New Carbamates and Ureas: Comparative Ability to Gel Organic Solvents

Abstract

Two series of novel amphiphilic compounds were synthesized based on carbamates and ureas structures, using a modification of the synthesis methods reported by bibliography. The compounds were tested for organic solvent removal in a model wastewater. The lipophilic group of all compounds was a hexadecyl chain, while the hydrophilic substituent was changed with the same modifications in both series. The structures were confirmed by FT-IR, NMR, molecular dynamic simulation and HR-MS and their ability to gel organic solvents were compared. The SEM images showed the ureas had a greater ability to gel organic solvents than the carbamates and formed robust supramolecular networks, with surfaces of highly interwoven fibrillar spheres. The carbamates produced corrugated and smooth surfaces. The determination of the minimum gelation concentration demonstrated that a smaller quantity of the ureas (compared to the carbamates, measured as the weight percentage) was required to gel each solvent. This advantage of the ureas was attributed to their additional N-H bond, which is the only structural difference between the two types of compounds, and their structures were corroborated by molecular dynamic simulation. The formation of weak gels was demonstrated by rheological characterization, and they demonstrated to be good candidates for the removal organic solvents.