Oleic Acid
- Formula: C18H34O2
- Molecular weight: 282.4614
- IUPAC Standard InChIKey: ZQPPMHVWECSIRJ-KTKRTIGZSA-N
- 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:
- 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
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Condensed phase thermochemistry data
Go To: Top, Phase change data, Reaction thermochemistry data, Gas Chromatography, 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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -182.8 | kcal/mol | Chyd | Rogers, Hoyte, et al., 1978 | Authors gave two values |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -2667.46 | kcal/mol | Ccb | Keffler, 1930 | At 293 °K; Corresponding ΔfHºliquid = -186.82 kcal/mol (simple calculation by NIST; no Washburn corrections) |
Phase change data
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas Chromatography, 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tfus | 289.45 | K | N/A | Mod, Magne, et al., 1962 | Uncertainty assigned by TRC = 0.3 K; TRC |
Tfus | 289.45 | K | N/A | Mod, Magne, et al., 1960 | Uncertainty assigned by TRC = 0.5 K; TRC |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
467.7 | 0.001 | Aldrich Chemical Company Inc., 1990 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
20.0 | 456. | A | Stephenson and Malanowski, 1987 | Based on data from 441. to 633. K.; 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 |
---|---|---|---|---|---|
449.7 to 633. | 5.04271 | 2555.604 | -127.258 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
9.46 | 286.5 | Domalski and Hearing, 1996 | AC |
Enthalpy of phase transition
ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
9.4646 | 286.45 | crystaline, α | liquid | Sato, Yoshimoto, et al., 1990 | High-melting, α-form.; DH |
12.404 | 289.35 | crystaline, β | liquid | Sato, Yoshimoto, et al., 1990 | Low-melting, β-form.; DH |
Entropy of phase transition
ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
33.08 | 286.45 | crystaline, α | liquid | Sato, Yoshimoto, et al., 1990 | High-melting,; DH |
42.85 | 289.35 | crystaline, β | liquid | Sato, Yoshimoto, et al., 1990 | Low-melting,; DH |
Reaction thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, 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 |
Gas Chromatography
Go To: Top, Condensed phase thermochemistry data, Phase change data, 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5MS | 2140. | Asuming, Beauchamp, et al., 2005 | 30. m/0.25 mm/0.25 μm, He, 50. C @ 10. min, 3. K/min, 250. C @ 5. min |
Capillary | SPB-1 | 2171. | Nagarajan, Rao, et al., 2001 | 30. m/0.32 mm/0.25 μm, He, 60. C @ 2. min, 2. K/min, 250. C @ 5. min |
Kovats' RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5MS | 2115. | Maia, Andrade, et al., 2000 | 30. m/0.25 mm/0.25 μm, He; Program: 40C => 2C/min => 60C => 4C/min => 260C |
Capillary | DB-5 | 2097. | Andrade, Santos, et al., 1998 | 30. m/0.25 mm/0.25 μm, He; Program: 40C => 2C/min => 60C => 4C/min => 260C |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5MS | 2102. | Benkaci-Ali, Baaliouamer, et al., 2007 | 30. m/0.25 mm/0.25 μm, He, 60. C @ 8. min, 2. K/min, 250. C @ 30. min |
Capillary | HP-5MS | 2175. | Vujisic L., Vuckovic I., et al., 2006 | 30. m/0.25 mm/0.25 μm, H2, 4.3 K/min; Tstart: 50. C; Tend: 285. C |
Capillary | HP-5MS | 2141. | Pino, Mesa, et al., 2005 | 30. m/0.25 mm/0.25 μm, He, 60. C @ 2. min, 4. K/min, 250. C @ 20. min |
Capillary | SPB-5 | 2137. | Pino, Marbot, et al., 2003 | 30. m/0.25 mm/0.25 μm, He, 60. C @ 2. min, 4. K/min, 250. C @ 20. min |
