Electrospray Ionization Mass Spectrometry Investigation of BTBP – Lanthanide(III) and Actinide(III) Complexes

Retegan, Teodora; Berthon, Laurence; Ekberg, Christian; Fermvik, Anna; Skarnemark, Gunnar; Zorz, Nicole

doi:10.1080/07366290903113991

Cited by 55 publications

(69 citation statements)

References 32 publications

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“…A modified Reissert-Henze reaction 17 of 4 with trimethylsilyl cyanide and N,N-dimethylcarbamyl chloride afforded the nitrile 6 18 in high yield (CAUTION: trimethylsilyl cyanide is a volatile hydrogen cyanide equivalent). 30 The reaction of 6 with hydrazine hydrate gave the carbohydrazonamide 7 19 which, on treatment with 3,3,6,6-tetramethylcyclohexane-1,2-dione 8 20,21 in THF/Et 3 N at reflux furnished the ligand 2 in 93% yield (see Supporting Information for the synthesis of compounds 4-7). The X-ray crystal structure of 2 is shown in Figure 2 together with the atomic numbering scheme.…”

Section: Synthesis and X-ray Crystallographymentioning

confidence: 99%

“…In the partitioning and transmutation (P&T) strategy, 1 it is intended that, following their separation from the trivalent lanthanides, the trivalent minor 30 actinides Am(III) and Cm(III) will be converted into shorter-lived or stable elements by neutron bombardment. Since many lanthanides have high neutron capture cross sections, efficient transmutation of the actinides is only possible once they have first been separated (partitioned) from the lanthanides.…”

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confidence: 99%

“…Once again the species distribution curve showed asymptotic behavior (see Figure 28 in the Supporting Information), suggesting incomplete complexation at the beginning of the titration. It is interesting to note that both 2 and CyMe 4 -BTTP 9, two ligands that share similar extraction structures of Yb(III) complexes can be determined unambiguously by an analysis of the paramagnetic shifts that it induces (which are essentially dipolar in nature), 32 this can only be applied to symmetrical complexes such as those formed by CyMe 4 -BTTP 9 27 or a related phenanthroline based bis-triazine 30 ligand. 10 Such an analysis on the Yb(III) complex of 2 is therefore not possible.…”

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confidence: 99%

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Complexation of lanthanides, actinides and transition metal cations with a 6-(1,2,4-triazin-3-yl)-2,2′:6′,2′′-terpyridine ligand: implications for actinide(iii)/lanthanide(iii) partitioning

et al. 2012

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The quadridentate N-heterocyclic ligand 6- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-1,2,4-benzotriazin-3-yl)-2,2′ : 6′,2′′-terpyridine (CyMe 4 -hemi-BTBP) has been synthesized and its interactions with Am(III), U(VI), Ln(III) and some transition metal cations have been evaluated by X-ray crystallographic analysis, Am(III)/Eu(III) solvent extraction experiments, UV absorption spectrophotometry, NMR studies and ESI-MS. Structures of 1 : 1 complexes with Eu(III), Ce(III) and the linear uranyl (UO 2 2+ ) ion were obtained by X-ray crystallographic analysis, and they showed similar coordination behavior to related BTBP complexes. In methanol, the stability constants of the Ln(III) complexes are slightly lower than those of the analogous quadridentate bis-triazine BTBP ligands, while the stability constant for the Yb(III) complex is higher. 1 H NMR titrations and ESI-MS with lanthanide nitrates showed that the ligand forms only 1 : 1 complexes with Eu(III), Ce(III) and Yb(III), while both 1 : 1 and 1 : 2 complexes were formed with La(III) and Y(III) in acetonitrile. A mixture of isomeric chiral 2 : 2 helical complexes was formed with Cu(I), with a slight preference (1.4 : 1) for a single directional isomer. In contrast, a 1 : 1 complex was observed with the larger Ag(I) ion. The ligand was unable to extract Am(III) or Eu(III) from nitric acid solutions into 1-octanol, except in the presence of a synergist at low acidity. The results show that the presence of two outer 1,2,4-triazine rings is required for the efficient extraction and separation of An(III) from Ln(III) by quadridentate N-donor ligands. † Electronic supplementary information (ESI) available: Procedures and characterization data for known compounds, Mercury plot of ligand 2 and its Eu, Ce and U complexes, NMR stack plots and species distribution curves, enlargements of mass peaks for La(III), Eu(III), Cu(I) and Ag(I) complexes of 2. CCDC 869233-869236. For ESI and crystallographic data in CIF or other electronic format see

