Modification conditions of poly-3-(2-aminoethylamino)propylsilsesquioxane with sulfur-containing groups as an instrument for influencing silver(I) sorption from multicomponent solutions

Ekaterina A. Melnik; Yulia S. Petrova; Victoria A. Osipova; Alexander V. Pestov; Lyudmila K. Neudachina

doi:10.15826/chimtech.9205

Modification conditions of poly-3-(2-aminoethylamino)propylsilsesquioxane with sulfur-containing groups as an instrument for influencing silver(I) sorption from multicomponent solutions

Ekaterina A. Melnik, Yulia S. Petrova, Victoria A. Osipova, Alexander V. Pestov, Lyudmila K. Neudachina

Abstract

The effect of modification conditions of poly-3-(2-aminoethylamino)propylsilsesquioxane with ammonium thiocyanate was studied. The possibility of varying the sorption properties of materials due to the formation of dithiobiuret or thiourea groups on the sorbent surface under certain conditions was established. The synthesized sorbents have high selectivity for silver(I) at pH from 0 to 8. The use of thiourea sulfuric acid solutions as a desorbent allows for a total desorption rate of up to 90%. An isochronous study of the stability of the sorption properties of modified polysilsesquioxanes was carried out for the first time: the sorption properties are preserved for 5 years. Modified poly-3-(2-aminoethylamino)propylsilsesquioxanes can be used for the selective and quantitative extraction of silver(I).

Keywords

polysilsesquioxane; sorption; silver; solid-phase extraction

Full Text:

PDF

References

Kinnunen V, Peramaki S, Matilainen R. Solid phase extraction materials as a key for improving the accuracy of silver nanoparticle characterization with single-particle inductively coupled plasma mass spectrometry in natural waters through dissolved silver removal. Spectrochim Acta Part B. 2022;193:106431. doi:10.1016/j.sab.2022.106431

Hamza MF, Abdel-Rahman AAH, Hawata MA, Araby RE, Guibal E, Fouda A, et al. Functionalization of magnetic chitosan microparticles – Comparison of trione and trithione grafting for enhanced silver sorption and application to metal recovery from waste X-ray photographic films. J Environ Chem. 2022;10(3):107939. doi:10.1016/j.jece.2022.107939

Elwakeel KZ, Al-Bogami AS, Guibal E. 2-Mercaptobenzimidazole derivative of chitosan for silver sorption – Contribution of magnetite incorporation and sonication effects on enhanced metal recovery. J Chem Eng. 2021;403:126265. doi:10.1016/j.cej.2020.126265

Huang T, Zhu J, Huang X, Ruan J, Xu Z. Assessment of precious metals positioning in waste printed circuit boards and the economic benefits of recycling. Waste Manag Res. 2022;139:105–115. doi:10.1016/j.wasman.2021.12.030

Andersson M; Söderman ML, Sandén BA. Challenges of recycling multiple scarce metals: The case of Swedish ELV and WEEE recycling. Resources Policy. 2019;63:101403. doi:10.1016/j.resourpol.2019.101403

Heo J, Park J, Park JH. Effect of pyro-processing conditions on impurity removal and precious metal enrichment in waste printed circuit board (WPCB) recycling process. Resour Conserv Recycl. 2022;179:106068. doi:10.1016/j.resconrec.2021.106068

Vikrant K, Kim KH. Nanomaterials for the adsorptive treatment of Hg(II) ions from water. J Chem Eng. 2019;358:264–282. doi:10.1016/j.cej.2018.10.022

Lachowicz E, Różańska B, Teixidor F, Meliani H, Barboiu M, Hovnanian N. Comparison of sulphur and sulphur–oxygen ligands as ionophores for liquid–liquid extraction and facilitated transport of silver and palladium. J Membrane Sci. 2002;210(2):279–290. doi:10.1016/S0376-7388(02)00388-5

Wang L, Xing R, Liu S, Yu H, Qin Y, Li K, et al. Recovery of silver(I) using a thiourea-modified chitosan resin. J Hazard Mater. 2010;180(1–3):577–582. doi:10.1016/j.jhazmat.2010.04.072

Yun JI, Bhattarai S, Yun YS, Lee YS. Synthesis of thiourea-immobilized polystyrene nanoparticles and their sorption behavior with respect to silver ions in aqueous phase. J Hazard Mater. 2018;344:398–407. doi:10.1016/j.jhazmat.2017.10.050

Ghiorghita CA, Lazar MM, Platon IV, Humelnicu D, Doroftei F, Dinu MV. Feather-weight cryostructured thiourea-chitosan aerogels for highly efficient removal of heavy metal ions and bacterial pathogens. Int J Biol Macromol. 2023;235:123910. doi:10.1016/j.ijbiomac.2023.123910

Tomina VV, Stolyarchuk NV, Melnyk IV, Kochkodan VM, Zub YL. Sorptive ceramic membranes functionalized with HS-groups. Microporous Mesoporous Mater. 2015;209:66–71. doi:10.1016/j.micromeso.2014.09.005

