Journal of Materials Science

, Volume 50, Issue 7, pp 2747–2758 | Cite as

Catalysis with solid lipid particles

  • Suzana Natour
  • Suheir Omar
  • Raed Abu-Reziq
Original Paper


We describe the preparation of catalytic solid lipid particles as a new heterogeneous catalytic system. This system was constructed by incorporating polyethyleneimine modified with oleic acid (PEI-C18) within solid lipid particles (SLPs) coated with a silica shell. The hot sonication technique was employed to emulsify the oil phase containing paraffin wax, PEI-C18, and tetraethyl orthosilicate (TEOS) in aqueous surfactant solution generating oil-in-water emulsion, followed by interfacial polymerization of TEOS in basic medium producing silica shell via the sol–gel route. The reactivity of catalyst PEI-C18 encapsulated within SLPs@SiO2 was tested in Knoevenagel condensation as a model reaction. This new catalyst showed high catalytic efficiency in the condensation of aromatic aldehydes with various active hydrogen compounds forming α,β-unsaturated compounds, while triple distilled water was utilized as a reaction medium. The catalyst was easily isolated from the reaction mixture using centrifuge technique and recycled over 5 times without any significant loss in its catalytic activity.


Fumed Silica Malononitrile Silica Shell Solid Lipid Polyethyleneimine 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Supplementary material

10853_2015_8830_MOESM1_ESM.docx (1.1 mb)
Supplementary material 1 (DOCX 1126 kb)


