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Choline Chloride-Based Deep Eutectic Solvents as Green Effective Medium for Quaternization Reactions
The Menshutkin reaction represents the alkylation of tertiary amines by alkyl halide where the reactants are neutral and the products, quaternary ammonium salts, are two ions with opposite signs. The most commonly used organic solvents in quaternization reactions are volatile organic solvents (VOSs)...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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MDPI
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9655353/ https://www.ncbi.nlm.nih.gov/pubmed/36364264 http://dx.doi.org/10.3390/molecules27217429 |
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author | Bušić, Valentina Molnar, Maja Tomičić, Vice Božanović, Dalia Jerković, Igor Gašo-Sokač, Dajana |
author_facet | Bušić, Valentina Molnar, Maja Tomičić, Vice Božanović, Dalia Jerković, Igor Gašo-Sokač, Dajana |
author_sort | Bušić, Valentina |
collection | PubMed |
description | The Menshutkin reaction represents the alkylation of tertiary amines by alkyl halide where the reactants are neutral and the products, quaternary ammonium salts, are two ions with opposite signs. The most commonly used organic solvents in quaternization reactions are volatile organic solvents (VOSs), namely acetone, anhydrous benzene, dry dichloromethane (DCM), dimethylformamide (DMF) and acetonitrile (ACN). The purpose of this work was to examine eutectic solvents as a “greener” alternative to conventional solvents so that quaternization reactions take place in accordance with the principles of green chemistry. Herein, sixteen eutectic solvents were used as replacements for volatile organic ones in quaternization reactions of isonicotinamide with substituted phenacyl bromides. The reactions were carried out at 80 °C by three synthetic approaches: conventional (4–6 h), microwave (20 min) and ultrasound (3 h). Microwave-assisted organic reactions produced the highest yields, where in several reactions, the yield was almost quantitative. The most suitable eutectic solvents were based on choline chloride (ChCl) as the hydrogen bond acceptor (HBA) and glycerol, oxalic or levulinic acid as hydrogen bond donors (HBDs). The benefits of these three deep eutectic solvents (DESs) as a medium for quaternization reactions are the simplicity of their preparation for large-scale production, with inexpensive, available and nontoxic starting materials, as well as their biodegradability. |
format | Online Article Text |
id | pubmed-9655353 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-96553532022-11-15 Choline Chloride-Based Deep Eutectic Solvents as Green Effective Medium for Quaternization Reactions Bušić, Valentina Molnar, Maja Tomičić, Vice Božanović, Dalia Jerković, Igor Gašo-Sokač, Dajana Molecules Article The Menshutkin reaction represents the alkylation of tertiary amines by alkyl halide where the reactants are neutral and the products, quaternary ammonium salts, are two ions with opposite signs. The most commonly used organic solvents in quaternization reactions are volatile organic solvents (VOSs), namely acetone, anhydrous benzene, dry dichloromethane (DCM), dimethylformamide (DMF) and acetonitrile (ACN). The purpose of this work was to examine eutectic solvents as a “greener” alternative to conventional solvents so that quaternization reactions take place in accordance with the principles of green chemistry. Herein, sixteen eutectic solvents were used as replacements for volatile organic ones in quaternization reactions of isonicotinamide with substituted phenacyl bromides. The reactions were carried out at 80 °C by three synthetic approaches: conventional (4–6 h), microwave (20 min) and ultrasound (3 h). Microwave-assisted organic reactions produced the highest yields, where in several reactions, the yield was almost quantitative. The most suitable eutectic solvents were based on choline chloride (ChCl) as the hydrogen bond acceptor (HBA) and glycerol, oxalic or levulinic acid as hydrogen bond donors (HBDs). The benefits of these three deep eutectic solvents (DESs) as a medium for quaternization reactions are the simplicity of their preparation for large-scale production, with inexpensive, available and nontoxic starting materials, as well as their biodegradability. MDPI 2022-11-01 /pmc/articles/PMC9655353/ /pubmed/36364264 http://dx.doi.org/10.3390/molecules27217429 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Bušić, Valentina Molnar, Maja Tomičić, Vice Božanović, Dalia Jerković, Igor Gašo-Sokač, Dajana Choline Chloride-Based Deep Eutectic Solvents as Green Effective Medium for Quaternization Reactions |
title | Choline Chloride-Based Deep Eutectic Solvents as Green Effective Medium for Quaternization Reactions |
title_full | Choline Chloride-Based Deep Eutectic Solvents as Green Effective Medium for Quaternization Reactions |
title_fullStr | Choline Chloride-Based Deep Eutectic Solvents as Green Effective Medium for Quaternization Reactions |
title_full_unstemmed | Choline Chloride-Based Deep Eutectic Solvents as Green Effective Medium for Quaternization Reactions |
title_short | Choline Chloride-Based Deep Eutectic Solvents as Green Effective Medium for Quaternization Reactions |
title_sort | choline chloride-based deep eutectic solvents as green effective medium for quaternization reactions |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9655353/ https://www.ncbi.nlm.nih.gov/pubmed/36364264 http://dx.doi.org/10.3390/molecules27217429 |
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