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Fabrication of magnetic functionalized m-carboxyphenyl azo calix[4]arene amine oxime derivatives for highly efficient and selective adsorption of uranium (VI)

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Abstract

A novel material called m-carboxyphenyl azo calix[4]arene amine oxime derivatives (M-CCAOD) was synthesized by diazotization-coupling reaction and substitution reaction. Then the composite consisting of Fe3O4 and M-CCAOD was prepared through a facile self-assembly method. The as-synthesized Fe3O4/M-CCAOD composite was used to remove U(VI) from aqueous solutions under different conditions. The calculated data indicate that the adsorption process of uranium by Fe3O4/M-CCAOD is an exothermic spontaneous process, which well fits with the pseudo-second-order and Freundlich model. More significantly, the composite showed high selectivity for uranium and excellent reusability, demonstrating that Fe3O4/M-CCAOD may be a potential uranium adsorbent material.

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References

  1. 1.

    Wang C, Xiao F-Z, Pu Y-Q, Xu Y-L, Xu D-Y, Zhang K, Liu Y, Peng G-W (2018) Preparation of p-carboxyphenyl azo calix [4] arene phosphate derivative and its extraction properties toward uranium (VI). J Radioanal Nucl Chem 317:1235–1241

  2. 2.

    Xiao F-Z, Huang T, Zhang S-W, Liu L-F, Wang C, Peng G-W, He S-Y (2019) Optimization analysis and mechanism exploration on the removal of cesium and the solidification of secondary residue wastes in electrokinetics. J Clean Prod 233:1207–1220

  3. 3.

    Peng G-W, Ding D-X, Xiao F-Z, Wang X-L, Hun N, Wang Y-D, Dai Y-M, Cao Z (2014) Adsorption of uranium ions from aqueous solution by amine-group functionalized magnetic Fe3O4 nanoparticle. J Radioanal Nucl Chem 301:781–788

  4. 4.

    Zhou L-M, Shang C, Liu Z-R, Huang G-L, Adesina AA (2012) Selective adsorption of uranium (VI) from aqueous solution using the ion-imprinted magnetic chitosan resins. J Colloid Interface Sci 366:165–172

  5. 5.

    Li Z-J, Huang Z-W, Guo W-L, Wang L, Zheng L-R, Chai Z-F, Shi W-Q (2017) Enhanced photocatalytic removal of uranium (VI) from aqueous solution by magnetic TiO/FeO and its graphene composite. Environ Sci Technol 51:5666–5674

  6. 6.

    Sun Y-B, Yang S-B, Chen Y, Ding C-C, Cheng W-C, Wang X-K (2015) Adsorption and desorption of U(VI) on functionalized graphene oxides: a combined experimental and theoretical study. Environ Sci Technol 49:4255–4262

  7. 7.

    Xiao C-L, Hassanzadeh Fard Z, Sarma D, Song T-B, Xu C, Kanatzidis MG (2017) Highly efficient separation of trivalent minor actinides by a layered metal sulfide (KInSn2S6) from acidic radioactive waste. J Am Chem Soc 139:16494–16497

  8. 8.

    Wang Y-X, Yin X-M, Liu W, Xie J, Chen J-F, Silver M-A, Sheng D-F, Chen L-H, Diwu J, Liu N, Chai Z-F, Albrecht-Schmitt T-E, Wang S-A (2018) Emergence of uranium as a distinct metal center for building intrinsic X-ray scintillators. Angew Chem Int Edit 57:7883–7887

  9. 9.

    Sun Y-B, Shao D-D, Chen C-L, Yang S, Wang X-K (2013) Highly efficient enrichment of radionuclides on graphene oxide-supported polyaniline. Environ Sci Technol 47:9904–9910

  10. 10.

    Sun Y-B, Wu Z-Y, Wang X-X, Ding C-C, Cheng W-C, Yu S-H, Wang X-K (2016) Macroscopic and microscopic investigation of U (VI) and Eu(III) adsorption on carbonaceous nanofibers. Environ Sci Technol 50:4459–4467

  11. 11.