Šesták J, Moravcová D, Křenková J, Planeta J, Roth M, Foret F. Bridged polysilsesquioxane-based wide-bore monolithic capillary columns for hydrophilic interaction chromatography. J Chromatogr A. 2017;1479:204–209. doi:10.1016/j.chroma.2016.11.062

Wang B, Wu K, Liu T, Cheng Z, Liu Y, Liu Y et al. Feasible synthesis of bifunctional polysilsesquioxane microspheres for robust adsorption of Hg(II) and Ag(I): Behavior and mechanism. J Hazard Mater. 2023;442:130121. doi:10.1016/j.jhazmat.2022.130121

Sun C, Li C, Qu R, Zhang Y, Bingdong Z, Kuang Y. Syntheses of diethylenetriamine-bridged polysilsesquioxanes and their structure–adsorption properties for Hg(II) and Ag(I). J Chem Eng. 2014;240:369–378. doi:10.1016/j.cej.2013.11.092

Melnik EA, Sysolyatina AA, Holmogorova AS, Neudachina LK, Osipova VA, Pestov AV. Selective Sorption of Silver Ions from Aqueous Solutions Using Poly(N-thiocarbamoyl‑3-aminopropylsilsesquioxane). Measurem Stand Ref Mater. 2022;18(2):57–71. doi:10.20915/2077-177-2022-18-2-57-71

Takagi T, Kawamura I, Oumi Y, Miwa Y, Yoshitake H. Absorption of Cu(II) in layered diaminoalkyl- and monoaminoalkyl-polysilsesquioxane. Polymer. 2017;132:227–234. doi:10.1016/j.polymer.2017.11.011

Barczak M, Borowski P, Dąbrowski A. Structure-adsorption properties of ethylene-bridged polysilsesquioxanes and polysiloxanes functionalized with different groups. Colloids Surf A Physicochem Eng Asp. 2009;347(1–3):114–120. doi:10.1016/j.colsurfa.2009.01.016

Ivanov PV. Characteristic features of polycondesation of organosilanols. Fine Chemical Technologies. 2011;6(3):3–22.

Doustkhah E, Tahawy R, Simon U, Tsunoji N, Ide Y, Hanaor DAH,et al. Bispropylurea bridged polysilsesquioxane: A microporous MOF-like material for molecular recognition. Chemosphere. 2021;276:130181. doi:10.1016/j.chemosphere.2021.130181

Schäfer S, Kickelbick G. Simple and high yield access to octafunctional azido, amine and urea group bearing cubic spherosilicates. Dalton Trans. 2017;46:221–226. doi:10.1039/c6dt03872g

Gavilan KC, Pestov AV, Garcia HM, Yatluk Y, Roussy J, Guibal E. Mercury sorption on a thiocarbamoyl derivative of chitosan. J Hazard Mater. 2009;165:415–426. doi:10.1016/j.jhazmat.2008.10.005

Vieira EG, Soares IV, Pires G, Ramos RAV, do Carmo DR, Filho NLD. Study on soluble heavy metals with preconcentration by using a new modified oligosilsesquioxane sorbent. J Hazard Mater. 2015;264:77–88. doi:10.1016/j.cej.2014.11.050

Timchenko VP, Novozhilov AL, Slepysheva OA. Kinetics of Thermal Decomposition of Thiourea. Russ J Gen Chem. 2004;74:1046–1050. doi:10.1023/B:RUGC.0000045862.69442.aa

Sun C, Li C, Qu R, Zhang Y, Bingdong Z, Kuang Y. Syntheses of diethylenetriamine-bridged polysilsesquioxanes and their structure–adsorption properties for Hg(II) and Ag(I). Chem Eng J. 2014;240:369–378. doi:10.1016/j.cej.2013.11.0925

Birinci E, Gulfen M, Aydin AO. Separation and recovery of palladium(II) from base metal ions by melamine–formaldehyde–thiourea (MFT) chelating resin. Hydrometallurgy. 2009;95(1–2):15–21. doi:10.1016/j.hydromet.2008.04.002

Liu J, Jin C, Wang C. Hyperbranched thiourea-grafted electrospun polyac rylonitrile fibers for efficient and selective gold recovery. J Colloid Interface Sci. 2020;561:449–458. doi:10.1016/j.jcis.2019.11.016

Petter PMH, Veit HM, Bernardes AM. Evaluation of gold and silver leaching from printed circuit board of cellphones. Waste Managemen. 2014;34(2):475–482. doi:10.1016/j.wasman.2013.10.032

Rao MD, Singh KK, Morrison CA, Love JB. Challenges and opportunities in the recovery of gold from electronic waste. RSC Adv. 2020;10(8):4300–4309. doi:10.1039/C9RA07607G

