Abstract
An ionic liquid-salt aqueous two-phase system (ILATPS) based on the hydrophilic ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate ([Bmim]BF4) and inorganic salt was developed for direct separation and analysis of macrolide antibiotics coupled with molecular fluorescence spectrophotometry. Liquid–liquid equilibria of [Bmim]BF4-salt aqueous two-phase systems were studied for different salts and temperatures. It was found that the salting-out ability of different salts may be related to the Gibbs energy of hydration of the ions, and the two-phase area was expanded with a decrease in temperature. The partition coefficients as well as extraction efficiencies of azithromycin and mydecamycin in [Bmim]BF4-salt aqueous two-phase system were influenced by the types of salts, concentration of salt, and the extracting temperature. Under the optimum conditions, the average partition coefficient of azithromycin in [Bmim]BF4-Na2CO3 ILATPS was 162, and that of mydecamycin in [Bmim]BF4- NaH2PO4 ILATPS was 90.9. This method has been satisfactorily applied to the determination of azithromycin and mydecamycin in real water samples with detection limits of 0.059 µg mL−1 and 0.019 µg mL−1. This extraction method is a simple, non-toxic and effective sample pretreatment technique with promise also for the separation of other small biomolecules.
Similar content being viewed by others
References
Lo TC (1996) Handbook of separations techniques for chemical engineers. In: Schwietzer PA (ed). McGraw-Hill, New York
Yin HQ, Mao M, Huang JB, Fu HL (2002) Two-phase region in the DTAB /SL mixed surfactant system. Langmiur 18:9198
Cai YQ, Cai Y, Shi YL, Liu JM, Mou SF, Lu YQ (2007) A liquid–liquid extraction technique for phthalate esters with water-soluble organic solvents by adding inorganic salts. Microchim Acta 157:73–79
Chen J, Ma GX, Li DQ (1999) HPCPC separation of proteins using polyethylene glycol-potassium phosphate aqueous two-phase. Prep Biochem Biotechnol 29:371
Rogers RD, Bauer CB (1996) Partitioning behavior of Group 1 and 2 cations in poly (ethylene glycol)-based aqueous biphasic systems. J Chromatogr B 680:237
Willauer HD, Huddleston JG, Rogers RD (2002) Solute partitioning in aqueous biphasic systems composed of polyethylene glycol and salt: the partitioning of small neutral organic species. Ind Eng Chem Res 41:1892
Helfrich MR, EI-Kouedi M, Etherton MR, Keating CD (2005) Partitioning and assembly of metal particles and their bioconjugates in aqueous two-phase systems. Langmuir 21:8478
Chen J, Spear SK, Huddleston JG, Rogers RD (2005) Polyethylene glycol and solutions of polyethylene glycol as green reaction media. Green Chem 7:4
Sheldon R (2001) Catalytic reactions in ionic liquids. Chem Commun 2399
Dupont J, de Souza RF, Suarez PAZ (2002) Ionic liquid (molten salt) phase organometallic catalysis. Chem Rev 102:3667
Huddleston JG, Willauer HD, Swatloski RP, Visser AE, Rogers RD (1998) Room temperature ionic liquids as novel media for ‘clean’ liquid–liquid extraction. Chem Commun 1765
Swatloski RP, Spear SK, Holbrey JD, Rogers RD (2002) Dissolution of cellose with ionic liquids. J Am Chem Soc 124:4974
Anderson JL, Ding J, Welton T, Armstrong DW (2002) Characterizing ionic liquids on the basis of multiple solvation interactions. J Am Chem Soc 124:14247
Gutowski KE, Broker GA, Willauer HD, Huddleston JG, Swatloski RP, Holbrey JD, Rogers RD (2003) 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 125:6632
Pei YC, Wang JJ, Liu L, Wu K, Zhao Y (2007) Liquid–liquid equilibria of aqueous biphasic systems containing selected imidazolium ionic liquids and salts. J Chem Eng Data 52:2026