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Section: Synthesis and X-ray Crystallographymentioning

confidence: 99%

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confidence: 99%

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confidence: 99%

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Complexation of lanthanides, actinides and transition metal cations with a 6-(1,2,4-triazin-3-yl)-2,2′:6′,2′′-terpyridine ligand: implications for actinide(iii)/lanthanide(iii) partitioning

et al. 2012

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“…High selectivity of actinides/lanthanides separation has been achieved when polynitrogen extractants were employed. [1][2][3][4][5][6][7][8][9] However, in spite of very high separation factors for americium/europium separation, some ligands proposed so far have demonstrated some disadvantages (e. g., low chemical stability, slow kinetics, and limited solubility in diluents).…”

Section: Introductionmentioning

confidence: 99%

N,N,N’,N’-Tetrabutyl-1,10-phenanthroline- 2,9-dicarboxamide as Very Effective Extraction Agent for Trivalent Europium and Americium

Makrlík

Vaňura

Selucký

et al. 2017

ACSi

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Solvent extraction of microamounts of Eu 3+ and Am 3+ from water into nitrobenzene by means of a mixture of hydrogen dicarbollylcobaltate (H + B -) and N,N,N',N'-tetrabutyl-1,10-phenanthroline-2,9-dicarboxamide (L) N,N,N',N'-tetrabutyl-1,10-phenanthroline-2,9-dicarboxamide) are extracted into the nitrobenzene phase. Extraction and stability constants of the cationic complex species in nitrobenzene saturated with water were determined and discussed. From the experimental results it is evident that this effective N,N,N',N'-tetrabutyl-1,10-phenanthroline-2,9-dicarboxamide receptor for the Eu 3+ and Am 3+ cations could be considered as a potential extraction agent for nuclear waste treatment.

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“…Another difference between the two extractants is that C5-BTBP is not stable under highly acidic conditions, due to -hydrogen abstraction from the side chains, which makes it less suitable for use in a highly acidic GANEX extraction step [27].…”

Section: Btbp Ligandsmentioning

confidence: 99%

Development of the Chalmers Grouped Actinide Extraction Process

et al. 2015

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Abstract. Several solvents for Grouped ActiNide EXtraction (GANEX) processes have been investigated at Chalmers University of Technology in recent years. Four different GANEX solvents; cyclo-GANEX (CyMe 4 --BTBP, 30 vol.% tri-butyl phosphate (TBP) and cyclohexanone), DEHBA-GANEX (CyMe 4 -BTBP, 20 vol.% N,N-di-2(ethylhexyl) butyramide (DEHBA) and cyclohexanone), hexanol-GANEX (CyMe 4 -BTBP, 30 vol.% TBP and hexanol) and FS-13-GANEX (CyMe 4 -BTBP, 30 vol.% TBP and phenyl trifl uoromethyl sulfone (FS-13)) have been studied and the results are discussed and compared in this work. The cyclohexanone based solvents show fast and high extraction of the actinides but a somewhat poor diluent stability in contact with the acidic aqueous phase. FS-13-GANEX display high separation factors between the actinides and lanthanides and a good radiolytic and hydrolytic stability. However, the distribution ratios of the actinides are lower, compared to the cyclohexanone based solvents. The hexanol-GANEX is a cheap solvent system using a rather stable diluent but the actinide extraction is, however, comparatively low.

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Electrospray Ionization Mass Spectrometry Investigation of BTBP – Lanthanide(III) and Actinide(III) Complexes

Cited by 55 publications

References 32 publications

Complexation of lanthanides, actinides and transition metal cations with a 6-(1,2,4-triazin-3-yl)-2,2′:6′,2′′-terpyridine ligand: implications for actinide(iii)/lanthanide(iii) partitioning

Complexation of lanthanides, actinides and transition metal cations with a 6-(1,2,4-triazin-3-yl)-2,2′:6′,2′′-terpyridine ligand: implications for actinide(iii)/lanthanide(iii) partitioning

N,N,N’,N’-Tetrabutyl-1,10-phenanthroline- 2,9-dicarboxamide as Very Effective Extraction Agent for Trivalent Europium and Americium

Development of the Chalmers Grouped Actinide Extraction Process

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