SYNTHESIS AND PROPERTIES OF 2-ALKYL-1-(2-AMINOETHYL)-2-IMIDAZOLINES
UDC 665.7.038.5
Key words: stearin, DETA, alkylimidazoline, cationic surfactant, aqueous solution, surface tension, critical micelle concentration, adsorption work, corrosion inhibitor.
For citation: Usevich A. I., Tsalko V. V., Asipionak K. M., Kuzemkin D. V. Synthesis and properties of 2-alkyl-1-(2-aminoethyl)-2-imidazolines. Proceedings of BSTU, issue 2, Chemical Engineering, Biotechnologies, Geoecology, 2021, no. 2 (247), pp. 144–152 (In Russian).DOI: https://doi.org/10.52065/2520-2669-2021-247-2-144-152.
Abstract
The features of diethylenetriamine (DETA) acylation reaction with C16–C18 saturated monocarboxylic acids have been studied, including the effect of an excess of DETA on the relative yield of its monoacyl derivative (aminoamide) and diacyl derivative (diamide). It was found that even a multiple excess of DETA does not suppress the formation of diamide, which negatively affects the subsequent stage of the aminoamide cyclization, leading to a decrease in the yield and quality of the target 2-alkyl-1- (2-aminoethyl) -2-imidazoline. The mechanism of the acylation and cyclization reactions during the interaction of diethylenetriamine with higher fatty acids is proposed, which explains the observed regularities. Based on the proposed mechanism, a procedure for the high yield synthesis of 2-alkyl-1-(2-aminoethyl)-2-imidazolines from fatty acids and diethylenetriamine in a one-pot system without the need for additional isolation and purification was developed and implemented. 1-(2-Aminoethyl)-2-pentadecyl-2- imidazoline and 1-(2-aminoethyl)-2-heptadecyl-2-imidazoline were synthesized from a technical mixture of palmitic and stearic acids without separation. Aqueous solutions of acetic acid salts of the obtained mixed surfactant were prepared and the isotherms of their surface tension at the interface with air were measured at temperatures of 20–60°С. The anticorrosive effect of the synthesized 2-alkyl-1-(2-aminoethyl)-2-imidazolines in relation to carbon steel in a water-salt solution has been studied.
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