Environmentally Friendly Solvents with Diverse Applications: Deep Eutectic Solvents (DESs)

When solid choline chloride (melting point 302 °C) and urea (melting point 133 °C) are mixed in a 1:2 ratio, they form a eutectic mixture (1) that remains liquid even at room temperature (freezing point 12 °C).¹⁾ This phenomenon has been reported for various combinations of hydrogen bond donors and acceptors, and such liquids are known as Deep Eutectic Solvents (DESs). Due to their many advantages, DESs have been studied for a wide range of applications similar to those of ionic liquids.²⁾
For example, reports include asymmetric organocatalytic reactions using solvent (2) and recovery/reuse of the catalyst-containing medium,³⁾ as well as Negishi-type C(sp²)–C(sp³) cross-coupling reactions carried out in a short time using solvent (1).⁴⁾ Beyond the field of organic synthesis, DESs have also been applied in enzyme-catalyzed biodiesel fuel synthesis using solvent (3),⁵⁾ as extraction solvents for natural products and biopolymers such as nucleic acids, and as electrolytes for batteries in bio- and materials-related fields. Thus, DESs are attracting considerable attention as highly valuable solvents for sustainable process development, recycling, and in the context of the SDGs.

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References

• 1) Novel solvent properties of choline chloride/urea mixtures
  • A. P. Abbott, G. Capper, D. L. Davies, R. K. Rasheed, V. Tambyrajah, Chem. Commun. 2003, 70.
• 2) Metal-Free Deep Eutectic Solvents: Preparation, Physical Properties, and Significance
  • B. Gurkan, H. Squire, E. Pentzer, J. Phys. Chem. Lett. 2019, 10, 7956.
• 3) L-Isoleucine in a Choline Chloride/Ethylene Glycol Deep Eutectic Solvent: A Reusable Reaction Kit for the Asymmetric Cross-Aldol Carboligation
  • N. Fanjul-Mosteirín, C. Concellón, V. delAmo, Org. Lett. 2016, 18, 4266.
• 4) Scalable Negishi Coupling between Organozinc Compounds and (Hetero)Aryl Bromides under Aerobic Conditions when using Bulk Water or Deep Eutectic Solvents with no Additional Ligands
  • G. Dilauro, C. S. Azzollini, P. Vitale, A. Salomone, F. M. Perna, V. Capriati, Angew. Chem. Int. Ed. 2021, 60, 10632.
• 5) Choline-based deep eutectic solvents for enzymatic preparation of biodiesel from soybean oil
  • H. Zhao, C. Zhang, T. D. Crittle, J. Mol. Catal. B Enzym. 2013, 85, 243.

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