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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.