    Mellah A, Chegrouche S, Barkat M (2007) The precipitation of ammonium uranyl carbonate (AUC): thermodynamic and kinetic investigations. Hydrometallurgy 85:163–171

  12. 12.

    Meunier N, Drogui P, Montané C, Hausler R, Mercier G, Blais JF (2006) Comparison between electrocoagulation and chemical precipitation for metals removal from acidic soil leachate. J Hazard Mater 137:581–590

  13. 13.

    Narayani M, Shetty KV (2013) Chromium-resistant bacteria and their environmental condition for hexavalent chromium removal: a review. Crit Rev Env Sci Tec 43:955–1009

  14. 14.

    Zondervan E, Roffel B (2007) Evaluation of different cleaning agents used for cleaning ultra filtration membranes fouled by surface water. J Membrane Sci 304:40–49

  15. 15.

    Yaftian M, Taheri R, Zamani A, Matt D (2004) Thermodynamics of the solvent extraction of thorium and europium nitrates by neutral phosphorylated ligands. J Radioanal Nucl Chem 262:455–459

  16. 16.

    Gao J, Sun S-P, Zhu W-P, Chung T-S (2014) Chelating polymer modified P84 nanofiltration (NF) hollow fiber membranes for highly efficient heavy metal removal. Water Res 63:252–261

  17. 17.

    Hua B, Deng B (2008) Reductive immobilization of uranium (VI) by amorphous iron sulfide. Environ Sci Technol 42:8703–8708

  18. 18.

    Akin I, Arslan G, Tor A, Cengeloglu Y, Ersoz M (2011) Removal of arsenate [As (V)] and arsenite [As (III)] from water by SWHR and BW-30 reverse osmosis. Desalination 281:88–92

  19. 19.

    Ladeira ACQ, Morais CAD (2005) Uranium recovery from industrial effluent by ion exchange—column experiments. Mine Eng 18:1337–1340

  20. 20.

    Tan J, Wang YF, Liu N, Liu MW (2018) Adsorption of uranium (VI) from aqueous solution by tetraphenylimidodiphosphinate. J Radioanal Nucl Chem 315:119–126

  21. 21.

    Huang T, Peng QK, Yu L, Li DW (2017) The detoxification of heavy metals in the phosphate tailing-contaminated soil through sequential microbial pretreatment and electrokinetic remediation. Soil Sediment Contam 26:308–322

  22. 22.

    Qian LP, Ma MH, Cheng DH (2015) Adsorption and desorption of uranium on nano goethite and nano alumina[J]. J Radioanal Nucl Chem 303:161–170

  23. 23.

    Ding CC, Cheng WC, Wang XX, Wu ZY, Sun YB, Chen CL, Wang XK, Yu SH (2016) Competitive sorption of Pb(II), Cu (II) and Ni (II) on carbonaceous nanofibers: a spectroscopic and modeling approach. J Hazard Mater 313:253–261

  24. 24.

    Olivelli MS, Curutchet GA, Sánchez Torres, Rosa M (2013) Uranium uptake by montmorillonite-biomass complexes. Ind Eng Chem Res 52:2273–2279

  25. 25.

    Bhatti AA, Memon S, Memon N (2014) Dichromate extraction by calix [4] arene appended amberlite XAD-4 resin. Sep Sci Technol 49:664–672

  26. 26.

    Bai Z-Q, Yuan L-Y, Zhu L, Liu Z-R, Chu S-Q, Zheng L-R, Chu S-Q, Zheng L-R, Zhang J, Chai Z-F, Shi W-Q (2015) Introduction of amino groups into acid-resistant MOFs for enhanced U(VI) sorption. J Mater Chem A 3:525–534

  27. 27.

    Ma S-L, Huang L, Ma L-J, Shim Y, Islam SM, Wang P-L, Zhao L-D, Wang S-C, Sun G-B, Yang X-J, Kanatzidis MG (2015) Efficient uranium capture by polysulfide/layered double hydroxide composites. J Am Chem Soc 137:3670–3677

  28. 28.

