ESTIMATION OF INTERRELATION BETWEEN STRUCTURE OF SOME NITROGEN-CONTAINING ALKYLARYL-SUBSTITUTED PHENOLS AND THEIR REACTIVITY AND FUNCTIONAL PROPERTIES

Abstract

The paper describes the results of the research of some N-containing 2,6-di-a-methylbenzylphenols as antioxidants, antimicrobial and antiwear additives to the lubricating oils. In the model reactions of oxidation of hydrocarbons it has been earlier shown the efficiency of some nitrogen-containing derivatives of α-methylbenzyl-substituted phenols. As it can be seen from the results of research of mechanism of inhibiting action of three 4-N-substituted aminomethyl-2,6-di-α-methylbenzylphenols they have approximate antiradical efficiency, К7=6-6.5.104 l/mol×s (60 °С), exceeding К7 of ionol (2.2·104 l/mol×s). The stoichiometric inhibition coefficients are f=2-2.6. 2,6-di-α-methylbenzyl-4-diethylaminomethylphenol has the highest reactivity and high catalytic factor. The same conclusion can be drawn from the results of quantum chemical calculations. To confirm the found regularities, they were tested in lubricating oils as antioxidants. Antimicrobial properties of the investigated compounds were studied in the composition of vaseline oil. The synthesized aminomethyl derivatives of 2,6-di-α-methylbenzylphenol at a concentration of 0.5-1% ensure the stability of the vaseline oil to biodeterioration, show antimicrobial, more antifungal activity. These compounds show better efficiency than the biocide used in practice - sodium pentachlorophenolate. The lubricating properties of the test compounds were evaluated by the wear spot diameter (Dw) on Four-Ball Wear Test Machine in accordance with RF State Standard 9490-75. Investigations of antiwear properties have shown that these compounds, along with antioxidant properties, have also lubricating properties. They are better than the known additive for the similar purpose - tricresyl phosphate in anti-wear efficiency. The analysis of interrelations of kinetic indicators (rate constant, stoichiometric coefficients), obtained in the model reactions of inhibition of hydrocarbons oxidation with quantum chemical parameters of inhibitors molecular structure (enthalpy, electron population, dipole moment) antioxidant and anti microbial properties of compounds in vaseline oil has been conducted..For citation:Babaev E.R. Estimation of interrelation between structure of some nitrogen-containing alkylaryl-substituted phenols and their reactivity and functional properties. Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. 2017. V. 60. N 5. P. 51-56