Abstract
Various toxic metal ions were successfully removed from solid matrix into supercritical CO2 (scCO2) by open-chain crown ether bridged diphosphates at 313.15 K and 20 MPa, these diphosphates with different ester side chains and different length of ethylene oxide bridge group are highly soluble in supercritical CO2. The extraction efficiency (E%) of heavy metals is between 55 and 89%. Mulliken charge distribution of ligand’s P=O coordination group was calculated to indicate the stability of metal complex. The ligand structure effects and the rationale for different selectivity were discussed. In addition, binding property of these diphosphates towards the alkaline earth metals was further studied following the same extraction procedures. Alkaline earth metal ions Ca2+, Sr2+ and Ba2+ were extracted with E% at 49–74%, 50–73% and 16–64%, respectively. DFT calculations were performed to investigate the interaction energy of the complexes and the correlation with the E% was discussed.
Funding source: Zhejiang Provincial Key R&D Program
Award Identifier / Grant number: 2018C00136
Funding source: Young Innovative Talents Program of Educational Commission of Guangdong Province
Award Identifier / Grant number: 2019GKQNCX057
Funding source: National Natural Science Foundation of China
Award Identifier / Grant number: 21436010 and 21776240
Funding source: Jieyang Science and Technology Project
Award Identifier / Grant number: 2017xm017
-
Research funding: This work is supported by National Natural Science Foundation of China (No. 21436010 and No. 21776240), Zhejiang Provincial Key R&D Program (2018C00136), Jieyang Science and Technology Project (No. 2017xm017) and Young Innovative Talents Program of Educational Commission of Guangdong Province (No. 2019GKQNCX057).
References
[1] K. Park, J. Lee, J. Sung. Chemosphere 91, 616 (2013).10.1016/j.chemosphere.2012.12.067Search in Google Scholar
[2] M. M. Matlock, K. R. Henke, D. A. Atwood. J. Hazard. Mater. 92, 129 (2002).10.1016/S0304-3894(01)00389-2Search in Google Scholar
[3] J. Wu, J. Lu, T. Chen, Z. He, Y. Su, X. Jin, X. Yao. Environ. Earth Sci. 60, 421 (2010).10.1007/s12665-009-0186-2Search in Google Scholar
[4] W. Liu, C. Weng, J. Zheng, X. Peng, J. Zhang, Z. Lin. Environ. Sci. Nano 6, 1657 (2019).10.1039/C9EN00120DSearch in Google Scholar
[5] C. M. Wai, S. Wang, Y. Liu, V. Lopez-Avila, W. F. Beckert. Talanta 43, 2083 (1996).10.1016/S0039-9140(96)01993-5Search in Google Scholar
[6] P. Hajeb, S. Jinap, S. Shakibazadeh, L. Afsah-Hejri, G. H. Mohebbi, I. S. M. Zaidul. Food Addit. Contam. Part A 31, 1712 (2014).10.1080/19440049.2014.942707Search in Google Scholar PubMed
[7] X. Yang, L. Chen, Y. Yang, Y. He, S. Zou, W. Feng, Y. Yang, N. Liu, J. Liao, L. Yuan. J. Hazard. Mater. 217-218, 171 (2012).10.1016/j.jhazmat.2012.03.010Search in Google Scholar PubMed
[8] W. Yantasee, G. E. Fryxell, R. S. Addleman, R. J. Wiacek, V. Koonsiripaiboon, K. Pattamakomsan, V. Sukwarotwat, J. Xu, K. N. Raymond. J. Hazard. Mater. 168, 1233 (2009).10.1016/j.jhazmat.2009.03.004Search in Google Scholar PubMed PubMed Central
[9] M. Atanassova. Solvent Extr. Ion Exch. 27, 159 (2009).10.1080/07366290802674655Search in Google Scholar
[10] J. A. Behles, J. M. DeSimone. Pure Appl. Chem. 73, 1281 (2001).10.1351/pac200173081281Search in Google Scholar
[11] W.-L. Chou, K.-C. Yang. J. Hazard. Mater. 154, 498 (2008).10.1016/j.jhazmat.2007.10.052Search in Google Scholar
[12] C. M. Wai, S. Wang. J. Chromatogr. A 785, 369 (1997).10.1016/S0021-9673(97)00679-1Search in Google Scholar
[13] P. B. Webb, P. C. Marr, A. J. Parsons, H. S. Gidda, S. M. Howdle. Pure Appl. Chem. 72, 1347 (2000).10.1351/pac200072071347Search in Google Scholar
[14] C. L. Phelps, N. G. Smart, C. M. Wai. J. Chem. Educ. 73, 1163 (1996).10.1021/ed073p1163Search in Google Scholar
[15] N. V. Rathod, A. Rao, P. Kumar, K. L. Ramakumar, D. D. Malkhede. Ind. Eng. Chem. Res. 54, 3933 (2015).10.1021/ie5045583Search in Google Scholar
[16] J. S. Wang, C. M. Wai, H.-K. Yak, K.-H. Chiu. Sep. Sci. Technol. 51, 1940 (2016).10.1080/01496395.2016.1185443Search in Google Scholar
[17] A. Leybros, A. Grandjean, N. Segond, M. Messalier, O. Boutin. J. Environ. Chem. Eng. 4, 1076 (2016).10.1016/j.jece.2016.01.009Search in Google Scholar
[18] J. Liu, W. Wang, G. Li. Talanta 53, 1149 (2001).10.1016/S0039-9140(00)00607-XSearch in Google Scholar
[19] B. Webb Paul, C. Marr Patricia, J. Parsons Andrew, S. Gidda Harmanjit, M. Howdle Steven. Pure Appl. Chem. 72, 1347 (2000).10.1351/pac200072071347Search in Google Scholar
[20] S. Du, G. Zhang, Z. Cui. J. Liq. Chromatogr. Relat. Technol. 28, 1487 (2005).10.1081/JLC-200058335Search in Google Scholar
[21] C. Kersch, G. F. Woerlee, G. J. Witkamp. Ind. Eng. Chem. Res. 43, 190 (2004).10.1021/ie030114uSearch in Google Scholar
[22] N. G. Smart, T. E. Carleson, S. Elshani, S. Wang, C. M. Wai. Ind. Eng. Chem. Res. 36, 1819 (1997).10.1021/ie960384vSearch in Google Scholar
