Catalyst-free synthesis of biodiesel precursors from biomass-based furfuryl alcohols in the presence of HO and air

• Published in: Green chemistry : an international journal and green chemistry resource : GC 2019-11, Vol.21 (23), p.6326-6334
• Main Authors: Qin, Shengxiang, Li, Teng, Zhang, Man, Liu, Hongyu, Yang, Xin, Rong, Nianxin, Jiang, Jun, Wang, Yalin, Zhang, Hua, Yang, Weiran
• Format: Article
• ISSN: 1463-9262; 1463-9270
• DOI: 10.1039/c9gc03179k

Production of biodiesel from biomass resources usually requires elongation of carbon numbers from typical C 5 and C 6 platform molecules through C-C coupling reactions, which were catalyzed by acid, base or metal catalysts traditionally. Herein, a catalyst-free method was developed to produce bis(furan-2-yl)methane derivatives (BFMs) from furfuryl alcohol derivatives (FAs) in the presence of H 2 O and air without any other additional catalysts. An 81% yield of bis(5-methylfuran-2-yl)methane (BMFM) can be obtained from 5-methylfurfuryl alcohol (5-MFA) and a 59% total yield of C 11 biodiesel was obtained from 5-methylfurfural (5-MF). In addition, a H 2 O and air mediated free radical decarboxylation mechanism was proposed based on the detailed mechanistic studies. This strategy offers a green, low-cost and environmentally friendly approach to synthesize biodiesel precursors from biomass based platform molecules. Dimerization of biomass-based furfuryl alcohols to biodiesel precursors was realized by using only H 2 O and air without adding any other catalysts.