948.0 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacliquid-11336.8 ± 2.1kJ/molCcbLebedeva, 1964Hfusion =10.81±0.10 kcal/mol; Corresponding «DELTA»fliquid = -891.28 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
Deltafsolid-912. ± 11.kJ/molCcbMedard and Thomas, 1952Reanalyzed by Cox and Pilcher, 1970, Original value = -897.9 kJ/mol; Author's hf291_condensed=-223.8 kcal/mol; ALS
Quantity Value Units Method Reference Comment
Deltacsolid-11290.79kJ/molCcbShkaraputa, Danilenko, et al., 1984Corresponding «DELTA»fsolid = -937.33 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacsolid-11271. ± 13.kJ/molCcbSwain, Silbert, et al., 1964Corresponding «DELTA»fsolid = -956.9 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacsolid-11316. ± 11.kJ/molCcbMedard and Thomas, 1952Reanalyzed by Cox and Pilcher, 1970, Original value = -11331.9 kJ/mol; Author's hf291_condensed=-223.8 kcal/mol; Corresponding «DELTA»fsolid = -912.07 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacsolid-11298.kJ/molCcbEmery and Benedict, 1911Corresponding «DELTA»fsolid = -930. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
solid,1 bar435.6J/mol*KN/ASingleton, Ward, et al., 1950Extrapolation below 90 K, 64.4 J/mol*K.; DH

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
501.55298.15Schaake, van Miltenburg, et al., 1982T = 80 to 355 K.; DH
561.9298.15Singleton, Ward, et al., 1950T = 154 to 350 K.; 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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil634.2KN/AAldrich Chemical Company Inc., 1990BS
Tboil631.15KN/AKrafft, 1880Uncertainty assigned by TRC = 5. K; TRC
Quantity Value Units Method Reference Comment
Tfus341. ± 3.KAVGN/AAverage of 31 out of 32 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple342.49KN/ASchaake, van Miltenburg, et al., 1982, 2Uncertainty assigned by TRC = 0.02 K; TRC
Ttriple341.85KN/ASpizzichino, 1956Uncertainty assigned by TRC = 0.5 K; TRC
Ttriple342.65KN/ASingleton, Ward, et al., 1950, 2Uncertainty assigned by TRC = 0.01 K; TRC
Quantity Value Units Method Reference Comment
Ptriple4.2663×10-8barN/ASpizzichino, 1956Uncertainty assigned by TRC = 1.9998×10-8 bar; TRC
Quantity Value Units Method Reference Comment
Tc805.09KN/AD'Souza and Teja, 1987Uncertainty assigned by TRC = 3.5 K; Ambrose's procedure; TRC
Quantity Value Units Method Reference Comment
Pc13.2658barN/AD'Souza and Teja, 1987Uncertainty assigned by TRC = 0.85 bar; Ambrose's procedure; TRC
Quantity Value Units Method Reference Comment
Deltasub204. ± 9.kJ/molTPDCappa, Lovejoy, et al., 2008AC

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
124.3364.AStephenson and Malanowski, 1987Based on data from 349. - 415. K.; AC
100.6472.AStephenson and Malanowski, 1987Based on data from 457. - 649. K.; AC
118.9 ± 2.0379.ME,TEde Kruif, Schaake, et al., 1982Based on data from 366. - 389. K.; AC
79.8515.ICramer, 1943AC

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
446.9 - 643.5.725443348.131-57.825Stull, 1947Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

DeltasubH (kJ/mol) Temperature (K) Method Reference Comment
158.5291. - 309.TPTDChattopadhyay and Ziemann, 2005AC
158.296. - 319.TPTDChattopadhyay, Tobias, et al., 2001Experimental values based on the TPTD method are often inconsistent with values determined using other experimental methods; AC
166.5 ± 4.2336.MEDavies and Malpass, 1961Based on data from 331. - 340. K. See also Cox and Pilcher, 1970, 2.; AC
167. ± 4.2330.89VDavies and Malpass, 1961, 2ALS

