Selective access to novel aryl alkyl disulfonates via photosulfochlorination process: An eco-benign approach to a highly active class of surfactants

Abstract

In this work we report the synthesis of a new family of surfactants based on aryl alkyl disulfonates; the latter compounds were derived from a mixture of linear alkylbenzene with the resulting disulfonate groups residing on the linear alkyl side-chain rather than the usual aromatic ring structure. The Reed sulfochlorination reaction was successfully utilized to selectively promote the formation of disulfonates on the alkyl group. A number of analytical methods in the form of liquid chromatography–mass spectrometry (LC–MS), gas chromatography–mass spectrometry (GC–MS), Fourier-transform infrared spectroscopy (FTIR) and nuclear magnetic resonance (NMR) were used to characterize the resulting compounds and intermediates. The critical micelle concentration, the surface tension at the critical micelle concentration, the surface excess concentration at surface tension, and the area per molecule were measured at different concentrations and temperatures. Thermodynamic parameters and Krafft temperature were also determined. The obtained results were compared to those of commercial n-dodecylbenzene sulfonates and linear alkylbenzene sulfonates surfactants, showing that these new synthesized surfactants present good surface properties