Design and synthesis of hydrophobic and chiral anions from amino acids as precursor for functional ionic liquids

Fukumoto, Ken-ichi; Ohno, Hiroyuki

doi:10.1039/b606613e

Cited by 140 publications

(78 citation statements)

References 25 publications

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“…[10] By measuring the solubility of these amino acid derived ILs in water, we found that a mixture of newly prepared IL and water exhibited unique phase behavior. The mixture showed phase separation with a lower critical solution temperature (LCST).…”

Section: Kenta Fukumoto and Hiroyuki Ohno*mentioning

confidence: 99%

“…[10] A tri-n-butyloctylphosphonium cation ([P 4448 ]) was also used as a more hydrophobic cation than [P 4444 [9a, 10] These phosphonium hydroxide aqueous solutions were mixed with a slightly smaller amount of trifluoromethanesulfonyl amino acid, and the ILs were extracted from the mixed solutions with chloroform. After evaporation, the product ( Figure 1) was dried in vacuo for at least 24 h at 80 8C.…”

Section: Kenta Fukumoto and Hiroyuki Ohno*mentioning

confidence: 99%

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LCST‐Type Phase Changes of a Mixture of Water and Ionic Liquids Derived from Amino Acids

2007

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Section: Kenta Fukumoto and Hiroyuki Ohno*mentioning

confidence: 99%

Section: Kenta Fukumoto and Hiroyuki Ohno*mentioning

confidence: 99%

LCST‐Type Phase Changes of a Mixture of Water and Ionic Liquids Derived from Amino Acids

2007

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“…The first example of an ionic liquid with a chiral anion was reported in 1999 by Seddons group in a study dealing with lactate ionic liquids. [33] Further ionic liquids with chiral anions were prepared later by the groups of Ohno, [34] Machado, [35] and Leitner, [36] derived from 19 natural amino acids, (S)-10-camphorsulfonate and (R)-1,10-bi-naphthylphosphate, and borate anions based on l-(À)-malic acid, respectively. Chiral cations are also accessible from the chiral pool.…”

Section: Introductionmentioning

confidence: 99%

Chirality Transfer in Imidazolium Camphorsulfonate Ionic Liquids through Ion Pairing Effects

et al. 2009

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The paper describes our studies on ion pair interactions in ionic liquids (IL) using an asymmetric hydrogenation reaction as probe. Three different ionic liquids carrying prochiral keto-functionalized cations were hydrogenated in the presence of their chiral, enantiomerically pure counter-ion using an achiral heterogeneous ruthenium catalyst. For the hydrogenation of N-(3'-oxobutyl)-N-methylimidazolium camphorsulfonate (2), N-(3'-oxobutyl)imidazolium camphorsulfonate (4) and N-(5'-oxohexyl)-Nmethylimidazolium camphorsulfonate (6) we found a strong dependency of the enantiomeric excess (ee in the cation) on the polarity of the solvent, the concentration of the IL and the structure of the IL. The highest ee values of up to 94% were found for the hydrogenation of 2 in ethanol. Interestingly, we observed that the ee (and consequently the strength of ion pair interaction) had a pronounced maximum for a certain concentration of the IL in the solvent depending on the nature of the solvent and on the substrate. Remarkably, the concentration leading to the maximum ee could be rationalized by independent determination of the degree of dissociation which was obtained by a combination of diffusion-ordered NMR spectroscopy and conductivity measurements.

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“…They have attracted much interest as novel solvents. [1][2][3][4][5][6][7][8][9][10][11][12][13][14] Some water-immiscible ILs can be used as extraction solvents for liquid-liquid extraction of metal cations. Unlike conventional extraction solvents such as hydrocarbons, ketones, ethers and alcohols, the ionic nature of ILs results in some unique properties, such as high polarity.…”

Section: Introductionmentioning

confidence: 99%

Extraction Behavior of Divalent Metal Cations in Ionic Liquid Chelate Extraction Systems Using 1-Alkyl-3-methylimidazolium Bis(trifluoromethanesulfonyl)imides and Thenoyltrifluoroacetone

2008

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The extraction behavior of several divalent metal cations (M 2+ ) in ionic liquid chelate extraction systems was investigated using several 1-alkyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide ionic liquids ([Rmim][Tf2N]) as extraction solvent and thenoyltrifluoroacetone (Htta) as extractant. The behavior was compared with that using less hydrophobic 1-alkyl-3-methylimidazolium hexafluorophosphates ([Rmim][PF6]). The extracted species in the [Rmim][Tf2N] systems were neutral M(tta)2 for M = Cu and anionic M(tta)3 -for M = Mn, Co, Ni, Zn and Cd. Conversion of ionic liquid anion from PF6 -to more hydrophobic Tf2N -resulted in changing the species extracted for Ni 2+ from hydrated neutral complex to hydrophobic anionic one. Furthermore, the extractability for these metals was governed by the hydrophobicity of ionic liquid ions. Thus, in the ionic liquid chelate extraction system, selection of a suitable ionic liquid as extraction phase seems to be an important factor for enhancement of extraction selectivity.

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Design and synthesis of hydrophobic and chiral anions from amino acids as precursor for functional ionic liquids

Abstract: Hydrophobic ionic liquids composed of tetrabutylphosphonium cation and chiral anions derived from amino acids modified with trifluoromethane sulfonyl groups have been synthesized using a simple method.

Cited by 140 publications

References 25 publications

LCST‐Type Phase Changes of a Mixture of Water and Ionic Liquids Derived from Amino Acids

LCST‐Type Phase Changes of a Mixture of Water and Ionic Liquids Derived from Amino Acids

Chirality Transfer in Imidazolium Camphorsulfonate Ionic Liquids through Ion Pairing Effects

Extraction Behavior of Divalent Metal Cations in Ionic Liquid Chelate Extraction Systems Using 1-Alkyl-3-methylimidazolium Bis(trifluoromethanesulfonyl)imides and Thenoyltrifluoroacetone

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