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Catalytic production of renewable lubricant base oils from bio-based 2-alkylfurans and enals

Liu, Sibao, Saha, Basudeb, Vlachos, Dionisios G.
Green chemistry 2019 v.21 no.13 pp. 3606-3614
alkanes, alkylation, biolubricants, biomass, catalysts, catalytic activity, ecological footprint, green chemistry, liquids, markets, molecular weight, oils, silica, sulfonic acids
Lubricants are an essential part of modern society with an over $146 billion market but have significant environmental footprint. Bio-based lubricant base oils can offer performance advantages over existing oils and mitigate environmental challenges. We describe, for the first time, the synthesis of new bio-based base oils with tunable molecular branches and properties in high yields (>80%) from biomass derived 2-alkylfurans with enals via conjugate addition-hydroxylalkylation/alkylation (CA-HAA) and hydrodeoxygenation reactions. Among several liquid and solid sulfonic acid catalysts tested for the CA-HAA condensation, Aquivion PW79S, a perfluorinated sulfonic acid resin, exhibits the best performance. Subsequent hydrodeoxygenation of the condensation products with an Ir-ReOₓ/SiO₂ catalyst gives up to an 88% yield of lubricant ranged branched alkanes with high selectivity and superior properties compared with commercial mineral group III and synthetic poly-α-olefin (PAO) base oils. Importantly, the molecular size and number of branches of the products can be tuned by varying the molecular size of substrates in the CA-HAA step. The as-synthesized base oils possess tunable properties and are promising for a wide range of applications.