Complex structure of An and Ln complexes with modified diglycolamides in solution and solid state using different analytical techniques
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1 First SACSESS International Workshop, Warsaw, Poland, April 2015 Complex structure of An and Ln complexes with modified diglycolamides in solution and solid state using different analytical techniques Andreas Wilden 1, G. Modolo 1, S. Lange 1, F. Sadowski 1, D. Kardhashi 1, Y. Li 1, P. Kowalsi 1, B. Beele 2,3, A. Skerencak-Frech 2, P. Panak 2,3, A. Geist 2, J. Rothe 2, K. Dardenne 2, S. Schäfer 4, A. T. Wagner 4, P. W. Roesky 4, W. Verboom 5 1 Forschungszentrum Jülich GmbH (FZJ), Institut für Energie- und Klimaforschung Nukleare Entsorgung und Reaktorsicherheit (IEK-6), Jülich, Germany 2 Karlsruher Institut für Technologie (KIT), Institut für Nukleare Entsorgung (INE), Karlsruhe, Germany 3 Ruprecht-Karls-Universität Heidelberg, Physikalisch Chemisches Institut (PCI), Heidelberg, Germany 4 Karlsruher Institut für Technologie, Institut für Anorganische Chemie, Karlsruhe, Germany 5 University of Twente, MESA+ Institute for Nanotechnology, P.O. Box 217, 7500 AE Enschede, The Netherlands Page 1
2 An(III) recovery: the multistep strategy Heterogeneous Recycling of MA PUREX HAR An(III) + Ln(III) co-extraction An(III)/Ln(III) separation Am Cm used nuclear fuel Highly Acidic: 3-4 mol/l HNO 3 U Pu Very Radioactive: (FP: Bq/L) Rather large volumes : 6 to 7 m 3 / t HMi Contains 100% of the MA and 80% of FP Large inventory of elements (>40) in different concentrations An(III) behave like Ln(III) Np FP 1 2 H He High Active Raffinate (HAR) Li Be B C N O F Ne Na Mg Al Si P S Cl Ar K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr Rb Sr Y Zr Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te I Xe Cs Ba Ln Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Po At Rn Fr Ra An Rf Db Sg Bh Hs Mt Uun Lanthanides La Ce Pr Nd Pm Sm Eu Gd Tb Dy Ho Er Tm Yb Lu Actinides Ac Th Pa U Np Pu Am Cm Bk Cf Es Fm Md No Lr Major Actinides Fission products Ln Minor Actinides (MA) Activation products Page 2
3 Introduction - Diglycolamides High affinity for An(III)/Ln(III) High distribution ratios of An(III)/Ln(III) at process relevant HNO 3 concentrations Easy/Cheap synthesis with various possible modifications CHON Good hydrolytic/radiolytic stability Several process demonstrations, e.g. TODGA/TBP (Jülich (spiked) and ITU, Karlsruhe (genuine fuel)) Modolo, G. et a. Solvent Extr. Ion Exch. 2008, 26 (1), Magnusson, D. et al. Solvent Extr. Ion Exch. 2009, 27 (1), SANEX-TODGA (CEA, France) Hérès, X. et al. Proceedings of GLOBAL 2009, Paris, France, T2EHDGA (India) Gujar, R.B. et al. Solvent Extr. Ion Exch. 2010, 28 (6), Stephan, H. et al. Solvent Extr. Ion Exch. 1991, 9 (3), and Page 3
4 Diglycolamides - Solubility DGA Solubility in H 2 O (mmol/l) Solubility in n-dodecane TPDGA 57 Very poor TBDGA 2.3 Poor TADGA 0.27 Soluble 100 THDGA 0.11 Soluble 40 TODGA Freely soluble 30 TDDGA Freely soluble 18 TdDDGA Freely soluble 11 c (M) org D c aq (M) D Am by 0.1 M DGA (1 M HNO 3 ) Sasaki, Y. et al. Solvent Extr. Ion Exch. 2001, 19 (1), Page 4
5 Diglycolamides - Derivatisation A lot of effort was drawn to vary R 1 -R 4 [1] Effect on solubility Branching improves 3 rd phase formation boundaries Higher loading of the solvent Selectivity Effect of substituents R 5 /R 6 was not studied yet! Synthesis of derivatives within the ACSEPT project [2-3] [1] Ansari, S.A. et al. Chem. Rev. 2012, 112 (3), pp [2] Iqbal, M. et al. Supramol. Chem. 2010, 22 (11), pp [3] Wilden, A. et al. Solvent Extr. Ion Exch. 2014, 32 (2), pp Page 5
