Studio della reattività del glicerol carbonato nella sintesi di derivati fenolici

Giliberti, Carlo (2016) Studio della reattività del glicerol carbonato nella sintesi di derivati fenolici. [Laurea magistrale], Università di Bologna, Corso di Studio in Chimica industriale [LM-DM270], Documento ad accesso riservato.
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Abstract

Supported by the increasing sustainable awareness, glycerol carbonate has gained much interest over the last 20 years because of its versatile reactivity and as a way to valorize waste glycerol. Numerous synthesis pathways for this molecule were identified, some of them very promising and on the verge of being applied at an industrial scale. Here, we report a study aimed at valorizing glycerol carbonate as chemical intermediate, in order to synthesize 2-hydroxymethyl-1,4-benzodioxane (HMB). This molecule finds important applications as key intermediate for the synthesis of a broad class of pharmaceuticals and therapeutic agents. Concerning the presence of a stereogenic center on the hydroxymethyl group, due to the pharmaceutical importance to obtain and isolate one single enantiomer, , nowadays HMB is obtained through batch scale process, using a multi-reaction approach and starting from reagents of the chiral pool. We carried out the reaction from a solution of glycerol carbonate and catechol 2:1. In the presence of a simple basic catalyst, at high temperatures, it was possible obtain total reactants conversion and high yield to HMB in few hours reaction time. Also, in the aim of developing a process which might adhere the principles of Green Chemistry, we avoided the use of solvents. Similar results were obtained using a 1:1 feed ratio of reactants, even if selectivity to HMB decrease, due to the presence of side reactions. A complete study of the reaction mechanism is proposed in this thesis.

Abstract
Tipologia del documento
Tesi di laurea (Laurea magistrale)
Autore della tesi
Giliberti, Carlo
Relatore della tesi
Correlatore della tesi
Scuola
Corso di studio
Ordinamento Cds
DM270
Parole chiave
glicerol carbonato alchilazione catecolo carbonati condensazione one-pot catalisi omogenea catalisi eterogenea
Data di discussione della Tesi
10 Ottobre 2016
URI

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