Abstract
Terpenoids, naturally occurring compounds derived from isoprene units present in pine oleoresin, are a valuable source of chemicals used in solvents, fragrances, flavors and have shown potential use as a biofuel. This paper describes a method to extract and analyze the terpenoids present in loblolly pine saplings and pine lighter wood. Various extraction solvents were tested over different times and temperatures. Samples were analyzed by pyrolysis-molecular beam mass spectrometry before and after extractions to monitor the extraction efficiency. The pyrolysis studies indicated that the optimal extraction method used a 1:1 hexane/acetone solvent system at 22°C for 1 h. Extracts from the hexane/acetone experiments were analyzed using a low thermal mass modular accelerated column heater for fast-GC/FID analysis. The most abundant terpenoids from the pine samples were quantified, using standard curves, and included the monoterpenes, α- and β- pinene, camphene and δ-carene. Sesquiterpenes analyzed included caryophyllene, humulene and α-bisabolene. Diterpenoid resin acids were quantified in derivatized extractions, including pimaric, isopimaric, levopimaric, palustric, dehydroabietic, abietic and neoabietic acids.
Highlights
Renewable chemicals, including fuels, solvents, fragrances, flavors, and pharmaceutical compounds, can be generated or extracted from renewable biomass sources
Monoterpenes (C10), sesquiterpenes (C15), and diterpenoid resin acids (C20), the main terpenoids found in pine oleoresin, are a Abbreviations: Bis(trimethylsilyl) trifluoroacetamide (BSTFA), N,O-Bis(trimethylsilyl)trifluoroacetamide; GC/FID, gas chromatography/flame ionization detector; LTM MACH, low thermal mass modular accelerated column heater; PLW, pine lighter wood; pine sapling cross section (PS), pine sapling; Pyrolysis-molecular beam mass spectrometry (py-MBMS), pyrolysis-molecular beam mass spectrometry
Py-MBMS analysis of the biomass samples before and after extraction indicated that the single step extraction using hexane/acetone extractions were efficient at extracting the maximum amount of terpenoid components and that the extractions should be performed over 1 h at 22°C
Summary
Renewable chemicals, including fuels, solvents, fragrances, flavors, and pharmaceutical compounds, can be generated or extracted from renewable biomass sources. Other biomass components, including lignin and oleoresin excretions from conifers, have been used as a source of renewable chemicals. Pine oleoresin is used to generate turpentine, a solvent and source of synthetic platform chemicals such as α-pinene (Palmer, 1943; Beglinger, 1958). Terpenoids, naturally occurring organic compounds derived from isoprene units, are the primary constituents of pine oleoresin (Palmer, 1943; Bohlmann and Keeling, 2008; Rodrigues-Corrêa et al, 2012). Monoterpenes (C10), sesquiterpenes (C15), and diterpenoid resin acids (C20), the main terpenoids found in pine oleoresin, are a Abbreviations: BSTFA, N,O-Bis(trimethylsilyl)trifluoroacetamide; GC/FID, gas chromatography/flame ionization detector; LTM MACH, low thermal mass modular accelerated column heater; PLW, pine lighter wood; PS, pine sapling; py-MBMS, pyrolysis-molecular beam mass spectrometry
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