Towards Novel Surfactants Derived from Bio-derived Starting Materials : A doctoral thesis submitted to Lancaster University for the degree of Doctor of Philosophy School of Chemistry

Callaway, Matt and Doulcet, Julien (2026) Towards Novel Surfactants Derived from Bio-derived Starting Materials : A doctoral thesis submitted to Lancaster University for the degree of Doctor of Philosophy School of Chemistry. PhD thesis, Lancaster University.

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Abstract

There exists a commercial demand for novel surfactants that are capable of stabilizing oil in water emulsions of non-petrochemical-based waxes. In the aim of meeting this demand, eighteen novel compounds derived from arginine and ricinoleic acid have been synthesised in an average of three steps using established techniques: modification of the nitro arginine carboxylic acid using thionyl chloride, subsequent amide bond formation with ricinoleic acid using amide coupling reagents and a final Pd/C hydrogenation in acidic conditions to remove the nitro protecting group. As low yields were observed, an in-depth study of the various side reaction products that occurred was performed, highlighting the propensity of ricinoleic acid to form oligomeric products. The dimeric products of the amidification were isolated for further investigation alongside the targeted compounds. Of these compounds, four were found to be water soluble enough to allow preliminary investigation of their efficacy as surfactants (Figure II-1). A UV-Vis spectroscopy using pyrene as a probe compound was adapted to provide values for their critical micelle concentrations. The novel compounds were found to have lower critical micelle concentrations than the structurally similar surfactant LAE. The results indicate that the surfactants could