Thinking in terms of structure-activity-relationships (T-SAR): A tool to better understand nanofiltration membranes

Membranes

Volumn 1, Issue 3, 2011, Pages 162-183

  Fernández, José F ^a   Jastorff, Bernd ^a   Störmann, Reinhold ^a,b   Stolte, Stefan ^a   Thöming, Jorg ^a  

^a UNIVERSITY OF BREMEN   (Germany)

^b Cheops GmbH   (Germany)

Author keywords

Characterization method; Ionic liquid; Molecular interaction potential; Nanofiltration; Performance; Property; Reactivity; Stereochemistry; Structure activity relationships

Indexed keywords

CHEMICAL ANALYSIS; IONIC LIQUIDS; MEMBRANE TECHNOLOGY; MEMBRANES; MOLECULAR INTERACTIONS; MOLECULAR STRUCTURE; NANOFILTRATION; REACTIVITY (NUCLEAR); SOLUTIONS; STEREOCHEMISTRY; STEREOSELECTIVITY;

CHARACTERIZATION METHODS; HYDROPHOBIC IONIC LIQUID; INTERACTION POTENTIALS; MEMBRANE CHARACTERISTICS; PERFORMANCE; PROPERTY; SEPARATION PERFORMANCE; STRUCTURE ACTIVITY RELATIONSHIPS;

NANOFILTRATION MEMBRANES;

EID: 80053213965     PISSN: None     EISSN: 20770375     Source Type: Journal    
DOI: 10.3390/membranes1030162     Document Type: Article

References (49)

