9-Octadecenoic acid (Z)-, methyl ester
- Formula: C19H36O2
- Molecular weight: 296.4879
- IUPAC Standard InChI: InChI=1S/C19H36O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19(20)21-2/h10-11H,3-9,12-18H2,1-2H3/b11-10-
- IUPAC Standard InChIKey: QYDYPVFESGNLHU-KHPPLWFESA-N
- CAS Registry Number: 112-62-9
- Chemical structure:
This structure is also available as a 2d Mol file - Stereoisomers:
- Other names: Oleic acid, methyl ester; Emery oleic acid ester 2301; Methyl cis-9-octadecenoate; Methyl oleate; (Z)-9-Octadecenoic acid methyl ester; cis-9-Octyldecenoic acid, methyl ester; Emery, oleic acid ester; Methyl 9-octadecenoate, cis-; Oleic acid, methyl ester, cis-; Emerest 2801; Kemester 205; Methyl (Z)-9-octadecenoate; Emery 2301; Priolube 1400; Witconol 2301; 9-octadecenoic acid, methyl ester (Z); cis-9-Octadecenoic acid, methyl ester; Methyl-cis-oleate; Methyl (Z)-9-oleate; (Z)-9-Methyl octadecenoate; 9-Octadecenoic acid (9Z)-, methyl ester; ADJ 100; Edenor Me 90/95V; Edenor MeTiO5; Esterol 112; Exceparl M-OL; Nissan Unister M 182A; Phytorob 926-67; Priolube 1403; Unister M 182A; Methyl 9-octadecenoate; Methyl (9z)-9-octadecenoate; Emerest 2301 (Salt/Mix); Kemester 213 (Salt/Mix); Emery 2219 (Salt/Mix)
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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°liquid | -727.64 | kJ/mol | Chyd | Rogers and Siddiqui, 1975 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -11832.4 ± 1.5 | kJ/mol | Ccb | Freedman, Bagby, et al., 1989 | Corresponding ΔfHºliquid = -789.27 kJ/mol (simple calculation by NIST; no Washburn corrections) |
| ΔcH°liquid | -11887. ± 12. | kJ/mol | Ccb | Keffler, 1937 | Reanalyzed by Cox and Pilcher, 1970, Original value = -11871. kJ/mol; See Keffler and McLean, 1935; Corresponding ΔfHºliquid = -734.46 kJ/mol (simple calculation by NIST; no Washburn corrections) |
Phase change 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 as indicated in comments:
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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔvapH° | 104. ± 6. | kJ/mol | AVG | N/A | Average of 6 values; Individual data points |
Reduced pressure boiling point
| Tboil (K) | Pressure (bar) | Reference | Comment |
|---|---|---|---|
| 491.7 | 0.027 | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
| ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 77.2 | 498. | GC | Husain, Sarma, et al., 1993 | Based on data from 453. to 543. K.; AC |
| 77.2 | 498. | GC | Husain, Sarma, et al., 1993 | Based on data from 453. to 543. K.; AC |
| 86.3 | 406. | A,MG,OM | Stephenson and Malanowski, 1987 | Based on data from 391. to 459. K. See also Scott, Macmillan, et al., 1952.; AC |
| 83.0 | 443. | A | Stephenson and Malanowski, 1987 | Based on data from 428. to 486. K. See also Rose and Schrodt, 1964.; AC |
| 84.39 | 293. | V | Scott, Macmillan, et al., 1952 | ALS |
| 86.7 | 416. | MG,OM | Scott, Macmillan, et al., 1952 | Based on data from 401. to 458. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
| Temperature (K) | A | B | C | Reference | Comment |
|---|---|---|---|---|---|
| 428.72 to 485.22 | 5.2252 | 2723.181 | -91.822 | Rose and Schrodt, 1964 | Coefficents calculated by NIST from author's data. |
References
Go To: Top, 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.
Rogers and Siddiqui, 1975
Rogers, D.W.; Siddiqui, N.A.,
Heats of hydrogenation of large molecules. I. Esters of unsaturated fatty acids,
J. Phys. Chem., 1975, 79, 574-577. [all data]
Freedman, Bagby, et al., 1989
Freedman, B.; Bagby, M.O.; Khoury, H.,
Correlation of heats of combustion with empirical formulas for fatty alcohols,
J. Am. Oil Chem. Soc., 1989, 66, 595-596. [all data]
Keffler, 1937
Keffler, L.J.P.,
Homology and isomerism in long-chain compounds. I. A thermochemical study of the n-alkyl esters derived from the monoethylenic monocarboxylic acids in C18,
J. Phys. Chem., 1937, 41, 715-721. [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]
Keffler and McLean, 1935
Keffler, L.; McLean, J.H.,
Homology in long-chain compounds, I. Oleic acid and the n-alkul oleates,
J. Soc. Chem. Ind., 1935, 178-185. [all data]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
Husain, Sarma, et al., 1993
Husain, Sajid; Sarma, P. Nageswara; Swamy, G.Y.S.K.; Devi, K. Sita,
Determination of physicochemical properties of some fatty acid methyl esters by gas liquid chromatography,
J Am Oil Chem Soc, 1993, 70, 2, 149-155, https://doi.org/10.1007/BF02542618
. [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]
Scott, Macmillan, et al., 1952
Scott, T.A., Jr.; Macmillan, D.; Melvin, E.H.,
Vapor pressures and distillation of methyl esters of some fatty acids,
Ind. Eng. Chem., 1952, 44, 172-175. [all data]
Rose and Schrodt, 1964
Rose, Arthur.; Schrodt, V.N.,
Vapor-Liquid Equilibria for the Methyl Oleate and Methyl Stearate Binary System.,
J. Chem. Eng. Data, 1964, 9, 1, 12-16, https://doi.org/10.1021/je60020a006
. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, References
- Symbols used in this document:
Tboil Boiling point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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