The aim of this PhD project is to investigate the reactivity of galactaric acid, also known as mucic acid, as a model molecule of the aldaric acids class of compounds. Galactaric acid was reacted to give 2‐pyrone derivatives, moieties present in molecules with a peculiar pharmacological activity. Those were then employed to obtain biosourced polycarboxylic aromatic acid derivatives through a sustainable pathway. Due to the importance of 2‐pyrones both in medicinal and synthetic chemistry, the optimization of the developed process was performed and this was transferred to a continuous flow reactor in order to open easy and fast access to those molecules. On the other hand, galactaric acid was manipulated to obtain new monomers for the synthesis of hydroxylated polyamides.
Lo scopo di questo progetto di dottorato è stato quello di indagare la reattività dell’acido galattarico, anche noto come acido mucico, come molecola rappresentativa per la classe degli acidi aldarici a sei atomi di carbonio. Nella prima fase del progetto, l’acido galattarico è stato impiegato come precursore per la sintesi di 2‐pironi, strutture che costituiscono il principio attivo di molti composti di interesse farmaceutico. I 2‐pironi stessi sono stati successivamente impiegati nella sintesi di acidi aromatici policarbossilici. Data l’importanza sia farmaceutica che sintetica dei 2‐pironi, il processo sviluppato per il loro ottenimento è stato ottimizzato e la sintesi è stata poi trasferita in un reattore in continuo al fine di facilitare e velocizzare la via di accesso a questa classe di composti. Nella seconda fase del progetto, l’acido galattarico è stato utilizzato per l’ottenimento di nuovi monomeri bifunzionali utilizzati nella sintesi di poliidrossi poliammidi.
Valorisation of galactaric acid and its derivatives for the sustainable synthesis of biobased molecules
RIGHETTI, GRAZIA ISA CARLA
2021/2022
Abstract
The aim of this PhD project is to investigate the reactivity of galactaric acid, also known as mucic acid, as a model molecule of the aldaric acids class of compounds. Galactaric acid was reacted to give 2‐pyrone derivatives, moieties present in molecules with a peculiar pharmacological activity. Those were then employed to obtain biosourced polycarboxylic aromatic acid derivatives through a sustainable pathway. Due to the importance of 2‐pyrones both in medicinal and synthetic chemistry, the optimization of the developed process was performed and this was transferred to a continuous flow reactor in order to open easy and fast access to those molecules. On the other hand, galactaric acid was manipulated to obtain new monomers for the synthesis of hydroxylated polyamides.File | Dimensione | Formato | |
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Tesi Dottorato Grazia Isa Carla Righetti.pdf
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https://hdl.handle.net/10589/187912