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Synthesis of p-(Cyclohexene-3-yl-ethyl)phenol and Characteristics of its Phosphatization with Phosphorous Trichloride
Corresponding Author(s) : M.R. Manafov
Asian Journal of Chemistry,
Vol. 30 No. 4 (2018): Vol 30 Issue 4
Abstract
Cycloalkenylation of phenol with 4-vinylcyclohexene was studied in the presence of zeolite-Y catalyst, saturated by orthophosphoric acid on the batch unit. Phenol and 4-vinylcyclohexene were used as initial products for the realization of cycloalkenylation reaction. Cyclo-dimerization is realized in liquid phase in the presence of copper on zeolite as a catalyst, which has high selectivity according to buta-1,3-diene. All the separated products of reaction were characterized and their physico-chemical properties were determined. Chromatographic analysis was identified on chromatographer LKhM-72 with thermal conductivity detector. Synthesized p-(cyclohexenylethyl)phenol was identified by NMR and IR techniques. It is evident that the yield of target product p-(cyclohexenylethyl)phenol at optimum regime amounts to 72.4 % on theoretically, but selectivity found to be 97.7 % according to the target product. Tri-[p-(cyclohexenylethyl)phenyl phosphite was obtained by the interaction of p-(cyclohexenylethyl)phenol with phosphorus trichloride and tested as an antioxidant for turbine oil T-46.
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References
B.N. Gorbunov, Y.A. Gurvich and I.P. Maslova, Chemistry and Technology of Stabilizers of Polymeric Materials, Khimiya, Moscow, p. 315 (1981).
Ch.K. Rasulov, A.G. Azizov, V. G. Mirzoev, R.K. Azimova, S.I. Abasov and S.Z. Alieva, Petroleum Chem., 49, 377 (2009); https://doi.org/10.1134/S0965544109050065.
V.G. Mirzayev, Process. Petrochem. Oil Refining, 17, 93 (2015).
A.M. Magerramov, M.R. Bairamov, G.M. Mekhtieva, M.A. Agaeva, P.Sh. Mamedova, D.M. Kulieva and I.G. Mamedov, Russ. J. Appl. Chem., 80, 665 (2007); https://doi.org/10.1134/S1070427207040295.
E.V. Kabilyanskiy and I.M. Vasilkevich, Issue Chem. Chemical Technol., 44, 102 (2008).
D.K. Korenev, V.A. Zavorotniy, V.B. Kelarev and T.A. Lagutina, Chem. Technol. Fuels Oils, 39, 72 (2003); https://doi.org/10.1023/A:1023297405336.
Ch.K. Rasulov, A. H. Azizov, R.K. Azimova, E.M. Abdullaev and S.I. Abasov, Petroleum Chem., 52, 352 (2012); https://doi.org/10.1134/S0965544112050106.
A.F. Markov, A.E. Prosenk and Y.Sh. Shvarch, Chem. Pharm. J., 45, 117 (2005).
K.I. Dyubchenko, V.V. Nikulina and E.I. Terax, Petroleum Chem., 45, 1 (2005).
I.V. Aleksandrova, Z.R. Tushakova and I. Lomakin, Oil Refining Petrochem., 12, 29 (2012).
J. Kang, X. Wang, X. Peng, Y. Yang and K. Cheng, Q. Zhang and Y. Wang, Ind. Eng. Chem. Res., 55, 13008 (2016); https://doi.org/10.1021/acs.iecr.6b03810.
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