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 results of arylalkylation of phenol with components of fraction 130-190 °C of pyrolysis products in the presence of KU-23 catalyst and the influence of various parameters on the yield and selectivity of the desired product are presented. Optimal conditions for the synthesis of p-aryl-alkylphenol are found. The reaction temperature was varied from 80 to 140 °C, the reaction time was 2 to 8 hours, the molar ratio of phenol to the fraction of 130-190 °C of pyrolysis products was from 1:1 to 1:3 mol/mol, the amount of catalyst from 4 to 15 %. It was found that the interaction of phenol with FLPP in the presence of KU-23 catalyst proceeds with the formation of p-substituted arylalkylphenol. It was determined that the reaction of arylalkylation of phenol with FLPP proceeds mainly with four components of the fraction. Chromatographic studies of FLPP before and after the phenol arylalkylation reaction showed that, mainly (91.5%), unsaturated hydrocarbons enter the reaction (styrene, α-methylstyrene, vinyltoluene, indene). In this case, the concentration of styrene in the FLPP after the reaction decreases from 33.65% to 3.78%, i.e. an obtained p-aryl-alkylphenol consisted of 95.0% p-α-methylbenzylphenol. Insofar as from unsaturated hydrocarbons FLPP mainly consists of 33.65% styrene, 6.15% α-methyl-styrene, 7.02% vinyltoluene, 4.85% indene, the reaction of the alkylation going with them. It is shown that under optimal conditions, the yield of the target p-arylalkylphenol is 74.7% of the theory, and the selectivity is 92.3%. On the basis of p-arylalkylphenol and acetic acid, 2-hydroxy-5-arylalkylacetophenon was synthesized and tested as a photostabilizer of polystyrene. It is shown that under optimal conditions, the yield of the target p-arylalkylphenol is 74.7% of the theory, and the selectivity is 92.3%. Physicochemical parameters of synthesized p-arylalkylphenol and 2-hydroxy-5-arylalkylacetophenone were determined. The use of arylalkylacetophenone as an inhibitor that increases the antioxidant stability of the polystyrene, used under both thermal and solar radiation, is proposed.For citation:Majidov E.A., Chalyshkan M.M., Bagirzade R.Z., Kuliev F.V., Rasulov Ch.K. Sintesis of 2-hidroxy-5-arylalkylacetofenone оn the basis of product of phenol reaction with the components of fraction 130-190 °C pirolysis products. Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. 2017. V. 60. N 7. P. 57-65.
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.
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.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.
hi@scite.ai
10624 S. Eastern Ave., Ste. A-614
Henderson, NV 89052, USA
Copyright © 2024 scite LLC. All rights reserved.
Made with 💙 for researchers
Part of the Research Solutions Family.