Oleic Acid

• Formula: C₁₈H₃₄O₂
• Molecular weight: 282.4614
• IUPAC Standard InChI: InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9- Copy

  
• IUPAC Standard InChIKey: ZQPPMHVWECSIRJ-KTKRTIGZSA-N Copy
• CAS Registry Number: 112-80-1
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Stereoisomers:
  • 9-Octadecenoic acid, (E)-
  • 9-Octadecenoic acid
• Other names: 9-Octadecenoic acid (Z)-; Δ9-cis-Oleic acid; cis-Oleic Acid; cis-9-Octadecenoic Acid; Emersol 211; Emersol 220 White Oleic Acid; Emersol 221 Low Titer White Oleic Acid; Oelsauere; Oleine 7503; Pamolyn 100; Vopcolene 27; Wecoline OO; Z-9-Octadecenoic acid; cis-Octadec-9-enoic acid; cis-Δ9-octadecenoic acid; cis-Δ9-Octadecenoate; neo-Fat 90-04; neo-Fat 92-04; Century cd fatty acid; Elaidoic acid; Emersol 210; Emersol 213; Emersol 6321; Glycon RO; Glycon WO; Groco 2; Groco 4; Groco 5l; Groco 6; Hy-phi 1055; Hy-phi 1088; Hy-phi 2066; Hy-phi 2088; Hy-phi 2102; K 52; L'Acide oleique; Metaupon; Tego-oleic 130; 9-Octadecenoic acid, cis-; Elaic acid; Industrene 105; Industrene 205; Industrene 206; Oleinic acid; Pamolyn; Wochem no. 320; (Z)-9-Octadecanoic acid; Emersol 6313 NF; Priolene 6906; 9-(Z)-octadecenoic acid; (Z)-Octadec-9-enoic acid; 9-Octadecenoic acid (9Z)-; D 100; Emersol 205; Extraolein 90
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • References
  • Notes
• Other data available:
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Options:
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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

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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Reduced pressure boiling point

Enthalpy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Enthalpy of fusion

Enthalpy of phase transition

Entropy of phase transition

Reaction thermochemistry data

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

References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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]

Keffler, 1930
Keffler, L.J.P., Calorimetric researches on geometrical isomerism. Part I. Preliminary studies on oleic and elaidic acids and esters from a comparison of their heats of combustion, J. Phys. Chem., 1930, 34, 1319-1325. [all data]

Mod, Magne, et al., 1962
Mod, R.R.; Magne, F.C.; Skau, E.L., J. Chem. Eng. Data, 1962, 7, 31. [all data]

Mod, Magne, et al., 1960
Mod, R.R.; Magne, F.C.; Skau, E.L., Pure Acid-Free Amides of C18 Fatty Acids. Their Preparation and Binary Freezing Point Behavior, J. Chem. Eng. Data, 1960, 5, 478. [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]

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]

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]

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]

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]

Notes

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

• Symbols used in this document:
  

  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔvapH	Enthalpy of vaporization

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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