{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,10]],"date-time":"2026-07-10T21:29:26Z","timestamp":1783718966041,"version":"3.55.0"},"reference-count":56,"publisher":"MDPI AG","issue":"15","license":[{"start":{"date-parts":[[2019,7,31]],"date-time":"2019-07-31T00:00:00Z","timestamp":1564531200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>A novel functional ion-exchange\/adsorption metal organic resin (MOR), TEBAC-HKUST-1, was prepared and characterized. Ethanedithiol was used as the grafting agent to introduce thiol groups onto HKUST-1, and 4-vinylbenzyl chloride was then grafted onto SH-HKUST-1 using thiol groups. Finally, the quaternary ammonium functional group was immobilized onto the carrier by performing a quaternization reaction. The structure and property of TEBAC-HKUST-1 MOR were characterized by TGA, N2 adsorption\u2013desorption, FTIR, SEM, and XRD. TEBAC-HKUST-1 MOR was used to remove metal cyanide complexes from wastewater. The adsorption was rapid, and the metal cyanide complexes including Pt(CN)42\u2212, Co(CN)63\u2212, Cu(CN)32\u2212, and Fe(CN)63\u2212 were removed in 30 min. TEBAC-HKUST-1 MOR exhibited a high stability in neutral and weak basic aqueous solutions. Furthermore, Pt(II) could be efficiently recovered through two-step elution. The recovery rate of Pt(II) for five cycles were over 92.0% in the mixture solution containing Pt(CN)42\u2212, Co(CN)63\u2212, Cu(CN)32\u2212, and Fe(CN)63\u2212. The kinetic data were best fitted with the pseudo second-order model. Moreover, the isothermal data were best fitted with the Langmuir model. The thermodynamic results show that the adsorption is a spontaneous and exothermic process. TEBAC-HKUST-1 MOR not only exhibited excellent ability for the rapid removal of metal cyanide complexes, but also provided a new idea for the extraction of noble metals from cyanide-contaminated water.<\/jats:p>","DOI":"10.3390\/molecules24152779","type":"journal-article","created":{"date-parts":[[2019,7,31]],"date-time":"2019-07-31T11:37:07Z","timestamp":1564573027000},"page":"2779","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["Two-Step Elution Recovery of Cyanide Platinum Using Functional Metal Organic Resin"],"prefix":"10.3390","volume":"24","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-9772-5643","authenticated-orcid":false,"given":"Muhan","family":"Chen","sequence":"first","affiliation":[{"name":"School of Chemistry Science and Engineering, Yunnan University, Cuihu North Road No. 2, Kunming 650091, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qun","family":"Ye","sequence":"additional","affiliation":[{"name":"School of Chemistry Science and Engineering, Yunnan University, Cuihu North Road No. 2, Kunming 650091, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shaosong","family":"Jiang","sequence":"additional","affiliation":[{"name":"School of Chemistry Science and Engineering, Yunnan University, Cuihu North Road No. 2, Kunming 650091, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Min","family":"Shao","sequence":"additional","affiliation":[{"name":"School of Chemistry Science and Engineering, Yunnan University, Cuihu North Road No. 2, Kunming 650091, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ci","family":"Jin","sequence":"additional","affiliation":[{"name":"School of Chemistry Science and Engineering, Yunnan University, Cuihu North Road No. 2, Kunming 650091, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7873-5582","authenticated-orcid":false,"given":"Zhangjie","family":"Huang","sequence":"additional","affiliation":[{"name":"School of Chemistry Science and Engineering, Yunnan University, Cuihu North Road No. 2, Kunming 650091, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2019,7,31]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"15929","DOI":"10.1007\/s11356-017-9081-7","article-title":"Cyanides in the environment-analysis-problems and challenges","volume":"24","author":"Jaszczak","year":"2017","journal-title":"Environ. Sci. Pollut. Res."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"5721","DOI":"10.1021\/ol062323r","article-title":"Acridinium salt based fluorescent and colorimetric chemosensor for the detection of cyanide in water","volume":"8","author":"Yang","year":"2006","journal-title":"Org. Lett."