Green synthesis of linear alkylbenzenes via diels-alder cycloaddition between furan and linear alkenes over niobic acid catalyst

Abstract

The synthesis of linear alkylbenzenes (LABs) from biomass-derived furan and linear alkenes via Diels-Alder cycloaddition followed by acid-catalyzed dehydration is presented. Furan was reacted with 1-dodecene, the alkene model compound, over the niobic acid catalyst in a laboratory-scale batch reactor. The effects of reaction temperature, catalyst loading, and initial reactant ratio were systematically investigated. Our experiments reveal that 1-alkene isomerization, furan alkylation to produce dodecylfuran, and self Diels-Alder cycloaddition of furan to produce benzofuran are the major side reaction pathways competing with LAB production. The highest conversion of 1-dodecene to 1-phenyldecane, our target LAB, was found to be at approximately 12 mmol/mol. The main reasons for this low LAB yields include high furan activity and volatility, coke formation, and mass transfer limitations. Despite low LAB yields, our work demonstrates for the first time that it is possible to synthesize LABs from biomass-derived furan and linear alkenes over solid acid catalysts. (Image Presented).