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(506d) Reaction Engineering for Bio-Renewable Furan-Derived Surfactants

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
Dauenhauer, P., University of Minnesota
Vlachos, D. G., University of Delaware
Despite years of technology development, most large-volume surfactants are made from petrochemical sources, while efforts to make renewable surfactants are focused on making existing surfactant structures from renewable sources. In this work, we demonstrate a new surfactant based on the natural structure and chemistry of plant-based oils and sugars with superior function and suitability as a replacement to petrochemicals. Furans obtained from lignocellulosic biomass can be acylated with natural oils-derived fatty acids and anhydrides in the presence of a heterogenous zeolite catalyst. The results obtained for the reaction of lauric anhydride with furan show that different pore sizes, structures and acidity of zeolites result in varying acylation activity. Following acylation, the molecule can be upgraded via several independent and sequential chemistries such as etherification, hydrogenation and aldol condensation and finally subjected to sulfonation to yield surfactant molecules termed as oleo-furan sulfonates (OFS) in high yield. Evaluation of surfactant performance of OFS revealed hundredfold better detergency and stability in hard water conditions in comparison with petroleum-derived counterparts. The synthesis of OFS molecules is highly tunable and selective where the number of carbon atoms in the linear or branched chain can be easily varied without compromising on reaction yields to achieve desired surfactant properties.

References

[1] Joseph, K. E., Park, D. S., Koehle, M., Krumm, C., Ren, L., Damen, J. N., Shete, M. S., Lee, H. S., Xiao, Z., Lee, B., Fan, W., Vlachos, D. G., Lobo, R., Tsapatsis, M., Dauenhauer, P. J. ACS Cent. Sci. 2016, 2, 820