6 Synthesis TODGA R 5 /R 6 derivatized TODGA Iqbal, M. et al. Supramol. Chem. 2010, 22 (11), pp Page 6
7 Solvent Extraction Distribution ratios decrease with introduction of additional Me groups reduced Sr co-extraction Org. 0.1 mol/l ligand in TPH Aq. var. HNO 3 concentrations, 10-4 M Sr, Am, 152 Eu tracer, 15 min., 22 C Page 7
8 Extraction of Ln(III) D-ratios strongly depend on degree of substitution Heavier Ln are better extracted Maximum in Ln-series shifts (Lu Er Dy) Page 8
9 Extraction mechanism: slope analysis Solvating mechanism is assumed K M nno ml ex M NO L n aq 3,aq org 3 n m,org logd m log L n log NO logk At constant nitrate concentrations linear relationship Slopes ~3 observed org 3,aq ex Am/Eu slopes not parallel for Me 2 -TODGA Org. var. ligand concentrations in TPH Aq. 3.1 mol/l HNO 3, 241 Am, 152 Eu tracer, 15 min., 22 C log (distribution ratio D) K y = x y = x y = x y = x y = x y = x log (ligand concentration [mol/l]) MNO 3 n m,org ex n n m M aq NO3,aq Lorg L MNO 3 L n D n M aq m org Am TODGA Am Me- TODGA Am Me2- TODGA Eu TODGA Eu Me- TODGA Eu Me2- TODGA Page 9
10 Additional insight into the complexation by TRLFS investigations Time Resolved Laser induced Fluorescence Spectroscopy Cm(III) and Eu(III) fluorescence is measured after excitation using monochromatic laser light Complexation of the metal ions with different ligands changes the fluorescence emission spectrum Single phase titration experiments in EtOH and extraction experiments into kerosene solution of ligand to confirm single phase data normalized intensity Cm a) + TODGA [TODGA] mol/l E-7 4.0E-7 8.8E-7 1.5E-6 2.3E-6 3.6E-6 5.4E-6 8.1E-6 1.2E-5 1.6E-5 2.3E-5 6.0E-5 a) 1,0 0,8 0,6 0,4 0,2 0,0 fit solv fit species 1 fit species 2 Solv Species 1 Species [nm] [TODGA] Page 10
11 TRLFS slope analysis 100 species 1 / Cm(solv)9 species 2 / species species 1 / Eu(solv)9 species 2 / species species ratio species ratio 1 0,1 0,1 1E-5 1E-4 Me 2 -TODGA [M] 0,01 1E -7 1E -6 1E- 5 Me 2 -TODGA [M] Species 1 identified as the 1:1 metal:ligand complex Species 2 identified as the 1:3 metal:ligand complex Same results for TODGA and Me-TODGA Page 11
12 Evaluation of Me-substituted Diglycolamides TRLFS confirmed threefold complexation Same trend in stability constants a) 1,0 0,8 0,6 0,4 0,2 fit solv fit species 1 fit species 2 Solv Species 1 Species 2 Same trends in SF Lifetime measurements suggest 0-1 H 2 O in the inner coordination shell log β 3 M = Cm log β 3 M = Eu M(III)-TODGA ± ± 0.22 b) 0,0 1,0 0,8 0,6 0,4 0,2 0, [TODGA] fit solv fit species 1 fit species 2 Solv Species 1 Species 2 M(III)-Me-TODGA ± ± [Me-TODGA] M(III)-Me 2 -TODGA ± ± 0.24 SF Eu/Am SF Eu/Cm solvent extraction TRLFS TODGA Me-TODGA c) 1,0 0,8 0,6 0,4 0,2 0,0 fit solv fit species 1 fit species 2 Solv Species 1 Species 2 Me 2 -TODGA [Me 2 -TODGA] Page 12
13 2-phase extraction experiments Comparison to 1-phase experiments a) extraction from 1.0 M nitric acid extraction from 2.0 M nitric acid extraction from 3.0 M nitric acid 1:3 complex species from titration experiment b) extraction from 1.0 M nitric acid extraction from 2.0 M nitric acid extraction from 3.0 M nitric acid 1:3 complex species from titration experiment normalized intensity Cm(III) normalized intensity Eu(III) [nm] [nm] In 2-phase extraction experiments, only the 1:3 complexes were observed Fluorescence lifetimes similar to single phase experiments Page 13
