Selective hydrogenation of benzene to cyclohexene with zirconium hydride catalysts

Pez, Guido P.; Crissey, Richard K.

doi:10.1016/0304-5102(93)80136-i

Cited by 13 publications

(2 citation statements)

References 10 publications

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“…The metal hydride chemistry of copper, ruthenium, rhodium, iron, cobalt, palladium, and nickel have seen broad application over the last two decades, providing catalytic platforms for the efficient diversification of simple chemical building blocks . However, the number of catalytic applications of zirconocene hydrides are few, despite the improved toxicity, orthogonal reactivity, and lower cost of zirconium in comparison to many late-transition-metal congeners. − …”

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confidence: 99%

Expanding Zirconocene Hydride Catalysis: In Situ Generation and Turnover of ZrH Catalysts Enabling Catalytic Carbonyl Reductions

2022

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Despite the wide use and popularity of metal hydride catalysis, methods utilizing zirconium hydride catalysts remain underexplored. Here, we report the development of a mild method for the in situ preparation and use of zirconium hydride catalysts. This robust method requires only 2.5−5 mol % of zirconocene dichloride in combination with a hydrosilane as the stoichiometric reductant and does not require careful air-or moisture-free techniques. A key finding of this study concerns an amine-mediated ligand exchange en route to the active zirconocene hydride catalyst. A mechanistic investigation supports the intermediacy of an oxo-bridged dimer precatalyst. The application of this method to the reduction of a wide variety of carbonylcontaining substrates, including ketones, aldehydes, enones, ynones, and lactones, is demonstrated with up to 92% yield and exhibits broad functional group tolerability. These findings open up alternative avenues for the catalytic application of chlorozirconocenes, potentially serving as the foundation for broader applications of zirconium hydride catalysis.

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confidence: 99%

Expanding Zirconocene Hydride Catalysis: In Situ Generation and Turnover of ZrH Catalysts Enabling Catalytic Carbonyl Reductions

2022

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“…[5] Numerous literature reports liquid phase hydrogenation of benzene to cyclohexene over unsupported ruthenium based alloy catalyst [6][7][8][9][10][11] or supported ruthenium based catalyst. [12][13][14][15][16][17][18][19][20][21][22][23][24][25] It has also been found that La, Cu, Zn, Ce, or Fe is introduced as promoter to improve the performance of the catalysts. [26][27][28][29][30] Although there are numerous literature on selective hydrogenation of benzene to cyclohexene, Asahi Chemical Industry Co. is the only one who has succeeded in the commercialization of the process for producing cyclohexene from benzene hydrogenation over metallic ruthenium-zinc particles catalyst.…”

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confidence: 99%

Hydrophilicity Modification of MCM-41 With Zirconia and Supported Ruthenium-Lanthanum for Benzene Hydrogenation to Cyclohexene

Liao

Zhang

Liu

et al. 2013

Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-

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Zirconia modified mesoporous molecular sieve MCM-41 supports were prepared by hydrothermal synthesis method, in situ synthesis method and precipitation method. Ruthenium and lanthanum supported on MCM-41 and zirconia modified MCM-41 catalysts were prepared via two solvents impregnation method. The catalysts were characterized by X-ray diffraction, transmission electron microscopy, nitrogen adsorption-desorption, and water/benzene static adsorptions techniques. It has been found that Ru-La supported on MCM-41 modified with zirconia by hydrothermal synthesis method (Ru-La/ZrO 2 -MCM-41-HS) leads to the biggest increase of the hydrophilicity. Ru-La/ZrO 2 -MCM-41-HS catalyst with the highest hydrophilicity shows the best performance in liquid phase hydrogenation of benzene to cyclohexene.

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Partial hydrogenation of benzene with ruthenium catalysts prepared by a chemical mixing procedure: Preparation and properties of the catalysts

Niwa

Mizukami

Isoyama

et al. 1986

J of Chemical Tech & Biotech

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Ruthenium catalysts were prepared in different alcohols by a chemical mixing technique, characterised by the preparation of a homogeneous solution containing catalyst components, and the uniform coagulation of the solution through hydrolysis. The technique has the potential for controlling the surface area of the catalysts and for making them porous. The ruthenium catalysts were much more effective for the partial hydrogenation of benzene to cyclohexene (maximum cyclohexene yield, 31.4%) in the absence of any poison such as alkali metal hydroxide or transitional metal sulphate in the reaction solution.

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Selective hydrogenation of benzene to cyclohexene with zirconium hydride catalysts

Cited by 13 publications

References 10 publications

Expanding Zirconocene Hydride Catalysis: In Situ Generation and Turnover of ZrH Catalysts Enabling Catalytic Carbonyl Reductions

Expanding Zirconocene Hydride Catalysis: In Situ Generation and Turnover of ZrH Catalysts Enabling Catalytic Carbonyl Reductions

Hydrophilicity Modification of MCM-41 With Zirconia and Supported Ruthenium-Lanthanum for Benzene Hydrogenation to Cyclohexene

Partial hydrogenation of benzene with ruthenium catalysts prepared by a chemical mixing procedure: Preparation and properties of the catalysts

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