Thermodynamics Research Center / ThermoML | Journal of Chemical Thermodynamics

Thermochemical properties of sesquiterpenes in natural products by correlation gas chromatography: Application to bergamotene oil

Orf, Megan, Kurian, Manu, Espinosa, Lorna, Nelson, Carissa, Simmons, Dan, Chickos, James
J. Chem. Thermodyn. 2018, 126, 128-136
ABSTRACT
The vapor pressures and vaporization enthalpies of the three major components of bergamotene oil have been evaluated by correlation gas chromatography. Three major components were identified by GCMS as E beta-caryophyllene, trans alpha-bergamotene and alpha-humulene. Two of the components, E beta-caryophyllene and alpha-humulene were also evaluated using commercial caryophyllene samples. Z-caryophyllene, present in the commercial sample was also evaluated. Two sets of hydrocarbon standards, n-alkanes and a series of relatively unrelated cyclic compounds that included adamantane and two alkyl derivatives, (-) alpha-pinene, diamantane and 1,4-di-t-butylbenzene, were used. Vaporization enthalpies of the targets at T = 298.15 K were reproduced within the specified uncertainties by both sets of standards as were vapor pressures from T = (298.15 to -400)K. Above 400 K, vapor pressures diverged. Equations for the evaluation of vapor pressure as a function of temperature are reported for all four compounds investigated.
Compounds
# Formula Name
1 C15H24 [1R-(1R*,4E,9S*)]-4,11,11-trimethyl-8-methylene-bicyclo[7.2.0]-4-undecene
2 C15H24 (-)-exo-.alpha.-bergamotene
3 C15H24 (E,E,E)-2,6,6,9-tetramethyl-1,4,8-cycloundecatriene
4 C15H24 (Z)-caryophyllene
Datasets
The table above is generated from the ThermoML associated json file (link above). POMD and RXND refer to PureOrMixture and Reaction Datasets. The compound numbers are included in properties, variables, and phases, if specificied; the numbers refer to the table of compounds on the left.
Type Compound-# Property Variable Constraint Phase Method #Points
  • POMD
  • 1
  • Molar enthalpy of vaporization or sublimation, kJ/mol ; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Gas
  • Correlation gas chromatography
  • 1
  • POMD
  • 1
  • Vapor or sublimation pressure, kPa ; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Gas
  • Gas chromatography
  • 18
  • POMD
  • 2
  • Molar enthalpy of vaporization or sublimation, kJ/mol ; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Gas
  • Correlation gas chromatography
  • 1
  • POMD
  • 2
  • Vapor or sublimation pressure, kPa ; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Gas
  • Gas chromatography
  • 18
  • POMD
  • 3
  • Molar enthalpy of vaporization or sublimation, kJ/mol ; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Gas
  • Correlation gas chromatography
  • 1
  • POMD
  • 3
  • Vapor or sublimation pressure, kPa ; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Gas
  • Gas chromatography
  • 17
  • POMD
  • 4
  • Molar enthalpy of vaporization or sublimation, kJ/mol ; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Gas
  • Correlation gas chromatography
  • 1
  • POMD
  • 4
  • Vapor or sublimation pressure, kPa ; Liquid
  • Temperature, K; Liquid
  • Liquid
  • Gas
  • Gas chromatography
  • 17