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Synthesis, stability, and biodegradability studies of a surface‐active amide
Author(s) -
Stjerndahl Maria,
Holmberg Krister
Publication year - 2005
Publication title -
journal of surfactants and detergents
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.349
H-Index - 48
eISSN - 1558-9293
pISSN - 1097-3958
DOI - 10.1007/s11743-005-0364-0
Subject(s) - chemistry , candida antarctica , lipase , pulmonary surfactant , amidase , biodegradation , amide , hydrolysis , critical micelle concentration , organic chemistry , micelle , aminolysis , ethylene glycol , catalysis , enzyme , biochemistry , aqueous solution
A homolog pure nonionic surfactant, tetra(ethylene glycol) mono‐ n ‐octaneamide, was synthesized. The surfactant was characterized by determining the critical micelle concentration, cloud point, and biodegradation. Hydrolysis catalyzed by an acid, an alkali, a peroxide, and enzymes [peptidase from porcine, amidase from Pseudomonas aeruginosa , and two lipases, Mucor miehei lipase (MML) and Candida antarctica lipase B (CALB)] was investigated using 1 H nuclear magnetic resonance. The surfactant was stable toward the acid, alkali, and peroxide. When subjected to peptidase and CALB, the amide was cleaved, although at a low rate. No reaction was obtained when using the amidase or MML. The biodegradation test resulted in more than 60% degradation after 28 d. Based on these results, the amide surfactant can be considered chemically stable, yet highly biodegradable, which generally is an ideal combination of properties for a surfactant.