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:
- 9-Octadecenoic acid, methyl ester, (E)-
- 9-Octadecenoic acid, methyl ester
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)
Permanent link for this species. Use this link for bookmarking this species for future reference.
Information on this page:
Other data available:
Options:
- Switch to calorie-based units

Data at NIST subscription sites:

NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Condensed phase thermochemistry data

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

Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_liquid	-727.64	kJ/mol	Chyd	Rogers and Siddiqui, 1975
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-11832.4 ± 1.5	kJ/mol	Ccb	Freedman, Bagby, et al., 1989	Corresponding Δ_fHº_liquid = -789.27 kJ/mol (simple calculation by NIST; no Washburn corrections)
Δ_cH°_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 Δ_fHº_liquid = -734.46 kJ/mol (simple calculation by NIST; no Washburn corrections)

Phase change data

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

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
Δ_vapH°	104. ± 6.	kJ/mol	AVG	N/A	Average of 6 values; Individual data points

Reduced pressure boiling point

T_boil (K)	Pressure (bar)	Reference	Comment
491.7	0.027	Weast and Grasselli, 1989	BS

Enthalpy of vaporization

Δ_vapH (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.

Reaction thermochemistry data

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

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

9-Octadecenoic acid (Z)-, methyl ester + =

By formula: C₁₉H₃₆O₂ + H₂ = C₁₉H₃₈O₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-122.4 ± 1.2	kJ/mol	Chyd	Rogers and Siddiqui, 1975	liquid phase; solvent: n-Hexane

References

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

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, Reaction thermochemistry data, References

Symbols used in this document:

T_boil	Boiling point
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions
Δ_rH°	Enthalpy of reaction 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
The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
Customer support for NIST Standard Reference Data products.