(2-Hydroxyethyl)ammonium lactates have been prepared by reactions of the corresponding (2-hydroxyethyl) amines with lactic acid and characterized by their 1 H NMR, IR, and mass spectra. They have been quantitatively analyzed by HPLC, and their water contents have been determined by the Karl-Fischer method. The title salts are low-melting solids or viscous liquids, and they belong to the class of polar, hydrophilic ionic liquids. The toxicity and chemical and biological degradation of the synthesized ionic liquids have been evaluated by methods described in European Standards. The measurements showed these ionic liquids to be highly biodegradable and only slightly toxic substances. Condensation reactions of benzaldehyde with ethyl cyanoacetate and with acetophenone have been performed in these materials as solvents. The possibility of simultaneously applying these ionic liquids as both solvents and catalysts for the mentioned reactions has been demonstrated, as well as repeated use of the same ionic liquid for a number of condensation reactions without any purification.
The alkylation reaction of the ambident 2-hydroxypyridine anion was examined in ionic liquid media. Ionic liquids increase the alkylation reaction rate in comparison with molecular liquids, as well as the level of impact on the reaction rates of the counter ion and/or additives, and the distribution of isomers of the reaction products in trans-formations of the ambident 2-hydroxypyridine anion.
Fragmentation pathways of some imidazolium based zwitterionic liquids-3-(3-alkyl-1-imidazolio)- propane sulfonates and 3-(2-methyl-3-alkyl-1-imidazolio)-propane sulfonates -- have been studied by tandem electrospray mass spectrometry and collision-induced dissociation. The relative abundances of the lowest energy fragment ions depend on the length of the alkyl chain at the (II)N of the imidazolium ring and the cone voltage. The first fragment ions originate from the scission of C(non aromatic)-N bond of compounds investigated, but with increasing collision energy, scission of C-C bonds occurs. Aggregates of the general formula [(M + H)(x) + (M)(y)](+) (x;y = 1-2) formed. Methyl substituted zwitterionic liquids show higher molecular stability than 3-(3-alkyl-1-imidazolio)-propane sulfonates.
Highly hydrophilic ionic liquids easily form in reactions between 2-hydroxyethyl amines and carboxylic acids. They have low toxicity and high biodegradability, serve both as reaction solvents and catalysts in condensation reactions, and they may be reused several times without any purification.
Alkylation of indole salts in different ionic liquids is reported. Ionic liquids increase the alkylation reaction rate of ambident indole anion and reduce the effects of counter ions and/or additives, the alkylation reaction rates being independent of the presence of small amounts of protic solvents or water.
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