Room temperature deep eutectic solvents of (1S)-(+)-10-camphorsulfonic acid and sulfobetaines: hydrogen bond-based mixtures with low ionicity and structure-dependent toxicity

Cardellini, Fabio; Germani, Raimondo; Cardinali, Gianluigi; Corte, Laura Della; Roscini, Luca; Spreti, Nicoletta; Tiecco, Marcello

doi:10.1039/c5ra03932k

Cited by 67 publications

(49 citation statements)

References 114 publications

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“…Among them, the DES prepared from N-cyclohexyl-N,N-dimethyl-3-ammonio-1-propanesulfonate and the sulfonic acid (3:2 molar ratio) was effective as catalytic reaction medium in the aldol condensation of benzaldehyde and acetophenone giving chalcone in 70% yield. [62] …”

Section: Scheme 10 Synthesis Of Imidazole Derivativesmentioning

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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Section: Scheme 10 Synthesis Of Imidazole Derivativesmentioning

confidence: 99%

Deep Eutectic Solvents: The Organic Reaction Medium of the Century

et al. 2016

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“…We tried the reaction in six DESs characterized by the presence of different acidic partner: glycolic acid (p K a = 3.8)/trimethylglycine ( Gly/TMG ); 15b (+)‐mandelic acid (p K a = 3.9)/trimethylglycine ( Man/TMG ); 15b benzoic acid (p K a = 4.2)/trimethylglycine ( Benz/TMG ); 15b 2‐chlorobenzoic acid(p K a = 2.9)/trimethylglycine ( 2‐Cl‐Benz/TMG ); 15b phenylacetic acid (p K a = 4.3)/octadecyldimethylamine N ‐oxide ( PhAA/AO‐18 ); 15c p ‐toluensulfonic acid (p K a = –1.3) monohydrate/benzyl‐trimethylammonium mesylate ( PTSA/BTMAMes ). [16b] Based on our previous findings, the reactions were performed in the presence of a catalytic amount of silver triflate (1 mol‐%) and by heating the reaction mixture at 60 °C by traditional conductive heat transfer (Table , entries 1–6). The progress of the reactions was monitored by TLC analysis.…”

Section: Resultsmentioning

confidence: 99%

“…However, with respect to ILs, DESs are less expensive, more biodegradable, and less‐or‐non toxic . DESs are typically prepared by blending quaternary onium salts (ammonium or phosphonium) with hydroxylated compounds able to act as hydrogen bonds donors, such as alcohols, phenols, polyols, carbohydrates, but also carboxylic acids and sulfonic acids . The strong interaction between the hydrogen‐bond donor and the hydrogen‐bond acceptor, namely the anion of the quaternary salt, is responsible for the reduction of the melting point of the eutectic mixture .…”

Section: Introductionmentioning

confidence: 99%

p‐TSA‐Based DESs as “Active Green Solvents” for Microwave Enhanced Cyclization of 2‐Alkynyl‐(hetero)‐arylcarboxylates: an Alternative Access to 6‐Substituted 3,4‐Fused 2‐Pyranones

et al. 2019

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In this paper, we describe the use of p‐TSA based Deep Eutectic Solvents (DESs) as alternative environmental‐friendly “active” solvents for the microwave‐mediated synthesis of 6‐substituted 3,4‐fused 2‐pyranones, and in particular isocoumarins, starting from 2‐alkynyl‐(hetero)arylcarboxylates. When the alkyne terminus bears a neutral or an electron‐donating group (EDG), the reactions are fast, clean and highly regioselective, to give the 6‐endo‐dig cyclization products in good to excellent yields. For substrates bearing an electron‐withdrawing group (EWG) on the alkyne end, the regioselectivity can be tuned by adding a small amount of silver(I) triflate as co‐catalyst. DES was demonstrated to be reusable without loss of efficiency in terms of reaction yields. Based on experimental evidence and previous findings, two competitive mechanisms working simultaneously are proposed to explain the outcomes and the regioselectivity issues.

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“…CB1‐12 was synthesized by a literature procedure . Sulfobetaine compounds were prepared by reaction of tertiary amines with propane or butane sultone following published procedures …”

Section: Experimental Chemoinformatics and Materialsmentioning

confidence: 99%

“…23 Sulfobetaine compounds were prepared by reaction of tertiary amines with propane or butane sultone following published procedures. 24,25 All obtained products were dried in vacuo over P 2 O 5 before use. Compound structure and their purity were verified by 1 H-NMR.…”

Section: Chemical Productsmentioning

confidence: 99%

Chemoinformatic design of amphiphilic molecules for methane hydrate inhibition

Profio

Canale

Marvulli

et al. 2018

Journal of Chemometrics

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Cationic surfactants and other low molecular weight compounds are known to inhibit nucleation and agglomeration of methane hydrates. In particular, tetralkylammonium salts are kinetic hydrate inhibitors; ie, they reduce the rate of hydrate formation. This work relates to the in‐silico determination of structural features of molecules modulating methane hydrate formation, as found experimentally, and the prediction of novel structures to be tested as candidate inhibitors. Experimental data for each molecule are the amount of absorbed methane. By inserting these numerical values into a chemoinformatic model, it was possible to find a mutual correlation between structural features and inhibition properties. A maximum amount of information is extracted from the structural features and experimental variables, and a model is generated to explain the relationship therebetween. Chemometric analysis was performed by using the software package Volsurf+ with the aim of finding a primary correlation between surfactant structures and their properties. Experimental parameters (pressure, temperature, and concentration) were further processed through an optimization procedure. A careful study of the chemometric analysis responses and the numerical descriptors of tested surfactants allowed to define the features of a good inhibitor, as far as the amount of absorbed gas is concerned. An external prediction is finally made to project external compounds, whose structures and critical micellar concentration are known, in a statistical model, to predict the inhibition properties of a particular molecule in advance of synthesis and testing. This method allowed to find novel amphiphilic molecules for testing as candidate inhibitors in flow‐assurance.

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Room temperature deep eutectic solvents of (1S)-(+)-10-camphorsulfonic acid and sulfobetaines: hydrogen bond-based mixtures with low ionicity and structure-dependent toxicity

Abstract: Preparation, properties and toxicity of room temperature deep eutectic solvents formed by (1S)-(+)-10-camphorsulfonic acid and aromatic, aliphatic and amphiphilic sulfobetaines.

Cited by 67 publications

References 114 publications

Deep Eutectic Solvents: The Organic Reaction Medium of the Century

Deep Eutectic Solvents: The Organic Reaction Medium of the Century

p‐TSA‐Based DESs as “Active Green Solvents” for Microwave Enhanced Cyclization of 2‐Alkynyl‐(hetero)‐arylcarboxylates: an Alternative Access to 6‐Substituted 3,4‐Fused 2‐Pyranones

Chemoinformatic design of amphiphilic molecules for methane hydrate inhibition

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