1. Freemantle, M. An Introduction to Ionic Liquids, 1st ed.; Royal Society of Chemistry: Cambridge, UK, 2010.
2. Plechkova, N.V.; Seddon, K.R. Applications of ionic liquids in the chemical industry. Chem. Soc. Rev. 2008, 37, 123-150.
3. Fernández, J.F.; Neumann, J.; Thöming, J. Regeneration, recovery and removal of ionic liquids. Curr. Org. Chem. 2011, 15, 1992-2014.
4. Kröckel, J.; Kragl, U. Nanofiltration for the separation of non-volatile products from solutions containing ionic liquids. Chem. Eng. Technol. 2003, 26, 1166-1168.
5. Jastorff, B.; Störmann, R.; Wölcke, U. Struktur-Wirkungs-Denken in der Chemie-eine Chance für mehr Nachhaltigkeit; Universitätsverlag Aschenbeck und Isensee: Oldenburg, Germany, 2003.
6. Jastorff, B.; Störmann, R.; Ranke, J. Thinking in structure-activity-relationships-A way forward towards sustainable chemistry. Clean Soil Air Water 2007, 35, 399-405.
7. Jastorff, B.; Störmann, R.; Ranke, J.; Mölter, K.; Stock, F.; Oberheitmann, B.; Hoffmann, W.; Hoffmann, J.; Nüchter, M.; Ondruschka, B.; et al. How hazardous are ionic liquids? Structure-activity-relationships and biological testing as important elements for sustainability evaluation. Green Chem. 2003, 5, 136-142.
8. Stolte, S.; Arning, J.; Bottin-Weber, U.; Matzke, M.; Stock, F.; Thiele, K.; Uerdingen, M.; Welz-Biermann, U.; Jastorff, B.; Ranke, J. Anion effects on the cytotoxicity of ionic liquids. Green Chem. 2006, 8, 621-629.
9. Arning, J.; Stolte, S.; Böschen, A.; Stock, F.; Pitner, W.R.; Welz-Biermann, U.; Jastorff, B.; Ranke, J. Qualitative and quantitative structure-activity-relationships for the inhibitory effects of cationic head groups, functionalised side chains and anions of ionic liquids on acetylcholinesterase. Green Chem. 2008, 10, 47-58.
10. Doose, C.A.; Ranke, J.; Stock, F.; Bottin-Weber, U.; Jastorff, B. Structure-activity-relationships of pyrithiones-IPC-81 toxicity tests with the antifouling biocide zinc pyrithione und structural analogs. Green Chem. 2004, 6, 259-266.
11. Arning, J.; Dringen, R.; Schmidt, M.; Thiessen, A.; Stolte, S.; Matzke, M.; Bottin-Weber, U.; Caesar-Geertz, B.; Jastorff, B.; Ranke, J. Structure-activity-relationships for the impact of selected isothiazol-3-one biocides on glutathione metabolism and glutathione reductase of the human liver cell line Hep G2. Toxicology 2008, 246, 203-212.
12. Weinhold, M.X.; Sauvageau, J.C.M.; Keddig, N.; Matzke, M.; Tartsch, B.; Grunwald, I.; Kübel, C.; Jastorff, B.; Thöming, J. Strategy to improve the characterization of chitosan for sustainable biomedical applications: SAR guided multi-dimensional analysis. Green Chem. 2009, 11, 498-509.
13. United Federation of Teachers-Universität Bremen. The UFT/Merck Ionic Liquids Biological Effects Database. Centre for Environmental Research and Technology (UFT): Bremen, Germany, 2011. Available online: http://www.il-eco.uft.uni-bremen.de/ (accessed on 24 May 2011).
14. Dow FilmTec Membranes. Basics of RO and NF: Membrane description. Tech Manual Excerpt Form No. 609-02004-504. The Dow Chemical Company: Midland, MI, USA, 2011. Available online: http://msdssearch.dow.com/PublishedLiteratureDOWCOM/dh_0042/0901b80380042dd8.pdf (accessed on 2 July 2011).
15. Cadotte, J.E. Reverse osmosis membrane. US Patent 4,259,183, 1981.
16. Cadotte, J.E. Interfacially synthesized reverse osmosis membrane. US Patent 4,277,344, 1981.
17. Williams, R. PKa Data. Available online: http://research.chem.psu.edu/brpgroup/pKa_compilation.pdf (accessed on 24 May 2011).
18. Harkema, S.; Gaymans, R.J. N,N'-(p-phenylene)dibenzamide. Acta Crystallogr. 1977, B33, 3609-3611.
19. Motherwell, W.D.S.; Shields, G.P.; Allen, F.H. Graph-set and packing analysis of hydrogen-bonded networks in polyamide structures in the Cambridge Structural Database. Acta Crystallogr. 2000, B56, 857-871.
20. Zheng, P.; Wang, W.; Duan, X. N,N'-Dibenzoylpiperazine. Acta Crystallogr. 2005, E61, 02513-02514.
21. Miron, Y.; McGarvey, B.R.; Morawetz, H. Rates of conformational transitions in solutions of randomly coiled polymers. I. Nuclear magnetic resonance study of transitions in the backbone of polyamides. Macromolecules 1969, 2, 154-161.
22. Kosobutskii, V.A.; Kagan, G.I.; Belyakov, V.K.; Tarakanov, O.G. Amide-imidol tautomerism in aromatic polyamides. J. Struct. Chem. 1972, 12, 753-760.
23. Tang, C.Y.; Kwon, Y.N.; Leckie, J.O. Effect of membrane chemistry and coating layer on physicochemical properties of thin film composite polyamide RO and NF membranes. I. FTIR and XPS characterization of polyamide and coating layer chemistry. Desalination 2009, 242, 149-167.
24. Tang, C.Y.; Kwon, Y.N.; Leckie, J.O. Effect of membrane chemistry and coating layer on physicochemical properties of thin film composite polyamide RO and NF membranes. II. Membrane physicochemical properties and their dependence on polyamide and coating layers. Desalination 2009, 242, 168-182.