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1016\/j.saa.2010.04.035","article-title":"A novel kinetic spectrophotometric method for the determination of ultra trace amount of cyanide","volume":"77","author":"Abbasi","year":"2010","journal-title":"Spectrochim. Acta A"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"164","DOI":"10.1016\/j.hydromet.2006.03.041","article-title":"A new technique for extraction of platinum group metals by pressure cyanidation","volume":"82","author":"Chen","year":"2006","journal-title":"Hydrometallurgy"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"249","DOI":"10.1016\/j.saa.2017.05.012","article-title":"A new azine derivative colorimetric and fluorescent dual-channel probe for cyanide detection","volume":"184","author":"Yu","year":"2017","journal-title":"Spectrochim. Acta A"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.jhazmat.2008.06.051","article-title":"Cyanide in industrial wastewaters and its removal: A review on biotreatment","volume":"163","author":"Dash","year":"2009","journal-title":"J. Hazard. Mater."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"387","DOI":"10.1016\/j.jhazmat.2007.07.009","article-title":"Treatment of metal cyanide bearing wastewater by simultaneous adsorption and biodegradation (SAB)","volume":"152","author":"Dash","year":"2008","journal-title":"J. Hazard. Mater."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"788","DOI":"10.1016\/j.mineng.2011.02.012","article-title":"Belkouch, Removal of cyanide in aqueous solution by oxidation with hydrogen peroxide in presence of copper-impregnated activated carbon","volume":"24","author":"Yeddou","year":"2011","journal-title":"Miner. Eng."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1078","DOI":"10.1007\/BF02707236","article-title":"Removal of heavy metal-cyanide complexes by ion exchange","volume":"19","author":"Kim","year":"2002","journal-title":"Korean J. Chem. Eng."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"19","DOI":"10.1016\/j.aca.2011.11.050","article-title":"Ionic liquid-modified materials for solid-phase extraction and separation: A review","volume":"715","author":"Vidal","year":"2012","journal-title":"Anal. Chim. Acta"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"27","DOI":"10.1016\/j.minpro.2017.02.017","article-title":"The extraction of platinum and palladium from a synthetic cyanide heap leach solution with strong base anion exchange resins","volume":"162","author":"Schoeman","year":"2017","journal-title":"Int. J. Miner. Process."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"7811","DOI":"10.1002\/anie.201600185","article-title":"A water-stable cationic metal-organic framework as a dual adsorbent of oxoanion pollutants","volume":"55","author":"Desai","year":"2016","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"25","DOI":"10.1016\/j.pmatsci.2017.01.002","article-title":"Metal-organic frameworks: Challenges and opportunities for ion-exchange\/sorption applications","volume":"86","author":"Kumar","year":"2017","journal-title":"Prog. Mater. Sci."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"8231","DOI":"10.1039\/c2cc33707j","article-title":"Fast capture and separation of, and luminescent probe for, pollutant chromate using a multi-functional cationic heterometal-organic framework","volume":"48","author":"Shi","year":"2012","journal-title":"Chem. Commun."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"7488","DOI":"10.1021\/jacs.5b03904","article-title":"High efficiency adsorption and removal of selenate and selenite from water using metal-organic frameworks","volume":"137","author":"Howarth","year":"2015","journal-title":"J. Am. Chem. Soc."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"168","DOI":"10.1016\/j.matchemphys.2015.04.021","article-title":"Highly selective adsorbents for removal of phosphate from water and urine","volume":"160","author":"Lin","year":"2015","journal-title":"Mater. Chem. Phys."