Confirmation of the reaction pathway for obtaining 1-(stearamidoethyl)-2-hepta-decyl-2-i midazoline

Abstract

2-lmidazolines are components of many products, used in industry and households. 1-(Stearamidoethyl)-2-heptadecyl-2-imidazoline is a surface active compound, which after quaternization with dimethyl sulfate, is used in lubricants, detergents, shampoos, softeners and cosmetics products. Due to its importance, it was essential to establish the exact reaction pathway for obtaining this compound. Diethylene triamine and stearic acid were used as the starting components. Using titrimetric analysis, and IR and 1H NMR spectros-copic analysis, as well as UV-Vis spectrophotometry it was established that the main intermediate was the 1,3-diamide bis(stearamidoethyl)amine. Earlier investigations conducted by some authors, using exclusively titrimetric analysis, showed that the main intermediate was the 1,2-diamide. In this paper it was proved that the assumption of these authors that salicylaldehiyde would react only with the primary and not the secondary amine groups was wrong. 1,2-Diamide is the main product of the hydrolysis of 1-(stearamido-ethyl)-2-heptadecyl-2-imidazoline. It was shown, in this paper that the reaction of diethylene triamine with stearic acid in xylene at the reflux temperature, yields the salt of 1-(stearamidoethyl)-2-heptadecyl-2-imidazoline and stearic acid.

2-imidazolini su jedinjenja koja ulaze u sastav velikog broja proizvoda koji se koriste u Industriji i domaćinstvima. 1-(2-stearamidoetil)-2-heptadecil-2-imidazolin je površinski aktivno jedinjenje, koje se posle kvaternizacije dimetilsulfatom, koristi kao aditiv lubrikansima, deterdžentima, šamponima, omekšivačima i kozmetičkim proizvodima. U raduje dat dokaz reakcionog puta do-bijanja 1-(2-stearamidoetil)-2-heptadecil-2-imidazolina. Do rezultata se došlo praćenjem reakcije između stearlnske klseline i dietilentriamina volumetrijskom metodom titracije i savremenim metodama IR i 1W NMR spektroskopije i UV-Vis spektrofotometrije. Utvrđeno je da je glavni intermedijer u reakciji dobijanja 1-(2-stearamidoetil)-2-heptadecil-2-imidazolina 1,3-diamid bis(stearamido-etil)amin. Pokazano je da je glavni proizvod reakcije dietilentriamina i stearin-ske kiseline u ksilenu, pod uslovima refluksa, so 1-(stearamidoetil)-2-hepta-decil-2-imidazolina istearinske kiseline.