Capillary | HP-5 | 2152. | Skaltsa, Demetzos, et al., 2003 | 30. m/0.25 mm/0.25 μm, He, 60. C @ 5. min, 4. K/min; Tend: 280. C |
Capillary | HP-5 | 2141. | Flamini, Cioni, et al., 2002 | 30. m/0.25 mm/0.25 μm, N2, 60. C @ 10. min, 5. K/min; Tend: 220. C |
Capillary | DB-5 | 2147. | Nogueira, Bittrich, et al., 2001 | 30. m/0.25 mm/0.25 μm, H2, 3. K/min; Tstart: 60. C; Tend: 240. C |
Capillary | HP-5MS | 2152. | Skaltsa, Mavrommati, et al., 2001 | 30. m/0.25 mm/0.25 μm, He, 60. C @ 5. min, 4. K/min; Tend: 280. C |
Capillary | Ultra-1 | 2113. | Richmond and Pombo-Villar, 1998 | 25. m/0.32 mm/0.52 μm, He, 15. K/min, 320. C @ 10. min; Tstart: 35. C |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | VF-5MS | 2146.1 | Tret'yakov, 2007 | 30. m/0.25 mm/0.25 μm, He; Program: Multi-step temperature program; T(initial)=60C; T(final)=270C |
Capillary | DB-5MS | 2130. | Varlet V., Knockaert C., et al., 2006 | 30. m/0.32 mm/0.5 μm, He; Program: 70C(1min) => 3C/min => 80C(1min) => 5C/min => 150C => 10C/min => 280C (4min) |
Van Den Dool and Kratz RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 3184. | Chung, Eiserich, et al., 1994 | He, 60. C @ 4. min, 3. K/min, 220. C @ 30. min; Column length: 60. m; Column diameter: 0.25 mm |
Capillary | DB-Wax | 3173. | Shiratsuchi, Shimoda, et al., 1994 | 60. m/0.25 mm/0.25 μm, He, 2. K/min, 230. C @ 60. min; Tstart: 50. C |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DP-5 | 2175. | Vijayakumar, Duraipandiyan, et al., 2012 | 30. m/0.25 mm/0.25 μm, Helium, 80. C @ 1. min, 4. K/min, 300. C @ 40. min |
Capillary | DP-5 | 2175. | Vijayakumar, Duraipandiyan, et al., 2012 | 30. m/0.25 mm/0.25 μm, Helium, 80. C @ 1. min, 4. K/min, 300. C @ 40. min |
Capillary | VF-5 MS | 2131. | Liu, Lu, et al., 2011 | 30. m/0.25 mm/0.25 μm, Helium, 40. C @ 3. min, 5. K/min, 250. C @ 3. min |
Capillary | DB-5 MS | 2141. | Stojanovic, RAdulovic, et al., 2011 | 30. m/0.25 mm/0.25 μm, Helium, 5. K/min, 290. C @ 10. min; Tstart: 70. C |
Capillary | HP-5 MS | 2147. | Jerkovic, Hegic, et al., 2010 | 30. m/0.25 mm/0.25 μm, Helium, 70. C @ 2. min, 3. K/min, 200. C @ 18. min |
Capillary | HP-5 MS | 2147. | Jerkovic, Tuberso, et al., 2010 | 30. m/0.25 mm/0.25 μm, Helium, 70. C @ 2. min, 3. K/min, 200. C @ 18. min |
Capillary | DB-1 | 2116. | Xu, Tang, et al., 2010 | 30. m/0.25 mm/0.25 μm, Helium, 50. C @ 2. min, 4. K/min, 220. C @ 2. min |
Capillary | HP-5 MS | 2146. | Radulovic, Blagojevic, et al., 2009 | 30. m/0.25 mm/0.25 μm, Helium, 5. K/min, 290. C @ 10. min; Tstart: 70. C |
Capillary | HP-1 | 2090. | Wetwiayaklung, Thavanapong, et al., 2009 | 25. m/0.32 mm/0.17 μm, 50. C @ 5. min, 1. K/min, 260. C @ 5. min |
Capillary | HP-101 | 2180. | Blazevic and Mastelic, 2008 | 25. m/0.20 mm/0.25 μm, Helium, 70. C @ 2. min, 3. K/min; Tend: 200. C |
Capillary | HP-101 | 2180. | Blazevic and Mastelic, 2008 | 25. m/0.20 mm/0.25 μm, Helium, 70. C @ 2. min, 3. K/min; Tend: 200. C |
Capillary | DB-5 | 2115. | Senatore, Landolfi, et al., 2006 | 30. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 2. K/min, 260. C @ 20. min |
Capillary | DB-5 | 2115. | Senatore, Apostolides Arnold, et al., 2005 | 30. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 2. K/min, 260. C @ 20. min |
Capillary | DB-5 | 2110. | Senatore, Rigano, et al., 2004 | 30. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 2. K/min, 250. C @ 20. min |
Capillary | DB-5 | 2161. | Priestap, van Baren, et al., 2003 | 30. m/0.2 mm/0.25 μm, He, 75. C @ 4. min, 3. K/min; Tend: 220. C |
Capillary | DB-5 | 2112. | Palmeira, Conserva, et al., 2001 | 30. m/0.25 mm/0.25 μm, He, 3. K/min; Tstart: 60. C; Tend: 270. C |
