Premium
Fatty Acids in Heterocyclic Synthesis. Part XIV: Synthesis of Surface Active Agents from Some Novel Class of Oxadiazole, Thiadiazole and Triazole Derivatives Having Microbiological Activities
Author(s) -
Gad ElKarim Iman A.,
Amine Mahasen S.,
Mahmoud Amal A.,
Gouda Alaa S.
Publication year - 2014
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/s11743-013-1530-9
Subject(s) - chemistry , chloroacetic acid , oxadiazole , semicarbazide , organic chemistry , hydrazine (antidepressant) , hydrate , hydrolysis , 1,2,4 triazole , acetic anhydride , acylation , myristic acid , nuclear chemistry , fatty acid , palmitic acid , chromatography , catalysis
Reaction of stearic acid with semicarbazide in refluxing POCl 3 afforded 2‐amino‐5‐heptadecyl 1,3,4‐oxadiazole. Acylation of the amino group with acetic anhydride, ethyl chloroacetate and chloroacetic acid gave amide and β‐amino acid derivatives. These compounds were cyclized to imidazo[2,1‐ b ]oxadiazole derivatives by two different techniques. Treating the starting oxadiazole compound with P 2 S 5 , hydroxyl amine and hydrazine hydrate in benzene afforded thiadiazole and triazole derivatives. Unexpectedly, triazolo[3,4‐ b ][1,3,4]oxadiazole derivative was obtained when 1,3,4‐oxadiazole derivative was refluxed with hydrazine hydrate in ethanol. The biological activities of the synthesized compounds were screened in vitro against some gram positive and gram negative bacteria and fungi. Addition of quantitative amount of propylene oxide units (3, 5, 7 mol) to the synthesized compounds afforded new nonionic surfactants. The physico‐chemical and surface properties of the novel synthesized surfactants such as surface and interfacial tension, cloud point, wetting time, emulsion stability, foam height, CMC, resistance to hydrolysis and their biodegradability were investigated. In addition, surface parameters including effectiveness ( π CMC ), efficiency (PC 20 ), maximum surface excess (Γ max ) and ( A min ) were examined.