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"10","DOI":"10.1016\/j.jhazmat.2015.10.030","article-title":"Aluminium fumarate metal-organic framework: A super adsorbent for fluoride from water","volume":"303","author":"Karmakar","year":"2016","journal-title":"J. Hazard. Mater."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1008","DOI":"10.1016\/j.cej.2015.07.010","article-title":"Perchlorate removal from aqueous solution with a novel cationic metal-organic frameworks based on amino sulfonic acid ligand linking with Cu-4,4\u2032-bipyridyl chains","volume":"281","author":"Li","year":"2015","journal-title":"Chem. Eng. J."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"6012","DOI":"10.1039\/c3dt53388c","article-title":"Zinc(II) and cadmium(II) metal-organic frameworks with 4-imidazole containing tripodal ligand: Sorption and anion exchange properties","volume":"43","author":"Chen","year":"2014","journal-title":"Dalton Trans."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"412","DOI":"10.1016\/j.matlet.2015.08.004","article-title":"Facile synthesis of metal-organic framework MOF-808 for arsenic removal","volume":"160","author":"Li","year":"2015","journal-title":"Mater. Lett."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"14090","DOI":"10.1002\/chem.201403382","article-title":"Alkenyl\/thiol-derived metal-organic frameworks (MOFs) by means of postsynthetic modification for effective mercury adsorption","volume":"20","author":"Liu","year":"2014","journal-title":"Chem. Eur. J."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1732","DOI":"10.1021\/je501115m","article-title":"Adsorptive removal of Pb(II) ions from aqueous samples with amino-functionalization of metal-organic frameworks MIL-101(Cr)","volume":"60","author":"Luo","year":"2015","journal-title":"J. Chem. Eng. Data"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"15292","DOI":"10.1039\/C5TA03201F","article-title":"Functionalized metal-organic framework as a new platform for efficient and selective removal of cadmium(II) from aqueous solution","volume":"3","author":"Wang","year":"2015","journal-title":"J. Mater. Chem. A"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"2864","DOI":"10.4067\/S0717-97072016000200004","article-title":"Solvent extraction of palladium(II) from alkaline cyanide solution by the dodecyl dimethhy-2-phenoxyethyl ammonium bromide","volume":"61","author":"Liu","year":"2016","journal-title":"J. Chil. Chem. Soc."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"1699","DOI":"10.1002\/jctb.5168","article-title":"Separation and recovery of Pd(II) and Pt(II) from cyanide liquors of Pd-Pt flotation concentrate via solvent extraction","volume":"92","author":"Chen","year":"2017","journal-title":"J. Chem. Technol. Biotechnol."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"73","DOI":"10.1016\/S0304-386X(03)00047-1","article-title":"Solvent extraction and stripping of gold(I) cyanide in the tetradecyldimethylbenzylammonium chloride system","volume":"70","author":"Jiang","year":"2003","journal-title":"Hydrometallurgy"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"1107","DOI":"10.1002\/jctb.489","article-title":"Extraction and recovery of gold from KAu(CN)2 using cetyltrimethylammonium bromide microemulsions","volume":"76","author":"Zhang","year":"2001","journal-title":"J. Chem. Technol. Biotechnol."},{"key":"ref_28","doi-asserted-by":"crossref","unstructured":"Zhang, Q., Chen, M., Zhong, L., Ye, Q., Jiang, S., and Huang, Z. (2018). Highly effective removal of metal cyanide complexes and recovery of palladium using quaternary-ammonium-functionalized MOFs. Molecules, 23.","DOI":"10.3390\/molecules23082086"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"293","DOI":"10.1016\/j.cej.2014.03.107","article-title":"Removing oil droplets from water using a copper-based metal organic frameworks","volume":"249","author":"Lin","year":"2014","journal-title":"Chem. Eng. J."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"344","DOI":"10.1016\/j.jcis.2016.06.032","article-title":"Excellent performance of copper based metal organic framework in adsorptive removal of toxic sulfonamide antibiotics from wastewater","volume":"478","author":"Azhar","year":"2016","journal-title":"J. Colloid Interface Sci."