Pd Nanoparticles in the Thermoregulated Ionic Liquid and Organic Biphasic System: An Efficient and Recyclable Catalyst f
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Pd Nanoparticles in the Thermoregulated Ionic Liquid and Organic Biphasic System: An Efficient and Recyclable Catalyst for Heck Reaction Yan Zeng • Yanhua Wang • Yicheng Xu Ying Song • Jingyang Jiang • Zilin Jin
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Received: 19 July 2012 / Accepted: 29 September 2012 / Published online: 12 October 2012 Ó Springer Science+Business Media New York 2012
Abstract A thermoregulated ionic liquid and organic biphasic system composed of ionic liquid [CH3(OCH2CH2)16 N?Et3][CH3SO3-] (ILPEG750) with ILPEG750-stabilized Pd nanoparticles and organic solvents, which allows for not only a highly efficient homogeneous catalytic reaction, but also an easy biphasic separation and reuse of catalyst attributed to the thermoregulated phase-transition property of the system, was employed for Heck reaction. The ILPEG750-stabilized Pd nanoparticle catalyst exhibited high efficiency, more importantly, after reaction the Pd nanoparticle catalyst could be separated from products by simple phase separation and recycled for six times without evident loss of activity. Keywords Thermoregulated ionic liquid and organic biphasic system Palladium Nanoparticle Catalyst recycling Heck reaction
1 Introduction Soluble transition-metal nanoparticles in catalysis have drawn much attention due to their high efficiency and unique properties. However, very similar to traditional homogeneous catalysts, one of the main disadvantages of soluble nanoparticle catalysts is the problem of separation the catalyst from the products [1, 2]. To deal with this problem, a range of methods has been reported, with most studies focusing on the liquid/ Electronic supplementary material The online version of this article (doi:10.1007/s10562-012-0919-9) contains supplementary material, which is available to authorized users. Y. Zeng Y. Wang (&) Y. Xu Y. Song J. Jiang Z. Jin State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, People’s Republic of China e-mail: [email protected]
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liquid biphasic system, for example, the use of fluorous/ organic biphasic system [3, 4], thermoregulated polyethylene glycol (PEG) biphasic system [5], thermoregulated phasetransfer aqueous/organic biphasic system [6, 7] and ionic liquid biphasic system [8, 9]. Ionic liquids with negligible vapour pressure and high thermal stability have gained increasing attention as promising reaction media or stabilizers for transition-metal nanoparticles. However, in most cases, the reaction systems involving ionic liquids are either monophase allowing for rapid transformation or biphase facilitating separation of product from catalyst [10–18]. Therefore, to search for new catalytic systems that might combine the advantages of both homogeneous and heterogeneous catalysis will have a significant impact. Very recently, our group has developed an effective approach for Rh nanoparticle catalyzed hydrogenation and hydroformylation of olefins in a thermoregulated ionic liquid and organic biphasic system [19, 20], wherein [CH3 (OCH2CH2)16N?Et3][CH3SO3-] (ILPEG
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