CMPO-calix[4]arenes with spacer containing intramolecular hydrogen bonding: Effect of local rigidification on solvent extraction toward f-block elements

Journal of Hazardous Materials

Volumn 264, Issue , 2014, Pages 211-218

  Chu, Hongzhu ^a   He, Lutao ^a   Jiang, Qian ^a   Fang, Yuyu ^a   Jia, Yiming ^a   Yuan, Xiangyang ^a   Zou, Shuliang ^a   Li, Xianghui ^a   Feng, Wen ^a   Yang, Yuanyou ^a   Liu, Ning ^a   Luo, Shunzhong ^b   Yang, Yanqiu ^b   Yang, Liang ^b   Yuan, Lihua ^a  

^a SICHUAN UNIVERSITY   (China)

^b RESEARCH CENTER OF LASER FUSION   (China)

Author keywords

CMPO calixarene; F Block elements; Hydrogen bonding; Solvent extraction

Indexed keywords

METAL IONS; PHENOLS; SOLVENT EXTRACTION; YTTERBIUM;

CALIX[4]ARENES; CMPO-CALIXARENE; COORDINATION ENVIRONMENT; EXTRACTABILITY; HINDERED ROTATIONS; INTRAMOLECULAR HYDROGEN BONDING; LIQUID-LIQUID EXTRACTION; SELECTIVE EXTRACTION;

HYDROGEN BONDS;

EUROPIUM; LANTHANUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; THORIUM; YTTERBIUM;

CHEMICAL BONDING; HYDROGEN; RIGIDITY; SOLVENT;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; COMPARATIVE STUDY; COMPLEX FORMATION; CONFORMATION; CONTROLLED STUDY; HYDROGEN BOND; HYDROGENATION; LIQUID LIQUID EXTRACTION; MASS SPECTROMETRY; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; PURIFICATION; REDUCTION; SOLVENT EXTRACTION; STOICHIOMETRY; SYNTHESIS;

CMPO-CALIXARENE; F-BLOCK ELEMENTS; HYDROGEN BONDING; SOLVENT EXTRACTION;

ACTINOID SERIES ELEMENTS; CALIXARENES; CARBAMYL PHOSPHATE; HYDROGEN BONDING; LANTHANOID SERIES ELEMENTS; LIQUID-LIQUID EXTRACTION;

EID: 84888393963     PISSN: 03043894     EISSN: 18733336     Source Type: Journal    
DOI: 10.1016/j.jhazmat.2013.11.021     Document Type: Article

References (48)

