Understanding the role of cholinium carboxylate ionic liquids in PEG-based aqueous biphasic systems

ACS Sustainable Chemistry and Engineering

Volumn 2, Issue 10, 2014, Pages 2426-2434

  Mourão, Teresa ^a   Tomé, Liliana C ^a   Florindo, Catarina ^a   Rebelo, Luís Paulo N ^a   Marrucho, Isabel M ^a  

^a INSTITUTO DE TECNOLOGIA QUÍMICA E BIOLÓGICA   (Portugal)

Author keywords

Antioxidants; Aqueous biphasic systems; Cholinium carboxylate ionic liquids; Poly(ethylene glycol) (PEG)

Indexed keywords

ALIPHATIC COMPOUNDS; ANTIOXIDANTS; CARBOXYLATION; ETHYLENE GLYCOL; MOLECULAR WEIGHT; NEGATIVE IONS; POLYETHYLENE GLYCOLS; POLYOLS; SOLVENT EXTRACTION;

ALKYL CHAIN LENGTHS; AQUEOUS BIPHASIC SYSTEM; EXTRACTION/SEPARATION; LOW MOLECULAR WEIGHT; NATURAL COMPOUNDS; PHASE SPLITTING; SEPARATION PROCESS; TERT-BUTYLHYDROQUINONE (TBHQ);

IONIC LIQUIDS;

EID: 84907841893     PISSN: None     EISSN: 21680485     Source Type: Journal    
DOI: 10.1021/sc500444w     Document Type: Article

References (42)

