Ion-Pair-Based Air-Assisted Liquid–Liquid Microextraction for the Extraction and Preconcentration of Phthalic Acids from Aqueous Samples
- 134 Downloads
- 2 Citations
Abstract
In the present study, a rapid, simple, and highly efficient sample preparation method based on ion-pair air-assisted liquid–liquid microextraction using a low-density extraction solvent followed by high performance liquid chromatography–diode array detection has been developed for the extraction, preconcentration, and determination of three phthalic acids (phthalic acid, iso-phthalic acid, and terephthalic acid) in aqueous samples. In this method, a mixture of tri-butyl amine (as an ion-pair reagent) and toluene (as an extraction solvent) is transferred into an aqueous sample solution. Fine organic solvent droplets are formed by aspirating and dispersing of the mixture via syringe needle. After that, the formed ion-pairs are extracted into toluene, and after centrifuging, the obtained collected phase is transferred into a microtube and is evaporated to dryness under a stream of nitrogen at room temperature. The residue is re-dissolved in mobile phase and injected into the separation system for analysis. Under the optimum extraction conditions, the method showed low limits of detection and quantification between 0.09–0.24 and 0.29–0.78 ng mL−1, respectively. Extraction recoveries and enrichment factors were from 88 to 98 % and 443 to 491, respectively. Relative standard deviations for the extraction of 5 ng mL−1 of each analyte were less than 8.4 % for intra-day (n = 6) and inter-days (n = 5) precisions. Finally, different aqueous samples were successfully analyzed using the proposed method, and the target analytes were determined in some of them at ng mL−1 level.
Keywords
Phthalic acids Air-assisted liquid–liquid microextraction Low-density extraction solvent High performance liquid chromatographyAbbreviations
- AALLME
Air-assisted liquid–liquid microextraction
- DAD
Diode array detection
- DLLME
Dispersive liquid–liquid microextraction
- EG
Ethylene glycol
- EU
European Union
- HPLC
High performance liquid chromatography
- LLE
Liquid–liquid extraction
- LPME
Liquid-phase microextraction
- MRL
Maximum residue level
- PET
Poly (ethylene terephthalate)
- SPE
Solid-phase extraction
- SPME
Solid-phase microextraction
- TPA
Terephthalic acid
- USAEME
Ultrasound-assisted emulsification microextraction
- VALLME
Vortex-assisted liquid–liquid microextraction
Notes
Acknowledgments
The authors thank the Research Council of University of Tabriz for financial support.
Funding
Mir Ali Farajzadeh has received research grants from the University of Tabriz.
Conflict of Interest
Mir Ali Farajzadeh declares that he has no conflict of interest. Mohammad Reza Afshar Mogaddam declares that he has no conflict of interest. Hamid Reza Shahbaazi declares that he has no conflict of interest. This article does not contain any studies with human or animal subjects.
References
- Baner A, Brandsch J, Franz R, Piringer O (1996) Migration of ethylene terephthalate oligomers from roasting bags into olive oil. Food Addit Contam 13:587–601CrossRefGoogle Scholar
- Begley TH, Hollifield HC (1990) High-performance liquid chromatographic determination of migrating poly(ethylene terephthalate) oligomers in corn oil. J Agric Food Chem 38:145–148CrossRefGoogle Scholar
- Begley TH, Dennison JL, Hollifield HC (1990) Migration into food of polyethylene terephthalate (PET) cyclic oligomers from PET microwave susceptor packaging. Food Addit Contam 7:797–803CrossRefGoogle Scholar
- Bianchi F, Careri M, Mangia A, Mattarozzi M, Musci M (2008) Experimental design for the optimization of the extraction conditions of polycyclic aromatic hydrocarbons in milk with a novel diethoxydiphenylsilane solid-phase microextraction fiber. J Chromatogr A 1196:41–46CrossRefGoogle Scholar
- Choodum A, Thavarungkul P, Kanatharana P (2007) Acetaldehyde residue in polyethylene terephthalate (PET) bottles. J Environ Sci Health Part B 42:577–583CrossRefGoogle Scholar
- Commission Regulation (EU) No 10/2011 of 14 January 2011 on plastic materials and articles intended to come into contact with food. Off. J. Eur. Union L12/1–L12/89 (2011).Google Scholar
- Cooper I (2007) Plastics and chemical migration into food. In: Chemical migration and food contact materials. Ed. by Karen A. CRC Press, New YorkGoogle Scholar
- Cunha SC, Fernandes JO, Oliveira MBPP (2009) Fast analysis of multiple pesticide residues in apple juice using dispersive liquid–liquid microextraction and multidimensional gas chromatography–mass spectrometry. J Chromatogr A 1216:8835–8844CrossRefGoogle Scholar
- Dabrowska A, Borcz A, Nawrocki J (2003) Aldehyde contamination of mineral water stored in PET bottles. Food Addit Contam 20:1170–1177CrossRefGoogle Scholar
- EC, Commission Directive No. 97/48/EC of 29 July 1997 amending for the second time Council Directive 82/711/EEC laying down the basic rules necessary for testing migration of the constituents of plastic materials and articles intended to come into contact with foodstuffs. Off. J. Eur. Communities L 222 (1997) 10–15Google Scholar
