New family of surfactants from biobased materials

Authors: Jackson, Michael - Mike; Evans, Kervin; Price, Neil; BLACKBURN, JUDITH - Retired ARS Employee; WARD, CHARLES - Iowa State University; Ray, Karen; Vermillion, Karl

Submitted to: ACS Sustainable Chemistry & Engineering
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 10/4/2021
Publication Date: 10/4/2021
Citation: Jackson, M.A., Evans, K.O., Price, N.P.J., Blackburn, J.A., Ward, C.J., Ray, K.J., Vermillion, K. 2021. New family of surfactants from biobased materials. ACS Sustainable Chemistry & Engineering. 9(41):13842-13850. https://doi.org/10.1021/acssuschemeng.1c04703.
DOI: https://doi.org/10.1021/acssuschemeng.1c04703

Interpretive Summary: In this project, we demonstrated that a new family of detergent molecules can be prepared by combining common and waste stream sugars with oil from a new row crop. These new detergents are based on agricultural products and could create a market for dairy waste and for Cuphea. The detergents are easily prepared using methods that are less environmentally impactful than those used in the preparation of other biobased detergents. We demonstrated that these detergents have antimicrobial activity which should expand the ways in which they can be used. This project was undertaken to help develop uses for crop residues and potential new crops. Commercialization of these new detergents would help develop these materials for new markets. Cuphea is a new row crop under development for its novel seed oil.

Technical Abstract: ß-C-glycoside ketone derivatives of glucose, lactose, and maltose were converted to amines via a reductive amination using 5 wt% Rh/Al2O3 in ammoniacal methanol under 34 bar H2. The amines were isolated and then were used as the amine in the reductive amination of 2-undecanone that can be prepared from the seed oil of Cuphea. The resulting ß-C-glycoside-2-aminoundecanes were characterized by MALDI-TOF mass spectrometry and 2D NMR. The critical micelle concentrations of the products as measured by isothermal calorimetry titration ranged from 1 to 5 mM and the micelles carry a positive charge as measured by zeta potentials. The ß-C-glycoside 2-aminoundecanes have antimicrobial activity against Bacillus subtilis, Pseudomonas aeruginosa, Erwinia amylovora, and Escherichia coli, with the C-glucoside derivative having the greatest activity with a minimum inhibitory concentration of 0.31 mM and a minimum bactericide concentration of 0.62 mM against the Gram positive organisms. Against the Gram negative Erwinia and Escherichia the MIC is 0.62 mM. This work introduces a new family of sustainable surfactants with potential uses in personal care and cleaning products.