    Monier M, Elsayed NH (2014) Selective extraction of uranyl ions using ion-imprinted chelating microspheres. J Colloid Interf Sc 423:113–122

  29. 29.

    Wang X-X, Yang S-B, Shi W-Q, Li J-X, Hayat T, Wang X-K (2015) Different interaction mechanisms of Eu(III) and 243Am (III) with carbon nanotubes studied by batch, spectroscopy technique and theoretical calculation. Environ Sci Technol 49:11721–11728

  30. 30.

    Wang X-X, Fan Q-H, Yu S-J, Chen Z-S, Ai Y-J, Sun Y-B, Hobiny A, Alsaedi A, Wang X-K (2016) High sorption of U(VI) on graphene oxides studied by batch experimental and theoretical calculations. Chem Eng J 287:448–455

  31. 31.

    Lu X, He S-N, Zhang D-X, Reda AT, Liu C, Feng J, Zhi Y (2016) Synthesis and characterization of amidoxime modified calix [8] arene for adsorption of U(VI) in low concentration uranium solutions. RSC Adv 6:101087–101097

  32. 32.

    Ogoshi T, Nishida Y, Yamagishi TA, Nakamoto Y (2010) Synthesis and host-guest properties of an alternating copolymer containing calix [4] arene and calix [6] arene in its main chain. Polym Chem UK 1:203–206

  33. 33.

    Kumar R, Lee YO, Bhalla V, Kumar M, Kim SJ (2014) Recent developments of thiacalixarene based molecular motifs. Chem Soc Rev 43:4824–4870

  34. 34.

    Tarbell DS, Weaver C (1941) The condensation of sulfoxides with p-toluenesulfonamide and substituted acetamides. J Am Chem Soc 63:2939–2942

  35. 35.

    Zhou J, Chen M, Xie J, Diao G-W (2013) Synergistically enhanced electrochemical response of host-guest recognition based on ternary nanocomposites: reduced graphene oxide-amphiphilic pillar [5] arene-gold nanoparticles. ACS Appl Mater Inter 5:11218–11224

  36. 36.

    Nie R, Chang X-J, He Q, Hu Z, Li Z-H (2009) Preparation of p-tert[(dimethylamino) methyl]-calix [4] arene functionalized aminopropylpolysiloxane resin for selective solid-phase extraction and preconcentration of metal ions. J Hazard Mater 169:203–209

  37. 37.

    Pu Y-Q, Xiao F-Z, He S-Y, Wang C, Peng G-W, Liu Y (2017) Synthesis of the p-tert-butyl calix [4] arene symmetrical sulfide derivatives and its extraction properties towards U (VI) from aqueous solution. J Radioanal Nucl Chem 314:2137–2143

  38. 38.

    Liu MC, Wen T, Wu XL, Chen CL, Hu J, Li J, Wang XK (2013) Synthesis of porous Fe3O4 hollow microspheres/graphene oxide composite for Cr(VI) removal. Dalton T 42:14710–14717

  39. 39.

    Chen Z-S, Wang J, Pu Z-X, Zhao Y-S, Jia D-S, Chen H-X, Wen T, Hu B, Alsaedi A, Hayat T, Wang X-K (2017) Synthesis of magnetic Fe3O4/CFA composites for the efficient removal of U (VI) from wastewater. Chem Eng J 320:448–457

  40. 40.

    Zhao Y-G, Li J-X, Zhao L-P, Zhang S-W, Huang Y-S, Wu X-L, Wang X-K (2014) Synthesis of amidoxime-functionalized Fe3O4@SiO2 core–shell magnetic microspheres for highly efficient sorption of U(VI). Chem Eng J 235:275–283

  41. 41.

    Arduini A, Pochini A, Reverberi S, Ungaro R, Anreetti G, Ugozzoli F (1986) The preparation and properties of a novel lipophilic sodium selective ether ester ligand derived from p-t-butylcalix[4]arene. Tetrahedron 42:2089–2100

  42. 42.

