Aggregation Behavior and Thiol-Thioester Exchange for Cationic Surfactants with Propylthioacetate Side Chain

Tsuyoshi Asakawa; Nao Arai; Akina Fujii; Katsunori Takahashi; Kazuki Takakuwa; Mitsunori Honda; Akio Ohta; Hitoshi Asakawa

doi:10.5650/jos.ess18032

Detergents, Surfactants, Interface and Colloid

Aggregation Behavior and Thiol-Thioester Exchange for Cationic Surfactants with Propylthioacetate Side Chain

Tsuyoshi Asakawa, Nao Arai, Akina Fujii, Katsunori Takahashi, Kazuki Takakuwa, Mitsunori Honda, Akio Ohta, Hitoshi Asakawa

Author information

Tsuyoshi Asakawa
School of Chemistry, College of Science and Engineering, Kanazawa University
Nao Arai
School of Chemistry, College of Science and Engineering, Kanazawa University
Akina Fujii
School of Chemistry, College of Science and Engineering, Kanazawa University
Katsunori Takahashi
School of Chemistry, College of Science and Engineering, Kanazawa University
Kazuki Takakuwa
School of Chemistry, College of Science and Engineering, Kanazawa University
Mitsunori Honda
School of Chemistry, College of Science and Engineering, Kanazawa University
Akio Ohta
School of Chemistry, College of Science and Engineering, Kanazawa University
Hitoshi Asakawa
School of Chemistry, College of Science and Engineering, Kanazawa University

Keywords: thioacetate surfactant, critical micelle concentration, micellar size, thiol-thioester exchange

JOURNAL FREE ACCESS

2018 Volume 67 Issue 8 Pages 969-976

DOI https://doi.org/10.5650/jos.ess18032

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Abstract

A series of cationic surfactants containing the thioacetate group, [C_nH_2n+1N(CH₃)₂(CH₂)₃SCOCH₃] Cl (C_n3SAc, n = 12, 14, 16), were prepared and their properties in aqueous solution were investigated by conductivity, fluorescence, and dynamic light scattering measurements. The critical micelle concentrations (CMCs) of C_n3SAc decreased to about half the value of the corresponding alkyltrimethylammonium chloride. Thioacetate was eliminated with the addition of dithiothreitol (DTT) as well as NaOH. HPLC (high performance liquid chromatography) analysis and NMR (nuclear magnetic resonance) spectroscopy showed that thiol surfactants, [C_nH_2n+1N(CH₃)₂(CH₂)₃SH]Cl (C_n3SH), were generated upon the addition of DTT in aqueous solution via thiol-thioester exchange, whereas gemini surfactants, [C_nH_2n+1N(CH₃)₂(CH₂)₃SS(CH₂)₃N(CH₃)₂C_nH_2n+1]2Cl (2C_n3SS), were generated upon incubation in alkaline solution via hydrolysis and air oxidation.

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