1. Tkac P., Vandegrift G.F., Lumetta G.J., Gelis A.V. Study of the interaction between HDEHP and CMPO and its effect on the extraction of selected lanthanides. Ind. Eng. Chem. Res. 2012, 51:10433-10444.
2. Nayak P.K., Kumaresan R., Venkatesan K.A., Antony M.P., Vasudeva Rao P.R. A new method for partitioning of trivalent actinides from high-level liquid waste. Sep. Sci. Technol. 2013, 48:1409-1416.
3. Kolarik Z. Complexation and separation of lanthanides (III) and actinides (III) by heterocyclic N-donors in solutions. Chem. Rev. 2008, 108:4208-4252.
4. 2 nuclear fuel scrap using dissolution and precipitation in carbonate media. J. Nucl. Mater. 2011, 418:93-97.
5. Griffiths T.R., Volkovich V.A., Yakimov S.M., May I., Sharrad C.A., Charnock J.M. Reprocessing spent nuclear fuel using molten carbonates and subsequent precipitation of rare earth fission products using phosphate. J. Alloys Compd. 2006, 418:116-121.
6. 7): nuclear waste form for the immobilization of plutonium and "minor" actinides. J. Appl. Phys. 2004, 95:5949-5971.
7. Raju C.S.K., Subramanian M.S. Sequential separation of lanthanides, thorium and uranium using novel solid phase extraction method from high acidic nuclear wastes. J. Hazard. Mater. 2007, 145:315-322.
8. Bhattacharyya A., Mohapatra P.K., Gadly T., Raut D.R., Ghosh S.K., Manchanda V.K. Liquid-liquid extraction and flat sheet supported liquid membrane studies on Am (III) and Eu (III) separation using 2,6-bis(5,6-dipropyl-1,2,4-triazin-3-yl) pyridine as the extractant. J. Hazard. Mater. 2011, 195:238-244.
9. Koma Y., Watanabe M., Nemoto S., Tanaka Y. Trivalent f-element intra-group separation by solvent extraction with CMPO-complexant system. J. Nucl. Sci. Technol. 1998, 35:130-136.
10. Hudson M.J., Harwood L.M., Laventine D.M., Lewis F.W. Use of soft heterocyclic N-donor ligands to separation actinides and lanthanides. Inorg. Chem. 2013, 52:3414-3428.
11. Radhika S., Kumar B.N., Kantam M.L., Reddy B.R. Liquid-liquid extraction and separation possibilities of heavy and light rare-earths from phosphoric acid solutions with acidic organophosphorus reagents. Sep. Purif. Technol. 2010, 75:295-302.
12. Nilsson M., Nash K.L. Review article: a review of the development and operational characteristics of the TALSPEAK process. Solv. Extr. Ion Exch. 2007, 25:665-701.
13. Yaftian M.R., Hassanzadeh L., Eshraghi M.E., Matt D. Solvent extraction of thorium (IV) and europium (III) ions by diphenyl-N,N-dimethylcarbamoylmethylphosphine oxide from aqueous nitrate media. Sep. Purif. Technol. 2003, 31:261-268.
14. Ramírez F.M., Tosheva T., Tashev E., García-Villafaña E., Shenkov S., Varbanov S. Synthesis of a para-tert-octylcalix[4]arene fitted with phosphinoyl pendant arms and its complexation properties towards f-elements. Polyhedron 2013, 56:123-133.
15. Park K.H., Mohapatra D., Nam C.-W. Two stage leaching of activated spent HDS catalyst and solvent extraction of aluminium using organo-phosphinic extractant, Cyanex 272. J. Hazard. Mater. 2007, 148:287-295.
16. Valsala T.P., Sonavane M.S., Kore S.G., Sonar N.L., De V., Raghavendra Y., Chattopadyaya S., Dani U., Kulkarni Y., Changrani R.D. Treatment of low level radioactive liquid waste containing appreciable concentration of TBP degraded products. J. Hazard. Mater. 2011, 196:22-28.
17. Dam H.H., Reinhoudt D.N., Verboom W. Multicoordinate ligands for actinide/lanthanide separations. Chem. Soc. Rev. 2006, 36:367-377.
18. Mokhtari B., Pourabdollah K., Dallali N. A review of calixarene applications in nuclear industries. J. Radioanal. Nucl. Chem. 2011, 287:921-934.
