硫杂冠醚的合成及其对废水中Ag(I)的选择性萃取研究
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摘要
针对当前含银废液综合回收利用率低,以及不当排放造成严重环境污染等问题.本研究以邻苯二酚为原料,经亲核取代、酰氯酰化、缩合反应制得一种全新结构硫杂冠醚7,10-二硫杂苯并-18-冠-6(硫杂冠醚3,Thia18C6),产物经核磁共振氢谱(~1H NMR)、X-射线衍射单晶进行了结构表征,进而采用溶剂萃取的方法考察了其对不同金属离子的选择性萃取能力.结果表明,在单一体系下,Thia18C6对银离子表现出较为优异的萃取能力,萃取率可达97.68%,而在多种杂质离子(Cu~(2+)、Pb~(2+)、Zn~(2+)和Ni~(2+))共存的复杂体系中,Thia18C6对银离子表现出了较强的选择性.
At present, silver-containing liquid waste has low recovery rate and may cause serious environmental issues. A novel thiacrown, 7,10-thia-18-crown-6(Thia18C6), was synthesized by nucleophilic substitution, chloride acylation and condensation. The structure was characterized by using proton nuclear magnetic resonance hydrogen spectrum(~1H NMR) and X-ray single crystal diffraction, and the extraction capacity and selectivity of Thia18C6 to various metal ions were further evaluated. The results showed that Thia18C6 has a high selective extraction capacity for Ag~+ with the co-existence of Cu~(2+), Pb~(2+), Zn~(2+) and Ni~(2+) ions, and exhibits an excellent extraction efficiency of 97.68% for Thia18C6 to Ag~+.
At present, silver-containing liquid waste has low recovery rate and may cause serious environmental issues. A novel thiacrown, 7,10-thia-18-crown-6(Thia18C6), was synthesized by nucleophilic substitution, chloride acylation and condensation. The structure was characterized by using proton nuclear magnetic resonance hydrogen spectrum(~1H NMR) and X-ray single crystal diffraction, and the extraction capacity and selectivity of Thia18C6 to various metal ions were further evaluated. The results showed that Thia18C6 has a high selective extraction capacity for Ag~+ with the co-existence of Cu~(2+), Pb~(2+), Zn~(2+) and Ni~(2+) ions, and exhibits an excellent extraction efficiency of 97.68% for Thia18C6 to Ag~+.
引文
陈立钦,汪玉庭.1990.硫杂冠醚的合成[J].有机化学,10(6):546-549
Celik Z,Gülfen M,Aydin A O.2010.Synthesis of a novel dithiooxamide-formaldehyde resin and its application to the adsorption and separation of silver ions[J].Journal of Hazardous Materials,174(1/3):556-562
Condomitti U,Silveira A T,Condomitti G W,et al.2014.Silver recovery using electrochemically active magnetite coated carbon particles[J].Hydrometallurgy,147-148(8):241-245
Dann J R,Chiesa P P,Jr J W G.1961.Sulfur-containing large-ring compounds.The preparation of 4,7,13,16-Tetraoxa-1,10-dithiacyclooctadecane and related compounds[J].Journal of Organic Chemistry,26(6):1991-1995
方秋生,李艳红,陈岭.2017.新型蒽并冠醚的合成及主客体键合行为[J].高等学校化学学报,38(9):1563-1567
韩建荣,张衡益,刘育.2005.双臂式苯并-15-冠-5的合成及其对金属离子的选择键合[J].高等学校化学学报,26(7):1273-1276
Han Z,Wei J,Zhao M,et al.2008.A method to recover silver from waste X-ray films with spent fixing bath[J].Hydrometallurgy,92(3/4):148-151
Hui M A,Yang T,Liu W,et al.2009.Study on reduction of silver with sodium sulfite from silver-containing liquid waste[J].Precious Metals,30(1):6-10
刘芳.2000.废液中银的回收[J].安阳师范学院学报,(4):38-39
李洲,朱屯.2008.溶剂萃取(现代分离科学与技术丛书)[M].北京:化学工业出版社.5-160
Lu X,Yin Q,Xin Z,et al.2010.Powerful adsorption of silver(I) onto thiol-functionalized polysilsesquioxane microspheres[J].Chemical Engineering Science,65(24):6471-6477
Nagai H,Suzaki Y,Osakada K.2015.Thiacrown ethers with oxygen and sulfur for coordination:formation of the Pd and Pt complexes and pseudorotaxane with dialkylammonium[J].European Journal of Inorganic Chemistry,2014(26):4376-4384
Oue M,Ishigaki A,Kimura K,et al.1985.Synthesis and cation-binding properties of poly-and bis(thiacrown ether)s[J].Journal of Polymer Science Polymer Chemistry Edition,23(7):2033-2042
Pedersen C J.1971.Crystalline complexes of macrocyclic polyethers with thiourea and related compounds[J].Journal of Organic Chemistry,36(12):254-257
秦圣英,金荣久,刘义远.1981.苯并-12-冠-4与二苯并-24-冠-8的“铸型”(模板)合成[J].化学试剂,(5):31-33
