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Branched Bio‐Lubricant Base Oil Production through Aldol Condensation
Author(s) -
Norton Angela M.,
Liu Sibao,
Saha Basudeb,
Vlachos Dionisios G.
Publication year - 2019
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201901838
Subject(s) - lubricant , hydrodeoxygenation , furfural , aldol condensation , chemistry , base oil , organic chemistry , furan , biomass (ecology) , lignocellulosic biomass , yield (engineering) , chemical engineering , materials science , catalysis , fermentation , geology , composite material , scanning electron microscope , oceanography , engineering , selectivity
Currently, lubricant base oils are derived from petroleum, a nonrenewable feedstock that contributes to greenhouse gas emissions. Bioderived, renewable lubricant base oils can mitigate environmental challenges and offer superior cold flow properties by incorporating branches to the base oil's hydrocarbon backbone with an appropriate synthetic strategy. A strategy was developed to synthesize branched alkanes for lubricant base oil in two steps from 12‐tricosanone, obtained from bioderived fatty acids, and furfural, obtained from lignocellulosic biomass. The reaction pathway involves carbon–carbon coupling through aldol condensation followed by hydrodeoxygenation (HDO). Various solvents (non‐polar, aprotic and polar, protic) and reaction conditions were screened to achieve a maximum yield of 94.3 % of aldol condensation products, containing the majority of a C 33 furan (79.5 %) followed by a C 28 furan (14.8 %). Subsequent HDO of aldol condensation products over an Ir‐ReO x /SiO 2 catalyst produced lubricant‐ranged branched alkanes (C 28 and C 33 ) with 61.4 % yield and small fractions (<11 %) of alkanes with carbon numbers between C 15 and C 10 . The viscous properties of the produced bio‐lubricant base oil were comparable to commercial petroleum‐derived Group III and Group IV base oils. This approach serves as a potential stepping‐stone to replace petroleumderived base oils and, in turn, reduce greenhouse gas emissions associated with current lubricant production.