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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)...

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Autores principales: Bušić, Valentina, Molnar, Maja, Tomičić, Vice, Božanović, Dalia, Jerković, Igor, Gašo-Sokač, Dajana
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
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.
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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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