1. Ragauskas, A. J.; Davison, B. H.; Liotta, C. L.; Mielenz, J. R.; H.Templer, R.; Tschaplinski, T. J. The path forward for biofuels and biomaterials Science 2006, 311, 484-489
2. Owen, N. A.; Inderwildi, O. R.; King, D. A. The status of conventional world oil reserves: Hype or cause for concern? Energy Policy 2010, 38 (8) 4743-4749
3. Raja, S.; Murty, V. R.; Thivaharan, V.; Rajasekar, V.; Ramesh, V. Aqueous two phase systems for the recovery of biomolecules-A review Sci. Technol. 2011, 1, 7-16
4. Martínez-Aragón, M.; Burghoff, S.; Goetheer, E. L. V.; de Haan, A. B. Guidelines for solvent selection for carrier mediated extraction of proteins Sep. Purif. Technol. 2009, 65 (1) 65-72
5. Rydberg, J.; Cox, M.; Musikas, C.; Choppin, G. R. Principles and Practices of Solvent Extraction; Marcel Dekker, Inc.: New York, 1992.
6. Patinha, D. J. S.; Alves, F.; Rebelo, L. P. N.; Marrucho, I. M. Ionic liquids based aqueous biphasic systems: Effect of the alkyl chains in the cation versus in the anion J. Chem. Thermodyn. 2013, 65, 106-112
7. Pereira, J. F. B.; Vicente, F.; Santos-Ebinuma, V. C.; Araújo, J. M.; Pessoa, A.; Freire, M. G.; Coutinho, J. A. P. Extraction of tetracycline from fermentation broth using aqueous two-phase systems composed of polyethylene glycol and cholinium-based salts Process Biochem. 2013, 48, 716-722
8. Deive, F. J.; Rodriguez, A.; Pereiro, A. B.; Araujo, J. M. M.; Longo, M. A.; Coelho, M. A. Z.; Lopes, J. N. C.; Esperanca, J. M. S. S.; Rebelo, L. P. N.; Marrucho, I. M. Ionic liquid-based aqueous biphasic system for lipase extraction Green Chem. 2011, 13 (2) 390-396
9. Deive, F. J.; Rodríguez, A.; Rebelo, L. P. N.; Marrucho, I. M. Extraction of Candida antarctica lipase A from aqueous solutions using imidazolium-based ionic liquids Sep. Purif. Technol. 2012, 97 (0) 205-210
10. Freire, M. G.; Neves, C. M. S. S.; Marrucho, I. M.; Lopes, J. N. C.; Rebelo, L. P. N.; Coutinho, J. A. P. High-performance extraction of alkaloids using aqueous two-phase systems with ionic liquids Green Chem. 2010, 12 (10) 1715-1718
11. Ribeiro, B. D.; Coelho, M. A. Z.; Rebelo, L. P. N.; Marrucho, I. M. Ionic liquids as additives for extraction of saponins and polyphenols from mate (Ilex paraguariensis) and tea (Camellia sinensis) Ind. Eng. Chem. Res. 2013, 52 (34) 12146-12153
12. Freire, M. G.; Claudio, A. F. M.; Araujo, J. M. M.; Coutinho, J. A. P.; Marrucho, I. M.; Lopes, J. N. C.; Rebelo, L. P. N. Aqueous biphasic systems: A boost brought about by using ionic liquids Chem. Soc. Rev. 2012, 41, 4966-4995
13. Albertsson, P. A. Partition of Cell Particles and Macromolecules; Wiley: New York, 1986.
14. Gutowski, K. E.; Broker, G. A.; Willauer, H. D.; Huddleston, J. G.; Swatloski, R. P.; Holbrey, J. D.; Rogers, R. D. Controlling the aqueous miscibility of ionic liquids: Aqueous biphasic systems of water-miscible ionic liquids and water-structuring salts for recycle, metathesis, and separations J. Am. Chem. Soc. 2003, 125 (22) 6632-6633
15. Docherty, K. M.; Kulpa, J. C. F. Toxicity and antimicrobial activity of imidazolium and pyridinium ionic liquids Green Chem. 2005, 7 (4) 185-189
16. Ranke, J.; Müller, A.; Bottin-Weber, U.; Stock, F.; Stolte, S.; Arning, J.; Störmann, R.; Jastorff, B. Lipophilicity parameters for ionic liquid cations and their correlation to in vitro cytotoxicity Ecotox. Environ. Safe 2007, 67 (3) 430-438
17. Li, Z.; Liu, X.; Pei, Y.; Wang, J.; He, M. Design of environmentally friendly ionic liquid aqueous two-phase systems for the efficient and high activity extraction of proteins Green Chem. 2012, 14 (10) 2941-2950
18. Petkovic, M.; Seddon, K. R.; Rebelo, L. P. N.; Silva Pereira, C. Ionic liquids: A pathway to environmental acceptability Chem. Soc. Rev. 2011, 40 (3) 1383-1403
19. Fukaya, Y.; Iizuka, Y.; Sekikawa, K.; Ohno, H. Bio ionic liquids: Room temperature ionic liquids composed wholly of biomaterials Green Chem. 2007, 9 (11) 1155-1157
20. Ohno, H.; Fukumoto, K. Amino acid ionic liquids Acc. Chem. Res. 2007, 40 (11) 1122-1129
21. Yu, Y.; Lu, X.; Zhou, Q.; Dong, K.; Yao, H.; Zhang, S. Biodegradable naphthenic acid ionic liquids: Synthesis, characterization, and quantitative structure-biodegradation relationship Chem.-Eur. J. 2008, 14 (35) 11174-11182
22. Petkovic, M.; Ferguson, J. L.; Gunaratne, H. Q. N.; Ferreira, R.; Leitao, M. C.; Seddon, K. R.; Rebelo, L. P. N.; Pereira, C. S. Novel biocompatible cholinium-based ionic liquids-toxicity and biodegradability Green Chem. 2010, 12 (4) 643-649
