Vol.:(0123456789) 1 3 Journal of Inorganic and Organometallic Polymers and Materials https://doi.org/10.1007/s10904-019-01139-7 Catalytic behavior of copper–amine complex supported on mesoporous silica SBA-15 toward mono-Aza-Michael addition: role of amine groups Aboubakr Hakiki 1  · Riad Mustpha Kerbadou 2  · Bouhadjar Boukoussa 1,3  · Hadjira Habib Zahmani 2  · Franck Launay 4  · Alain Pailleret 5  · Françoise Pillier 5  · Salih Hacini 2  · Abdelkader Bengueddach 1  · Rachida Hamacha 1 Received: 23 December 2018 / Accepted: 14 March 2019 © Springer Science+Business Media, LLC, part of Springer Nature 2019 Abstract This work concerns the preparation and modifcation of mesoporous silica SBA-15 with diferent amine-copper complexes in order to study their impact on the catalytic behavior via Aza Michael addition. Firstly, SBA-15 was prepared hydrothermally, then functionalized by mono-, di- and tri-amine, and in the second step, copper (II) was anchored. The catalytic activity of these solids was evaluated at room temperature under liquid-phase conditions. Efects of catalyst nature, catalyst mass, reaction time and the starting reagents nature were investigated. Cu@SBA-15 (non-aminated) was shown to be efcient in the Aza Michael addition, but after its second re-use, a progressive decrease in the product yield was obtained due to copper leaching. The catalytic behavior of all prepared catalysts showed a selective reaction via the mono-Aza-Michael addition. Amongst all the catalysts, the one containing the monoamine-copper complex led to the highest yield. This catalyst was used in four consecutive cycles without signifcant loss of activity, which confrms its stability. Keywords Mesoporous silica · SBA-15 · Functionalization · Copper complex · Aza Michael 1 Introduction Mesoporous silicas have been widely used in the catalysis and adsorption feld due to their diferent remarkable proper- ties such as a high surface area, large pore size and a huge pore volume compared to zeolites [1–5]. In particular, SBA- 15 is the most used in catalysis due to its larger pore size and wall thickness [5–7], giving its high mechanical and thermal stability. However, due to its inactive surface exhibiting only silanol groups [4, 8], SBA-15 cannot be used in catalysis without modifcation [5, 7]. To date, several attempts have been proposed to improve their performance in catalysis, such as the incorporation of a heteroatom [7, 9], the immo- bilization of polymers [10, 11], the dispersion of oxides [12, 13], ion-exchange [14, 15] or the functionalization of surface by organic groups or metal complexes [5, 6, 16–27]. Recently, a particular interest has been devoted to the use of mesoporous silicas bearing metal complexes due to their several advantages [6, 16–27] such as dispersion of a signif- cant amount of metal compared to the conventional methods (such as ions exchange) [24], anchoring of diferent cationic metals [6, 20, 23, 26, 27], limitation of the metal leaching in the reaction medium and reuse in several catalytic cycles Electronic supplementary material The online version of this article (https://doi.org/10.1007/s10904-019-01139-7) contains supplementary material, which is available to authorized users. * Bouhadjar Boukoussa bouhadjar.boukoussa@univ-usto.dz; bbouhdjer@yahoo.fr 1 Laboratoire de Chimie des Matériaux L.C.M, Université Oran1 Ahmed Ben Bella, El-Mnaouer, BP 1524, 31000 Oran, Algeria 2 Laboratoire de Chimie Fine L.C.F, Université Oran 1 Ahmed Ben Bella, El-Mnaouer, BP 1524, 31000 Oran, Algeria 3 Département de Génie des Matériaux, Faculté de Chimie, Université des Sciences et de la Technologie Mohamed Boudiaf, El-Mnaouer, BP 1505, Oran, Algeria 4 Sorbonne Université, Faculté des Sciences et Ingénierie, CNRS, Laboratoire de Réactivité de Surface (LRS, UMR 7197), 4 Place Jussieu (case courrier 197), 75005 Paris, France 5 Sorbonne Université, Faculté des Sciences et Ingénierie, CNRS, Laboratoire Interfaces et Systèmes Electrochimiques (LISE, UMR 8235), 4 place Jussieu (case courrier 133), 75005 Paris, France