In this review the reactivity of the bio-based platform compounds D-sorbitol and isosorbide with green reagents and solvent Dimethyl Carbonate is reported. Dehydration of D-sorbitol via Dimethyl Carbonate in the presence of catalytic amounts of base is an efficient and viable process for the preparation of the industrially relevant anhydro sugar isosorbide. This procedure is “chlorine-free”, one-pot, environmental friendly and high yielding. The reactivity of isosorbide with DMC is equally interesting as it can lead to the formation of dicarboxymethyl isosorbide, a potential monomer for isosorbide-based polycarbonate, and dimethyl isosorbide, a high boiling green solvent. The peculiar reactivity of isosorbide and the non-toxic properties of Dimethyl Carbonate represent indeed a green match leading to several industrial appealing potential applications.

However, it should be pointed out that, despite D-sorbitol and isosorbide are renewable materials, their derivatizations do not always follow the green chemistry principles. In this prospect, the present work is focussed on the reactivity of D-sorbitol and isosorbide with the green reagent and solvent Dimethyl Carbonate.

Dimethyl carbonate the simplest among the dialkyl carbonate (DAC) family, is nowadays produced by a clean and halogen-free process. This compound has been extensively employed as green substitute of highly toxic phosgene in carboxymethylation reactions and methyl halides or other noxious methylating agents in methylation reactions.

The reactions between the bio-based chemicals D-sorbitol or isosorbide and DMC, are very appealing as they encompass the preparation, as well as the transformation of a renewable resource into industrially relevant products via a chlorine-free and green approach.

Synthesis of isosorbide via dimethyl carbonate

In this view, a different synthetic approach to isosorbide employs the versatile, green reagent and solvent Dimethyl Carbonate as dehydrating agent.

Reactivity of isosorbide with Dimethyl Carbonate.