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Method Reference Comment
61.300342.75N/ASato, Yoshimoto, et al., 1990DH
60.4338.3N/AMoore, Koelmel, et al., 2007AC
63.2342.8DSCMoreno, Cordobilla, et al., 2007AC
57.8344.1DSCTeixeira, Gonçalves da Silva, et al., 2006AC
50.93340.2ACYu, Meng, et al., 2000AC
61.21342.5N/ADomalski and Hearing, 1996AC
68.450342.65N/ASingleton, Ward, et al., 1950DH
64.643326.1N/AEykman, 1889DH

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
178.8342.75Sato, Yoshimoto, et al., 1990DH
1998.342.65Singleton, Ward, et al., 1950DH
198.326.1Eykman, 1889DH

Enthalpy of phase transition

DeltaHtrs (kJ/mol) Temperature (K) Initial Phase Final Phase Reference Comment
61.208342.49crystaline, IliquidSchaake, van Miltenburg, et al., 1982DH

Entropy of phase transition

DeltaStrs (J/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
178.12342.49crystaline, IliquidSchaake, van Miltenburg, et al., 1982DH

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:


Reaction thermochemistry data

Go To: Top, 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

Oleic Acid + Hydrogen = Octadecanoic acid

By formula: C18H34O2 + H2 = C18H36O2

Quantity Value Units Method Reference Comment
Deltar-123.6 ± 1.6kJ/molChydRogers, Hoyte, et al., 1978liquid phase; solvent: Hexane; Authors gave two values
Deltar-125.1 ± 0.8kJ/molChydRogers, Hoyte, et al., 1978liquid phase; solvent: Hexane; Authors gave two values

2Hydrogen + Linoelaidic acid = Octadecanoic acid

By formula: 2H2 + C18H32O2 = C18H36O2

Quantity Value Units Method Reference Comment
Deltar-248.8 ± 0.5kJ/molChydRogers, Hoyte, et al., 1978liquid phase; solvent: Hexane

3Hydrogen + 9,12,15-Octadecatrienoic acid, (Z,Z,Z)- = Octadecanoic acid

By formula: 3H2 + C18H30O2 = C18H36O2

Quantity Value Units Method Reference Comment
Deltar-380.2 ± 1.9kJ/molChydRogers, Hoyte, et al., 1978liquid phase; solvent: Hexane

9-Octadecenoic acid, (E)- + Hydrogen = Octadecanoic acid

By formula: C18H34O2 + H2 = C18H36O2

Quantity Value Units Method Reference Comment
Deltar-120.2 ± 2.0kJ/molChydRogers, Hoyte, et al., 1978liquid phase; solvent: Hexane

2Hydrogen + 9,12-Octadecadienoic acid (Z,Z)- = Octadecanoic acid

By formula: 2H2 + C18H32O2 = C18H36O2

Quantity Value Units Method Reference Comment
Deltar-254.4 ± 1.5kJ/molChydRogers, Hoyte, et al., 1978liquid phase; solvent: Hexane

IR Spectrum

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), References, Notes

Data compiled by: Coblentz Society, Inc.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director


Mass spectrum (electron ionization)

Go To: Top, 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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Mass spectrum
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Additional Data

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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 NIST Mass Spectrometry Data Center, 1998.
NIST MS number 290961

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


References

Go To: Top, 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.

