Hydrolysis Reactions of Two Benzoyl Chlorides as a Probe to Investigate Reverse Micelles Formed by the Ionic Liquid-Surfactant bmim-AOT
| Autor: | Nahir Dib, R. Darío Falcone, Luis García-Río |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
chemistry.chemical_classification
Reaction mechanism 010405 organic chemistry Chemistry Organic Chemistry Inorganic chemistry Reaction intermediate 010402 general chemistry 01 natural sciences Chloride Micelle 0104 chemical sciences Solvent chemistry.chemical_compound Benzoyl chloride Ionic liquid medicine Counterion medicine.drug |
| Zdroj: | The Journal of organic chemistry. 85(23) |
| ISSN: | 1520-6904 |
| Popis: | In this work, two hydrolysis reactions were used as a probe to investigate the properties of reverse micelles (RMs) formed by the ionic liquid-surfactant 1-butyl-3-methylimidazolium 1,4-bis-2-ethylhexylsulfosuccinate (bmim-AOT). The results were compared with those found for RMs generated with sodium 1,4-bis-2-ethylhexylsulfosuccinate (Na-AOT). As external nonpolar solvents, n-heptane (n-Hp), isopropyl myristate (IPM), and methyl laurate (ML) were used. Thus, the effect of changing the Na+ cation by bmim+ was analyzed, as well as the impact of the replacement of a conventional external nonpolar solvent by biocompatible solvents. The kinetics of the hydrolysis reactions of 4-methoxybenzoyl chloride (OMe) and 4-(trifluoromethyl)benzoyl chloride (CF3) were studied. The results indicate that the replacement of the Na+ counterion by bmim+ in AOT RMs alters the rates of reactions carried out in them and produces changes in the reaction mechanism. In bmim-AOT RMs, the bmim+ cation is located between the surfactant molecules; this has an important influence on the reaction intermediates' stability and, therefore, in the reaction rates and mechanisms. Also, the results indicate that when IPM is used as an external solvent instead of ML or n-Hp, interfacial water molecules have larger nucleophilicity due to the higher interface penetration of IPM. |
| Databáze: | OpenAIRE |
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