Abstract
The reactivity of glycerol with trimethyl orthoformate is here described with an emphasis on developing a reliable synthetic approach for glycerol valorization. The glycerol based orthoester 4-(dimethoxymethoxy)methyl)-2-methoxy-1,3-dioxolane (3) was synthesized, under catalytic as well as catalyst-free conditions, by taking advantage of the thermodynamically controlled equilibrium between intermediates. Both Brønsted and Lewis acid catalysts accelerated the attainment of such an equilibrium, particularly Brønsted acidic ionic liquids BSMImHSO4 and BSMImBr were the most effective compounds for this reaction. The kinetic profiles allowed the proposal of a mechanism that accounts for the selectivity of the reaction.
Highlights
Glycerol (Glyc) is one of the most important biomass-derived platform chemicals [1]
In a search to further expand this chemistry and to identify new bio-building blocks, we considered orthoesters (OEs) as another family of electrophilic partners for the upgrading of Glyc
The reactivity between Glyc and HC(OMe)3 was first tested in the absence of any catalyst, in aim to develop new reliable synthetic protocols for glycerol exploitation
Summary
Glycerol (Glyc) is one of the most important biomass-derived platform chemicals [1]. Over the last few decades, the overabundance of this bio-diesel by-product stimulated academic and industrial interests towards its conversion into renewable high value-added chemicals [2,3,4,5,6,7]. In this field, our research group has explored different thermal and catalytic synthetic approaches by reacting Glyc with formaldehyde, acetone, dimethyl carbonate, and enol esters to yield acetals, ketals, and other sustainable derivatives [8,9,10,11,12,13]. A fascinating use of OEs in the synthesis of dynamic cryptands has been proposed, employed for the controlled release of metal ion guests [20,21]
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