Octadecanoic acid
- Formula: C18H36O2
- Molecular weight: 284.4772
- IUPAC Standard InChIKey: QIQXTHQIDYTFRH-UHFFFAOYSA-N
- CAS Registry Number: 57-11-4
- Chemical structure:
This structure is also available as a 2d Mol file - Other names: Stearic acid; n-Octadecanoic acid; Humko Industrene R; Hydrofol Acid 150; Hystrene S-97; Hystrene T-70; Hystrene 80; Industrene R; Kam 1000; Kam 2000; Kam 3000; Neo-Fat 18; Neo-Fat 18-53; Neo-Fat 18-54; Neo-Fat 18-55; Neo-Fat 18-59; NAA 173; PD 185; Stearex Beads; Stearophanic acid; Steric acid; Vanicol; 1-Heptadecanecarboxylic acid; Heptadecanecarboxylic acid; Neo-fat 18-61; Pearl stearic; Century 1240; Dar-chem 14; Emersol 120; Emersol 132; Emersol 150; Formula 300; Glycon DP; Glycon TP; Glycon S-70; Glycon S-80; Glycon S-90; Groco 54; Groco 55; Groco 55L; Groco 58; Groco 59; Hy-phi 1199; Hy-phi 1205; Hy-phi 1303; Hy-phi 1401; Hydrofol acid 1655; Hydrofol acid 1855; Hydrofol 1895; Hystrene 4516; Hystrene 5016; Hystrene 7018; Hystrene 9718; Industrene 5016; Neo-Fat 18-S; Tegostearic 254; Tegostearic 255; Tegostearic 272; Cetylacetic acid; Industrene 8718; Industrene 9018; Barolub FTA; Loxiol G 20; Lunac S 20; Emersol 153; Century 1210; Century 1220; Century 1230; Emersol 6349; Hystrene 7018 FG; Hystrene 9718 NF FG; Industrene 4518; Industrene 7018 FG; n-Octadecylic acid; Pristerene 4904; Promulsin; Proviscol wax; Stearex; Tsubaki; Vis-Plus; Prifac 2918; Adeka Fatty Acid SA 910; Century 1224; Edenor C18; Hydrofol Acid 1895; Kiri stearic acid; Lunac S 40; SA 400 (fatty acid); WO 2 (fatty acid); Octadecanoic acid (stearic acid); Emersol 110 (Salt/Mix); Emery 400 (Salt/Mix)
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Phase change data
Go To: Top, 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 634.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 631.15 | K | N/A | Krafft, 1880 | Uncertainty assigned by TRC = 5. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 341. ± 3. | K | AVG | N/A | Average of 31 out of 32 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 342.49 | K | N/A | Schaake, van Miltenburg, et al., 1982 | Uncertainty assigned by TRC = 0.02 K; TRC |
Ttriple | 341.85 | K | N/A | Spizzichino, 1956 | Uncertainty assigned by TRC = 0.5 K; TRC |
Ttriple | 342.65 | K | N/A | Singleton, Ward, et al., 1950 | Uncertainty assigned by TRC = 0.01 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ptriple | 4.2105×10-8 | atm | N/A | Spizzichino, 1956 | Uncertainty assigned by TRC = 1.9736×10-8 atm; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 805.09 | K | N/A | D'Souza and Teja, 1987 | Uncertainty assigned by TRC = 3.5 K; Ambrose's procedure; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 13.0923 | atm | N/A | D'Souza and Teja, 1987 | Uncertainty assigned by TRC = 0.84 atm; Ambrose's procedure; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 49. ± 2. | kcal/mol | TPD | Cappa, Lovejoy, et al., 2008 | AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
29.71 | 364. | A | Stephenson and Malanowski, 1987 | Based on data from 349. to 415. K.; AC |
24.04 | 472. | A | Stephenson and Malanowski, 1987 | Based on data from 457. to 649. K.; AC |
28.42 ± 0.48 | 379. | ME,TE | de Kruif, Schaake, et al., 1982 | Based on data from 366. to 389. K.; AC |
19.1 | 515. | I | Cramer, 1943 | AC |
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 |
---|---|---|---|---|---|
446.9 to 643. | 5.71973 | 3348.131 | -57.825 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
37.88 | 291. to 309. | TPTD | Chattopadhyay and Ziemann, 2005 | AC |
37.8 | 296. to 319. | TPTD | Chattopadhyay, Tobias, et al., 2001 | Experimental values based on the TPTD method are often inconsistent with values determined using other experimental methods; AC |
39.8 ± 1.0 | 336. | ME | Davies and Malpass, 1961 | Based on data from 331. to 340. K. See also Cox and Pilcher, 1970.; AC |
39.8 ± 1.0 | 330.89 | V | Davies and Malpass, 1961, 2 | ALS |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
14.651 | 342.75 | N/A | Sato, Yoshimoto, et al., 1990 | DH |
14.4 | 338.3 | N/A | Moore, Koelmel, et al., 2007 | AC |
15.1 | 342.8 | DSC | Moreno, Cordobilla, et al., 2007 | AC |
13.8 | 344.1 | DSC | Teixeira, Gonçalves da Silva, et al., 2006 | AC |
12.17 | 340.2 | AC | Yu, Meng, et al., 2000 | AC |
14.63 | 342.5 | N/A | Domalski and Hearing, 1996 | AC |
16.360 | 342.65 | N/A | Singleton, Ward, et al., 1950, 2 | DH |
15.450 | 326.1 | N/A | Eykman, 1889 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
42.73 | 342.75 | Sato, Yoshimoto, et al., 1990 | DH |
477.5 | 342.65 | Singleton, Ward, et al., 1950, 2 | DH |
47.3 | 326.1 | Eykman, 1889 | DH |
Enthalpy of phase transition
ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
14.629 | 342.49 | crystaline, I | liquid | Schaake, van Miltenburg, et al., 1982, 2 | DH |
Entropy of phase transition
ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
42.572 | 342.49 | crystaline, I | liquid | Schaake, van Miltenburg, et al., 1982, 2 | DH |
References
Go To: Top, Phase change data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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
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
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
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]
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, 143-146. [all data]
Eykman, 1889
Eykman, J.F.,
Zur kryoskopischen Molekulargewichtsbestimmung,
Z. Physik. Chem., 1889, 4, 497-519. [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. Thermodynam., 1982, 14, 771-778. [all data]
Notes
Go To: Top, Phase change data, References
- Symbols used in this document:
Pc Critical pressure Ptriple Triple point pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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