Nucleophilic Addition to Acetylenes in Superbasic Catalytic Systems: X. Catalytic Effect of Alkali Metal Hydroxides in the Vinylation of 1-Heptanol |
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| Authors: | L N Parshina L A Oparina O V Gorelova T Preiss J Henkelmann and B A Trofimov |
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| Institution: | (1) Siberian Division, Russian Academy of Sciences, Favorskii Irkutsk Institute of Chemistry, ul. Favorskogo 1, Irkutsk, 664033, Russia;(2) Ammonia Laboratory, BASF Actiengesellschaft, Ludwigshafen, Germany |
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| Abstract: | The catalytic activity of alkali metal hydroxides in base-catalyzed addition of 1-heptanol to acetylene depends on the alkali metal nature and degree of hydration of its hydroxide. In a closed system, the catalytic activity of alkali metal hydroxides decreases in the series 2KOH·H2O > RbOH·H2O > CsOH·H2O > NaOH. The corresponding series for a flow system is as follows: RbOH·H2O > CsOH·H2O > 2KOH·H2O > NaON > KOH·H2O. The difference is explained by participation of the catalyst in side reactions with both 1-heptanol and acetylene. Addition of dimethyl sulfoxide to the catalytic system accelerates the vinylation process. |
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