Choline chloride based eutectic solvent: an efficient and reusable solvent system for the synthesis of primary amides from aldehydes and from nitriles

Patil, Umakant B.; Singh, Abhilash S.; Nagarkar, Jayashree M.

doi:10.1039/c3ra43552k

Cited by 62 publications

(39 citation statements)

References 53 publications

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“…7 On the contrary, due to its low-cost, biodegradable, and environmentalfriendly starting material, DESs are believed to be more effective and environmental-friendly. [15][16][17][18] Most of the earlier studies focused on ChCl-based DESs. 1,4,[12][13][14] N,N-Diethyl ethanol ammonium chloride (EAC) and 2-hydroxy-N,N,N-trimethylethanaminium chloride known as (choline chloride) (ChCl)-based DESs were previously reported in different studies along with their physical properties.…”

Section: Introductionmentioning

confidence: 99%

Evaluation of toxicity and biodegradability for cholinium-based deep eutectic solvents

2015

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This study presented the toxicological and biodegradable assessment of different cholinium-based deep eutectic solvents (DESs). They were formed from choline chloride (ChCl) and N,N-diethyl ethanol ammonium chloride (EAC) as salts and four hydrogen bond donors, namely ethylene glycol (EG), glycerol (Gly), urea (U), malonic acid (MA), in addition to a metal salt, i.e. zinc chloride (ZnCl 2 ), and a hydrated metal salt, i.e. zinc nitrate hexahydrate (ZnN). The toxicity towards Aspergillus niger of pure and aqueous DESs was evaluated by observing the inhibition zone using an agar well diffusion assay, and the minimum inhibition concentration (MIC) using a broth dilution assay, respectively. The MIC values of the DESs varied from 1 to 650 mg mL À1 , whereas the inhibition zones changed according to the DES dose amount. Another test for acute toxicity was performed by evaluating the lethal concentration at 50% (LC 50 ) of the same DESs on Cyprinus carpio fish. The LC 50 of DESs ranged from practically harmless (e.g.ChCl : EG-DES aq ) to highly toxic (e.g. EAC : ZnCl 2 -DES aq ). The toxicity profile of the DESs depended on their concentration, type of individual components, and interaction with living organisms. Moreover, the DESs recorded higher toxicity compared to their individual components on fungi. However, lower toxicity was found for the DESs tested on Cyprinus carpio. Types I (organic salts and metal salt) and II (organic salt and hydrate metal salt) eutectics exhibited significantly higher toxicity than type III (organic salts and HBD). This was due to the presence of the innate toxicity of the metal salts. The biodegradability was appraised by a closed bottle test in which all the DESs were found to be readily biodegradable. To the best of our knowledge, there are no previous studies reported regarding the toxicity of cholinium-based DESs on freshwater fish or fungi and the biodegradability of EAC-based DESs. Therefore, this investigation can be used as a benchmark for future development of DESs. Table 1 Structures, names, and abbreviations of the individual components of the tested DESs Ammonium salts Hydrogen bond donors/metal salt/hydrate metal salt This journal is

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Section: Introductionmentioning

confidence: 99%

Evaluation of toxicity and biodegradability for cholinium-based deep eutectic solvents

2015

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“…[82] The same DES has been effectively used, in this case acting as solvent as well, in a one-pot transformation of aromatic-and ,-unsaturated aldehydes to amides through a Beckmann rearrangement, as well as in the hydrolysis of nitriles to amides (Scheme 19). [83] Concerning recyclability and reusability, the DES was recycled for five times but with a marked decrease in the product yield (98 to 82 %). Pillar[n]arenes are supramolecular macrocyclic hosts with important applications in supramolecular chemistry.…”

Section: Miscellaneous Reactionsmentioning

confidence: 99%

Deep Eutectic Solvents: The Organic Reaction Medium of the Century

et al. 2016

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This microreview summarizes the use of deep eutectic solvents (DES) and related melts in Organic Synthesis. This type of solvents combine the great advantages of other proposed environmentally benign alternative solvents, such as low toxicity, high availability, low inflammability, high recyclability, low volatility and low price, avoiding many disadvantages of these neoteric media. The fact that many of the components of the mixture come directly from Nature assures their biodegradability and renewability. The classification and distribution of the reactions in different sections along this microreview, as well as the emphasis paid to their scope, easily allows a general reader to understand the actual state of art, and the great opportunities opened, not only for academic proposes but also for industry.

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“…The metal-catalyzed rearrangement of aldoximes, a process closely related to the well-known Beckmann rearrangement of ketoximes (100,101), has emerged in recent years as an appealing tool for the generation of primary amides (102)(103)(104)(105). In this sense, Nagarkar and co-workers reported the synthesis of primary amides in the eutectic mixture 1ChCl/2ZnCl 2 , via in situ generation of the corresponding aldoxime intermediates (starting directly from aldehydes) and concomitant isomerization reaction of the aldoxime into the desired amide (see Scheme 5) (106). The authors proposed that coordination of the ZnCl 2 to the nitrogen atom of the aldoxime is one of the key steps in this isomerization reaction.…”

Section: Metal-catalyzed Isomerization Reactionsmentioning

confidence: 98%

Deep Eutectic Solvents: Environmentally Friendly Media for Metal-Catalyzed Organic Reactions

García‐Álvarez

2014

ACS Symposium Series

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Deep Eutectic Solvents (DESs), also known in the literature as Deep Eutectic Ionic Liquids (DEILs), Low Melting Mixtures (LMMs) or Low Transition Temperature Mixtures (LTTMs), are defined as combinations of two or three safe and inexpensive components which are able to establish hydrogen bond interactions with each other to form an eutectic mixture, that is a liquid at the desired temperature, with a melting point lower than that of the each individual component. Due to the advantages of DESs (i.e., low cost of components, easy to prepare, tuneable physicochemical properties, negligible vapour pressure, biorenewability and biodegradability) when compared with traditional ionic liquids (ILs), these eutectic mixtures have been used as Green and biorenewable solvents in different metal-catalyzed organic reactions like: i) dehydration of carbohydrates to 5-hydroxymethyl-furfural (HMF); ii) production of furfural (furan-2-carbaldehyde) from Xylose or Xylan; iii) cross-coupling reactions; iv) Click Chemistry processes; v) isomerization procedures; and vi) hydrogenation reactions.

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Choline chloride based eutectic solvent: an efficient and reusable solvent system for the synthesis of primary amides from aldehydes and from nitriles

Cited by 62 publications

References 53 publications

Evaluation of toxicity and biodegradability for cholinium-based deep eutectic solvents

Evaluation of toxicity and biodegradability for cholinium-based deep eutectic solvents

Deep Eutectic Solvents: The Organic Reaction Medium of the Century

Deep Eutectic Solvents: Environmentally Friendly Media for Metal-Catalyzed Organic Reactions

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