Systematic Green Solvent Selection for the Hydroformylation of Long-Chain Alkenes

When selecting solvents, not only thermodynamic criteria but also environmental, health, and safety (EHS) properties should be considered. To this end, we present a fully automated solvent selection approach for the homogeneous catalyzed hydroformylation of 1-decene in a temperature-dependent thermomorphic multicomponent system (TMS) using the conductor-like screening model for real solvents (COSMO-RS). The state-of-the-art TMS uses N,N-dimethylformamide (DMF) as the catalyst carrier, which is developmentally toxic, thereby demanding replacement. In order to evaluate the EHS properties holistically, 30 predictive EHS models for 15 different properties are considered in the solvent selection framework, as well as the reliability of the predictions. From a database containing approximately 7800 molecules, the most promising candidates are identified. The best solvent among them, diethyl sulfoxide (DESO), is predicted as outperforming DMF as a catalyst solvent in the hydroformylation. The evidence suggests that DESO may be a broadly applicable environmentally benign substitute solvent for DMF.