A novel statistical approach for the synthesis of Chalcones viaClaisen-Schmidt condensation catalyzed by Pd nanoparticles modified mesoporous TiO2 as an efficient heterogeneous catalyst
Graphical abstract
Introduction
In chemistry, and like any other discipline in applied sciences, it is quite common to face significant hurdle when it is about manipulating carefully materials and their parameters. This is still considered as the main challenge in many researches works in such manner more undertakings efforts must be made in the researchers' community to deeply innovate and develop modern industrial processes. In fact, the development of existing catalytic technologies for synthesis of important organic compounds is viewed as a heavy-duty challenge in research. Such advances have been at the cutting edge of research for several generations. The base-catalyzed organic transformations such Knoevenagel, aldol, Claisen–Schmidt Condensations, and transesterification reactions are of great importance in both industry and research activities.
The heterogeneous catalytic condensation of Aldol and Cross Aldol Condensation (Claisen-Schmidt) is a powerful tool for the formation of a carbon‑carbon bond in many types of carbonyl compounds [1,2]. Chalcones with α, β unsaturated carbonyl moiety is one of the most important compounds and versatile synthons for various chemical transformations. It is used as a precursor of various heterocyclic compounds [3,4].
Chalcones and their derivatives have been widely used in a large number of biological active compounds or synthetic origin exhibiting diverse pharmacological activities [5,6], such as antioxidant [2,7], anti-inflammatory [8,9], anti-cardiac [10], antifungal [11], antimalarial [12], antibacterial [13,14], anti-osteogenic [15], anti-cancer [16], anti-HIV [17], antimicrobial [18], anti-tubercular [19], antidiabetic [20], anti-leishmanial [21] and antihypertensive activities [22].
The most common used example of CSC is the synthesis of chalcones because of their importance [[23], [24], [25]]. However, heterogeneous catalysts are preferred for the synthesis of chalcones [1]. The most used ones in CSC are alkaline-doped activated carbons (Na- and Cs-Norit) [26], alumina [27], Ba(OH)2 [28], hydrotalcites [29], natural phosphates modified with sodium nitrate [1], Nanoporous AlSBA−15 [30], Hierarchical Cs-Pollucite Nanozeolite [31] andKF–Al2O3 [32].
Because of its thermal stability, PdNPs modified Titania is considered as very promising in regards to the huge number of applications in various industrial processes [[33], [34], [35], [36]]. Further, more other advantages can be cited, namely active surface area [37], porosity [38,39], specific active sites [40,41]. All these characteristics reflect the fact that PdNPs is very appropriate to use as an heterogeneous catalyst in organic synthesis.
RSM is quite possibly the most mainstream experimental design methodology considered by analysts in a wide scope of fields, particularly in chemistry where experiences need the highest level of precision [[42], [43], [44]]. The main motivation behind is the creation of an experiment environment which facilitates the building of the optimal design under the available working conditions. Further, it is generally recognized that RSM is a powerful modeling approach for understanding and analyzing different processes in chemistry field [[45], [46], [47]].It was approved in several works that the Box-Behnken design is recommended in such experimentations requiring both human attention and huge number of iterations. Hence, the major challenge is, of course, saving money and time in downstream industrial cycles. This strategy can consider and important number of variables, alongside three levels of test conditions (low, medium and high levels) [48]. For this reason, among others, the Box-Behnken design remains more efficient than the other response design techniques. Also, it should be mentioned that the Box-Behnken design effectiveness is confirmed by enabling huge number of trials and parameters to be incorporated in the process.
In one concerns of continuation in achieving a set of ongoing projects mainly focused on nanomaterials and their various applications, this research complements noteworthy efforts that are underway within our research team [38,45,[48], [49], [50], [51], [52], [53]]. It proposes an efficient, clean, economical, and easy heterogeneous reaction process for the synthesis of chalcones based on the use of PdNPs modified Titania as a new heterogeneous catalyst. Within this framework, a modeling approach by Box Behkhen Design on RSM for assessing the different parameters effects on the chalcone yield will be carried out. It permits to detect the interactions between the chosen parameters while considering the best conditions among the process.
Section snippets
Reagents
Titanium isopropoxide (IV) [C12H28O4Ti, (97%)], acetic acid [CH3 COOH, (20%)], Pluronic P123 [EO20PO70EO20, 99.99%], palladium nitrate hexahydrate [Pd (NO3)2.2H2O, (99,99%)], Ethanol [C2H5OH, (99%)],]. Acetophenone [CH3COC6H5, (≤99%), benzaldehyde [C6H5 CHO, (≤99%)], ethanol [CH3CH2OH, pure]. Every chemical product was purchased from Sigma Aldrich.
Preparation of catalyst
Mesoporous Titania was prepared by an easy hydrothermal-assistant sol-gel method using P123 as a structure-directing agent just like reported in our
Box-Behnken Design
The Box-Behnken Design was used to highlight elements supposed to be critical on the creation of chalcone reaction. Altogether, three factors were assessed and recorded in Table 1: Concentration of PdNPs on TiO2 (A), temperature of reaction (B), and a reaction time (C). Every factor was tested at three thresholds: low (− 1), central (0) and high (+1).
To distinguish the factors that effectively affect the reactions (response yield) statistical indicators were used [54,55]. All computations and
N2 adsorption–desorption isotherms
The Brunauer-Emmett-Teller (BET) theory is known as a useful method for studying the surface texture properties of materials. The N2 adsorption-desorption isotherms and pore size distribution of the prepared materials are shown in Fig. 1a. Pure Titania and Pd-doped mesoporous Titania materials exhibit type IV adsorption-isotherms characteristic of mesoporous materials according to the IUPAC [49,56]. A sharp inflection at a relative pressure around ~0.5–0.8 and a narrow pore size distribution
Conclusion
In this work, chalcones were successfully synthesized via Claisen-Schmidt condensation of aromatic aldehydes. This very simple and effective process is based on the use of PdNPs doped mesoporous Titania as a heterogeneous catalyst. The obtained yield was very promising by using 0.1Pd/TiO2 over a short period of time. The process was carried out by assessing the impact of three parameters: PdNPs concentration, temperature and time of the reaction on the yield of chalcones. The appropriateness of
Declaration of Competing Interest
The authors declare that they have no conflict of interest.
Acknowledgements
The authors are grateful to the Algerian Direction Gnérale de la Recherche Scientifique et du Développement Technologique (DGRSDT-MESRS), the University of Tlemcen and Ain Temouchent for funding this work.
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