Some physico-chemical properties of ethanolamine ionic liquids: Behavior in different solvents

Simijonović, Dušica; Petrović, Zorica D.; Petrović, Vladimir P.

doi:10.1016/j.molliq.2012.12.020

Cited by 19 publications

(10 citation statements)

References 39 publications

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“…[93] In the case of the ion pair formed by the methylimidazolium cation and the dicyanamide anion, the PCM reveals free energies of solvation increasing in the series water, DMSO, and acetonitrile, and even more in solvents with lower dielectric constants. [94] Similarly, the binding energy of the EMI cation [95] as well as ethanolaminic cations [96] with several anions has been demonstrated to increase significantly in solvents with lower dielectric constants. For the ion pair composed by MMIM and the methylsulphate anion, PCM calculations in water and ethanol suggest ion pair separation.…”

Section: Quantum Mechanical Investigationsmentioning

confidence: 98%

Imidazolium Salt Ion Pairs in Solution

Stassen

Ludwig

Wulf

et al. 2015

Chemistry A European J

167

151

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The formation, stabilisation and reactivity of contact ion pairs of non-protic imidazolium ionic liquids (ILs) in solution are conceptualized in light of selected experimental evidence as well theoretical calculations reported mainly in the last ten years. Electric conductivity, NMR, ESI-MS and IR data as well as theoretical calculations support not only the formation of contact ion pairs in solution, but also the presence of larger ionic and neutral aggregates even when dissolved in solvents with relatively high dielectric constants, such as acetonitrile and DMSO. The presence of larger imidazolium supramolecular aggregates is favoured at higher salt concentrations in solvents of low dielectric constant for ILs that contain shorter N-alkyl side chains associated with anions of low coordination ability. The stability and reactivity of neutral contact species are also dependent on the nature of the anion, imidazolium substituents, and are more abundant in ILs containing strong coordinating anions, in particular those that can form charge transfer complexes with the imidazolium cation. Finally, some ILs display reactivities as contact ion pairs rather than solvent-separated ions.

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Section: Quantum Mechanical Investigationsmentioning

confidence: 98%

Imidazolium Salt Ion Pairs in Solution

Stassen

Ludwig

Wulf

et al. 2015

Chemistry A European J

167

151

View full text Add to dashboard Cite

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“…[HS] ILs were synthesized according to literature procedures. 26 In summary, alkyl amines and the corresponding acids were mixed in a stoichiometric molar ratio of 1:1. Before mixing, the amines were diluted with distilled water to approximately 75% v/v.…”

Section: Both [Teoh][oac] and [Tea]mentioning

confidence: 99%

“…To address the issue, a few low-cost protic ILs have been reported. 21,[23][24][25][26] These protic ILs can be prepared by simple mixing of lowcost bases (e.g., alkanolamines, alkylamines) and acids (e.g., acetic acid, sulfuric acid, phosphoric acid). It was demonstrated that a comparably high glucose yield and an even better thermal stability can be achieved.…”

Section: Introductionmentioning

confidence: 99%

Generation of ionic liquid tolerant Pseudomonas putida KT2440 strains via adaptive laboratory evolution

et al. 2020

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“…III is further transformed in the presence of the IL catalyst. In our recent study, ethanolamine based ILs were proved to behave as separated ions in polar solvents (Simijonović et al, 2013). Bearing in mind that the reaction was performed in ethanol as the reaction medium, the presence of triethanolammonium cations and chloroacetic anions in the reaction mixture can be expected.…”

Section: Resultsmentioning

confidence: 97%

“…Synthesis of the Mannich product 2-[1-(N-phenylamino)-1-(4-hydroxy-3-methoxyphenyl)]methylcyclohexanone (MB-H) was performed using [HTEA] [ClAc] as the catalyst (Simijonović et al, 2013). All components (aniline and vanillin (1 mmol), cyclohexanone (1.5 mmol), and ionic liquid as the catalyst (15 mol %)) were stirred in 1 mL of ethanol at room temperature for 24 h. The precipitated product was filtrated and washed with ethanol.…”

Section: Methodsmentioning

confidence: 99%

Formation of a vanillic Mannich base – theoretical study

et al. 2015

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One-pot anti-Mannich reaction of vanillin, aniline and cyclohexanone was successfully catalyzed by ionic liquid triethanolammonium chloroacetate, at room temperature. Yield of the obtained Mannich base was very good and excellent diastereoselectivity was achieved. Mechanism of the reaction was investigated using the density functional theory. The reaction started with a nucleophilic attack of aniline nitrogen at the carbonyl group of vanillin. The intermediate α-amino alcohol formed in this way was further subjected to protonation by the triethanolammonium ion yielding the imminium ion. Theoretically, the obtained imminium ion and the enol form of cyclohexanone can build the protonated Mannich base via the anti and syn pathways. The chloroacetic anion spontaneously abstracts the proton yielding the final product of the reaction anti 2-[1-(N-phenylamino)-1-(4-hydroxy-3-methoxyphenyl)]methylcyclohexanone (MB-H). The syn pathway requires lower activation energy but the anti pathway yields a thermodynamically more stable product, which implies that the examined Mannich reaction is thermodynamically controlled.

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Some physico-chemical properties of ethanolamine ionic liquids: Behavior in different solvents

Cited by 19 publications

References 39 publications

Imidazolium Salt Ion Pairs in Solution

Imidazolium Salt Ion Pairs in Solution

Generation of ionic liquid tolerant Pseudomonas putida KT2440 strains via adaptive laboratory evolution

Formation of a vanillic Mannich base – theoretical study

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