Marina M. SEITKALIEVA1, Anna V. VAVINA1, Ksenia S. EGOROVA1, Alexey S. KASHIN1, Valentine P. ANANIKOV1
1N.D. Zelinsky Institute of Organic Chemistry, Moscow, Russian Federation
The past few decades have witnessed the rise of ionic liquids (ILs) as new alternative solvents, and many diverse applications have been suggested for this class of compounds. They are used as unique media for chemical reactions, electrochemical processes, analytical chemistry, cellulose dissolution, biological aid, etc. [1-2]
However, the non-renewable nature of the initial reagents for synthesis of most ILs affects their cost and environmental impact. Along with toxicity and the problem with purification and regeneration of ILs, these limits their wide industrial application. Using renewable, bio-based starting materials can significantly reduce the cost of finale ILs and their environmental impact. The presence of natural molecules depending on the place of the bio-fragment (in the cation or/and anion) can affect the toxicity of new compounds. [3-4]
While studying the advantages of various bio-derived ILs, we synthesized new ammonium ionic liquids from 5-hydroxymethylfurfural (5-HMF). [5] 5-HMF is a valuable platform-chemical, derived directly from cellulose and a good alternative to non-renewable aromatic sources. Protic ILs were synthesized by reductive amination of 5-HMF and subsequent protonation with strong inorganic acids. Aprotic ILs with quaternary ammonium cationic center were obtained with anions of weak acids. The new ILs based on 5-HMF had improved physicochemical properties and showed higher cytotoxicity compared to 5-HMF and commercially available ILs. The substituents in the cationic core had a prominent impact on the cytotoxicity of the ILs. Some 5-HMF-derived ILs showed antimicrobial activity in relation to gram-positive and gram-negative bacteria. The possible application of some 5-HMF derived ILs for cellulose dissolution was demonstrated.
Acknowledgements
The part of the work was supported by the Russian Science Foundation (RSF Project #21-73-10262).
References
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