The paper deals with the results of cycloalkylation of phenol with 1-methylcyclopentene, 1(3)-methylcyclohexene in the presence of aluminum phenolate catalyst and influence of various parameters on the yield of the target product. The reaction temperature was varied from 220 to 280 °C, the reaction time - from 1 to 7 h, molar ratio of phenol to cyclene – from 1:1 to 1:3 mol/mol, the catalyst amount – from 10 to 25%. Maximum yield of 2,6-di[1(3)-methylcycloalkyl]phenols is obtained under the following conditions: temperature - 260-280 °C, duration - 5-6 h, molar ratio of phenol to 1(3)-methylcycloalkene - 1:2 mol/mol and the catalyst amount is 20% based on taken phenol. Simultaneously, the yield of the target products - 2,6-di-[1(3)-methylcycloalkyl] phenols is 44.3-47.1% per taken phenol, the selectivity is 67.4 71.2% on the target product. The structure of the synthesized products was determined by 1H NMR and IR spectroscopy. The IR spectra of the samples were recorded on the ALPHA IR Fourier spectrometer (BRUKER company, Germany) in the wave number range of 600–4000 cm-1. The 1H NMR spectra were recorded on the Bruker-300 instrument (Germany) at room temperature of CCl4 with an internal standard, tetramethylsiloxane. As a result of the chromatographic studies of the products of phenol cycloalkylation with 1(3)-methylcycloalkenes in the presence of aluminum phenolate catalyst it became clear that the alkylate mainly contains 2,6-dicycloalkyl-substituted phenols (87.4-92.3%). After rectification of the alkylate at low pressure (20 mm Hg), the target products were obtained with a purity of 96.7-98.1% and their physico-chemical properties were determined. The resulting 2,6-di-[1(3)-methylcycloalkyl]phenols were aminomethylated by formaldehyde and aminoethylnonylimidazoline at the ratio of 1:2:2. From theoretical point of view, Mannich bases were obtained with yield of 65.7-71.7% by the interaction of 2,6-di-[1(3)-methylcycloalkyl]phenols with formaldehyde and aminoethylnonyl imidazoline. Physico-chemical properties of synthesized 4-hydroxy-3,5-di-[1(3)-methylcycloalkyl]benzylaminoethylnonylimidazolines were determined.

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.

2-hydroxy-3-(methylcyclohexenyl-isopropyl)-5-methylbenzylaminoethylnonylimidazolines were synthesized by the interaction of 2-(methylcyclohexynylisopropyl-4-methylphenols and aminoethylnonylimidazoline. Aminocompounds are purified from cycloalkylphenol by transferring them to hydrochloride salt. Further, aqueous solution of the hydrochloric acid amine salt is treated with a concentrated solution of NH4OH and free aminecompounds are isolated. The resulting amine is separated from water by benzene extraction. After benzene distillation, the residue is undergone to distillation under vacuum. Its physico-chemical characteristics and purity of the products are determined. The obtained products are tested as the thermostabilizers to polypropylene.

The paper deals with the results of cycloalkylation of phenol with 1-methylcyclopentene, 1(3)-methylcyclohexene in the presence of aluminum phenolate catalyst and influence of various parameters on the yield of the target product. The reaction temperature was varied from 220 to 280 °C, the reaction time - from 1 to 7 h, molar ratio of phenol to cyclene – from 1:1 to 1:3 mol/mol, the catalyst amount – from 10 to 25%. Maximum yield of 2,6-di(1(3)-methylcycloalkyl)phenols is obtained under the following conditions: temperature - 260-280 °C, duration - 5-6 h, molar ratio of phenol to 1(3)-methylcycloalkene - 1:2 mol/mol and the catalyst amount is 20% based on taken phenol. Simultaneously, the yield of the target products - 2,6-di-(1(3)-methylcycloalkyl)phenols is 44.3-47.1% per taken phenol, the selectivity is 67.4 71.2% on the target product. As a result of the chromatographic studies of the products of phenol cycloalkylation with 1(3)-methylcycloalkenes in the presence of aluminum phenolate catalyst it became clear that the alkylate mainly contains 2,6-dicycloalkyl-substituted phenols (87.4-92.3%). After rectification of the alkylate at low pressure (20 mm Hg), the target products were obtained with a purity of 96.7-98.1% and their physico-chemical properties were determined. The resulting 2,6-di-(1(3)-methylcycloalkyl)phenols were aminomethylated by formaldehyde and aminoethylnonylimidazoline at the ratio of 1:2:2.From theoretical point of view, Mannich bases were obtained with yield of 65.7-71.7% by the interaction of 2,6-di-[1(3)-methylcycloalkyl]phenols with formaldehyde and aminoethylnonyl imidazoline. Physico-chemical properties of synthesized 4-hydroxy-3,5-di-(1(3)-methylcycloalkyl)benzylaminoethylnonylimidazolines were determined.

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