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

• Asakawa Tsuyoshi

  School of Chemistry, College of Science and Engineering, Kanazawa University

• Arai Nao

  School of Chemistry, College of Science and Engineering, Kanazawa University

• Fujii Akina

  School of Chemistry, College of Science and Engineering, Kanazawa University

• Takahashi Katsunori

  School of Chemistry, College of Science and Engineering, Kanazawa University

• Takakuwa Kazuki

  School of Chemistry, College of Science and Engineering, Kanazawa University

• Honda Mitsunori

  School of Chemistry, College of Science and Engineering, Kanazawa University

• Ohta Akio

  School of Chemistry, College of Science and Engineering, Kanazawa University

• Asakawa Hitoshi

  School of Chemistry, College of Science and Engineering, Kanazawa University

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.

Journal

• Journal of Oleo Science

  Journal of Oleo Science 67 (8), 969-976, 2018

  Japan Oil Chemists' Society

Keywords

• thioacetate surfactant
• critical micelle concentration
• micellar size
• thiol-thioester exchange

Details

• CRID: 1390001288049807104
• NII Article ID: 130007429130
• NII Book ID: AA11503337
• DOI: 10.5650/jos.ess18032
• ISSN: 13473352
• ISSN: 13458957
• NDL BIB ID: 029116472
• PubMed: 30012900
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I029116472
• Web Site: https://www.jstage.jst.go.jp/article/jos/67/8/67_ess18032/_pdf
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • PubMed
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed