α-Pinene

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

  
• IUPAC Standard InChIKey: GRWFGVWFFZKLTI-UHFFFAOYSA-N Copy
• CAS Registry Number: 80-56-8
• 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.
• Species with the same structure:
  • α-Pinene
• Stereoisomers:
  • (1S)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene
  • (1R)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene
• Other names: Bicyclo[3.1.1]hept-2-ene, 2,6,6-trimethyl-; 2-Pinene; 2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene; Pinene, α; 2,6,6-Trimethylbicyclo(3.1.1)-2-hept-2-ene; 2,6,6-Trimethylbicyclo[3.1.1]-2-heptene; Acintene A; 4,6,6-Trimethylbicyklo(3,1,1)hept-3-en; UN 2368; alpha-Pinene; PC 500; Bicyclo[3.1.1]hept-2-ene, 2,6,6-trimethyl-, (.+/-.)-; Sylvapine A; (.+/-.)-α-Pinene; NSC 7727; Pinene; (+)-α-pinene; 2,6,6-trimethylbicyclo[3,1,1]-heptene (α-pinene); α-Pinene [1R-(+), 1S-(-) ]; 2,6,6-trimethylbicyclo-[3,1,1]-2-heptene (α-pinene); pin-2(3)-ene
• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • References
  • Notes
• Other data available:
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
• 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Enthalpy of vaporization

Antoine Equation Parameters

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

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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]

Hawkins and Eriksen. W.T., 1954
Hawkins, J.E.; Eriksen. W.T., J. Am. Chem. Soc., 1954, 76, 2669. [all data]

Timmermans, 1952
Timmermans, J., Freezing points of organic compounds. VVI New determinations., Bull. Soc. Chim. Belg., 1952, 61, 393. [all data]

Anonymous, 1942
Anonymous, R., , Am. Pet. Inst. Res. Proj. 6, Natl. Bur. Stand., 1942. [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]

An, Hu, et al., 1987
An, Xuwu; Hu, Riheng; Wang, Hu; Wu, Mali; Zou, Yongkuang, Enthalpies of Vaporization of α- and β-Pinene, Acta Phys. Chim. Sin., 1987, 3, 6, 668-671, https://doi.org/10.3866/PKU.WHXB19870621 . [all data]

Rodrigues and Bernardo-Gil, 1996
Rodrigues, M. Fátima; Bernardo-Gil, M. Gabriela, Vapor-Liquid Equilibrium Data of α-Pinene + β-Pinene + Limonene at 80 kPa and 101 kPa, J. Chem. Eng. Data, 1996, 41, 3, 581-585, https://doi.org/10.1021/je950324g . [all data]

Reich and Sanhueza, 1993
Reich, Ricardo; Sanhueza, Vilma, Vapor-liquid equilibria for .alpha.-pinene or .beta.-pinene with anisole, J. Chem. Eng. Data, 1993, 38, 3, 341-343, https://doi.org/10.1021/je00011a001 . [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]

Bukala, Majewski, et al., 1954
Bukala, M.; Majewski, J.; Rodzinski, W., Przem. Chem., 1954, 10, 6. [all data]

Hawkins and Armstrong, 1954
Hawkins, J.E.; Armstrong, G.T., Physical and thermodynamic properties of terpenes. III. The vapor pressures of α-pinene and β-pinene, J. Am. Chem. Soc., 1954, 76, 3756-37. [all data]

Hawkinds and Armstrong, 1954
Hawkinds, J.E.; Armstrong, G.T., Physical and Thermodynamic Properties of Terpenes. III. The Vapor Pressures of α-Pinene and β-Pinene, J. Am. Chem. Soc., 1954, 76, 14, 3756-3759, https://doi.org/10.1021/ja01643a051 . [all data]

Notes

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

• Symbols used in this document:
  

  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  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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