Ruck EB, Amikam G, Darom Y, Manor-Korin N, Gendel Y. Catalytic selective recovery of silver from dilute aqueous solutions and e-waste leachates. Sep Purif Technol. 2022;285:120303. doi:10.1016/j.seppur.2021.120303

Zhang M, Zhang Y, Helleur R. Selective adsorption of Ag+ by ion-imprinted O-carboxymethyl chitosan beads grafted with thiourea–glutaraldehyde. J Chem Eng. 2015;264:56–65. doi:10.1016/j.cej.2014.11.062

Niu Y, Qu R, Liu X, Mu L, Bu B, Sun Y, et al. Thiol-functionalized polysilsesquioxane as efficient adsorbent for adsorption of Hg(II) and Mn(II) from aqueous solution. Mater Res Bull. 2014;52:134–142. doi:10.1016/j.materresbull.2014.01.024

Melnik EA, Sysolyatina AA, Petrova YuS, Kholmogorova AS, Neudachina LК, Osipova VA, Pestov AV. A study of silver sorption from aqueous solutions by solid-phase modified poly(n-thiocarbamoyl-3-aminopropyl silsesquioxane). Analitika i Kontrol. 2023;27(1):42–50. doi:10.15826/analitika.2023.27.1.004

Talut IE. Application of silicas chemically modified with thiourea derivatives for the concentration and determination of zinc, cadmium, silver and copper [dissertation]. Moscow (Russian Federation): Moscow State University:1993. 18.

Tokalioglu S, Oymak T, Kartal S. Determination of palladium in various samples by atomic ab-sorption spectrometry after preconcentration with dimethylglyoxime on silica gel. Anal Chim Acta. 2004;511(2):255–260. doi:10.1016/j.aca.2004.02.015

Hiskey JB, Atluri VP. Dissolution chemistry of gold and silver in different lixiviants. Miner Process Extr Metall Rev. 1988;4(1–2):95–134. doi:10.1080/08827508808952634

Danilenko NV, Kononova ON, Kachin SV, Kholmogorov AG, Dmitrieva ZhV, Plotnikova EA. Sorption and separation of thiocyanate gold and silver complexes and determination of gold by diffuse reflectance spectroscopy. B Korean Chem Soc. 2004;25(7):1019–1024. doi:10.5012/bkcs.2004.25.7.1019

Deng S, Huang J, Guo M, Sun X, Ren X, Zhong J, Xu R. Preparation and adsorption behavior of amino-functionalized bridged organosilicas for the removal of Ag(I) from aqueous solutions. Desalin Water Treat. 2021;229:322–330. doi:10.5004/dwt.2021.27380

Stolyarchuk NV, Kolev H, Kanuchova M, Keller R, Vaclavikova M, Melnyk IV. Synthesis and sorption properties of bridged polysilsesquioxane microparticles containing 3-mercaptopropyl groups in the surface layer. Colloids Surf A Physicochem Eng Asp. 2018;538:694–702 doi:10.1016/j.colsurfa.2017.11.049

Lu X, Yin Q, Xin Z, Zhang Z. Powerful adsorption of silver(I) onto thiol-functionalized polysilsesquioxane microspheres. Chem Eng Sci. 2010;65(24):6471-6477. doi:10.1016/j.ces.2010.10.001

Ladhe AR, Frailie P, Hua D, Darsillo M, Bhattacharyya D. Thiol-functionalized silica–mixed matrix membranes for silver capture from aqueous solutions: Experimental results and modeling. J Membr Sci. 2009;326(2):460–471. doi:10.1016/j.memsci.2008.10.025

Quang DV, Lee JE, Kim JK, Kim YN, Shao GN, Kim HT. A gentle method to graft thiol-functional groups onto silica gel for adsorption of silver ions and immobilization of silver nanoparticles. Powder Technol. 2013;235:221–227. doi:10.1016/j.powtec.2012.10.015

Wang S, Li H, Chen X, Yang M, Qi Y. Selective adsorption of silver ions from aqueous solution using polystyrene-supported trimercaptotriazine resin. J Environ Sci. 2012;24(12):2166–2172. doi:10.1016/S1001-0742(11)61052-8

Luan L, Tang B, Liu Y, Wang A, Zhang B, Xu W, Niu Y. Selective capture of Hg(II) and Ag(I) from water by sulfur-functionalized polyamidoamine dendrimer/magnetic Fe3O4 hybrid materials. Sep Purif Technol. 2021;257:117902. doi:10.1016/j.seppur.2020.117902ed

DOI: https://doi.org/10.15826/chimtech.9205

Copyright (c) 2025 Ekaterina A. Melnik, Yuliya S. Petrova, Victoria A. Osipova, Alexander V. Pestov, Ludmila К. Neudachina

This work is licensed under a Creative Commons Attribution 4.0 International License.

Chimica Techno Acta, 2014–2025
eISSN 2411-1414
Copyright Notice

Username
Password
Remember me