Roper E D,Talanov V S,Butcher R J.2008.Selective recognition of thallium(I) by calix[4]arene-bis(crown-6 Ether):A new talent of the known ionophore[J].Supramolecular Chemistry,20(1/2):217-229
田欢,张梦龙,王莉莎,等.2018.4,13-二硫杂苯并-18-冠-6的合成及对Ag+的选择性萃取[J].高等学校化学学报,39(6):1191-1196
Virolainen S,Tyster M,Haapalainen M,et al.2015.Ion exchange recovery of silver from concentrated base metal-chloride solutions[J].Hydrometallurgy,152:100-106
张志远,陈鸿伟,于海龙,等.2017.冠醚对准东煤水洗液中碱-碱土金属离子萃取动力学[J].煤炭学报,42(3):768-774
Zhang S,Lu W,Liu X,et al.2011.Fast and effective identification of the bioactive compounds and their targets from medicinal plants via computational chemical biology approach[J].Med Chem Commun,2(6):471-477
Zheng T X,Yide N N.2016.A cobalt supramolecular compound constructed from 4,6-Di(1-imidazolyl)- 1,3,5-triazine-2-one: Synthesis,characterization and magnetic property[J].Chemical Research in Chinese Universities,32(2):184-187
Celik Z,Gülfen M,Aydin A O.2010.Synthesis of a novel dithiooxamide-formaldehyde resin and its application to the adsorption and separation of silver ions[J].Journal of Hazardous Materials,174(1/3):556-562
Condomitti U,Silveira A T,Condomitti G W,et al.2014.Silver recovery using electrochemically active magnetite coated carbon particles[J].Hydrometallurgy,147-148(8):241-245
Dann J R,Chiesa P P,Jr J W G.1961.Sulfur-containing large-ring compounds.The preparation of 4,7,13,16-Tetraoxa-1,10-dithiacyclooctadecane and related compounds[J].Journal of Organic Chemistry,26(6):1991-1995
方秋生,李艳红,陈岭.2017.新型蒽并冠醚的合成及主客体键合行为[J].高等学校化学学报,38(9):1563-1567
韩建荣,张衡益,刘育.2005.双臂式苯并-15-冠-5的合成及其对金属离子的选择键合[J].高等学校化学学报,26(7):1273-1276
Han Z,Wei J,Zhao M,et al.2008.A method to recover silver from waste X-ray films with spent fixing bath[J].Hydrometallurgy,92(3/4):148-151
Hui M A,Yang T,Liu W,et al.2009.Study on reduction of silver with sodium sulfite from silver-containing liquid waste[J].Precious Metals,30(1):6-10
刘芳.2000.废液中银的回收[J].安阳师范学院学报,(4):38-39
李洲,朱屯.2008.溶剂萃取(现代分离科学与技术丛书)[M].北京:化学工业出版社.5-160
Lu X,Yin Q,Xin Z,et al.2010.Powerful adsorption of silver(I) onto thiol-functionalized polysilsesquioxane microspheres[J].Chemical Engineering Science,65(24):6471-6477
Nagai H,Suzaki Y,Osakada K.2015.Thiacrown ethers with oxygen and sulfur for coordination:formation of the Pd and Pt complexes and pseudorotaxane with dialkylammonium[J].European Journal of Inorganic Chemistry,2014(26):4376-4384
Oue M,Ishigaki A,Kimura K,et al.1985.Synthesis and cation-binding properties of poly-and bis(thiacrown ether)s[J].Journal of Polymer Science Polymer Chemistry Edition,23(7):2033-2042
Pedersen C J.1971.Crystalline complexes of macrocyclic polyethers with thiourea and related compounds[J].Journal of Organic Chemistry,36(12):254-257
秦圣英,金荣久,刘义远.1981.苯并-12-冠-4与二苯并-24-冠-8的“铸型”(模板)合成[J].化学试剂,(5):31-33
Roper E D,Talanov V S,Butcher R J.2008.Selective recognition of thallium(I) by calix[4]arene-bis(crown-6 Ether):A new talent of the known ionophore[J].Supramolecular Chemistry,20(1/2):217-229
田欢,张梦龙,王莉莎,等.2018.4,13-二硫杂苯并-18-冠-6的合成及对Ag+的选择性萃取[J].高等学校化学学报,39(6):1191-1196
Virolainen S,Tyster M,Haapalainen M,et al.2015.Ion exchange recovery of silver from concentrated base metal-chloride solutions[J].Hydrometallurgy,152:100-106
张志远,陈鸿伟,于海龙,等.2017.冠醚对准东煤水洗液中碱-碱土金属离子萃取动力学[J].煤炭学报,42(3):768-774
Zhang S,Lu W,Liu X,et al.2011.Fast and effective identification of the bioactive compounds and their targets from medicinal plants via computational chemical biology approach[J].Med Chem Commun,2(6):471-477
Zheng T X,Yide N N.2016.A cobalt supramolecular compound constructed from 4,6-Di(1-imidazolyl)- 1,3,5-triazine-2-one: Synthesis,characterization and magnetic property[J].Chemical Research in Chinese Universities,32(2):184-187