Hydroxylation of Benzene to Phenol by H2O2 over an Inorganic-Organic Dual Modified Heteropolyacid

doi:10.1016/j.cjche.2014.09.041

Abstract

Abstract: Various catalysts, including the heteropolyacid (HPA) H₄PMo₁₁VO₄₀, its cesiumsalts, and inorganic-organic dual modified HPA catalyst,were prepared and characterized by Fourier transform infrared spectroscopy (FT-IR), nuclearmagnetic resonance (¹³C NMR), N₂ adsorption, acid-base titration, electron spin resonance (ESR) and X-ray diffraction (XRD) techniques as well as elemental analysis. These prepared catalysts were used in the hydroxylation of benzene to phenol by H₂O₂ as oxidant. The inorganic-organic dual modified HPA Cs_2.5(MIMPS)_1.5 PMo₁₁VO₄₀, prepared by partially exchanging Cs⁺ with protons in H₄PMo₁₁VO₄₀ and followed by the immobilization of 3-(1-methylimidazolium-3-yl)propane-1-sulfonate (MIMPS), led to a liquid-solid biphasic catalysis system in the hydroxylation, which showed the best catalytic performance in terms of reusability and catalytic activity. The high reusability of Cs_2.5(MIMPS)_1.5PMo₁₁VO₄₀ in the heterogeneous hydroxylation was probably due to its high resistance in leaching of bulk HPA into the reaction medium. The slightly enhanced catalytic activity for the catalyst was due to the acid sites available from MIMPS beneficial to the hydroxylation.

Key words: Heteropolyacids, Hydroxylation, Phenols, Hydrophobic interaction, Liquid-phase oxidation

摘要： Various catalysts, including the heteropolyacid (HPA) H₄PMo₁₁VO₄₀, its cesiumsalts, and inorganic-organic dual modified HPA catalyst,were prepared and characterized by Fourier transform infrared spectroscopy (FT-IR), nuclearmagnetic resonance (¹³C NMR), N₂ adsorption, acid-base titration, electron spin resonance (ESR) and X-ray diffraction (XRD) techniques as well as elemental analysis. These prepared catalysts were used in the hydroxylation of benzene to phenol by H₂O₂ as oxidant. The inorganic-organic dual modified HPA Cs_2.5(MIMPS)_1.5 PMo₁₁VO₄₀, prepared by partially exchanging Cs⁺ with protons in H₄PMo₁₁VO₄₀ and followed by the immobilization of 3-(1-methylimidazolium-3-yl)propane-1-sulfonate (MIMPS), led to a liquid-solid biphasic catalysis system in the hydroxylation, which showed the best catalytic performance in terms of reusability and catalytic activity. The high reusability of Cs_2.5(MIMPS)_1.5PMo₁₁VO₄₀ in the heterogeneous hydroxylation was probably due to its high resistance in leaching of bulk HPA into the reaction medium. The slightly enhanced catalytic activity for the catalyst was due to the acid sites available from MIMPS beneficial to the hydroxylation.

关键词: Heteropolyacids, Hydroxylation, Phenols, Hydrophobic interaction, Liquid-phase oxidation

Li Jing, Fumin Zhang, Yijun Zhong, Weidong Zhu . Hydroxylation of Benzene to Phenol by H₂O₂ over an Inorganic-Organic Dual Modified Heteropolyacid[J]. , 2014, 22(11/12): 1220-1225.

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Hydroxylation of Benzene to Phenol by H₂O₂ over an Inorganic-Organic Dual Modified Heteropolyacid

Hydroxylation of Benzene to Phenol by H₂O₂ over an Inorganic-Organic Dual Modified Heteropolyacid

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