Hydroxymethylfurfural (HMF) is one of the feedstocks that can be produced from glucose; it is a useful precursor for the synthesis of biofuels and polymers. Many catalysts have been developed for production of HMF, including Brønsted and Lewis acids dissolved in the biphasic system consisting of water and organic solvent. However, it is challenging to improve the selectivity of HMF due to the possibility of side products which can be controlled by using appropriate organic solvent for the biphasic system.<br/>In this regard, here solvent effects on glucose conversion to HMF were thoroughly analyzed. First, HMF yields were measured by experiments for 13 water-organic biphasic systems. To explain the solvent effects on production of HMF, computational study of reaction mechanisms was performed using density functional theory (DFT) with the implicit solvation model. It should be noted that this approach can incorporate only one solvent phase, so the COSMO-SAC model was adopted for reliable description of solvent effects in two phases. Next, the molecular descriptors relevant to solvent effect on HMF yield were derived from those calculations. Finally, the multivariate model was developed which correlates HMF yield with these descriptors. It showed reliable accuracy in predicting HMF yield for four new systems as well as that for 13 cases, and also gave chemical interpretations of solvent effects leading to differences in HMF formation. It is expected that this multivariate analysis with the COSMO-SAC model can be applied to solvent screening for other target products of biomass conversion reactions. In particular, the COSMO-SAC is also capable of accounting for heterogeneity of the biphasic system, such as immiscibility, azeotropic behavior, and vapor-liquid equilibrium, which implies its potential applicability to broader scope of reactions.

Addressing the solvent effect of biphasic systems on glucose conversion to hydroxymethylfurfural through multivariate analysis with the COSMO-SAC model

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.