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We report on the characterisation of 16 protic ionic liquids (PILs) prepared by neutralisation of primary or tertiary amines with a range of simple carboxylic acids, or salicylic acid. The extent of proton transfer was greater for simple primary amine ILs compared to tertiary amines. For the latter case, proton transfer was increased by providing a better solvation environment for the ions through the addition of a hydroxyl group, either on the tertiary amine, or by formation of PIL/molecular solvent mixtures. The library of PILs was characterised by differential scanning calorimetry and a range of transport properties (i. e. viscosity, conductivity and diffusivity) were measured. Using the (fractional) Walden rule, the conductivity and viscosity results were analysed with respect to their deviation from ideal behaviour. The validity of the Walden plot for PILs containing ions of varying sizes was also verified for a number of samples by directly measuring self-diffusion coefficients using pulsed-field gradient spin-echo (PGSE) NMR. Ionicity was found to decrease as the alkyl chain length and degree of branching of both the cations and anions was increased. These results aim to develop a better understanding of the relationship between PIL properties and structure, to help design ILs with optimal properties for applications.
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http://dx.doi.org/10.1002/cphc.202000242 | DOI Listing |
Molecules
February 2025
Department of Metallurgical and Materials Engineering, Federal University of Ceará (UFC), Fortaleza 60440-900, CE, Brazil.
The inhibitory performance of three distinct protic ionic liquids (PILs), namely, 2-hydroxyethyl ammonium formate (PIL 01), 2-hydroxyethyl ammonium propionate (PIL 02), and 2-hydroxyethyl ammonium pentanoate (PIL 03), was evaluated to determine their suitability as eco-friendly corrosion inhibitors for carbon steel (ASTM A36) in a 3.5 wt. % NaCl aerated neutral electrolyte solution.
View Article and Find Full Text PDFInt J Biol Macromol
March 2025
Beijing Key Laboratory of Ionic Liquids Clean Process, CAS Key Laboratory of Green Process and Engineering, Institute of Process Engineering, Chinese Academy of Sciences, Beijing 100190, China; School of Chemical and Engineering, University of Chinese Academy of Sciences, Beijing 100049, China.
Ionic liquids (ILs) are highly effective in lignocellulose pretreatment due to their excellent solvation properties. However, the single-phase nature of conventional IL pretreatment not only causes component mixing, complicating separation and utilization, but also limits large-scale application due to the high cost. To address these challenges, this study developed a biphasic pretreatment system combining the protic IL [BHEM]mesy with aqueous pentanol, aiming to efficiently fractionate corn stover under mild conditions.
View Article and Find Full Text PDFJ Phys Chem A
March 2025
Department of Chemistry, University of Southern California, Los Angeles, California 90089, United States.
The ionization of protic molecules such as HO and NH in the condensed phase initiates ion-molecule reactions, which remain poorly understood. Studies of the structure and reactivity of small ionic clusters in molecular beams have yielded a wealth of information on protonated clusters. However, unprotonated radical cation clusters have a low concentration in a typical experiment and thus remain challenging.
View Article and Find Full Text PDFChemistryOpen
February 2025
School of Chemical Sciences, University of Auckland, 23 Symonds Street, Auckland, 1010, New Zealand.
The transformation of chitin and its monomer N-acetylglucosamine (NAG) to high-value organonitrogen chemicals has attracted increasing interest, with 3-acetamido-5-acetylfuran (3A5AF) proposed as a versatile platform chemical. The preparation of 3A5AF from NAG has relied on high boiling organic solvents, ionic liquids (ILs) or deep eutectic solvents (DES). While these methods have met with some success, the isolation of 3A5AF and recycling of the solvent remains problematic for non-IL methods whereas most IL methods utilize inherently expensive aprotic ILs with substantial environmental footprints.
View Article and Find Full Text PDFPhys Chem Chem Phys
March 2025
Department of Materials Chemistry, Faculty of Engineering, Shinshu University, 4-17-1 Wakasato, Nagano, 380-8553, Japan.
In recent years, there has been growing interest in rechargeable batteries utilizing protons or hydronium ions as charge carriers, driven by the rapid ionic conduction enabled by the proton-specific Grötthuss mechanism. However, the use of acidic aqueous electrolytes introduces side reactions, such as irreversible hydrogen evolution and the dissolution of active materials into the electrolyte, which are influenced by the reaction potential of the active materials. These challenges complicate the identification and development of active materials.
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