TY - JOUR
T1 - Potential antioxidants for biodiesel from a softwood lignin pyrolyzate
AU - Larson, Richard A.
AU - Sharma, Brajendra K.
AU - Marley, Karen A.
AU - Kunwar, Bidhya
AU - Murali, Dheeptha
AU - Scott, John
N1 - Funding Information:
Authors thank Illinois Sustainable Technology Center (ISTC), a division of Prairie Research Institute of the University of Illinois at Urbana Champaign for providing funds through Illinois Hazardous Waste Research Fund (Grant No. HWR12220 ). The Fund had no role in the design, writing, or submission of this manuscript. The authors also thank Joe Loveshe of Columbus Foods (Des Plaines, IL) for providing samples of soybean methyl ester.
Publisher Copyright:
© 2017 Elsevier B.V.
PY - 2017/12/15
Y1 - 2017/12/15
N2 - Softwood lignin was pyrolyzed to afford a “bio-oil” distillate in which phenols were major products. Extraction with alkali gave a range of lignin-related phenols having molecular weights (MWs) from 110 to 344 amu. The total phenolic extract was at least equal in antioxidant activity to the synthetic compound 2,6-di(tert)butyl-4- methylphenol (BHT). The extract was separated by chromatographic techniques to characterize components potentially responsible for the activity. A series of phenols in the extract exhibited MWs of 274, 302, 316, 330, and 344 and are likely to be dimers responsible for the majority of the observed antioxidant properties. Several of these compounds appear by mass spectrometry to be bifunctional phenolic compounds containing catechol or guaiacol groups. We hypothesize that a type of effective antioxidant for fatty acid esters will contain one phenolic hydroxyl group hydrogen-bonded to the ester and another at a radical-quenching site; monophenols are likely to be ineffective in this system due to the predominance of hydrogen bonding (kinetic solvent effect).
AB - Softwood lignin was pyrolyzed to afford a “bio-oil” distillate in which phenols were major products. Extraction with alkali gave a range of lignin-related phenols having molecular weights (MWs) from 110 to 344 amu. The total phenolic extract was at least equal in antioxidant activity to the synthetic compound 2,6-di(tert)butyl-4- methylphenol (BHT). The extract was separated by chromatographic techniques to characterize components potentially responsible for the activity. A series of phenols in the extract exhibited MWs of 274, 302, 316, 330, and 344 and are likely to be dimers responsible for the majority of the observed antioxidant properties. Several of these compounds appear by mass spectrometry to be bifunctional phenolic compounds containing catechol or guaiacol groups. We hypothesize that a type of effective antioxidant for fatty acid esters will contain one phenolic hydroxyl group hydrogen-bonded to the ester and another at a radical-quenching site; monophenols are likely to be ineffective in this system due to the predominance of hydrogen bonding (kinetic solvent effect).
KW - Bio-oil
KW - Free radical quenching
KW - Kinetic solvent effect
KW - Phenolic dimers
KW - Pyrolysis
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U2 - 10.1016/j.indcrop.2017.08.053
DO - 10.1016/j.indcrop.2017.08.053
M3 - Article
AN - SCOPUS:85028965978
SN - 0926-6690
VL - 109
SP - 476
EP - 482
JO - Industrial Crops and Products
JF - Industrial Crops and Products
ER -