Abstract
Bis(cyclo-carbonate) was successfully synthesized from D-sorbitol (Sorb-BisCC) through an environmentally friendly process with dimethyl carbonate (DMC) as a reactant. In agreement with green chemistry principles, solvent free reactions were catalyzed and took place at low temperature. The reaction yield was increased until 50%, with the use of 1.3.5-triazabicyclo[4.4.0]dec-5-ene as catalyst and a continuous DMC feed to limit the side-reactions or the loss of reactant by azeotropic flux with a reactional subsidiary product. The obtained Sorb-BisCC is a remarkable platform molecule which could compete with others polycyclic platform molecules (isosorbide). Sorb-BisCC can be e.g., used to synthesize different chemicals such as short and long polyols, or novel biobased non-isocyanate polyurethanes (NIPU). Two Sorb-BisCC molecules have been coupled to obtain novel cyclic diols with pendant side chains. Polyether polyols were also obtained by anionic ring opening polymerization. According to the synthesis conditions, these synthetized polyether polyols range from partially to highly cross-linked materials. Finally, NIPU were synthesized with short and biobased fatty diamines. These different modifications and synthesis highlight the versatility of the Sorb-BisCC and demonstrated its high potential as building block. Sorb-BisCC can be considered as a platform molecule to open the way to different original and biobased chemical architectures.
Highlights
D-sorbitol (Table 1) is a widely available and low-cost sugar alcohol which is mainly obtained from D-glucose hydrogenation[1]
Mazurek-Budzynska et al.[19] reported the synthesis of this molecule working with 10 eq of dimethyl carbonate (DMC) toward D-sorbitol in methanol catalyzed by potassium carbonate with a global yield of 40%
To show that Sorb-BisCC is a platform molecule, it was used as a basis leading to the elaboration of different products
Summary
D-sorbitol (Table 1) is a widely available and low-cost sugar alcohol which is mainly obtained from D-glucose hydrogenation[1]. The Enichem process uses carbon monoxide and oxygen as reactants, but its current production derived of CO2 is on the rise, positioning DMC as a green reactive solvent[16]. The D-sorbitol-based and five-membered bis(cyclo-carbonate) (Sorb-BisCC) is composed of two cyclo-carbonate groups and a tetrahydrofuran ring It can be compared (Table 1) to another important polycyclic sorbitol derivative which is largely used as a building block with a large industrial production: the isosorbide[20,21]. The annual production and price of the Sorb-BisCC cannot be assessed as it is not produced at industrial scale
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