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Activation of Vegetable Oils by Reaction with Maleic Anhydride as a Renewable Source in Chemical Processes: New Experimental and Computational NMR Evidence
Authors:Francesco Lanero  Bianca Maria Bresolin  Anna Scettri  Marco Nogarole  Elisabetta Schievano  Stefano Mammi  Giacomo Saielli  Alessia Famengo  Alessandra Semenzato  Giovanni Tafuro  Paolo Sgarbossa  Roberta Bertani
Abstract:Vegetable oils are bio−based and sustainable starting materials that can be used to develop chemicals for industrial processes. In this study, the functionalization of three vegetable oils (grape, hemp, and linseed) with maleic anhydride was carried out either by conventional heating or microwave activation to obtain products that, after further reactions, can enhance the water dispersion of oils for industrial applications. To identify the most abundant derivatives formed, trans-3-octene, methyl oleate, and ethyl linoleate were reacted as reference systems. A detailed NMR study, supported by computational evidence, allowed for the identification of the species formed in the reaction of trans-3-octene with maleic anhydride. The signals in the 1H NMR spectra of the alkenyl succinic anhydride (ASA) moieties bound to the organic chains were clearly identified. The reactions achieved by conventional heating were carried out for 5 h at 200 °C, resulting in similar or lower amounts of ASA units/g of oil with respect to the reactions performed by microwave activation, which, however, induced a higher viscosity of the samples.
Keywords:vegetable oil   maleic anhydride   Alder reaction   ene reaction   2D COSY   HSQC   HMBC and 1D CSSF-TOCSY NMR experiments
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