[23] D. Duan, B. Su, Z. Zhang, Z. Bao, Y. Yang, Q. Ren. J. Supercrit. Fluids 81, 103 (2013).10.1016/j.supflu.2013.05.004Search in Google Scholar
[24] D. Duan, B. Su, Z. Bao, Y. Yang, Q. Ren. J. Supercrit. Fluids 147, 42 (2019).10.1016/j.supflu.2019.01.022Search in Google Scholar
[25] M. Ouchi, Y. Inoue, H. Sakamoto, A. Yamahira, M. Yoshinaga, T. Hakushi. J. Org. Chem. 48, 3168 (1983).10.1021/jo00167a007Search in Google Scholar
[26] H. Zhang, R. Li, B. Su, H. Xing, Y. Yang, Q. Ren. J. Chem. Eng. Data 57, 1991 (2012).10.1021/je300232aSearch in Google Scholar
[27] M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. MontgomeryJr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox. Gaussian 09, Revision A.02, Gaussian Inc., Wallingford, CT (2009).Search in Google Scholar
[28] S. Wang, S. Elshani, C. M. Wai. Anal. Chem. 67, 919 (1995).10.1021/ac00101a019Search in Google Scholar
[29] M. Ashraf-Khorassani, L. T. Taylor. Anal. Chim. Acta 379, 1 (1999).10.1016/S0003-2670(98)00648-5Search in Google Scholar
[30] A. V. Yazdi, E. J. Beckman. Ind. Eng. Chem. Res. 35, 3644 (1996).10.1021/ie9601211Search in Google Scholar
© 2020 IUPAC & De Gruyter. This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License. For more information, please visit: http://creativecommons.org/licenses/by-nc-nd/4.0/
Articles in the same Issue
- Frontmatter
- In this issue
- Preface
- Selected papers from the 36th International Conference on Solution Chemistry (ICSC-36)
- Conference papers
- Using computational chemistry to explore experimental solvent parameters – solvent basicity, acidity and polarity/polarizability
- Solution chemistry in the surface region of aqueous solutions
- Water confined in solutions of biological relevance
- Real-time in-situ 1H NMR of reactions in peptide solution: preaggregation of amyloid-β fragments prior to fibril formation
- Free energy profile of permeation of Entecavir through Hepatitis B virus capsid studied by molecular dynamics calculation
- Dielectric relaxation spectroscopy: an old-but-new technique for the investigation of electrolyte solutions
- Excess spectroscopy and its applications in the study of solution chemistry
- Structure of aqueous sodium acetate solutions by X-Ray scattering and density functional theory
- Desymmetrization in geometry optimization: application to an ab initio study of copper(I) hydration
- Interactions between adsorbents and adsorbates in aqueous solutions
- Modeling vapor-liquid-liquid-solid equilibrium for acetone-water-salt system
- Apparent molar volumes of sodium arsenate aqueous solution from 283.15 K to 363.15 K at ambient pressure: an experimental and thermodynamic modeling study
- Extraction of various metal ions by open-chain crown ether bridged diphosphates in supercritical carbon dioxide
- Solvation heterogeneity in ionic liquids as demonstrated by photo-chemical reactions
- The structure and composition of solid complexes comprising of Nd(III), Ca(II) and D-gluconate isolated from solutions relevant to radioactive waste disposal
- Separation of phenols from oils using deep eutectic solvents and ionic liquids
Articles in the same Issue
- Frontmatter
- In this issue
- Preface
- Selected papers from the 36th International Conference on Solution Chemistry (ICSC-36)
- Conference papers
- Using computational chemistry to explore experimental solvent parameters – solvent basicity, acidity and polarity/polarizability
- Solution chemistry in the surface region of aqueous solutions
- Water confined in solutions of biological relevance
- Real-time in-situ 1H NMR of reactions in peptide solution: preaggregation of amyloid-β fragments prior to fibril formation
- Free energy profile of permeation of Entecavir through Hepatitis B virus capsid studied by molecular dynamics calculation
- Dielectric relaxation spectroscopy: an old-but-new technique for the investigation of electrolyte solutions
- Excess spectroscopy and its applications in the study of solution chemistry
- Structure of aqueous sodium acetate solutions by X-Ray scattering and density functional theory
- Desymmetrization in geometry optimization: application to an ab initio study of copper(I) hydration
- Interactions between adsorbents and adsorbates in aqueous solutions
- Modeling vapor-liquid-liquid-solid equilibrium for acetone-water-salt system
- Apparent molar volumes of sodium arsenate aqueous solution from 283.15 K to 363.15 K at ambient pressure: an experimental and thermodynamic modeling study
- Extraction of various metal ions by open-chain crown ether bridged diphosphates in supercritical carbon dioxide
- Solvation heterogeneity in ionic liquids as demonstrated by photo-chemical reactions
- The structure and composition of solid complexes comprising of Nd(III), Ca(II) and D-gluconate isolated from solutions relevant to radioactive waste disposal
- Separation of phenols from oils using deep eutectic solvents and ionic liquids