Thermal Stability Study of 4-(1-Adamantyl)phenol
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mal Stability Study of 4-(1-Adamantyl)phenol V. A. Shakuna, *, T. N. Nesterovaa, S. V. Tarazanovb, and V. S. Sarkisovaa aSamara
b
State Technical University, Samara, 443100 Russia All-Russia Research Institute for Petroleum Processing, Moscow, 111116 Russia *e-mail: [email protected] Received June 6, 2020; revised July 3, 2020; accepted July 10, 2020
Abstract—The thermal stability of 4-(1-adamantyl)phenol has been studied in the temperature range of 703– 753 K, the components of the thermolysis reaction mixture have been identified, and the rate constants and parameters of the Arrhenius equation for the thermal degradation of the compound under study have been calculated. It has been found that of the thermal stability of 4-(1-adamantyl)phenol significantly surpasses that of 4-tert-butylphenol. Keywords:4-(1-adamantyl)phenol, thermal stability, thermal degradation, isomerization, kinetics, rate constant, Arrhenius equation DOI: 10.1134/S0965544120110171
It is known that the modification of organic compounds and polymers with adamantane and its derivatives imparts additional resistance against extreme mechanical impacts to materials and increases their thermo-oxidative stability. Currently, a great deal of attention is being paid to carboxylic acid esters of the adamantane series as promising components of thermally stable lubricating oils. Thus, Bagrii and Maravin [1] evaluated the viscosity–temperature properties and thermo-oxidative stability of alkyl esters of 5,7-dimethyladamantane1,3-dicarboxylic acids and showed their advantages over conventional lubricating oils. The cited authors have recommended using such structures as thermally stable synthetic lubricating oils for gas turbine power plants and as cable oil in view of strong electrical insulation properties. The results of extensive studies [2–5] on the physicochemical characteristics and thermooxidative stability of esters of dicarboxylic acids of the adamantane series also show serious advantages of this type of compounds in the development of unique lubricating materials. Adamantane derivatives are also of great interest in the creation of advanced polymers. For example, it has been shown in [6, 7] that epoxy resins based on 1,3bis(4-hydroxyphenyl)adamantane are characterized by increased hardness and thermal stability and have improved dielectric properties. According to the data of the patent [8], copolymers of dialkyladamantane and di-tert-butylbenzenes possess a high glass transition point (182°C), are resistant to extreme temperatures and thermo-oxidative degradation and find application as protective coatings.
The results of the studies devoted to adamantylphenols show the possibility of their effective application as inhibitors and antioxidants. Sokolenko et al. [9] have shown that 4-(1-adamantyl)phenol and 2,4-di(1-adamantyl)phenol exhibit high antioxidant activity by way of example of the model reaction of cumene oxidation. The prospects for application of adamantyl-substituted phenols, cresols, catechol, and hydroquinone as radical chain poly
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