D-Limonene

• Formula: C₁₀H₁₆
• Molecular weight: 136.2340
• IUPAC Standard InChI: InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3/t10-/m1/s1 Copy

  
• IUPAC Standard InChIKey: XMGQYMWWDOXHJM-SNVBAGLBSA-N Copy
• CAS Registry Number: 5989-27-5
• 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:
  • Limonene
  • Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (S)-
  • Limonene
• Other names: Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (R)-; p-Mentha-1,8-diene, (R)-(+)-; (+)-(R)-Limonene; (+)-(4R)-Limonene; (+)-p-Mentha-1,8-diene; (+)-Limonene; (R)-(+)-Limonene; Carvene; D-(+)-Limonene; Limonene, (D)-; Limonene, (+)-; (R)-1-methyl-4-(1-methylethenyl)cyclohexene; Dextro-limonene; (R)-4-Isopropenyl-1-methyl-1-cyclohexene; 4-Isopropenyl-1-methyl-1-cyclohexene-, (R)-; (R)-Limonene; (+)-Dipentene; (4R)-(+)-Limonene; (4R)-Limonene; (R)-(+)-p-Mentha-1,8-diene; (R)-p-Mentha-1,8-diene; Biogenic SE 374; Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (4R)-; EC 7; Glidesafe; Glidsafe; Refchole
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Phase change data
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
• Options:
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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

Enthalpy of vaporization

Enthalpy of fusion

References

Go To: Top, Phase change data, Notes

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

Gomes, Serrano, et al., 1988
Gomes, A.; Serrano, L.; Fareio, F., Solid-Liquid Equilibria in 1,8-Cineole/TErpenic Hydrocarbon Systems, J. Chem. Eng. Data, 1988, 33, 194. [all data]

Clara, Marigliano, et al., 2009
Clara, Rene A.; Marigliano, Ana C. Gomez; Solimo, Horacio N., Density, Viscosity, and Refractive Index in the Range (283.15 to 353.15) K and Vapor Pressure of α-Pinene, d -Limonene, (±)-Linalool, and Citral Over the Pressure Range 1.0 kPa Atmospheric Pressure, J. Chem. Eng. Data, 2009, 54, 3, 1087-1090, https://doi.org/10.1021/je8007414 . [all data]

Hoskovec, Grygarová, et al., 2005
Hoskovec, Michal; Grygarová, Dana; Cvacka, Josef; Streinz, Ludvík; Zima, Jirí; Verevkin, Sergey P.; Koutek, Bohumír, Determining the vapour pressures of plant volatiles from gas chromatographic retention data, Journal of Chromatography A, 2005, 1083, 1-2, 161-172, https://doi.org/10.1016/j.chroma.2005.06.006 . [all data]

van Roon, Parsons, et al., 2002
van Roon, André; Parsons, John R.; Govers, Harrie A.J., Gas chromatographic determination of vapour pressure and related thermodynamic properties of monoterpenes and biogenically related compounds, Journal of Chromatography A, 2002, 955, 1, 105-115, https://doi.org/10.1016/S0021-9673(02)00200-5 . [all data]

Chickos, Hosseini, et al., 1995
Chickos, James S.; Hosseini, Sarah; Hesse, Donald G., Determination of vaporization enthalpies of simple organic molecules by correlations of changes in gas chromatographic net retention times, Thermochimica Acta, 1995, 249, 41-62, https://doi.org/10.1016/0040-6031(95)90670-3 . [all data]

Atik, Saito, et al., 1987
Atik, Zadjia; Saito, Yoshihiro; Kusano, Kazuhito, Thermodynamic properties of liquid enantiomers I. Enthalpies of vaporization of fenchones, α-methylbenzylamines, and limonenes at 298.15 K, The Journal of Chemical Thermodynamics, 1987, 19, 1, 99-102, https://doi.org/10.1016/0021-9614(87)90167-4 . [all data]

Steele, Chirico, et al., 2002
Steele, W.V.; Chirico, R.D.; Cowell, A.B.; Knipmeyer, S.E.; Nguyen, A., Thermodynamic Properties and Ideal-Gas Enthalpies of Formation for Methyl Benzoate, Ethyl Benzoate, ( R )-(+)-Limonene, tert -Amyl Methyl Ether, trans -Crotonaldehyde, and Diethylene Glycol, J. Chem. Eng. Data, 2002, 47, 4, 667-688, https://doi.org/10.1021/je0100847 . [all data]

Espinosa Diaz, Guetachew, et al., 1999
Espinosa Diaz, M.A.; Guetachew, T.; Landy, P.; Jose, J.; Voilley, A., Experimental and estimated saturated vapour pressures of aroma compounds, Fluid Phase Equilibria, 1999, 157, 2, 257-270, https://doi.org/10.1016/S0378-3812(99)00016-3 . [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]

Gallis, van den Berg, et al., 1996
Gallis, H.E.; van den Berg, G.J.K.; Oonk, H.A.J., Thermodynamic Properties of Crystalline d -Limonene Determined by Adiabatic Calorimetry, J. Chem. Eng. Data, 1996, 41, 6, 1303-1306, https://doi.org/10.1021/je960094l . [all data]

Notes

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• Symbols used in this document:
  

  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔfusH	Enthalpy of fusion
  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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