Methods have been developed for the synthe-sis of a series of monomeric and dimeric surfactants functionalized by an oxime group based on imid-azole, pyridine and alkylamines. Alkyl radicals of varying degrees of branching were used, both as sub-stituents at the nitrogen atom of the head group and as spacers in the formation of dimeric products. This allowed to create a whole spectrum of supramo-lecular systems with different physicochemical pro-perties and reactivity.
Methods of obtaining a number of intermedi-ate products were improved, primarily for the reac-tion of the imidazole alkylation using interphase ca-talysis conditons — solid phase-liquid. The method of obtaining surfactants based on imidazole consisted in the interaction of alkylimidazoles with chloro-acetaloxime in a suitable solvent or with chloro-acetone and subsequent reaction with a hydroxyla-mine solution. In the preparation of pyridine-based surfactants, the corresponding oxo-substituted pyri-dine was reacted with a hydroxylamine solution, fol-lowed by reaction of the obtained product with al-kyl halide. A method has been developed for the syn-thesis of functionalized surfactants based on alipha-tic amines, where for monomeric products a path is chosen that is associated with the sequential alkyla-tion of 1-chloroacetoxime with dimethylamine and dodecyl bromide, and for dimeric ones, the direct interaction of 1,3-dichloroacetoxime with 1,1-dime-thyl-1-dodecylamine.
The composition, structure and purity of the obtained compounds were confirmed by NMR spec-troscopy, thin-layer chromatography and elemental analysis. NMR spectra were recorded on a BRUKER Avance II 400 instrument (400 MHz), TMS was used as an internal standard. Chromatography in a thin layer of silica gel was performed on Merck Si-licaGel 60 F254 plates (eluent — chloroform: meth-anol = 10:1).
The data presented by us testify to the pro-spects of the chosen pathway for structural modifica-tion of surfactants functionalized by the oxime group, and give direction for the further design of such microheterogeneous systems.
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