Octadecanoic acid
- Formula: C18H36O2
- Molecular weight: 284.4772
- IUPAC Standard InChI: InChI=1S/C18H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-17H2,1H3,(H,19,20)
- 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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Condensed phase thermochemistry data
Go To: Top, Reaction 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:
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 | -213.1 ± 0.5 | kcal/mol | Ccb | Lebedeva, 1964 | Hfusion =10.81±0.10 kcal/mol; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -2696.01 ± 0.45 | kcal/mol | Ccb | Adriaanse, Dekker, et al., 1965 | Reanalyzed by Cox and Pilcher, 1970, Original value = -2695.84 ± 0.45 kcal/mol; Hfusion=63.0 kJ/mol; Corresponding ΔfHºliquid = -226.6 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -2709.57 ± 0.51 | kcal/mol | Ccb | Lebedeva, 1964 | Hfusion =10.81±0.10 kcal/mol; Corresponding ΔfHºliquid = -213.02 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔfH°solid | -218.0 ± 2.7 | kcal/mol | Ccb | Medard and Thomas, 1952 | Reanalyzed by Cox and Pilcher, 1970, Original value = -214.6 kcal/mol; Author's hf291_condensed=-223.8 kcal/mol; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -2698.564 | kcal/mol | Ccb | Shkaraputa, Danilenko, et al., 1984 | Corresponding ΔfHºsolid = -224.03 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°solid | -2693.9 ± 3.2 | kcal/mol | Ccb | Swain, Silbert, et al., 1964 | Corresponding ΔfHºsolid = -228.7 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°solid | -2704.6 ± 2.7 | kcal/mol | Ccb | Medard and Thomas, 1952 | Reanalyzed by Cox and Pilcher, 1970, Original value = -2708.40 kcal/mol; Author's hf291_condensed=-223.8 kcal/mol; Corresponding ΔfHºsolid = -217.99 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°solid | -2700.3 | kcal/mol | Ccb | Emery and Benedict, 1911 | Corresponding ΔfHºsolid = -222. kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°solid,1 bar | 104.1 | cal/mol*K | N/A | Singleton, Ward, et al., 1950 | Extrapolation below 90 K, 64.4 J/mol*K.; DH |
Constant pressure heat capacity of solid
| Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 119.87 | 298.15 | Schaake, van Miltenburg, et al., 1982 | T = 80 to 355 K.; DH |
| 134.3 | 298.15 | Singleton, Ward, et al., 1950 | T = 154 to 350 K.; DH |
Reaction thermochemistry data
Go To: Top, 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 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
+
=
By formula: C18H34O2 + H2 = C18H36O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -29.54 ± 0.38 | kcal/mol | Chyd | Rogers, Hoyte, et al., 1978 | liquid phase; solvent: Hexane; Authors gave two values |
| ΔrH° | -29.9 ± 0.2 | kcal/mol | Chyd | Rogers, Hoyte, et al., 1978 | liquid phase; solvent: Hexane; Authors gave two values |
2 +
=
By formula: 2H2 + C18H32O2 = C18H36O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -59.5 ± 0.1 | kcal/mol | Chyd | Rogers, Hoyte, et al., 1978 | liquid phase; solvent: Hexane |
3 +
=
By formula: 3H2 + C18H30O2 = C18H36O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -90.87 ± 0.45 | kcal/mol | Chyd | Rogers, Hoyte, et al., 1978 | liquid phase; solvent: Hexane |
+
=
By formula: C18H34O2 + H2 = C18H36O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -28.73 ± 0.48 | kcal/mol | Chyd | Rogers, Hoyte, et al., 1978 | liquid phase; solvent: Hexane |
2 +
=
By formula: 2H2 + C18H32O2 = C18H36O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -60.80 ± 0.36 | kcal/mol | Chyd | Rogers, Hoyte, et al., 1978 | liquid phase; solvent: Hexane |
References
Go To: Top, Condensed phase thermochemistry 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.
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]
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, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid S°solid,1 bar Entropy of solid at standard conditions (1 bar) ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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