(582d) Tunable Oleo-Furan Surfactants Via Acylation of Biomass-Derived Furans

Authors: 
Joseph, K. E., University of Minnesota
Park, D. S., University of Minnesota
Krumm, C., Sironix Renewables
Tsapatsis, M., University of Minnesota
Lobo, R. F., University of Delaware
Vlachos, D. G., University of Delaware
Dauenhauer, P., University of Minnesota
Surfactants are widely used in household detergents, cleaners, emulsifiers, foaming agents, and personal care products. Limited selectivity and tunability of petroleum-derived, commercial surfactants such as linear alkylbenzene sulfonates result in poor hard water performance, thereby demanding the use of expensive and toxic chelants in detergent formulations. We propose a new, renewable pathway to produce surfactants made from biomass-derived feedstocks, such as furan obtained from the sugar, xylose, in biomass and lauric acid obtained from the hydrolysis of triglycerides found in natural oils such as coconut and soybean oil. The key chemistry enables acylation of furan with lauric acid or anhydride in the presence of a heterogenous catalyst such as a zeolite or a homogenous catalyst such as trifluoroacetic anhydride. The synthesis of these oleo-furan molecules is highly tunable, where surfactant properties can be selected by using different sources of triglycerides and by coupling various chemistries to obtain a wide range of surfactants incorporating linear or branched structure, or different chemical functionalities. Oleo-furan surfactants (OFS) demonstrates a hundredfold improvement in hard water stability when compared to conventional surfactants, thereby bypassing the need for chelants. The ability to tailor furans with the functionality desired in the final surfactant molecule enables the expansion of this chemistry to make a wide variety of OFS and opens the doors to explore the potential of furan-based surfactants for other applications.
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