23. Weaver, K. D.; Kim, H. J.; Sun, J.; MacFarlane, D. R.; Elliott, G. D. Cyto-toxicity and biocompatibility of a family of choline phosphate ionic liquids designed for pharmaceutical applications Green Chem. 2010, 12 (3) 507-513
24. Blusztajn, J. K. Choline, a vital amine Science 1998, 281 (5378) 794-795
25. Nockemann, P.; Thijs, B.; Driesen, K.; Janssen, C. R.; Van Hecke, K.; Van Meervelt, L.; Kossmann, S.; Kirchner, B.; Binnemans, K. Choline saccharinate and choline acesulfamate: Ionic liquids with low toxicities J. Phys. Chem. B 2007, 111 (19) 5254-5263
26. Shahriari, S.; Tomé, L. C.; Araujo, J. M. M.; Rebelo, L. P. N.; Coutinho, J. A. P.; Marrucho, I. M.; Freire, M. G. Aqueous biphasic systems: A benign route using cholinium-based ionic liquids RSC Adv. 2013, 3 (6) 1835-1843
27. Neves, C. M. S. S.; Ventura, S. P. M.; Freire, M. G.; Marrucho, I. M.; Coutinho, J. A. P. Evaluation of cation influence on the formation and extraction capability of ionic-liquid-based aqueous biphasic systems J. Phys. Chem. B 2009, 113 (15) 5194-5199
28. Ventura, S. P. M.; Neves, C. M. S. S.; Freire, M. G.; Marrucho, I. M.; Oliveira, J.; Coutinho, J. A. P. Evaluation of anion influence on the formation and extraction capacity of ionic-liquid-based aqueous biphasic systems J. Phys. Chem. B 2009, 113 (27) 9304-9310
29. Passos, H.; Sousa, A. C. A.; Pastorinho, M. R.; Nogueira, A. J. A.; Rebelo, L. P. N.; Coutinho, J. A. P.; Freire, M. G. Ionic-liquid-based aqueous biphasic systems for improved detection of bisphenol A in human fluids Anal. Methods 2012, 4 (9) 2664-2667
30. Liu, X.; Li, Z.; Pei, Y.; Wang, H.; Wang, J. (Liquid-liquid) equilibria for (cholinium-based ionic liquids + polymers) aqueous two-phase systems J. Chem. Thermodyn. 2013, 60, 1-8
31. Pereira, J. F. B.; Kurnia, K. A.; Cojocaru, O. A.; Gurau, G.; Rebelo, L. P. N.; Rogers, R. D.; Freire, M. G.; Coutinho, J. A. P. Molecular interactions in aqueous biphasic systems composed of polyethylene glycol and crystalline vs. liquid cholinium-based salts Phys. Chem. Chem. Phys. 2014, 16 (12) 5723-5731
32. Freire, M. G.; Pereira, J. F. B.; Francisco, M.; Rodríguez, H.; Rebelo, L. P. N.; Rogers, R. D.; Coutinho, J. A. P. Insight into the interactions that control the phase behaviour of new aqueous biphasic systems composed of polyethylene glycol polymers and ionic liquids Chem.-Eur. J. 2012, 18 (6) 1831-1839
33. Tome, L. I. N.; Pereira, J. F. B.; Rogers, R. D.; Freire, M. G.; Gomes, J. R. B.; Coutinho, J. A. P. "Washing-out" ionic liquids from polyethylene glycol to form aqueous biphasic systems Phys. Chem. Chem. Phys. 2014, 16 (6) 2271-2274
34. Pinchuk, I.; Shoval, H.; Dotan, Y.; Lichtenberg, D. Evaluation of antioxidants: Scope, limitations and relevance of assays Chem. Phys. Lipids 2012, 165 (6) 638-647
35. Carocho, M.; Ferreira, I. C. F. R. A review on antioxidants, prooxidants and related controversy: Natural and synthetic compounds, screening and analysis methodologies and future perspectives Food Chem. Toxicol. 2013, 51, 15-25
36. Sindhi, V.; Gupta, V.; Sharma, K.; Bhatnagar, S.; Kumari, R.; Dhaka, N. Potential applications of antioxidants-A review J. Pharm. Res. 2013, 7 (9) 828-835
37. Goulart, L. A.; Teixeira, A. R. L.; Ramalho, D. A.; Terezo, A. J.; Castilho, M. Development of an analytical method for the determination of tert-butylhydroquinone in soybean biodiesel Fuel 2014, 115, 126-131
38. Eskandani, M.; Hamishehkar, H.; Ezzati Nazhad Dolatabadi, J. Cytotoxicity and DNA damage properties of tert-butylhydroquinone (TBHQ) food additive Food Chem. 2014, 153, 315-320
39. Tomé, L. C.; Patinha, D. J. S.; Ferreira, R.; Garcia, H.; Silva Pereira, C.; Freire, C. S. R.; Rebelo, L. P. N.; Marrucho, I. M. Cholinium-based supported ionic liquid membranes: A sustainable route for carbon dioxide separation ChemSusChem 2014, 7 (1) 110-113
40. Deive, F. J.; Rodríguez, A.; Marrucho, I. M.; Rebelo, L. P. N. Aqueous biphasic systems involving alkylsulfate-based ionic liquids J. Chem. Thermodyn. 2011, 43 (11) 1565-1572
41. Marcus, Y. Thermodynamics of solvation of ions. Part 5. Gibbs free energy of hydration at 298.15 K J. Chem. Soc., Faraday Trans. 1991, 87 (18) 2995-2999
42. - in polyethylene/poly(propylene glycol)-based aqueous biphasic systems J. Chromatogr., Biomed. Appl. 1996, 680 (1-2) 231-236