19. Dam H.H., Reinhoudt D.N., Verboom W. Influence of the platform in multicoordinate ligands for actinide partitioning. New J. Chem. 2007, 31:1620-1632.
20. Matthews S.E., Saadioui M., Böhmer V., Barboso S., Arnaud-Neu F., Schwing-Weill M.-J., Carrera A.G., Dozol J.-F. Conformationally mobile wide rim carbamoylmethylphosphine oxide (CMPO)-calixarenes. J. Prakt. Chem. 1999, 341:264-273.
21. Mikulášek L., Grüner B., Danila C., Bohmer V., Čáslavský J., Selucký P. Synergistic effect of ligating and ionic functions, prearranged on a calix[4]arene. Chem. Commun. 2006, 4001-4003.
22. Reinoso-García M.M., Verboom W., Reinhoudt D.N., Brisach F., Arnaud-Neu F., Liger K. Solvent extraction of actinides and lanthanides by CMP(O)- and N-Acyl(thio)urea-tetrafunctionalized cavitands: strong synergistic effect of cobalt bis(dicarbollide) ions. Solv. Extr. Ion Exch. 2005, 23:425-437.
23. Boerrigter H., Verboom W., Reinhoudt D.N. Novel resorcinarene cavitand-based CMP(O) cation ligands: synthesis and extraction properties. J. Org. Chem. 1997, 62:7148-7155.
24. Sharova E.V., Artyushin O.I., Turanov A.N., Karandashev V.K., Meshkova S.B., Topilova Z.M., Odinets I.L. N-tris[(2-aminoethyl)-2-(diphenylphosphoryl)acetamide)]-novel CMPO tripodand: synthesis, extraction studies and luminescent properties of lanthanide complexes. Cent. Eur. J. Chem. 2012, 10:146-156.
25. Reinoso-García M.M., Jańczewski D., Reinhoudt D.N., Verboom W., Malinowska E., Pietrzak M., Hill C., Báča J., Grüner B., Selucky P., Grüttner C. CMP(O) tripodands: synthesis, potentiometric studies and extractions. New J. Chem. 2006, 30:1480-1492.
26. Guo Z.J., Niu Y.N., Zhang W.G., Tan M.Y. Liquid-liquid extraction of thorium (IV) and uranium (VI) with three ether-amide type tripodands. J. Radioanal. Nucl. Chem. 2004, 262:331-337.
27. Peters M.W., Werner E.J., Scott M.J. Enhanced selectivity for actinides over lanthanides with CMPO ligands secured to a C3-symmetric triphenoxymethane platform. Inorg. Chem. 2002, 41:1707-1716.
28. Matloka K., Gelis A., Regalbuto M., Vandegrift G., Scott M.J. Highly efficient binding of trivalent f-elements from acidic media with a C3-symmetric tripodal ligand containing diglycolamide arms. Dalton Trans. 2005, 3719-3721.
29. Arnaud-Neu F., Browne J.K., Byrne D., Marrs D.J., McKervey M.A., O'Hagan P., Schwing-Weill M.J., Walker A. Extraction and complexation of alkali, alkaline earth, and f-element cations by calixaryl phosphine oxides. Chem. Eur. J. 1999, 5:175-186.
30. Arduini A., Böhmer V., Delmau L., Desreux J.-F., Dozol J.-F., Carrera M.A.G., Lambert B., Musigmann C., Pochini A., Shivanyuk A., Ugozzoli F. Rigidified calixarenes bearing four carbamoylmethylphosphineoxide or carbamoylmethylphosphoryl functions at the wide rim. Chem. Eur. J. 2000, 6:2135-2144.
31. Carolan A.N., Mroz A.E., Ojaimi M.E., VanDerveer D.G., Thummel R.P., Hancock R.D. Metal-ion-complexing properties of 2-(pyrid-2'-yl)-1,10-phenanthroline, a more preorganized analogue of terpyridyl. A crystallographic, fluorescence, and thermodynamic study. Inorg. Chem. 2012, 51:3007-3015.
32. Zhong L.J., Chen L., Feng W., Zou S.L., Yang Y.A., Liu N., Yuan L.H. Shape-persistent macrocycles: efficient extraction towards lanthanide and actinide elements. J. Incl. Phenom. Macrocycl. Chem. 2012, 72:367-373.
33. Yang Y.A., Feng W., Hu J.H., Zou S.L., Gao R.Z., Yamato K., Kline M., Cai Z.H., Gao Y., Wang Y.B., Li Y.B., Yang Y.L., Yuan L.H., Zeng X.C., Gong B. Strong aggregation and directional assembly of aromatic oligoamide macrocycles. J. Am. Chem. Soc. 2011, 133:18590-18593.
