Synthesis, Characterization and Surface Activity of Hexadecyl o ‐Xylene Sulfonate Isomers

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.

Section: Resultsmentioning

confidence: 99%

Section: Surface Tensionmentioning

confidence: 99%

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

Daoudi

Sehailia

Tazerouti

2022

“…The data are collected in Table 2. The CMC decreased with increasing alkyl chain length, probably because of the increasing hydrophobic effect [22,23].…”

Section: Surface Properties Of Npasmentioning

confidence: 99%

Synthesis and Characterization of Novel Aryl Alkyl Sulfonates Based on Nonylphenol

Niu

Wang

Song

et al. 2016

A series of nonylphenol-substituted alkyl sulfonates (C x NPAS, x = 8,10,12,14,16) with two hydrocarbon chains and two different hydrophilic groups has been synthesized from a-olefins and nonylphenol. The respective products have a ''pseudo-gemini'' surfactant structure. The structures of the C x NPAS have been characterized by IR, UV, 1 H nuclear magnetic resonance, electrospray ionization mass spectrometry, and elemental analysis. The effects of carbon chain length of the obtained surfactants on properties such as the critical micelle concentrations (CMC) in aqueous solutions, surface tension at the CMC (c CMC ), and efficiency of adsorption at the water/ air interface (pC 20 ) have been determined. The c CMC of the surfactants first decreased and then increased with increasing length of the carbon chain x, and reached a minimum of 29.25 mN/m at x = 10, which is much lower than that of a-olefin sulfonate (AOS) (33.52 mN/m). The CMC decreased and pC 20 increased with increasing x. The introduction of the hydroxyl group is responsible for multiple molecular conformations at the water/air interface and leads to a greater molecular area A min and smaller C max than those of AOS.

Synthesis, Characterization and Surface Activity of Alkyl m‐Xylene Sulfonate Isomers

Luan

Cheng

et al. 2012

This paper deals with the synthesis of a series of alkyl m‐xylene sulfonate isomers (with the m‐xylene located at the eighth carbon atom along the long alkyl chain) by the Friedel–Crafts reaction, and the Grignard reaction followed by hydrogenation. The structures were confirmed by 1H NMR. All analytical methods indicated high levels of purity of the isomers with the eighth carbon atom at the long alkyl chain. The critical micelle concentration (CMC), surface tension and maximum surface excess concentration at the CMC and area per molecule at the interface were determined. As the long alkyl chains increased the surfactant molecule tends to pack closely at the gas–liquid interface. Accordingly, the CMC decreased, the adsorption density increased, and the surface tension reduction was strengthened.