14 Synthesis of single crystals Use of short-chained analogues of Me-TODGA and Me 2 -TODGA (as lipophilic ligands don t yield crystals) Crystallisation experiments of Ln-complexes with these ligands X-ray single crystal structure analysis Crystal structures reported for La, Pr, Nd, Sm, Eu, and Gd with TEDGA: Kawasaki, T. et al. Bull. Chem. Soc. Japan 2014, 87 (2), pp Page 14
15 Obtained crystal structures TMDGA TEDGA La Sm Eu La Sm Eu Yb Crystals with methylated derivatives were grown but not measured, yet. Page 15
16 Single crystal structure analysis Trends visible in Ln-O bond lengths TMDGA Intra-ligand bond lengths constant O Carbonyl -Ln-O Carbonyl angle decreases with increasing r(ln) Isostructural to [Pu IV (TMDGA) 3 ] [1] and [Ln(TEDGA) 3 ] [2] crystal structures reported for La, Pr, Nd, Sm, Eu, and Gd [1] Reilly S. D. et al. Chem. Comm. 2012, 48 (78), pp [2] Kawasaki, T. et al. Bull. Chem. Soc. Japan 2014, 87 (2), pp Bond length / Å Bond length / Å r(ln) CN9 from lit. / Å r(ln) CN9 from lit. / Å Ln-OEther Ln-OCarbonyl OEther-CEther OCarbony-CCarbonyl CEther-CCarbonyl TEDGA Ln-OEther Ln-OCarbonyl OEther-CEther OCarbony-CCarbonyl CEther-CCarbonyl Page 16
17 XAFS measurements XANES/EXAFS ANKA synchrotron, Karlsruhe Real life samples of 243 Am, 239 Pu(IV), La, Eu, Yb were prepared by extraction from nitric acid 0.1 mol/l ligand in kerosene Phase separation and measurement of the organic phase Some samples have not been measured, yet Org-. metal concentration resembled by edge jump TODGA > Me-TODGA > Me 2 -TODGA M-(Me 2 -TODGA) intensities partly very low Page 17
18 EXAFS of Eu-TODGA complex Single crystal data of [Eu(TEDGA) 3 ] complex was used as the structure model Best fit using 6 O at 2.40 Å (carbonyl) 3 O at 2.50 Å (ether) 6 C at 3.26 Å (C ) 6 C at 3.47 Å (C ) [6 N at 4.7 Å] Primary k 3 χ(k) Eu EXAFS data and fit Eu R N C R O C O C C Consistent with reported EXAFS data on a solid complex of [Eu(TODGA) 3 ][BiCl 4 ] 3 [1] O N R R 3 Fourier transform of the k 3 χ(k) Eu EXAFS data and fit [1] Antonio M.R. et al. Dalton Trans. 2012, 44 (2), pp Page 18
19 Ab-initio DFT-based computational study TMDGA with shortest length of amide groups was used Formation La 3+ Eu 3+ Am 3+ energies [kj/mol] PBE PBE+U TMDGA Me-TMDGA Me 2 -TMDGA Trends observed in solvent extraction experiments are reproduced! Page 19
20 Conclusions and Outlook Methylated TODGA derivatives show very promising properties towards process development D Sr <1, but D An/Ln >1 at high nitric acid concentrations Fast kinetics Stripping may be improved Extraction mechanism was studied by solvent extraction and TRLFS Both methods show 1:3 metal:ligand complexes Conditional stability constants were determined by TRLFS and show the same trends as observed in solvent extraction Single crystal data gives structural information in solid state (to be continued) EXAFS data gives structural information in organic phase (to be continued) Again, both methods show 1:3 metal:ligand complexes DFT-based calculations support the experimental results This fundamental study gives a thorough insight into the impact of systematic structural changes of ligands towards their complexation and extraction behaviour On this basis further optimizations of the extractants will follow Page 20
21 Acknowledgements All collaborating partners Financial support FP7-Fission NUK020E Thank you for your kind attention Page 21
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