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pp. 11831-11838 | Article Number: ijese.2016.859
Published Online: November 25, 2016
Abstract
The article deals with the results of investigation of the process of catalytical photocyclization of aniline and aniline hydrochloride with α-olefins (hexene-1, heptene-1 and octene-1). The following compounds of d- and f-metals are tested as probable catalysts: CuSO4•5H2O, EuCl3•6H2O, PrCl3•6H2O, TbCl3•6H2O, La2O3, MnO2, NiSO4•6H2O, NiCl2•6H2O, Ni(NO3)2•6H2O, [Ni(NH3)4]Cl2 and [(C6H5)3P]2NiCl2. Catalytic effect in the reaction of photocyclization is only detected for nickel compounds. The products of catalytical photocyclization are 2-alkylquinolines. Maximum output is observed for 2-propylquinoline and is equal to 45 % at conversion of aniline of 57 %. Photosynthesis of quinolinic bases proceeds under the influence of UV-radiation at room temperature. Catalytical activity of nickel ions in a series of investigated compounds marginally depends on ligand environment. The influence of solvents’ nature on the efficiency of catalytical photocyclization is detected. The output of the target product decreased in the following series: EtOH ˃ DMSO ˃ DMFA ˃ Toluol ˃ Hexane ˃ solventless system. Catalytical photocyclization of hydrochloride aniline with α-olefine in water environment relates to ecologically friendly way of 2-alkylquinolines synthesis.
Keywords: Photocyclization, catalysis, aniline, aniline hydrochloride, alkene, 2-alkylquinoline
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