- European Union Commission Directive 2002/72/EC, 2005–1895–ECGoogle Scholar
- Farajzadeh MA, Dj D, Afshar Mogaddam MR, Nourozi J (2012) Determination of phthalate esters in cow milk samples using dispersive liquid–liquid microextraction coupled with gas chromatography followed by flame ionization and mass spectrometric detection. J Sep Sci 35:742–749CrossRefGoogle Scholar
- He Y, Lee HK (1997) Liquid-phase microextraction in a single drop of organic solvent by using a conventional microsyringe. Anal Chem 69:4634–4639CrossRefGoogle Scholar
- Hou L, Lee HK (2002) Application of static and dynamic liquid-phase microextraction in the determination of polycyclic aromatic hydrocarbons. J Chromatogr A 976:377–385CrossRefGoogle Scholar
- Jeannot MA, Cantwell FF (1996) Solvent microextraction into a single drop. Anal Chem 68:2236–2240CrossRefGoogle Scholar
- Kashtock M, Breder CV (1980) Migration of ethylene glycol from polyethylene terephthalate bottles into 3 % acetic acid. J AOAC 63:168–172Google Scholar
- Kim DJ, Lee KT (2012) Determination of monomers and oligomers in polyethylene terephthalate trays and bottles for food use by using high performance liquid chromatography–electrospray ionization mass spectrometry. Poly Test 31:490–499CrossRefGoogle Scholar
- Kim H, Gilbert SG, Johnson JB (1990) Determination of potential migrants from commercial amber polyethylene terephthalate bottle wall. Pharm Res 7:176–179CrossRefGoogle Scholar
- KOREA FDA. Food Code, 2010, Part 7. Standards and specifications for articles, containers and packagesGoogle Scholar
- Lee J, Lee HK (2011) Fully automated dynamic in-syringe liquid-phase microextraction and on-column derivatization of carbamate pesticides with gas chromatography/mass spectrometric analysis. Anal Chem 83:6856–6861CrossRefGoogle Scholar
- Life Hygiene Bureau of Japanese Welfare Ministry (LHBJWM) Food hygiene law, part 3. Specifications and standards for articles, containers and packages (1999). pp. 1048–1084Google Scholar
- Liu H, Dasgupta PK (1996) Analytical chemistry in a drop. Solvent extraction in a microdrop. Anal Chem 68:1817–1821CrossRefGoogle Scholar
- Monteiro M, Nerín C, Reyes FGR (1996) Determination of UV stabilizers in PET bottles by high performance-size exclusion chromatography. Food Addit Contam 13:575–586CrossRefGoogle Scholar
- Mutsuga M, Kawamura Y, Sugita–Konishi Y, Hara–Kudo Y, Takatori K, Tanamoto K (2006) Migration of formaldehyde and acetaldehyde into mineral water in polyethylene terephthalate (PET) bottles. Food Addit Contam 23:212–218CrossRefGoogle Scholar
- Park HJ, Lee YJ, Kim MR, Kim KM (2008) Safety of polyethylene terephthalate food containers evaluated by HPLC, migration test, and estimated daily intake. J Food Sci 73:T 83–T 89CrossRefGoogle Scholar
- Rezaee M, Assadi Y, Hosseini MRM, Aghaeem E, Ahmadi F, Berijani S (2006) Determination of organic compounds in water using dispersive liquid–liquid microextraction. J Chromatogr A 1116:1–9CrossRefGoogle Scholar
- Sanagi MM, Abbas HH, Ibrahim WAW, Aboul-Enien Y (2012) Dispersive liquid–liquid microextraction method based on solidification of floating organic droplet for the determination of triazine herbicides in water and sugarcane samples. Food Chem 133:557–562CrossRefGoogle Scholar
- Schmid P, Kohler M, Meierhofer R, Luzi S, Wegelin M (2008) Does the reuse of PET bottles during solar water disinfection pose a health risk due to the migration of plasticisers and other chemicals into the water? Water Res 42:5054–5060CrossRefGoogle Scholar
- Turner C, Mathiasson L (2000) Determination of vitamins A and E in milk powder using supercritical fluid extraction for sample clean-up. J Chromatogr A 874:275–283CrossRefGoogle Scholar
- USFDA. Code of federal regulation. 2010. Chapter 21, Parts 170–199Google Scholar
- Wang P, Yang X, Wang J, Cui J, Dong AJ, Zhao HT, Zhang LW, Wang ZY, Xu RB, Li WJ, Zhang YC, Zhang H, Jing J (2012) Multi-residue method for determination of seven neonicotinoid insecticides in grains using dispersive solid-phase extraction and dispersive liquid–liquid micro-extraction by high performance liquid chromatography. Food Chem 134:1691–1698CrossRefGoogle Scholar
- Wegelin M, Canonica S, Alder AC, Marazuela D, Suter MJF, Bucheli TD, Heafliger OP, Zenobi R, McGuigan KG, Kelly MT, Ibrahim P, Larroque M (2001) Does sunlight change the material and content of polyethylene terephthalate (PET) bottles? Journal of Water Supply Research Technology AQUA 50:125–133Google Scholar
- Yang ZH, Liu DH, Zhao WT, Wu T, Zhou ZQ, Wang P (2013) Low-density solvent-based vortex-assisted surfactant-enhanced emulsification liquid–liquid microextraction and its application. J Sep Sci 36:916–922CrossRefGoogle Scholar
- Yebra–Pimentel I, Martinez–Carballo E, Regueiro J, Simal–Gandara J (2013) The potential of solvent-minimized extraction methods in the determination of polycyclic aromatic hydrocarbons in fish oils. Food Chem 139:1036–1043CrossRefGoogle Scholar
- Zhu L, Ee HK, Zhao L, Lee HK (2002) Analysis of phenoxy herbicides in bovine milk by means of liquid–liquid–liquid microextraction with a hollow-fiber membrane. J Chromatogr A 963:335–343CrossRefGoogle Scholar