N-Geranylated Amino Acid Surfactants with Low Critical Micelle Concentrations from Abundant, Naturally Derived Starting Materials

Abstract

In this work, a simple method for the preparation of N-alkylated amino acid surfactants in 1–2 steps is reported. These products perform comparably to existing ionic surfactants, with N-tetrahydrogeranylated serine having a critical micelle concentration (CMC) of only 7.4 mmol·L−1. The suite of multiply charged surfactants generally possesses CMCs comparable to existing ionic surfactants. Further, their synthesis is simple, high-yielding, scalable, and does not require complex purification. The most hydrophobic surfactant (N-geranylated glycine) was found to have a log n-octanol-water partition coefficient (Pow) of 1.6 (indicating low bioaccumulative potential), and a single-step product (N-geranylated aspartic acid) was assessed for detergency potential via swatch testing. Show more