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Regioselective acylation of methyl-α-d-glucopyranoside with different acylating agents catalysed by micro/mesoporous materials

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Abstract

The composite microporous/mesoporous material ZSM-5/MCM-48 was successfully prepared by hydrothermal synthesis using a simple one-step crystallization process. The material was a mesoporous composite containing zeolite and crystals of ZSM-5. The textural and structural features of this material were characterized by use of powder XRD, nitrogen sorption, FTIR spectroscopy, SEM, and TEM. The mesoporous material obtained, Al-MCM-48, and the composite material, ZSM-5/MCM-48, were used as catalysts for acylation of methyl-α-d-glucopyranoside. Fatty acids (n = 10, 14, and 16) and fatty acid chlorides were used, individually, as acylating agents for this reaction. The effects of solvent, type of catalyst, and nature of the fatty acids on the acylation reaction were investigated. Reaction yields in the range 50–70 % were achieved by use of this synthetic pathway. The products resulting from the acylation reaction are new nonionic bio-surfactants.

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Authors and Affiliations

  1. Laboratoire de chimie des matériaux L.C.M, Université d’Oran, BP, 1524, Oran El-Mnaouer, Algérie

    Bouhadjar Boukoussa, Rachida Hamacha & Abdelkader Bengueddach

  2. Laboratoire de Synthèse Organique Appliquée L.S.O.A, Université d’Oran, BP, 1524, Oran El-Mnaouer, Algérie

    Fatiha Sebih, Salima Bellahouel & Aicha Derdour

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  1. Bouhadjar Boukoussa
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  2. Fatiha Sebih
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  3. Rachida Hamacha
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  4. Salima Bellahouel
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Correspondence to Bouhadjar Boukoussa.

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Boukoussa, B., Sebih, F., Hamacha, R. et al. Regioselective acylation of methyl-α-d-glucopyranoside with different acylating agents catalysed by micro/mesoporous materials. Res Chem Intermed 41, 2221–2233 (2015). https://doi.org/10.1007/s11164-013-1340-8

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