Thermodynamically stable structure of hydroxy alkane sulfonate surfactant monomers in water achieving high water solubility and a low CMC

Abstract

Although sodium internal olefin sulfonates (IOSs) derived from petrochemicals are known to act as anionic surfactants, these compounds have few practical applications and their interfacial properties have not been examined in detail because they have complex compositions and are challenging to prepare. However, IOSs obtained from vegetable oils have recently been applied to detergents. The present work represents the first study of the IOS sodium 5-hydroxyhexadecane-4-sulfonate (C16-4S-5OH) as a pure substance. The properties of C16-4S-5OH in aqueous solution were assessed by differential scanning calorimetry, equilibrium surface tension measurements, Fourier transform infrared spectroscopy and proton nuclear magnetic resonance spectroscopy. This compound was found to have a low Krafft point and a low CMC, both of which are necessary for a modern sustainable surfactant. Although these two characteristics are normally difficult to achieve simultaneously, this work demonstrated that C16-4S-5OH in aqueous solution has a highly fixed stereostructure that enables both properties to be achieved. The C16 main carbon chain of this compound acts as a C12 and a C4 chain both oriented in the same direction, while the hydrophilic sulfo and hydroxy head groups form a rigid cyclic moiety including two carbons of the C16 alkyl chain based on hydrogen bonding. This highly fixed molecular structure of the C16-4S-5OH in water is maintained in the monomer and micellar states below and above the CMC, respectively.