Capillary | DB-5 | 2115. | Palmeira, Conserva, et al., 2001 | 30. m/0.25 mm/0.25 μm, He, 3. K/min; Tstart: 60. C; Tend: 270. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | VF-5 MS | 2131. | Liu, Lu, et al., 2011 | 30. m/0.25 mm/0.25 μm, Helium; Program: not specified |
Capillary | DB-1 | 2152. | Xu, Tang, et al., 2010 | 30. m/0.25 mm/0.25 μm, Helium; Program: not specified |
Capillary | ZB-1 MS | 2175. | Al-Reza, Rahman, et al., 2009 | 30. m/0.25 mm/0.25 μm, Helium; Program: 50 0C 3 0C/min -> 150 0C (10 min) 10 0C/min -> 250 0C |
Capillary | HP-5 MS | 2120. | Mancini, Arnold, et al., 2009 | 30. m/0.25 mm/0.25 μm, Helium; Program: 40 0C (5 min) 2 0C/min -> 270 0C -> 260 0C (20 min) |
Capillary | RTX-5 MS | 2173. | Mebazaa, Mahmoudi, et al., 2009 | 30. m/0.25 mm/0.25 μm, Helium; Program: 50 0C (5 min) 2 0C/min -> 100 0C (5 min) 5 0C/min -> 300 0C |
Capillary | RTX-5 MS | 2161. | Mebazaa, Mahmoudi, et al., 2009 | 30. m/0.25 mm/0.25 μm, Helium; Program: not specified |
Capillary | HP-1 | 2098. | Wetwiayaklung, Thavanapong, et al., 2009 | 25. m/0.32 mm/0.17 μm; Program: not specified |
Capillary | HP-5MS | 2112. | Ning, Zheng, et al., 2008 | 30. m/0.25 mm/0.25 μm, He; Program: 40 0C (2 min) 3 0C/min -> 180 0C (2 min) 15 0C -> 280 0C |
Capillary | HP-5 | 2146. | Zhao, Li, et al., 2008 | 30. m/0.25 mm/0.25 μm; Program: 40 0C (2 min) 5 0C/min -> 80 0C 7 oC/min -> 160 0C 9 0C/min -> 200 0C 20 0C/min -> 280 0C (10 min) |
Capillary | HP-5 | 2141. | Zhao, Li, et al., 2008 | 30. m/0.25 mm/0.25 μm; Program: not specified |
Capillary | HP-5MS | 2155. | Alissandrakis, Kibaris, et al., 2005 | 30. m/0.25 mm/0.25 μm, He; Program: 40C(3min) => 2C/min => 180C => 10C/min => 250C(5min) |
Normal alkane RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 3172. | Guo, Wu, et al., 2008 | 30. m/0.25 mm/0.25 μm, Helium, 60. C @ 2. min, 10. K/min, 250. C @ 10. min |
Capillary | TC-WAX FFS | 3142. | Miyazawa, Maehara, et al., 2002 | He, 3. K/min; Column length: 60. m; Column diameter: 0.25 mm; Tstart: 60. C; Tend: 240. C |
Capillary | TC-Wax | 3150. | Miyazawa, Kurose, et al., 2001 | He, 4. K/min, 250. C @ 47. min; Column length: 60. m; Column diameter: 0.25 mm; Tstart: 80. C |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Innowax | 3157. | Noorizadeh, Farmany, et al., 2011 | 60. m/0.25 mm/0.33 μm; Program: not specified |
Capillary | HP Innowax | 3157. | Mancini, Arnold, et al., 2009 | 50. m/0.20 mm/0.25 μm, Helium; Program: 40 0C (5 min) 2 0C/min -> 270 0C -> 260 0C (20 min) |
Capillary | DB-FFAP | 3184. | Mebazaa, Mahmoudi, et al., 2009 | 30. m/0.25 mm/0.25 μm, Helium; Program: not specified |
Capillary | Innowax FSC | 3200. | Baser, Özek, et al., 2004 | 60. m/0.25 mm/0.25 μm, He; Program: 60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas Chromatography, Notes
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,
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Calorimetric researches on geometrical isomerism. Part I. Preliminary studies on oleic and elaidic acids and esters from a comparison of their heats of combustion,
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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,
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Chemical composition of the volatiles of Decalepis hamiltonii (Wight Arn),
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Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas Chromatography, 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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