Haeckl, Katharina and Muhlbauer, Andrea and Ontiveros, Jesus F. and Marinkovic, Sinisa and Estrine, Boris and Kunz, Werner and Nardello-Rataj, Veronique (2018) Carnitine alkyl ester bromides as novel biosourced ionic liquids, cationic hydrotropes and surfactants. JOURNAL OF COLLOID AND INTERFACE SCIENCE, 511. pp. 165-173. ISSN 0021-9797, 1095-7103
Full text not available from this repository. (Request a copy)Abstract
Hypothesis: In contrast to anionic and nonionic amphiphilic substances, bio-based cationic ones are very rare. Cationic amphiphiles are mostly based on quaternary ammonium, pyridinium or imidazolium groups that are either badly biodegradable or have toxic residues even after degradation. In the search for green alternatives to cationic hydrotropes and amphiphiles, natural L-carnitine could be a promising candidate for a cationic headgroup. Experiments: By esterification of carnitine in one step and with low cost, cationic molecules with alkyl chain length of n = 2-14 could be obtained. Their thermal properties, aggregation behaviour and cytotoxicity were determined. Hydrophobic compounds were solubilized in their aqueous solutions and the PIT slope method was applied to determine a relative hydrophilicity. Findings: It was found that some pure carnitine ester bromides were liquid at room temperature and thus can be classified as ionic liquids. They are highly water-soluble, and in aqueous solutions, they showed hydrotrope or surfactant behaviour depending on their alkyl chain length. Their high hydrotropic efficiency was demonstrated by solubilizing Disperse Red 13, while also biomolecules, like vanillin, could be dissolved in reasonable amounts. In all tests, they performed at least as good as the tested reference substances, while showing similar cytotoxicity towards human skin keratinocytes, thus demonstrating their potential as green functional amphiphilic molecules of positive charge. (C) 2017 Elsevier Inc. All rights reserved.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | SOLUBILIZATION; WATER; TEMPERATURE; MIXTURES; TOXICITY; BEHAVIOR; QUANTIFICATION; EXTRACTION; INVERSION; ETHER; Carnitine alkyl esters; Cationic; Ionic liquids; Hydrotropes, surfactants |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Physikalische und Theoretische Chemie > Chair of Chemistry VI - Physical Chemistry (Solution Chemistry) > Prof. Dr. Werner Kunz |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 20 Mar 2020 14:39 |
| Last Modified: | 20 Mar 2020 14:39 |
| URI: | https://pred.uni-regensburg.de/id/eprint/15168 |
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