Synthesis of Linear Alkylbenzenes from Biomass-Derived Furan over Solid Acid Catalysts

Linear alkybenzenes (LABs) are the precursors of linear alkylbenzene sulfonate, the world’s largest commodity biodegradable synthetic surfactant. Commercially, LABs are produced from petroleum-derived feedstocks via alkylation of benzene with C₁₀−C₁₄ linear alpha olefins (i.e., 1-alkenes). Three different types of catalysts are typically employed: hydrogen fluoride (HF), aluminum chloride (AlCl₃), or UOP’s proprietary DA-114. HF and AlCl₃ are both highly toxic and corrosive, while DA-114, although not toxic and corrosive, requires HF during its synthesis. There is therefore a critical need for a new LAB production process that utilizes both environmental friendly catalysts and renewable feedstocks. In this work, a new LAB synthesis pathway from biomass-derived furan and C₁₂−C₁₆ linear alpha olefins over two different types of solid acid catalysts is studied. The reaction proceeds through Diel-Alder mechanism between furan and linear alpha olefins, followed by dehydration over acid catalysts. The product yields are dependent on several critical parameters, such as reaction temperature, reaction time, reactant ratio, and catalytic loading. Key reaction pathways leading to main and side reaction products are identified.