25. Rayne, S.; Forest, K.; Friesen, K. Examining the PM6 semiempirical method for pKa prediction across a wide range of oxyacids. Nature Precedings 2009. Available online: http://precedings.nature.com/documents/2981/version/1 (accessed on 24 May 2011).
26. SciFinder. CAS: Columbus, OH, USA, 2011. Available online: http://scifinder.cas.org/ (accessed on 24 May 2011).
27. Hilal, N.; Al-Zoubi, H.; Darwish, N.A.; Mohammad, A.W. Characterisation of nanofiltration membranes using atomic force microscopy. Desalination 2005, 177, 187-199.
28. Boussu, K.; Zhang, Y.; Cocquyt, J.; van der Meeren, P.; Volodin, A.; van Haesendonck, C.; Martens, J.A.; van der Bruggen, B. Characterization of polymeric nanofiltration membranes for systematic analysis performance. J. Membr. Sci. 2006, 278, 418-427.
29. Artug, G.; Roosmasari, I.; Richau, K.; Hapke, J. A comprehensive characterization of commercial nanofiltration membranes. Sep. Sci. Technol. 2007, 42, 2947-2986.
30. Petersen, R.J. Composite reverse osmosis and nanofiltration membranes. J. Membr. Sci. 1993, 83, 81-150.
31. Nghiem, L.D.; Schäfer, A.I.; Elimelech, M. Removal of natural hormones by nanofiltration membranes: Measurement, modelling, and mechanisms. Environ. Sci. Technol. 2004, 38, 1888-1896.
32. Bowen, W.R.; Mohammad, A.W.; Hilal, N. Characterisation of nanofiltration membranes for predictive purposes-Use of salts, uncharged solutes and atomic force microscopy. J. Membr. Sci. 1997, 126, 91-105.
33. Zhang, Y.; Xiao, C.; Liu, E.; Du, Q.; Wang, X.; Yu, H. Investigations on the structures and performances of a polypiperazine amide/polysulfone composite membrane. Desalination 2006, 191, 291-295.
34. Gevers, L.E.M.; Meyen, G.; De Smet, K.; van de Velde, P.; Du Prez, F.; Vankelecom, I.F.J.; Jacobs, P.A. Physico-chemical interpretation of the SRNF transport mechanism for solutes through dense silicone membranes. J. Membr. Sci. 2006, 274, 173-182.
35. Norberg, D.; Hong, S.; Taylor, J.; Zhao, Y. Surface characterization and performance evaluation of commercial fouling resistant low-pressure RO membranes. Desalination 2007, 202, 45-52.
36. Nghiem, L.D.; Schäfer, A.I.; Elimelech, M. Nanofiltration of hormone mimicking trace organic contaminants. Sep. Sci. Technol. 2005, 40, 2633-2649.
37. Simon, A.; Nghiem, L.D.; Le-Clech, P.; Khan, S.J.; Drewes, J.E. Effects of membrane degradation on the removal of pharmaceutically active compounds (PhACs) by NF/RO filtration processes. J. Membr. Sci. 2009, 340, 16-25.
38. Nghiem, L.D. Removal of Emerging Trace Organic Contaminants by Nanofiltration and Reverse Osmosis. Ph.D. Thesis, University of Wollongong: Bega, Australia, 2005.
39. Vankelecom, I.F.J.; De Smet, K.; Gevers, L.E.M.; Jacobs, P.A. Nanofiltration membranes materials and preparation. In Nanofiltration: Principles and Applications, 1st ed.; Schäfer, A.I., Fane, A.G., Walte, T.D., Eds.; Elselvier Ltd.: Oxford, UK, 2005; pp. 33-65.
40. Eckstein, M.; Villela Filho, M.; Liese, A.; Kragl, U. Use of an ionic liquid in a two-phase system to improve an alcohol dehydrogenase catalysed reduction. Chem. Commun. 2004, 9, 1084-1085.
41. Hussain, W.; Pollard, D.J.; Truppo, M.; Lye, G.J. Enzymatic ketone reductions with co-factor recycling: Improved reactions with ionic liquid co-solvents. J. Mol. Catal. B: Enzym. 2008, 55, 19-29.
42. Pfruender, H.; Amidjojo, M.; Kragl, U.; Weuster-Botz, D. Efficient whole-cell biotransformation in a biphasic ionic liquid/water system. Angew. Chem., Int. Ed. 2004, 43, 4529-4531.
43. Pfruender, H.; Jones, R.; Weuster-Botz, D. Water immiscible ionic liquids as solvents for whole cell biocatalysis. J. Biotechnol. 2006, 124, 182-190.
44. Bräutigam, S.; Bringer-Meyer, S.; Weuster-Botz, D. Asymmetric whole cell biotransformations in biphasic ionic liquid/water systems by use of recombinant Escherichia coli with intracellular cofactor regeneration. Tetrahedron Asymmetry 2007, 18, 1883-1887.
45. Bräutigam, S.; Dennewald, D.; Schürmann, M.; Lutje-Spelberg, J.; Pitner, W.R.; Weuster-Botz, D. Whole-cell biocatalysis: Evaluation of new hydrophobic ionic liquids for efficient asymmetric reduction of prochiral ketones. Enzyme Microb. Technol. 2009, 45, 310-316.
46. Dennewald, D.; Pitner, W.R.; Weuster-Botz, D. Recycling of the ionic liquid phase in process integrated biphasic whole-cell biocatalysis. Process Biochem. 2011, 46, 1132-1137.
47. Preiss, U.P.R.M.; Slaterry, J.M.; Krossing, I. In silico prediction of molecular volumes, heat capacities, and temperature-dependent densities of ionic liquids. Ind. Eng. Chem. Res. 2009, 48, 2290-2296.
48. Preiss, U.; Emel'yanenko, V.N.; Verevkin, S.P.; Himmel, D.; Paulechka, Y.U.; Krossing, I. Temperature-dependent prediction of the liquid entropy of ionic liquids. Eur. J. Chem. Phys. Phys. Chem. 2010, 11, 3425-3431.
49. Ranke, J.; Müller, A.; Bottin-Weber, U.; Stock, F.; Stolte, S.; Arning, J.; Störmann, R.; Jastorff, B. Liphophilicity parameters for ionic liquid cations and their correlation to in vitro cytotoxicity. Ecotoxicol. Environ. Saf. 2007, 67, 430-438.