  1. 1.
    Smith GV, Notheisz F (1999) Heterogeneous catalysis in organic chemistry. Academic Press, San DiegoGoogle Scholar
  2. 2.
    Hutchings GJ (2009) Heterogeneous catalysts-discovery and design. J Mater Chem 19:1222CrossRefGoogle Scholar
  3. 3.
    Anastas PT, Bartlett LB, Kirchhoff MM, Williamson TC (2000) The role of catalysis in the design, development, and implementation of green chemistry. Catal Today 55:11CrossRefGoogle Scholar
  4. 4.
    Banon-Caballero A, Guillena G, Najera C, Faggi E, Sebastian RM, Vallribera A (2013) Recoverable silica-gel supported binam-prolinamides as organocatalysts for the enantioselective solvent-free intra- and intermolecular aldol reaction. Tetrahedron 69:1307CrossRefGoogle Scholar
  5. 5.
    Chen H-T, Trewyn BG, Wiench JW, Pruski M, Lin VSY (2010) Urea and thiourea-functionalized mesoporous silica nanoparticle catalysts with enhanced catalytic activity for Diels-Alder reaction. Top Catal 53:187CrossRefGoogle Scholar
  6. 6.
    Hajek M (2001) Heterogeneous catalysis in organic chemistry. In: Gerhard V. Smith, Ferenc Notheisz (eds). React Funct Polym 47:159Google Scholar
  7. 7.
    Schulz K, Ratjen L, Martens J (2011) Homo- and heterogeneous organocatalysis: enantioselective Mannich addition of ketones to endocyclic carbon–nitrogen double bonds. Tetrahedron 67:546CrossRefGoogle Scholar
  8. 8.
    Xu DQ, Luo SP, Wang YF et al (2007) Organocatalysts wrapped around by poly(ethylene glycol)s (PEGs): a unique host-guest system for asymmetric Michael addition reactions. Chem Commun 42:4393–4395CrossRefGoogle Scholar
  9. 9.
    Zhang Z, Wang Y, Wang Z, Hodge P (1999) Asymmetric synthesis of α-amino acids using polymer-supported chiral phase transfer catalysts. React Funct Polym 41:37CrossRefGoogle Scholar
  10. 10.
    Corma A, Garcia H (2008) Crossing the borders between homogeneous and heterogeneous catalysis: developing recoverable and reusable catalytic systems. Top Catal 48:8CrossRefGoogle Scholar
  11. 11.
    Poe SL, Kobašlija M, McQuade DT (2006) Microcapsule enabled multicatalyst system. J Am Chem Soc 128:15586CrossRefGoogle Scholar
  12. 12.
    Corma A, Garcia H (2006) Silica-bound homogeneous catalysts as recoverable and reusable catalysts in organic synthesis. Adv Synth Catal 348:1391CrossRefGoogle Scholar
  13. 13.
    Dohi T, Fukushima K-I, Kamitanaka T, Morimoto K, Takenaga N, Kita Y (2012) An excellent dual recycling strategy for the hypervalent iodine/nitroxyl radical mediated selective oxidation of alcohols to aldehydes and ketones. Green Chem 14:1493CrossRefGoogle Scholar
  14. 14.
    Li P, Wang L, Zhang Y, Wang G (2008) Silica gel supported pyrrolidine-based chiral ionic liquid as recyclable organocatalyst for asymmetric Michael addition to nitrostyrenes. Tetrahedron 64:7633CrossRefGoogle Scholar
  15. 15.
    Kristensen TE, Hansen T (2010) Polymer-supported chiral organocatalysts: synthetic strategies for the road towards affordable polymeric immobilization. Eur J Org Chem 17:3179–3204CrossRefGoogle Scholar
  16. 16.
    Gleeson O, Davies G-L, Peschiulli A, Tekoriute R, Gun’ko YK, Connon SJ (2011) The immobilisation of chiral organocatalysts on magnetic nanoparticles: the support particle cannot always be considered inert. Org Biomol Chem 9:7929CrossRefGoogle Scholar
  17. 17.
    Shi JY, Wang CA, Li ZJ, Wang Q, Zhang Y, Wang W (2011) Heterogeneous organocatalysis at work: functionalization of hollow periodic mesoporous organosilica spheres with MacMillan catalyst. Chem Eur J 17:6206CrossRefGoogle Scholar
  18. 18.
    Shylesh S, Schuenemann V, Thiel WR (2010) Magnetically separable nanocatalysts: bridges between homogeneous and heterogeneous catalysis. Angew Chem Int Ed 49:3428CrossRefGoogle Scholar
  19. 19.
    Kalbasi RJ, Kolahdoozan M, Rezaei M (2012) Synthesis and characterization of polyvinyl amine–SiO2–Al2O3 as a new and inexpensive organic–inorganic hybrid basic catalyst. J Ind Eng Chem 18:909CrossRefGoogle Scholar
  20. 20.
    Shylesh S, Zhou Z, Meng Q et al (2010) Sustainable, green protocols for heterogenized organocatalysts: N-phenylthiazolium salts heterogenized on organic–inorganic hybrid mesoporous supports. J Mol Catal A Chem 332:65CrossRefGoogle Scholar
  21. 21.
    Saupe A, Rades T (2006) In: Mozafari MR (ed) Nanocarrier technologies. Springer, DordrechtGoogle Scholar
  22. 22.
    Wissing SA, Kayser O, Müller RH (2004) Solid lipid nanoparticles for parenteral drug delivery. Adv Drug Deliv Rev 56:1257CrossRefGoogle Scholar
  23. 23.
    Atterholt CA, Delwiche MJ, Rice RE, Krochta JM (1999) Controlled release of insect sex pheromones from paraffin wax and emulsions. J Control Release 57:233CrossRefGoogle Scholar
  24. 24.
    Ekambaram P, Abdul HSA, Priyanka K (2012) Solid lipid nanoparticles: a review. Sci Rev Chem Commun 2:80Google Scholar
  25. 25.
    Gupta R, Rousseau D (2012) Surface-active solid lipid nanoparticles as Pickering stabilizers for oil-in-water emulsions. Food Funct 3:302CrossRefGoogle Scholar
  26. 26.
    Mehnert W, Mader K (2012) Solid lipid nanoparticles production, characterization and applications. Adv Drug Deliv Rev 64:83CrossRefGoogle Scholar
  27. 27.
    Spada G, Gavini E, Cossu M, Rassu G, Giunchedi P (2012) Solid lipid nanoparticles with and without hydroxypropyl-beta-cyclodextrin: a comparative study of nanoparticles designed for colonic drug delivery. Nanotechnology 23:1CrossRefGoogle Scholar
  28. 28.
    Kumar S, Randhawa JK (2013) High melting lipid based approach for drug delivery: solid lipid nanoparticles. Mater Sci Eng C 33:1842CrossRefGoogle Scholar
  29. 29.
    Fireman S, Toledano O, Neimann K, Loboda N, Dayan N (2011) A look at emerging delivery systems for topical drug products. Dermatol Ther 24:477CrossRefGoogle Scholar
  30. 30.
    Abu-Reziq R, Wang D, Post M, Alper H (2008) Separable catalysts in one-pot syntheses for greener chemistry. Chem Mater 20:2544CrossRefGoogle Scholar
  31. 31.
    Benita S (1996) Microencapsulation: methods and industrial applications. Marcel Dekker, New YorkGoogle Scholar
  32. 32.
    Arshady R, Margel S, Pichot C (1998) Microspheres, microspheres, microcapsules & liposomes. Plenum, New YorkGoogle Scholar
  33. 33.
    Brinker C, Scherer G (1990) Sol–gel science: the physics and chemistry of sol–gel processing. Academic Press, San DiegoGoogle Scholar
  34. 34.
    Marini M, Pourabbas B, Pilati F, Fabbri P (2008) Functionally modified core–shell silica nanoparticles by one-pot synthesis. Colloids Surf A 317:473CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  1. 1.Institute of Chemistry, Casali Center of Applied Chemistry and Center for Nanoscience and NanotechnologyThe Hebrew University of JerusalemJerusalemIsrael

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