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 paper deals with the results of cycloalkylation of phenol with 1-methylcyclopentene, 1(3)-methylcyclohexene in the presence of KU-23 catalyst and influence of various parameters on the yield of the target product. The reaction temperature was varied from 80 to 140 °C, the reaction time - from 2 to 8 h, molar ratio of phenol to cyclene – from 1:2 to 2:1 mol/mol, the catalyst amount – from 5 to 15%. Maximum yield of para-[1(3)-methylcycloalkyl] phenols is obtained under the following conditions: temperature – 110-120 °C, duration – 5-6 h, molar ratio of phenol to 1(3)-methylcycloalkene – 1:1 mol/mol and the catalyst amount is 10% based on taken phenol. Simultaneously, the yield of the target products – para-[1(3)-methylcycloalkyl] phenols is 68.6-73.5% per taken phenol, the selectivity is 91.8-94.3% 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 KU-23 catalyst it becames clear that the alkylate mainly contains paracycloalkyl-substituted phenols (89.6-94.1%). After rectification of the alkylate at low pressure (10 mm Hg), the target products were obtained with a purity of 97.6-98.2% and their physico-chemical properties were determined. The resulting para-[1(3)-methylcycloalkyl] phenols were aminomethylated by formaldehyde and aminoethylnonylimidazoline at the ratio of 1:2:2. As a result, Mannich bases were obtained with yield of 68.3-76.7% from theory. The synthesized methylcycloalkylbenzylaminoethylnonylimidazolines were tested as antioxidants of M-8 engine oil. The oxidation resistance of the oil has been investigated without the addition and with the addition of ИХП-21 antioxidants, known benzylphenylamines and the compounds of the invention. Addition of the obtained compounds to the base oil leads to enhancement of its antioxidant properties, at application of which viscosity increase is 14.07-15.28%, and precipitate - 0.45-0.57%.
The present study deals with the investigation of catalytic cycloalkylation reactions of phenol with 1-methylcyclopentene. KU-23 and aluminum phenolate were used as catalysts for the process. The effect of kinetic parameters (temperature, duration, molar ratios of the initial components and the amount of catalyst) on the yield and selectivity of methylcyclopentyl phenols obtained as a result of scientific research was investigated. As a result, effective conditions were found for the production of para- and ortho-, ortho- (1-methylcyclopentyl) phenols with high yield and selectivity. It was determined that high yield of target product in the presence of phenol, 1-methylcyclopentene and catalyst KU-23, was 71.2% for phenol and selectivity for target product - 92.8% is obtained under the following conditions of cycloalkylation reaction: temperature 110°C, reaction time-5 hours, molar ratio phenol to methylcyclopentene-1 : 1, the amount of catalyst-10% according to the phenol taken. The cycloalkylation reaction of phenol with 1-methylcyclopentene in the presence of aluminum phenolate catalyst was carried out in an autoclave in a nitrogen environment and effective conditions were found: temperature 260°C, reaction time - 5 hours, molar ratio of phenol to 1-methylcyclopentene 1: 2, amount of catalyst 20% according to the phenol taken. Under these conditions, the yield of the target product is 44.3% for the phenol taken, and the selectivity is 87.6% for the target product. The chemical structures of the synthesized para- and ortho-, ortho- (1-methylcyclopentyl) phenols were confirmed by IR-, 1H and NMR spectroscopy, and physicochemical parameters were determined.
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.
The paper studies the regularities of the reaction of catalytic cycloalkylation of phenol with methyl-cyclohexane in the presence of ceolite-U saturated with ortho-phosporic acid. To obtain a target product with the maximum yield, the effect of input variables, i.e. reaction temperature, duration, mole ratio of the initial components, and the catalyst amount has been analyzed. Mathematic interpretation of the experimental data enabled to obtain individual dependences of the output parameter of each input factor in the form of an equation of the second order. The generalized equation of the dependence of the output parameter of the optimization simultaneously on the all input variables has been developed. The optimum conditions of the reaction of obtaining para- (methylcyclo-hexyl) of phenol have been specified.
The paper presents the results of studies of the reaction of the interaction of phenol with cyclohexene (CH) in the presence of a Zeolite-Y catalyst impregnated with phosphoric acid and studying the dependence on the yield and selectivity of the target product on various parameters. As a result of the study of the phenol cycloalkylation by cyclohexene, optimal conditions were found, the yield of which is 81.6 % of theory for the taken CH, and the selectivity is 94.0 % for the target product. The developed mathematical model of the processes of the interaction of phenol with cyclohexene in the form of a regression polynomial made it possible to find the optimal values of the input variables.
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