34. Zou S.L., He Y.Z., Yang Y.A., Zhao Y., Yuan L.H., Feng W., Yamato K., Gong B. Improving the efficiency of forming 'unfavorable' products: eight-residue macrocycles from folded aromatic oligoamide precursors. Synlett 2009, 1437-1440.
35. Yang L.Q., Zhong L.J., Yamato K., Zhang X.H., Feng W., Deng P.C., Yuan L.H., Zeng X.C., Gong B. Aromatic oligoamide macrocycles from the bimolecular coupling of folded oligomeric precursors. New J. Chem. 2009, 33:729-733.
36. Feng W., Yamato K., Yang L.Q., Ferguson J.S., Zhong L.J., Zou S.L., Yuan L.H., Zeng X.C., Gong B. Efficient kinetic macrocyclization. J. Am. Chem. Soc. 2009, 131:2629.
37. Yang X.S., Chen L., Yang Y.A., He Y.Z., Zou S.L., Feng W., Yang Y.Y., Liu N., Liao J.L., Yuan L.H. Synthesis of crescent aromatic oligoamides with preorganized chelating groups and their extraction towards transition metal ions. J. Hazard. Mater. 2012, 217-218:171-176.
38. Dudic M., Colombo A., Sansone F., Casnati A., Donofrio G., Ungaro R. A general synthesis of water soluble upper rim calix[n]arene guanidinium derivatives which bind to plasmid DNA. Tetrahedron 2004, 60:11613-11618.
39. Yuan L.H., Sanford A.R., Feng W., Zhang A.M., Zhu J., Zeng H.Q., Yamato K., Li M.F., Ferguson J.S., Gong B. Synthesis of crescent aromatic oligoamides. J. Org. Chem. 2005, 70:10660-10669.
40. Arnaud-Neu F., Böhmer V., Dozol J.-F., Grüttner C., Jakobi R.A., Kraft D., Mauprivez O., Rouquette H., Schwing-Weill M.-J., Simon N., Vogt W. Calixarenes with diphenylphosphoryl acetamide functions at the upper rim. A new class of highly efficient extractants for lanthanides and actinides. J. Chem. Soc., Perkin Trans. 1996, 2:1175-1182.
41. Cao R.K., Zhou J.J., Wang W., Feng W., Li X.H., Zhang P.H., Deng P.C., Yuan L.H., Gong B. Oligoamide duplexes as organogelators. Org. Lett. 2010, 12:2958-2961.
42. Ramírez F.M., Varbanov S., Padilla J., Bünzli J.-C.G. Physicochemical properties and theoretical modeling of actinide complexes with a para-tert-butylcalix[6]arene bearing phosphinoyl pendants. Extraction capability of the calixarene toward f elements. J. Phys. Chem. B 2008, 112:10976-10988.
43. Yaftian M.R., Razipour M.R., Matt D. Extraction of thorium (IV) and europium (III) by a phosphorylated calix[4]arene in dichloromethane. J. Radioanal. Nucl. Chem. 2006, 270:357-361.
44. Panja S., Mohapatra P.K., Tripathi S.C., Manchanda V.K. Facilitated transport of uranium(VI) across supported liquid membranes containing T2EHDGA as the carrier extractant. J. Hazard. Mater. 2011, 188:281-287.
45. Tashkhourian J., Moradi Abdoluosofi L., Pakniat M., Montazerozohori M. Sodium dodecyl sulfate coated alumina modified with a new Schiff's base as a uranyl ion selective adsorbent. J. Hazard. Mater. 2011, 187:75-81.
46. Schmidt C., Saadioui M., Böhmer V., Host V., Spirlet M.-R., Desreux J.F., Brisach F., Arnaud-Neu F., Dozol J.-F. Modification of calix[4]arenes with CMPO-functions at the wide rim. Synthesis, solution behavior, and separation of actinides from lanthanides. Org. Biomol. Chem. 2003, 1:4089-4096.
47. Motornaya A., Vatsouro I., Shokova E., Hubscher-Bruder V., Alyapyshev M., Babain V., Karavan M., Arnaud-Neu F., Böhmer V., Kovalev V. Adamantylcalixarenes with CMPO groups at the wide rim: synthesis and extraction of lanthanides and actinides. Tetrahedron 2007, 63:4748-4755.
48. Karavan M., Arnaud-Neu F., Hubscher-Bruder V., Smirnov I., Kalchenko V. Novel phosphorylated calixarenes for the recognition of f-elements. J. Incl. Phenom. Macrocycl. Chem. 2010, 66:113-123.