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:
  • Condensed phase thermochemistry data
  • Phase change data
  • References
  • Notes
• Other data available:
  • IR Spectrum
  • Mass spectrum (electron ionization)
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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

Enthalpy of vaporization

Enthalpy of fusion

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.

Hawkins and Eriksen, 1954
Hawkins, J.E.; Eriksen, W.T., Physical and thermodynamic properties of terpenes. II. The heats of combustion of some terpene hydrocarbons, J. Am. Chem. Soc., 1954, 76, 2669-26. [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]

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
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  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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