Hydrogenation and hydrogenolysis. XVII. The selectivities of platinum group metals in catalytic hydrogenation of 2-naphthol and tetrahydro-2-naphthols.
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概要
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Catalytic hydrogenation of 2-naphthol (NL) with the six platinum metals has been studied in <I>t</I>-BuOH at 80 °C and 4–5 MPa H<SUB>2</SUB> pressure. Selectivities for formation of 1,2,3,- and 5,6,7,8-tetrahydro-2-naphthols (<I>ac</I>- and <I>ar</I>-TLs) have been determined by application of a kinetic equation. <I>ar</I>-TL was formed more predominantly than <I>ac</I>-TL over all the metals. The hydrogenation of <I>ac</I>- and <I>ar</I>-TLs has also been studied under the same conditions for comparison. The hydrogenation of NL and <I>ar</I>-TL was accompanied by extensive hydrogenolysis to give decalins over Os, Ir, and Pt, whereas the hydrogenolysis occurred only slightly over Ru, Rh, and Pd. In general the hydrogenolysis occurred to much lesser extents with <I>ac</I>-TL. The amounts of 2-decalone formed in hydrogenation of <I>ar</I>-TL have been determined by application of the kinetic equation. The 2-decalone was the <I>cis</I> isomer only except with Pd. For formation of the <I>cis</I> products at the ring juncture, hydrogenation of <I>ar</I>-TL was highly stereoselective with Ru, Rh, Os, and Ir, while hydrogenation of <I>ac</I>-TL was the most stereoselective with Os and Ir. The course of hydrogenolysis and the stereochemistry of hydrogenation are discussed from the comparative results on NL, <I>ar</I>-TL, and <I>ac</I>-TL.
著者
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Nishimura Shigeo
Department Of Applid Chemistry For Resources Tokyo University Of Agriculture And Technology
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OKADA YASUHIRO
Department of Chemical Engineering, Nara National College of Technology
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Ikeno Kiyoshi
Department of Applied Chemistry for Resources, Tokyo University of Agriculture and Technology
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Ohbuchi Shin-ichi
Department of Applied Chemistry for Resources, Tokyo University of Agriculture and Technology
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Okada Yasuhiro
Department of Applied Chemistry for Resources, Tokyo University of Agriculture and Technology
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