Kinetics of Acylation of 2-Methylfuran with Fatty Acid Anhydride and AlMCM41.

The conversion of lignocellulosic biomass to fuels and chemicals provides a sustainable alternative to crude oil-based consumer products. For example, oleo-furan sulphonate (OFS) surfactants [1] are a new-class of renewable surfactants with a tunable structure and properties for application as a laundry detergent. These renewable surfactants are synthesized from furans obtained from biomass and long-chain (C₁₂-C₂₀) fatty acid derivatives such as anhydrides obtained from plant-oils. Friedel Crafts acylation reaction to form acylated furans in the presence of solid Brønsted acid catalysts is the main synthetic step to produce OFS surfactants. In this work, we study the acylation of 2-methylfuran and n-octanoic anhydride as a model system using Al-MCM-41 as a mesoporous catalyst. Although, Friedel Crafts reaction is well-known, there is a limited understanding of the kinetics specifically using furanic substrates and long carbon chain acylating agents. The apparent activation energy and rate orders were obtained using a flow reactor set-up. A possible reaction mechanism is proposed to explain the experimental rate orders. This understanding will help in the catalyst design and scale-up of OFS surfactants.

References:

1. Park, D. S., Joseph, K. E., Koehle, M., Krumm, C., Ren, L., Damen, J. N., Shete, M. H., Lee, H. S., Zuo, X., Lee, B., Fan, W., Vlachos, D. G., Lobo, R. F., Tsapatsis, M. and Dauenhauer, P. J. ACS Cent. Sci. 2, 820–824 (2016).