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Review
. 2016 Oct 26:12:2256-2266.
doi: 10.3762/bjoc.12.218. eCollection 2016.

Isosorbide and dimethyl carbonate: a green match

Fabio Aricò  1 , Pietro Tundo  1
Affiliations
Review

Isosorbide and dimethyl carbonate: a green match

Fabio Aricò et al. Beilstein J Org Chem. .

Abstract

In this review the reactivity of the bio-based platform compounds D-sorbitol and isosorbide with green reagents and solvent dimethyl carbonate (DMC) is reported. Dehydration of D-sorbitol via DMC 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 DMC represent indeed a green match leading to several industrial appealing potential applications.

Keywords: D-sorbitol; carbohydrate chemistry; dimethyl carbonate; green chemistry; isosorbide.

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Figures

Figure 1
Figure 1
The DOE “Top 10” report [2].
Figure 2
Figure 2
Chemical structure of isosorbide and its epimers isomannide and isoidide.
Scheme 1
Scheme 1
Conversion of D-sorbitol to isosorbide via twofold dehydration reaction.
Scheme 2
Scheme 2
Possible reaction mechanism for the conversion of D-sorbitol to isosorbide.
Scheme 3
Scheme 3
Methoxycarbonylation of isosorbide via DMC chemistry.
Scheme 4
Scheme 4
Isosorbide homo- and co-polycarbonate via melt polycondensation.
Scheme 5
Scheme 5
Synthesis of DMI via DMC chemistry.
Scheme 6
Scheme 6
Comparison of the reactivity of isosorbide with other secondary alcohols in methylation reaction. Reaction conditions: Isosorbide DMC 1:50 equiv; reaction time 20 h; 90 °C.
Figure 3
Figure 3
Chemical structure of isosorbide and its epimers isomannide and isoidide.
See this image and copyright information in PMC

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