Poly(lactic acid)-Based Stereocomplexes as Recyclable Organic Support for Pd-Nanoparticles (Abstract/Poster in atti di convegno)

Type
Label
  • Poly(lactic acid)-Based Stereocomplexes as Recyclable Organic Support for Pd-Nanoparticles (Abstract/Poster in atti di convegno) (literal)
Anno
  • 2013-01-01T00:00:00+01:00 (literal)
Alternative label
  • Capozzoli, Laura; Oberhauser, Werner; Bartoli, Mattia; Frediani, Marco; Petrucci, Giorgio (2013)
    Poly(lactic acid)-Based Stereocomplexes as Recyclable Organic Support for Pd-Nanoparticles
    in Nanotech Italy, Venice, 27.-29.11.2013
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Capozzoli, Laura; Oberhauser, Werner; Bartoli, Mattia; Frediani, Marco; Petrucci, Giorgio (literal)
Note
  • Poster (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Centro di Microscopie (CEME)-ICCOM ICCOM Dipartimento di Chimica, Università di Firenze (literal)
Titolo
  • Poly(lactic acid)-Based Stereocomplexes as Recyclable Organic Support for Pd-Nanoparticles (literal)
Abstract
  • The partial hydrogenation of alkynes to alkenes is of special relevance in bulk and fine chemical industry [1, 2]. This latter catalytic process is most conveniently performed with the Lindlar catalyst (i.e. Palladium nanoparticles (NPs) supported onto quinoline-promoted CaCO3 which is partially poisoned with lead [3]). The presence of an organic surface modifier [4], which is mainly involved in the rearrangement process of Pd-(NPs) [5] revealed to be mandatory for obtaining high chemo- and regioselectivity in the partial hydrogenation of alkynes. The organic modifier has always to be added to the catalytic reaction solution after each catalytic cycle and consequently separated from it which is a clear drawback of the latter heterogeneous catalyst. Hence other heterogeneous catalysts have been developed such as carbon-based nanomaterials [6], inorganic materials [7], functional organic polymers [8], resins [9], porous organic polymers [10] and organic-inoragnic composite materials [11]. In this context, we propose poly(lactic acid) (PLA)-based stereocomplexes [12] which are build up by either bipyridine end-functionalized PLA-PCL (poly-capro-lactone) copolymers (Scheme 1) or PLA as new recyclable polymer-based supports for Pd-(NPs). Stereocomplexation of PLA which is based on the CH3...O(carbonyl oxygen atom) hydrogen bonds confers high mechanical and thermal stability as well as hydrolysis resistance to PLA [13]. Indeed, Pd-(NPs) located in the PCL-phase showed much higher catalytic activity compared to Pd-(NPs) supported directly onto the PLA-stereocomplex. The obtained polymer-based catalytic systems were used to catalyze the partial hydrogenation of phenylacetylene to styrene in THF under very mild reaction conditions (i.e. 25 °C, p(H2) = 3bar). The heterogeneous catalyst is also active under solventless experimental reaction conditions. The polymer-based catalysts proved to be recyclable for at least four consecutive catalytic cycles maintaining its activity as well as chemoslectcivity. References [1] M. Crespo-Quesada, F. Cádenas-Lizana, A.-L. Dessimoz, L. Kiwi-Minsker, ACS Catal.12, 1773-1786, 2012. [2] B. Chen, U. Dingerdissen, J. G. E. Krautler, H.G.J. Lansink Rotgerink, K. Möbus, D. J. Ostgard, P. Panster, T. H. Riermeier, S. Seebald, T. Tacke, H. Trauthwein, Appl. Catal. A: Gen. 280, 17-46, 2005. [3] H. Lindlar, Hel. Chim. Acta 57, 446-450, 1952. [4] S. G. Kwon, G. Krylova, A. Sumer, M. M: Schwartz, E. E. Bunel, Ch. L. Marshall, S. Chattopadhyay, B. Lee, J. Jellinek, E. V. Shevchenko, Nano Lett 12, 5382-5388, 2012. [5] W. F. Maier, S. J. Chettle, R. S. Rai, G. Thomas, J. Am. Chem. Soc. 108, 2608-2616, 1986. [6] A. Jung, A. Jess, T. Schubert, W. Schütz, Appl. Catal. A: Gen. 362, 95-105, 2009. [7] Ch. Na-Chiangmai, N. Tiengchad, P. Kittisakmontree, O. Mekasuwandumrong, J. Powell, J. Panpranot, Catal. Lett. 141, 1149-1155, 2011. [8] M. Králik, A. Biffis, J. Mol. Catal. A: Chem. 177, 113-138, 2001. [9] A. Drelinkiewicz, W. Stanuch, A. Knapik, A. Ghanem, R. Kosydar, A. Bukowska, W. Bukowska, J. Mol. Catal. A: Chem. 300, 8-18, 2009. [10] P. Kaur, J. T. Hupp, S. T. Nguyen, ACS Catal. 1, 819-835, 2011. [11] W. Long, N. A. Brunelli, S. A. Didas, E. W. Ping, Ch. W. Jones, ACS Catal. 3, 1700-1708, 2013. [12] H. Tsuji, Macromol. Biosci. 5, 569-597, 2005. [13] H. Tsuji, Polymer 43, 1789-1796, 2002. (literal)
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