Hydrogenation and Hydrogenolysis. XIV. The Hydrogenation of Ethyl <I>p</I>-Tolyl Ether over Platinum Metal Catalysts
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概要
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The hydrogenation of ethyl <I>p</I>-tolyl ether (<B>1</B>) in ethanol has been studied with five unsupported platinum metals as catalysts, mainly with the purpose of estimating the yields of ethyl 4-methyl-1-cyclohexenyl ether (<B>2</B>) formed as intermediate. Except for ruthenium catalyst, the hydrogenation of <B>1</B> in ethanol was accompanied by the formation of acetal <B>3</B>, ketone <B>4</B> and alcohol <B>5</B> which seem to be related to the formation of <B>2</B>. The amounts of <B>2</B> and the related compounds which were desorbed from the catalyst surface have been estimated to be 32–33% for Ru, 32–34% for Rh, 72–76% for Pd, 3.7% for Ir and 4.7% for Pt, by application of both kinetic and extrapolation methods. A good agreement was obtained between the results from the two methods. The proportion of hydrogenolysis increased for the catalyst metals in the order Pd<Ru<<Rh<Ir<Pt. With platinum catalyst a noticeable amount of toluene was formed along with methylcyclohexane. The hydrogenation of ethyl 4-methyl-3-cyclohexenyl ether (<B>6</B>), one of the other intermediates of the hydrogenation of <B>1</B>, has also been studied in ethanol. Hydrogenolysis occurred extensively with palladium and rhodium catalysts, but much less with ruthenium, iridium and platinum catalysts. The hydrogenation route of <B>1</B> and its relation to hydrogenolysis and stereochemistry of hydrogenation of <B>1</B> are discussed with reference to the formation and hydrogenation of its intermediates.
- 公益社団法人 日本化学会の論文
著者
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Nishimura Shigeo
Department Of Applid Chemistry For Resources Tokyo University Of Agriculture And Technology
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Watanabe Tetsuo
Department of Chemistry Faculty of Science Tokyo Metropolitan University
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Uramoto Masayoshi
Department of Industrial Chemistry, Tokyo University of Agriculture and Technology
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