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"211","DOI":"10.1016\/j.jiec.2015.02.016","article-title":"Adsorption of hexavalent chromium by metal organic frameworks from aqueous solution","volume":"28","author":"Maleki","year":"2015","journal-title":"J. Ind. Eng. Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"36","DOI":"10.1016\/j.jhazmat.2011.08.069","article-title":"Thiol-functionalization of metal-organic framework by a facile coordination-based postsynthetic strategy and enhanced removal of Hg2+ from water","volume":"196","author":"Ke","year":"2011","journal-title":"J. Hazard. Mater."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"57","DOI":"10.1016\/S0167-577X(99)00230-X","article-title":"The influence of cationic surfactants on rheological properties of bentonite-water systems","volume":"43","author":"Alemdar","year":"2000","journal-title":"Mater. Lett."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"104","DOI":"10.1021\/ic101358q","article-title":"Structures of Pd(CN)2 and Pt(CN)2: Intrinsically Nanocrystalline Materials?","volume":"50","author":"Hibble","year":"2011","journal-title":"Inorg. Chem."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"13742","DOI":"10.1039\/c2jm31536j","article-title":"Fine tuning of the metal-organic framework Cu3(BTC)2 HKUST-1 crystal size in the 100 nm to 5 micron range","volume":"22","author":"Wee","year":"2012","journal-title":"J. Mater. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"54119","DOI":"10.1039\/C6RA03317B","article-title":"Immobilization of a thiol-functionalized ionic liquid onto HKUST-1 through thiol compounds as the chemical bridge","volume":"6","author":"Chen","year":"2016","journal-title":"RSC Adv."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"436","DOI":"10.1016\/j.microc.2018.09.033","article-title":"Nanoporous metal-organic framework (MOF-199): Synthesis, characterization and photocatalytic degradation of Basic Blue 41","volume":"144","author":"Mahmoodi","year":"2019","journal-title":"Microchem. J."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"120","DOI":"10.1016\/j.jcis.2011.09.060","article-title":"Adsorption of CH4 and CO2 on Zr-metal organic frameworks","volume":"366","author":"Abid","year":"2012","journal-title":"J. Colloid Interface Sci."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"108","DOI":"10.1016\/j.micromeso.2007.09.016","article-title":"High pressure methane adsorption in the metal-organic frameworks Cu3(btc)2, Zn2(bdc)2dabco, and Cr3F(H2O)2O(bdc)3","volume":"112","author":"Senkovska","year":"2008","journal-title":"Microporous Mesoporous Mater."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"2246","DOI":"10.1039\/C3CE42390E","article-title":"Synthesis and characterization of different nanostructured copper(II) metal-organic frameworks by a ligand functionalization and modulation method","volume":"16","author":"Alavi","year":"2014","journal-title":"Crystengcomm"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"105","DOI":"10.1016\/j.elspec.2004.10.001","article-title":"Photoelectron spectroscopy study of irradiation damage and metal-sulfur bonds of thiol on silver and copper surfaces","volume":"142","author":"Laiho","year":"2005","journal-title":"J. Electron Spectrosc."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"23","DOI":"10.1016\/j.jcis.2012.09.003","article-title":"Synthesis of nanoparticle\/ligand composite thin films by sequential ligand self assembly and surface complex reduction","volume":"389","author":"Muench","year":"2013","journal-title":"J. Colloid Interface Sci."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"404","DOI":"10.1016\/j.apsusc.2016.07.095","article-title":"13C NMR and XPS characterization of anion adsorbent with quaternary ammonium groups prepared from rice straw, corn stalk and sugarcane bagasse","volume":"389","author":"Cao","year":"2016","journal-title":"Appl. Surf. Sci."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"65","DOI":"10.1016\/j.jssc.2016.10.031","article-title":"Gold nano-particle formation from crystalline AuCN: Comparison of thermal, plasma- and ion-beam activated decomposition","volume":"246","author":"Beck","year":"2017","journal-title":"J. Solid State Chem."