Glycerol remains a bottleneck for the biodiesel industry as well as an opportunity from the biorefinery perspective, having a notable reactivity as a platform chemical. In particular, glycerol ketals can be envisaged as oxygenates for fuel formulation. In this study, we have focused on the green synthesis of glycerol ketals by reacting glycerol with acyclic (acetone, butanone) and cyclic (cyclohexanone) ketones in the presence of an acid activated clay Tunisian AC in homogeneous systems under quasi-solventless conditions. These reactions were followed by on-line Fourier Transform Infrared Spectroscopy (FTIR) (namely, ReactIR 10). Firstly, the contacting time was selected studying the activity, stability and chemical characteristics of a set of catalysts. The 1-h activated clay AC was further characterized by X-Ray diffraction (XRD), Fourier Transform Infrared Spectroscopy (FTIR) and Scanning Electronic Microscopy with Energy Dispersive Spectroscopy (SEM/EDS). Finally, the effect of the main operational variables (catalyst concentration, reagents molar ratio, time and temperature) were checked and we reflected on adequate second-order kinetic models with partial first-order deactivation.
The production of solketal and conversion of glycerol takes a major importance in the field of the sustainability of the biodiesel industry. The synthesis of (2,2-dimethyl-1,3-dioxolan-4-yl)methanol by the acetalization of glycerol with acetone successfully applied out using various Algerian acid activated clays (maghnia-H+) under autogenous pressure and without solvent. The acid catalyst clays are prepared by an easy technique by activation with the available and low-cost Maghnia clay. The purified Maghnia clay named ALC and the resulting series of acid-activated clays AL1, AL2, AL3, and AL4 are characterized by X-ray Fluorescence (XRF) investigation, N2-adorption/desorption Brunauer–Emmett–Teller (BET) surface area, X-rays Diffraction (XRD), Fourier Transform Infra Red (FT-IR) spectroscopy, SEM microscopy and the cation exchange capacity (CEC) with copper bisethylenediamine complex method, in order to study the effect of activation at the acid and the catalytic behaviour in the acetalization reaction. The results show a high catalytic activity whose that the yield of solketal production interest reached 95 % at a temperature of 40 °C for a reaction time of 48 hours with full selectivity and glycerol conversion reaching up to 89 %. A mechanistic is proposed to explain the chemoselective of solketal production. These results indicate the potential of this Algerian acid activated clays catalysts for the acetalization of glycerol for an environmentally benign process. Copyright © 2018 BCREC Group. All rights reservedReceived: 28th March 2018; Revised: 17th October 2018; Accepted: 30th October 2018; Available online: 25th January 2019; Published regularly: April 2019How to Cite: Alali, K., Lebsir, F., Amri, S., Rahmouni, A., Srasra, E., Besbes, N. (2019). Algerian Acid Activated Clays as Efficient Catalysts for a Green Synthesis of Solketal by Chemoselective Acetalization of Glycerol with Acetone. Bulletin of Chemical Reaction Engineering & Catalysis, 14 (1): 130-141 (doi:10.9767/bcrec.14.1.2445.130-141)Permalink/DOI: https://doi.org/10.9767/bcrec.14.1.2445.130-141
A new heterogeneous acid catalyst based on a natural resource, Tunisian clay (Clay-H0.5), has been prepared and characterized by FT-IR, FE-SEM, and powder X-ray diffraction (XRD), as well as chemical composition, cation exchange capacity, specific surface area, and pore volume. Acid treatment for 0.5 h enlarged the surface area from 78.24 to 186.10 m 2 /g and pore volume (PV) from 0.186 to 0.281 cm 3 /g. The catalytic activity of this material was investigated in ketalization reaction under mild solvent-free conditions. This achieved up to 92% isolated yield for only 10 wt.% of the catalyst. This environmentally friendly method has advantages such as simple work-up procedure, avoidance of organic solvents, and good performance in ketalization reactions. Importantly, the Clay-H0.5 catalyst showed good recyclability where insignificant activity loss was exhibited even after six runs. Synthesized cyclic ketals were tested for their possible antileishmanial and antibacterial activities as well as antifungal activity. Biological screening showed that compound 11 had important antileishmanial activity against both L. major and L. infantum, while compound 14 also had significant antibacterial activity against four gram-positive and two gram-negative bacteria, and antifungal activity against Candida albicans, with minimal inhibitory concentration values ranging from 15.62 µg/mL to 125 µg/mL.
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