Ionic liquids derived from prolinium esters, previously described as fully green and stable, were found to decompose in the presence of water by ester hydrolysis. To avoid this problem, a new family of these biodegradable salts incorporating an alcohol instead of the ester group is proposed. From this family, two novel ionic liquids that incorporate the prolinolium cation [HOPro] and the [DS] or [DBS] anion were selected (DS=dodecylsulfate; DBS=dodecylbenzenesulfonate). Both salts are liquid at room temperature, a property not usually found in ionic surfactants, and are also chemically and thermally stable. Moreover, they are more effective in reducing the surface tension of water than the corresponding traditional surfactants in the form of sodium salts, being useful for applications related to their aggregation capacity. They were tested for surfactant enhanced oil recovery and an optimal formulation for reservoirs at high salinity and temperature, able to produce ultra-low interfacial tension, was found with [HOPro][DBS].

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The transformation of two solid Active Pharmaceutical Ingredients (APIs) into new ionic liquids (IL)s that incorporate APIs (API-ILs) is reported. The structures of the APIs (indomethacin and mebendazole) were selected by their susceptibility to being transformed into API-ILs (either to form the cation or the anion) and their limited bioavailability due to their low solubility in water. The counterions, such as those derived from 2-dimethylaminoethanol (DMEA), tetramethylguanidine (TMG), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), 1,4-diazabicyclo[2.2.2] (TED), <i>p</i>-toluensulfonic acid, glycolic acid, methanesulfonic acid, and saccharin, were carefully chosen, aiming for high biocompatibility, low toxicity, and high water solubility. The synthesis was carried out by direct treatment of the API with the corresponding selected acid or base. Finally, the solubility in water of all the synthesized salts was determined.

A new procedure to prepare ε-caprolactam by the Beckmann rearrangement of cyclohexanone oxime is described.

A mild and efficient procedure for the oxyselenocyclization of unsaturated alcohols by treatment with phenylselenyl chloride using ionic liquids as solvents/catalyzers has been developed. The reaction proceeds instantaneously under mild conditions with absolute regioselectivity, using primary, secondary, tertiary, and aromatic alcohols, as well as monosubstituted, disubstituted, and trisubstituted alkenols. This procedure provides a new method for the synthesis of substituted tetrahydrofurans and tetrahydropyrans ethers, the precursors of many biologically active metabolites, avoiding the use of toxic and corrosive catalysts. There are no previous reports of seleniummediated cyclofuncionalization reactions in ionic liquids. Taking into the account the good results obtained with [MMIM][MSO 4 ], its ease preparation, low viscosity, low price, and its capacity to be recovered and reused, it was selected as the solvent/catalyzer. Quantum-chemical calculations (MP2(fc)/ 6-311 + G**//B3LYP/6-311 + G**) has shown that the intramolecular cyclization is promoted by the hydrogen bond formed between the ionic liquid anion and the hydroxyl group of the alkenol.