Zafarani-Moattar MT, Hamzehzadeh S (2007) Liquid–liquid equilibria of aqueous two-phase systems containing 1-butyl-3-methylimidazolium bromide and potassium phosphate or dipotassium hydrogen phosphate at 298.15 K. J Chem Eng Data 52:1686
Deng Y, Chen J, Zhang D (2007) Phase diagram data for several salt + salt aqueous biphasic systems at 298.15 K. J Chem Eng Data 52:1332
Bridges NJ, Gutowski KE, Rogers RD (2007) Investigation of aqueous biphasic systems formed from solutions of chaotropic salts with kosmotropic salts (salt-salt ABS). Green Chem 9:177
Zafarani-Moattar MT, Hamzehzadeh S (2009) Phase diagrams for the aqueous two-phase ternary system containing the ionic liquid 1-butyl-3- methylimidazolium bromide and tri-potassium citrate at T = (278.15, 298.15 and 318.15)K. J Chem Eng Data 54:833
He C, Li S, Liu H, Li K, Liu F (2005) Extraction of testosterone and epitestosterone in human urine using aqueous two-phase systems of ionic liquid and salt. J Chromatogr A 1082:143–149
Li S, He C, Liu H, Li K, Liu F (2005) Ionic liquid-based aqueous two-phase system, a sample pretreatment procedure prior to high-performance liquid chromatography of opium alkaloids. J Chromatogr B 826:58
Du Z, Yu Y, Wang J (2007) Extraction of proteins from biological fluids by use of an ionic liquid/aqueous two-phase system. Chem Eur J 13:2130
Liu QF, Yu J, Li WL, Hu XS, Xia HS, Liu HZ, Yang P (2006) Partitioning behavior of penicillin G in aqueous two phase system formed by ionic liquids and phosphate. Sep Sci Technol 41:2849
Soto A, Arce A, Khoshkbarchi MK (2005) Partitioning of antibiotics in a two-liquid phase system formed by water and a room temperature ionic liquid. Sep Purif Technol 44:242
Horie M, Takegami H, Toya K, Nakazawa H (2003) Determination of macrolide antibiotics in meat and fish by liquid chromatography–electrospray mass spectrometry. Anal Chim Acta 49:2187
Kanfer I, Skinner MF, Walker RB (1998) Analysis of macrolide antibiotics. J Chromatogr A 812:255
Omura S (Ed) Macrolide antibiotics: chemistry, biology and practice. Academic, Orlando, 1984, p 26
Wu B, Zhang YM, Wang HP (2008) Phase behavior for ternary systems composed of ionic liquid + saccharides + water. J Phys Chem B 112:426
Marcus Y (1993) Thermodynamics of solvation of ions: Part 6. The standard partial molar volumes of aqueous ions at 298.15 K. J Chem Soc Faraday Trans 89:713
Marcus Y (1991) Thermodynamics of solvation of ions: Part 5. Gibbs free energy of hydration at 298.15 K. J Chem Soc Faraday Trans 87:2995
Li CX, Han J, Wang Y, Yan YS, Pan JM, Xu XH, Zhang ZL (2009) Phase behavior for the aqueous two-phase systems containing the ionic liquid 1- butyl-3-methylimidazolium tetrafluoroborate and kosmotropic salts. J Chem Eng Data. In press, doi:10.1021/je900533h
Trindade JR, Visak ZP, Blesic M, Marrucho IM, Coutinho João AP, Lopes José NC, Rebelo Luis PN (2007) Salting-outing effects in aqueous ionic liquid solutions: cloud-point temperature shifts. J Phys Chem B 111:4737–4741
Acknowledgements
This work has been supported by the National Natural Science Foundation of China (No. 20777029, No. 20876071 and No. 20976074) and the Ph.D. Programs Foundation of Ministry of Education of China (No. 200807100004).
Author information
Authors and Affiliations
Electronic supplementary material
Below is the link to the electronic supplementary material.
ESM 1
(DOC 504 kb)
Rights and permissions
About this article
Cite this article
Han, J., Wang, Y., Kang, W. et al. Phase equilibrium and macrolide antibiotics partitioning in real water samples using a two-phase system composed of the ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate and an aqueous solution of an inorganic salt. Microchim Acta 169, 15–22 (2010). https://doi.org/10.1007/s00604-010-0298-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00604-010-0298-0