Lebedeva, 1964
Lebedeva, N.D., Heats of combustion of monocarboxylic acids, Russ. J. Phys. Chem. (Engl. Transl.), 1964, 38, 1435-1437. [all data]

Adriaanse, Dekker, et al., 1965
Adriaanse, N.; Dekker, H.; Coops, J., Heats of combustion of normal saturated fatty acids and their methyl esters, Rec. Trav. Chim. Pays/Bas, 1965, 84, 393-407. [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]

Medard and Thomas, 1952
Medard, L.; Thomas, M., Determination des chaleurs de combustion de douze composes organiques utilises dans les poudres et enplosies, Mem. Poudres, 1952, 34, 421-442. [all data]

Shkaraputa, Danilenko, et al., 1984
Shkaraputa, L.N.; Danilenko, V.V.; Sklyar, V.T.; Kendis, M.Sh.; Ratushnaya, V.I., Changes in enthalpy in the reaction of stearic acid with dextramine, Neftepererab. Neftekhim. (Moscow), 1984, 27, 31-32. [all data]

Swain, Silbert, et al., 1964
Swain, H.A., Jr.; Silbert, L.S.; Miller, J.G., The heats of combustion of aliphatic long chain peroxyacids, t-butyl peroxyesters, and related acids and esters, J. Am. Chem. Soc., 1964, 86, 2562-2566. [all data]

Emery and Benedict, 1911
Emery, A.G.; Benedict, F.G., The heat of combustion of compounds of physiological importance, Am. J. Physiol., 1911, 28, 301-307. [all data]

Singleton, Ward, et al., 1950
Singleton, W.S.; Ward, T.L.; Dollear, F.G., Physical properties of fatty acids. I. Some dilatometric and thermal properties of stearic acid in two polymorphic forms, J. Am. Oil Chem. Soc., 1950, 27, 143-146. [all data]

Schaake, van Miltenburg, et al., 1982
Schaake, R.C.F.; van Miltenburg, J.C.; De Kruif, C.G., Thermodynamic properties of the normal alkanoic acids. II. Molar heat capacities of seven even-numbered normal alkanoic acids, J. Chem. Thermodynam., 1982, 14, 771-778. [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]

Krafft, 1880
Krafft, F., The production of laurinaldehyde c(12)h(24)o, myristinaldehyde c(14)h(28)o, palmitinaldehyde c(16)h(32)o, stearinaldehyde c(18)h(36)o: I investigation of aldehydes, Ber. Dtsch. Chem. Ges., 1880, 13, 1413-8. [all data]

Schaake, van Miltenburg, et al., 1982, 2
Schaake, R.C.F.; van Miltenburg, J.C.; De Kruif, C.G., Thermodynamic properties of the normal alkanoic acids. II. Molar heat capacities of seven even-numbered normal alkanoic acids., J. Chem. Thermodyn., 1982, 14, 771-8. [all data]

Spizzichino, 1956
Spizzichino, C., Contribution a l'etude des tensions de vapeur et des chaleurs de vaporisation des acides gras, esters methyliques et alcools gras a des pressions inferieures a 1 mm de mercure, J. des Recherches du C.N.R.S., 1956, 34, 1-24. [all data]

Singleton, Ward, et al., 1950, 2
Singleton, W.S.; Ward, T.L.; Dollear, F.G., Physical Properties of Fatty Acids I. Some Dilatometric and Thermal Properties of Stearic Acid in Two Polymorphic Forms, J. Am. Oil Chem. Soc., 1950, 27, 143. [all data]

D'Souza and Teja, 1987
D'Souza, R.; Teja, A.S., The prediction of the vapor pressures of carboxylic acids, Chem. Eng. Commun., 1987, 61, 13. [all data]

Cappa, Lovejoy, et al., 2008
Cappa, Christopher D.; Lovejoy, Edward R.; Ravishankara, A.R., Evaporation Rates and Vapor Pressures of the Even-Numbered C 8 -C 18 Monocarboxylic Acids, J. Phys. Chem. A, 2008, 112, 17, 3959-3964, https://doi.org/10.1021/jp710586m . [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]

de Kruif, Schaake, et al., 1982
de Kruif, C.G.; Schaake, R.C.F.; van Miltenburg, J.C.; van der Klauw, K.; Blok, J.G., Thermodynamic properties of the normal alkanoic acids III. Enthalpies of vaporization and vapour pressures of 13 normal alkanoic acids, The Journal of Chemical Thermodynamics, 1982, 14, 8, 791-798, https://doi.org/10.1016/0021-9614(82)90176-8 . [all data]

