Preparation of Diglycolamides via Schotten–Baumann Approach and Direct Amidation of Esters

Leoncini, Andrea; Huskens, Jurriaan; Verboom, Willem

doi:10.1055/s-0035-1561495

Cited by 23 publications

(12 citation statements)

References 4 publications

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“…TEDGA was synthesized according to the literature. [11] TRLFS experiments were performed at 298 K with a Nd : YAG (Surelite II laser, Continuum) pumped dye laser system (NarrowScan D-R; Radiant Dyes Laser Accessories GmbH). A wavelength of 396.6 nm (Cm(III)) was used to excite the metal ions.…”

Section: Methodsmentioning

confidence: 99%

Spectroscopic Study on the Complexation of trivalent Actinide and Lanthanide ions with TEDGA in Solution

Sittel,

Meißner,

Keller

et al. 2024

Eur J Inorg Chem

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NMR spectroscopy studies on the complexation of La(III), Sm(III), Lu(III), Y(III) and Am(III) with N,N,N’,N’‐tetraethyldiglycolamide (TEDGA) have been performed. Initial studies concerning the stoichiometry of the complexes prove the formation of [M(TEDGA)3]3+ in D2O and [M(TEDGA)1‐3]3+ in CD3CN. Decreasing the solvent polarity translates to an increase of the complex stability as shown by complementary TRLFS studies with Cm(III). Due to delocalization of the lone electron pair of the amide nitrogen atom, the M(III)‐O interaction has been studied indirectly by collecting 13C and 15N NMR data. The observed chemical shifts prove that the interaction of the trivalent ions, An(III) and Ln(III), and TEDGA is almost identical.

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Section: Methodsmentioning

confidence: 99%

Spectroscopic Study on the Complexation of trivalent Actinide and Lanthanide ions with TEDGA in Solution

Sittel,

Meißner,

Keller

et al. 2024

Eur J Inorg Chem

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“…To prepare a DGE ligand containing an aromatic substituent (see cationic ligands in Figure ), 2,5-furandicarboxylic acid (20 mmol) was transferred into a 250 mL RBF along with an excess (200 mmol) of thionyl chloride (SOCl 2 ). Five drops of N , N -dimethylformamide ( N , N -DMF) were added to the flask, and its contents were then refluxed at 50 °C for 24 h until a homogeneous clear solution was obtained . Excess SOCl 2 was removed under reduced pressure using a rotary evaporator, and the resulting furan-2,5-dicarbonyl dichloride was reacted with 1-octanol using the same procedure outlined for diglycolyl chloride.…”

Section: Methodsmentioning

confidence: 99%

“…Five drops of N,N-dimethylformamide (N,N-DMF) were added to the flask, and its contents were then refluxed at 50 °C for 24 h until a homogeneous clear solution was obtained. 39 Excess SOCl 2 was removed under reduced pressure using a rotary evaporator, and the resulting furan-2,5-dicarbonyl dichloride was reacted with 1-octanol using the same procedure outlined for diglycolyl chloride. The following DGE ligands were prepared and characterized using 13 C and 1 H NMR (spectra are provided in the Supporting Information):…”

Section: Preparation and Characterization Of Cationic Ligandsmentioning

confidence: 99%

Ultra-Low Viscosity and High Magnetic Susceptibility Magnetic Ionic Liquids Featuring Functionalized Diglycolic Acid Ester Rare-Earth and Transition Metal Chelates

et al. 2023

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Magnetic ionic liquids (MILs) comprise a subcategory of ionic liquids (ILs) and contain a paramagnetic metal center allowing them to be readily manipulated by an external magnetic field. While MILs are popularly employed as solvents in catalysis, separations, and organic synthesis, most low viscosity combinations possess a hydrophilic character that limits their use in aqueous matrices. To date, no study has reported the synthesis and characterization of hydrophobic MILs with viscosities similar to those of hydrophilic MILs and organic solvents while simultaneously exhibiting enhanced magnetic and thermal properties. In this study, diglycolic acid esters are employed as ligands to chelate with paramagnetic metals to produce cations that are paired with metal chelates composed of hexafluoroacetylacetonate ligands to form MILs incorporating multiple metal centers in the cation and anion. Viscosity values below 31.6 cP were obtained for these solvents, the lowest ever reported for hydrophobic MILs. Solubilities in nonpolar solvents such as benzene were observed to be as high as 50% (w/v) MIL-to-solvent ratio while being insoluble in water at concentrations as low as 0.01% (w/v). Effective paramagnetic moment values for these solvents ranged from 5.33 to 15.56 Bohr magnetons (μB), with mixed metal MILs containing multiple lanthanides in the anion generally offering higher magnetic susceptibilities. MILs composed of ligands containing octyl substituents were found to possess thermal stabilities up to 190 °C. The synthetic strategies explored in this study exploit the highly tunable nature of the employed cation and anion pairs to design versatile ultra-low viscosity magnetoactive solvents that possess tremendous potential and applicability in liquid–liquid separation systems, catalysis, and microfluidics where the mechanical movement of the solvent can be easily facilitated using electromagnets.

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“…The extractants, TODGA and PTD, were synthesized by authors of this work (at Twente and Parma, respectively). , The extractant CyMe 4 -BTBP and the complexing agent SO 3 -Ph-BTP were synthesized by Karlsruhe Institute for Technology (KIT). The SO 3 -Ph-BTP was provided and used as the tetra-sodium salt.…”

Section: Methodsmentioning

confidence: 99%

Liquid/Liquid Extraction Kinetics of Eu(III) and Am(III) by Extractants Designed for the Industrial Reprocessing of Nuclear Wastes

Simonin

Rollet

et al. 2020

Ind. Eng. Chem. Res.

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Results about the kinetics of extraction of Eu(III) and Am(III) by extractants designed for the industrial reprocessing of nuclear wastes are reported. They were obtained using the rotating membrane cell technique (RMC). Extraction and stripping kinetic rate constants were determined for various compositions of the aqueous and organic phases. The transfer was studied at liquid/liquid interfaces between an aqueous nitric acid solution and an organic solvent containing the diglycolamide extractant molecule TODGA, or a mixture of the bipyridine molecule CyMe 4 BTBP with TODGA (the latter being used as a phase-transfer catalyst), dissolved in an aliphatic diluent. In some experiments, an aqueous ligand (a sulfonated bis triazinyl pyridine, SO 3-Ph-BTP, 1 or a PyTri-diol) was added to the aqueous phase as a stripping agent. The diffusion coefficients of Eu(III) and Am(III), that are key in the analysis of the kinetic data, were measured using the RMC and the closed capillary technique. Whenever possible, mechanisms are proposed to interpret the experimental results.

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Preparation of Diglycolamides via Schotten–Baumann Approach and Direct Amidation of Esters

Cited by 23 publications

References 4 publications

Spectroscopic Study on the Complexation of trivalent Actinide and Lanthanide ions with TEDGA in Solution

Spectroscopic Study on the Complexation of trivalent Actinide and Lanthanide ions with TEDGA in Solution

Ultra-Low Viscosity and High Magnetic Susceptibility Magnetic Ionic Liquids Featuring Functionalized Diglycolic Acid Ester Rare-Earth and Transition Metal Chelates

Liquid/Liquid Extraction Kinetics of Eu(III) and Am(III) by Extractants Designed for the Industrial Reprocessing of Nuclear Wastes

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