Highly Selective Catalytic Preparation Of Bis (4-Oxo-Benzo-2-Cyclohexen-1-yl) Amine (BOBCHA) From 1-Naphthylamine Oxidation Over Metalloporphyrin Catalysts By Molecular Oxygen Under Air Pressure And By Hydrogen Peroxide

This thesis introduces that 1-Naphthylamine was catalytically converted into Bis (4-oxo-benzo-2-cyclohexen-1-yl) amine (BOBCHA) by metalloporphyrin catalysts through an oxidative-coupling way with oxidants of O₂ or H₂O₂. The product was separated and characterized. A spectrophotometric method was established for quantitative analysis of the product. A possible catalytic mechanism was proposed based on in situ EPR and UV-Vis determinations and influences on reaction were examined for optimizing catalytic conditions.In addition, we found the new ways to synthesize and separate water-soluble meso-Tetra (4-Aminophenyl) Porphyrin Znic tetra-hydroxy [TAPPZn(OH)₄]. The thesis is divided into 5 chapters.In chapter 1, the metalloporphyrin complexes and the study background of catalytic oxidation of hydrocarbons are concisely introduced. The research progresses of the oxidative-coupling of naphthylamine and the sythesis of the water-soluble porphyrin are summarized. Finally, the signification of this work was also described.In chapter 2, The catalytic conversion of 1-Naphthylamine (1-NA) to bis (4-oxo-benzo -2-cyclohexen-1-yl) amine (BOBCHA) over metalloporphyrin catalysts through an oxidative-coupling way in the presence of hydrogen peroxide was discussed in detail. The yield of BOBCHA reachs 51% with the selectivity of 100%. UV-Vis, IR, NMR, MS, m. p. determinations and elemental analysis were employed for product characterization. While keeping other reaction conditions changeless, H₂O₂ was taken place by O₂, 1-NA was also catalytically converted into BOBCHA. The yield of BOBCHA was 46 % with the same selectivity. A spectrophotometric method was established for quantitative analysis of the product according to its characteristic absorption at λ_max = 465 nm.In chapter 3, based on in situ UV-Vis and EPR determinations of FeTPPCl with H₂O₂, a possible catalytic mechanism was proposed.In chapter 4, the influences on reaction, such as solvents, temperature, reaction time, medium...