Cramer, 1943
Cramer, K.S.N., Chem. Zentr. II, 1943, 2234. [all data]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [all data]

Chattopadhyay and Ziemann, 2005
Chattopadhyay, Sulekha; Ziemann, Paul J., Vapor Pressures of Substituted and Unsubstituted Monocarboxylic and Dicarboxylic Acids Measured Using an Improved Thermal Desorption Particle Beam Mass Spectrometry Method, Aerosol Science and Technology, 2005, 39, 11, 1085-1100, https://doi.org/10.1080/02786820500421547 . [all data]

Chattopadhyay, Tobias, et al., 2001
Chattopadhyay, Sulekha; Tobias, Herbert J.; Ziemann, Paul J., A Method for Measuring Vapor Pressures of Low-Volatility Organic Aerosol Compounds Using a Thermal Desorption Particle Beam Mass Spectrometer, Anal. Chem., 2001, 73, 16, 3797-3803, https://doi.org/10.1021/ac010304j . [all data]

Davies and Malpass, 1961
Davies, Mansel; Malpass, V.E., 212. Heats of sublimation of straight-chain monocarboxylic acids, J. Chem. Soc., 1961, 1048, https://doi.org/10.1039/jr9610001048 . [all data]

Cox and Pilcher, 1970, 2
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [all data]

Davies and Malpass, 1961, 2
Davies, M.; Malpass, V.E., Heats of sublimation of straight-chain monocarboxylic acids, J. Chem. Soc., 1961, 1048-10. [all data]

Sato, Yoshimoto, et al., 1990
Sato, K.; Yoshimoto, N.; Suzuki, M.; Kobayashi, M.; Kaneko, F., Structure and transformation in polymorphism of petroselinic acid (cis-w-12-octadecenoic acid), J. Phys. Chem., 1990, 94, 3180-3185. [all data]

Moore, Koelmel, et al., 2007
Moore, David J.; Koelmel, Donald; Laura, Donna; Bedford, Eilidh, Infrared spectroscopy and differential scanning calorimetry studies of binary combinations of cis-6-octadecenoic acid and octadecanoic acid, Chemistry and Physics of Lipids, 2007, 150, 1, 109-115, https://doi.org/10.1016/j.chemphyslip.2007.06.217 . [all data]

Moreno, Cordobilla, et al., 2007
Moreno, Evelyn; Cordobilla, Raquel; Calvet, Teresa; Cuevas-Diarte, M.A.; Gbabode, Gabin; Negrier, Philippe; Mondieig, Denise; Oonk, Harry A.J., Polymorphism of even saturated carboxylic acids from n-decanoic to n-eicosanoic acid, New J. Chem., 2007, 31, 6, 947, https://doi.org/10.1039/b700551b . [all data]

Teixeira, Gonçalves da Silva, et al., 2006
Teixeira, A.C.T.; Gonçalves da Silva, A.M.P.S.; Fernandes, A.C., Phase behaviour of stearic acid--stearonitrile mixtures, Chemistry and Physics of Lipids, 2006, 144, 2, 160-171, https://doi.org/10.1016/j.chemphyslip.2006.09.001 . [all data]

Yu, Meng, et al., 2000
Yu, S.; Meng, S.; Tan, Z.; Li, L.; Zhang, J., Taiyangneng Xuebao, 2000, 21, 2, 171. [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]

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

Rogers, Hoyte, et al., 1978
Rogers, D.W.; Hoyte, O.P.A.; Ho, R.K.C., Heats of hydrogenation of large molecules. Part 2. Six unsaturated and polyunsaturated fatty acids, J. Chem. Soc. Faraday Trans. 1, 1978, 74, 46-52. [all data]


Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References