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"685","DOI":"10.1016\/j.jcis.2016.11.100","article-title":"One-pot synthesis of binary metal organic frameworks (HKUST-1 and UiO-66) for enhanced adsorptive removal of water contaminants","volume":"490","author":"Azhar","year":"2017","journal-title":"J. Colloid Interface Sci."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"2393","DOI":"10.1081\/SS-100102345","article-title":"The effect of functional group structure on the elution of metal cyanide complexes from ion exchange resins","volume":"35","author":"Lukey","year":"2000","journal-title":"Sep. Sci. Technol."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"11","DOI":"10.1016\/j.mineng.2013.09.001","article-title":"The extraction of Pt, Pd and Au from an alkaline cyanide simulated heap leachate by granular activated carbon","volume":"55","author":"Mpinga","year":"2014","journal-title":"Miner. Eng."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"14","DOI":"10.1016\/j.mineng.2015.06.013","article-title":"Factors affecting the elution of Pt, Pd and Au cyanide from activated carbon","volume":"80","author":"Snyders","year":"2015","journal-title":"Miner. Eng."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"1621","DOI":"10.1039\/an9962101621","article-title":"Ion-pair solid-phase extraction with membranes: Group contributions and steric effects of ions on the extraction behaviour","volume":"121","author":"Taguchi","year":"1996","journal-title":"Analyst"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"211","DOI":"10.1016\/j.cej.2005.07.009","article-title":"Ion-exchange equilibria of Cu(II) and Zn(II) from aqueous solutions with Chelex 100 and Amberlite IRC 748 resins","volume":"112","author":"Lin","year":"2005","journal-title":"Chem. Eng. J."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"217","DOI":"10.1016\/S0304-386X(00)00071-2","article-title":"Selective elution of copper and iron cyanide complexes from ion exchange resins using saline solutions","volume":"56","author":"Lukey","year":"2000","journal-title":"Hydrometallurgy"},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"1921","DOI":"10.1055\/s-1999-2976","article-title":"Anti-markovnikov addition of thiols across double bonds catalyzed by H-Rho-zeolite","volume":"12","author":"Kumar","year":"1999","journal-title":"Synlett"},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"790","DOI":"10.1055\/s-0029-1219350","article-title":"Solvent-free anti-markovnikov addition of thiols to alkenes using anhydrous cerium(III) chloride as catalyst","volume":"2010","author":"Silveira","year":"2010","journal-title":"Synlett"},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"513","DOI":"10.1002\/cssc.201403022","article-title":"Alkaline stability of quaternary ammonium cations for alkaline fuel cell Membranes and Ionic Liquids","volume":"8","author":"Marino","year":"2015","journal-title":"Chemsuschem"},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"59","DOI":"10.1016\/j.molcata.2003.09.025","article-title":"Kinetic study of dichlorocyclopropanation of 4-vinyl-1-cyclohexene by a novel multisite phase transfer catalyst","volume":"210","author":"Wang","year":"2004","journal-title":"J. Mol. Catal. A Chem."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"2490","DOI":"10.1039\/C3GC42414F","article-title":"Conversion of fructose into 5-hydroxymethylfurfural catalyzed by recyclable sulfonic acid-functionalized metal\u2013Organic frameworks","volume":"16","author":"Chen","year":"2014","journal-title":"Green Chem."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/24\/15\/2779\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T13:11:28Z","timestamp":1760188288000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/24\/15\/2779"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,7,31]]},"references-count":56,"journal-issue":{"issue":"15","published-online":{"date-parts":[[2019,8]]}},"alternative-id":["molecules24152779"],"URL":"https:\/\/doi.org\/10.3390\/molecules24152779","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,7,31]]}}}