Isosorbide:Structure and Properties, Syntheses and Applications

The use of biosourced carbon resources is a promising approach to the synthesis of "petroleum-free" products. However, this approach comes up against a price issue when comparing these biosourced compounds with petrochemical derivatives. Experience shows that it is generally not enough to reproduce existing petrochemical molecules in biosourced form in order to achieve viable commercial value. In many cases, biobased alternatives are expected to have superior application properties to those of products currently on the market.

Glucose, a C6 molecule, represents a major renewable carbon resource. This makes it a particularly attractive starting molecule for the production of high-tonnage materials. However, to produce a wide variety of end-use products, it often needs to be chemically transformed. The molecule can be oxidized, reduced, oligomerized, functionalized or cut into smaller building blocks (C1, C2, ..., C5). Isosorbide is one of the compounds derived from glucose whose carbon number is conserved (C6). Its agro-sourced origin and, above all, its particularly singular structure open the door to numerous applications, which are rapidly diversifying. The commercial success of isosorbide has been made possible by the fact that the molecule is marketed with very high levels of purity.

This article presents the isosorbide molecule, its structure and origin. The aim is also to present the various synthetic routes, often catalytic, that have been developed to efficiently access the molecule. Aspects such as reaction selectivity and polymerization of reaction intermediates all contribute to limiting reaction yields. The article then looks at the industrial advantages of incorporating the molecule into materials, and the chemical transformations that can be used to modulate its properties for increasingly diverse applications.