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Dimethylcarbonate-Assisted Ring-Opening of Biobased Valerolactones with Methanol

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Dipartimento di Scienze Molecolari e Nanosistemi, Università Ca’ Foscari Venezia, Via Torino 155, 30172 Venezia Mestre, Italy
Cite this: ACS Sustainable Chem. Eng. 2016, 4, 11, 6193–6199
Publication Date (Web):August 23, 2016
https://doi.org/10.1021/acssuschemeng.6b01863
Copyright © 2016 American Chemical Society

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    Abstract

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    The methanolysis reaction of renewable γ-valerolactone and α-methyl-γ-valerolactone in the presence of dimethylcarbonate and under acid conditions can be tuned to yield selectively each of three acyclic biobased products: 4-hydroxy-methylpentanoate 1, 4-methoxy-methylpentanoate 2, and methyl-pent-3-enoate 3. The reaction was studied in batch and in continuous flow, and a reaction mechanism based on experimental and computational evidence was proposed. The protocol is based on a set of greener chemical technologies and was implemented in continuous flow.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acssuschemeng.6b01863.

    • Complete experimental data and full spectral (NMR and MS) characterization of all compounds (PDF)

    • Rotable image and Cartesian coordinates for [GVL–CH(OMe)2]+, [GVL–H–DMC]+, and the transition state for the reaction between MeOH and the [GVL–H–DMC]+ adduct (XYZ)

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