Synthesis of Ethyl Ether of 4(4-Hydroxyphenyl)- and 4′-Methyl-4(4-Hydroxyphenyl)cyclohexancarbonic Acids and Their Aminomethylated Derivatives

Abstract

The article presents the results of cycloalkylation of phenol with ethyl cyclohexane- and 4-methylcyclohexenecarboxylic esters in the presence of a zeolite-Y catalyst impregnated with phosphoric acid. It has been established that to perform the cycloalkylation of phenol with ethyl cyclohexenecarboxylic acid in the presence of a zeolite-Y catalyst impregnated with orthophosphoric acid, the optimal conditions are: temperature 120 °С, reaction time 5 h, molar ratio of phenol to ether 1 : 1 mol/mol. And amount of catalyst is 10% for taken phenol. The yield of the target product was 74.7% of the theory for taken phenol, and selectivity - 93.8% for the target products. It was found that under optimal reaction conditions cycloalkylation (temperature 110 °C, reaction time 4 h, the ratio of phenol to ether 1 : 1, the amount of catalyst 7%) of phenol with ethyl 4-methylcyclohexenecarboxylic acid yield of ethyl 4 (4-hydroxyphenyl) -4'-methylcyclohexane-carboxylic) acid was 78.3% of the theory per phenol taken, and the selectivity was 95.7% for the desired product. The synthesis of aminomethyl derivatives of 4-hydroxyphenylcyclohexanecarboxylic acids in the presence of formalin and aniline was also carried out. As a result of aminomethylation, ethyl esters of 4 (4-hydroxy-3-phenylaminobenzyl) cyclohexane- and 4 (4-hydroxy-3-phenylaminobenzyl) -4'-methylcyclohexanecarboxylic acid were obtained. The yields of the target products were 67.3 and 71.7%, respectively, from the theory on taken ether. The structure and composition of the products were determined using IR and 1H NMR spectroscopy. And the purity of the products obtained was studied by chromatographic analysis. Ethyl esters of 4 (4-hydroxy-3-phenylaminobenzyl) cyclohexane- and 4 (4-hydroxy-3-phenylaminobenzyl) -4'-methylcyclohexanecarboxylic acid can be used as an antioxidant to diesel fuel and turbine oil T-46.

SYNTHESIS AND STUDY OF ANTIOXIDATIVE PROPERTIES OF AMINOMETHYLATED DERIVATIVES OF p-(CYCLOHEXENE3-YL-ETHYLPHENOL)

“…Among a large number of petrochemical products, alkylphenols are widely used as initial reagents in the synthesis of fuel additives and stabilizers, inhibitors of freeradical oxidation of organic and bioorganic substrates, herbicides, fragrances, etc. [1][2][3][4][5][6].…”

“…As a result, it found that at a temperature of 80 °C, reaction t i m e o f 2 h , 1 : 2 : 2 m o l a r r a t i o o f palkylphenol to formalin and aniline, the yield of 2-hydroxy-5-alkylbenzylphenylamines amounts to 82. 3…”

Impact on Humans of Pollutants in Moscow

“…Источниками загрязнения почвы являются химические вещества и микроорганизмы, присутствие которых изменяет физические, химические и биологические свойства почвы, что приводит к снижению плодородия почвы [9]. Попав в почву или грунтовые воды, данные вещества способны не только оказывать токсическое воздействие, но и накапливаться как в почве, так и в воде [6,11,13].…”

“…Попав в почву или грунтовые воды, данные вещества способны не только оказывать токсическое воздействие, но и накапливаться как в почве, так и в воде [6,11,13]. Контроль уровня загрязнения атмосферного воздуха осуществляется с помощью дискретных измерений разовых концентраций загрязняющих веществ с интервалом времени 20-30 мин, а также путем непрерывного отбора проб в течение суток [9,14]. В результате чего определяются -максимальная разовая Cмр и среднесуточная Cсс концентрации загрязняющих веществ [23].…”

“…Кроме перечисленных веществ, также в атмосферный воздух поступают различные специфические вещества, выбрасываемые отдельными производствами, предприятиями, цехами. Действие данных веществ (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18) может приводить к атмосферным загрязнениям, к изменению рН и, как следствие, может сказаться как на почве, так и на организме человека.…”