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

Cleaning Up Surfactants: Realising critical micelle concentrations lower than sodium dodecyl sulfate with sustainable surfactants prepared from amino acids and naturally occurring aldehydes.

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 (P _ow) of 1.6 (indicating low bioaccumulative potential), and a single-step product (N-geranylated aspartic acid) was assessed for detergency potential via swatch testing.

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