Synthesis of an ionic sugar-amino acid based surfactant in aqueous media

• Published in: Journal of molecular liquids 2020-11, Vol.318, p.114269, Article 114269
• Main Authors: Esmaeilian, Nima, Dabir, Bahram, Malek, Reza Mohammad Ali, Arami, Mokhtar, Mazaheri, Firooz Mehr
• Format: Article
• Language: English
• Subjects: Closed bottle test; Connolly solvent accessible area; Micellar catalysis; Sugar based cationic surfactant
• ISSN: 0167-7322; 1873-3166
• DOI: 10.1016/j.molliq.2020.114269

Micellar catalysis has been used to synthesis a sugar-amino acid based cationic surfactant (N,N,N-trimethyl-2-oxo-2-(((2R,3S,4S,5R)-3,4,5-trihydroxy-6-(tetradecyloxy)tetrahydro-2H-pyran-2-yl)methoxy)ethan-1-aminium iodide) with renewable raw materials in aqueous media. The micellar catalysis method was compared with the method that uses dimethylformamide (DMF) as solvent. The results confirm the superiority of micellar catalysis method in terms of efficiency, energy consumption and environmental issues. Common physicochemical properties of surfactants like critical micelle concentration (CMC), the minimum surface area per molecule (Amin) and Krafft temperature were determined to evaluate the behavior of synthesized surfactant properties at the air-water interface. Computational chemistry method (DFT (B3LYP/6-311g(d)) was conducted to calculate the dimensional properties of the surfactant to determine the shape, size and aggregation number of micelles at their CMC by an approach that uses Connolly solvent accessible area as the effective area of surfactant head groups. Dynamic light scattering method (DLS) was used to determine the size of micelles. The results of DLS tests show good agreement with the calculation method. Finally, the biodegradability of synthesized natural based cationic surfactant was studied by close bottle standard test to investigate the biodegradation of synthesized surfactant. •Micellar catalysis enables transesterification of betaine and alkyl glucoside.•Alkyl glucoside cationization in water is greener and cheaper than in the DMF.•Connolly surface area of surfactant head corresponds to the effective surface area.•Addition of betaine to alkyl glucoside structure increases the biodegradability.