    Khan MH, Warwick P, Evans N (2006) Spectrophotometric determination of uranium with arsenazo-III in perchloric acid. Chemosphere 63:1165–1169

  43. 43.

    Pan Y, Wu Z-M, Zhou J-Z, Zhao J, Ruan X-X, Liu J-Y, Qian G-R (2013) Chemical characteristics and risk assessment of typical municipal solid waste incineration (MSWI) fly ash in China. J Hazard Mater 261:269–276

  44. 44.

    Xu S, Zhang L-Y, Freeman SPHT, Hou X-L, Shibata Y, Sanderson D, Cresswell A, Doi T, Tanaka A (2015) Speciation of radiocesium and radioiodine in aerosols from Tsukuba after the Fukushima nuclear accident. Environ Sci Technol 49:1017–1024

  45. 45.

    Ulusoy Halil İbrahim, Şimşek Selçuk (2013) Removal of uranyl ions in aquatic mediums by using a new material: gallocyanine grafted hydrogel. J Hazard Mater 254:397–405

  46. 46.

    Liu ZR, Liu DQ, Cai ZW, Wang Y, Zhou LM (2018) Synthesis of new type dipropyl imide chelating resin and its potential for uranium (VI) adsorption. J Radioanal Nucl Chem 318(2):1219–1227

  47. 47.

    He Y, Wang XQ, Nie XQ, Zou H, Pan N (2018) Uranium (VI) removal from aqueous solutions by a chelating fiber. J Radioanal Nucl Chem 317:1005–1012

  48. 48.

    Şimşek Selçuk, Şenol Zeynep Mine, Ulusoy Halil Ibrahim (2017) Synthesis and characterization of a composite polymeric material including chelating agent for adsorption of uranyl ions. J Hazard Mater 338:437–446

  49. 49.

    Yang PP, Liu Q, Liu JY, Zhang HS, Li ZS, Li RM, Liu LH, Wang J (2017) Interfacial growth of a metal–organic framework (UiO-66) on functionalized graphene oxide (GO) as a suitable seawater adsorbent for extraction of uranium (VI). R Soc Chem 5:17933–17942

  50. 50.

    Wu Y-J, Zhang L-J, Gao C-L, Ma J-Y, Ma X-H, Han R-P (2009) Adsorption of copper ions and methylene blue in a single and binary system on wheat stra. J Chem Eng Data 54:3229–3234

  51. 51.

    Saito T, Brown S, Chatterjee S, Kim J, Tsouris C, Mayes RT, Kuo LJ, Gill G, Oyola Y, Janke CJ, Dai S (2014) Uranium recovery from seawater: development of fiber adsorbents prepared via atom-transfer radical polymerization. J Mater Chem A 2:14674–14681

  52. 52.

    Gao Q, Zhao A-W, Gan Z-B, Tao W-Y, Li D, Zhang M-F, Guo H-Y, Wang D-P, Sun H-H, Mao R-R, Liu E-H (2012) Facile fabrication and growth mechanism of 3D flower-like Fe3O4 nanostructures and their application as SERS substrates. CrystEngComm 14:4834–4842

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Acknowledgements

We are grateful to acknowledge the support of this work from National Natural Science Foundation of China (CN) (NO.11705085), National Natural Science Foundation of China (NO.51574152).

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Correspondence to Fangzhu Xiao or Guowen Peng.

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Xu, Y., Zhang, K., Wang, C. et al. Fabrication of magnetic functionalized m-carboxyphenyl azo calix[4]arene amine oxime derivatives for highly efficient and selective adsorption of uranium (VI). J Radioanal Nucl Chem 323, 1145–1155 (2020). https://doi.org/10.1007/s10967-020-07029-4

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Keywords

  • Carboxylation
  • Amine oxime
  • Magnetic functionalization
  • Calix[4]arene
  • Uranium