Determination of Diphenylamine Residue in Fruit Samples Using Dispersive Liquid-Liquid Microextraction Coupled with Ion Mobility Spectrometry

Document Type : Research Article

Authors

Phase Separation and FIA Laboratory, Department of Chemistry, Faculty of Science, University of Zanjan, Zanjan, I.R. IRAN

Abstract

In this study, a simple, fast, and inexpensive method is introduced to extract and determine remaining diphenylamine (DPA) in fruit samples by the combination of Dispersive Liquid-Liquid MicroExtraction (DLLME) and Ion Mobility Spectrometry (IMS). The main parameters such as the type and volume of extraction solvent, volume of dispersive solvent, salt addition, centrifugation time, and sample pH that affected the extraction efficiency were evaluated by performing single-factor variable experiments. Chlorobenzene was selected as the extraction solvent, which was dispersed into samples with methanol as the dispersive solvent. In the optimized experimental conditions, the suggested technique showed good linearity in the range of 25-550 µg/L with a correlation coefficient (R2) 0.997. The detection limits were obtained based on S/N of 3 as 7.5 µg/L in the standard solution and 17µg/kg in apple and pear samples. The repeatability and reproducibility of the method expressed as intraday (n=5) and interday (n=3) relative standard deviations were 6.0 and 7.5%, respectively at a concentration level of 150 µg/L DPA, and the enrichment factor was 36.0. Analysis of fruit samples for measurement of DPA showed that the introduced method has great potential to extract and determine the DPA in real samples.

Keywords

Main Subjects

References

[1] Lurie S., Watkins C.B.,  Superficial Scald, Its Etiology and Control, Postharvest Biol. Technol., 65: 44-60 (2012).
[2] Granado V.L.V., Gutiérrez-Capitán M., Fernández-Sánchez C., Gomes M.T., Rudnitskay A., Jimenez-Jorquera C., Thin-Film Electrochemical Sensor for Diphenylamine Detection using Molecularly Imprinted Polymers, Anal. Chim. Acta, 809: 141-147 (2014).
[3] Farokhcheh A., Alizadeh N., Determination of Diphenylamine Residue in Fruit Samples Using Spectrofluorimetry and Multivariate Analysis, LWT-Food Sci. Technol., 54(1): 6-12 (2013).
[4] Santovito A., Cervella P., Delpero M., Micronucleus Frequency in Human Lymphocytes after Exposure to Diphenylamine in Vitro, Mutat. Res., Genet. Toxicol. Environ. Mutagen., 747(1): 135-137 (2012).
[5] European Food Safety Authority, Conclusion on the Peer Review of the Pesticide Risk Assessment of the Active Substance Diphenylamine, EFSA Journal, 10(1): 2486 (2012).
[6] Robatscher P., Eisenstecken D., Sacco F., Pöhl H., Berger J.,  Zanella A., Oberhuber M., Diphenylamine Residues in Apples Caused by Contamination in Fruit Storage Facilities, J. Agric. Food Chem., 60(9): 2205-2211 (2012).
[7] Drouillet-Pinard P., Boisset M., Periquet A., Lecerf J. M., Casse F., Catteau M., Barnat S., Realistic Approach of Pesticide Residues and French Consumer Exposure within Fruit & Vegetable Intake, J. Environ. Sci. Health, Part B, 46(1): 84-91 (2010).
[8] Saad B., Haniff N.H., Saleh M.I., Hashim N.H., Abu A., Ali N., Determination of Ortho-Phenylphenol, Diphenyl and Diphenylamine in Apples and Oranges using HPLC with Fluorescence Detection, Food Chem., 84(2): 313-317 (2004).
 [9] Garciäa-Reyes JF., Ortega-Barrales P., Molina-Diäaz A., Rapid Determination of Diphenylamine Residues in Apples and Pears with a Single Multicommuted Fluorometric Optosensor, J. Agric. Food Chem., 53(26): 9874-9878 (2005).
[10] Kovalczuk T., Lacina O., Jech M., Poustka J., Hajšlová J., Novel Approach to Fast Determination of Multiple Pesticide Residues using Ultra-Performance Liquid Chromatography-Tandem Mass Spectrometry (UPLC-MS/MS), Food Addit. Contam. Part A, 25(4): 444-457 (2008).
[11] Song J., Forney C.H., Jordan M.A., A Method to Detect Diphenylamine Contamination of Apple Fruit and Storages Using Headspace Solid Phase Micro-Extraction and Gas Chromatography/Mass Spectroscopy, Food Chem., 160: 255-259 (2014).
[12] Rezaei F., Yamini Y., Asiabi H., Moradi M., Determination of Diphenylamine Residue in Fruit Samples by Supercritical Fluid Extraction Followed by Vesicular Based-Supramolecular Solvent Microextraction, J. Supercrit. Fluids, 100: 79-85 (2015).
[13] Sedghi R., Heidari B., Yassari M., Novel Molecularly Imprinted Polymer based on Β-Cyclodextrin@Graphene Oxide: Synthesis and Application for Selective Diphenylamine Determination, J. Colloid Interface Sci., 503: 47-56 (2017).
[14] Kalhor H., Alizadeh N., Enhancing Sensitivity of Ion Mobility Spectrometry Determination of Aldehydes by In Situ Gas Phase Derivatization with Dibutylamine, Int. J. Ion Mobility Spectrom., 16(3): 199-205 (2013).
 [15] Alizadeh N., Kamalabadi M., Mohammadi A., Determination of Histamine and Tyramine in Canned Fish Samples by Headspace Solid-Phase Microextraction Based on a Nanostructured Polypyrrole Fiber Followed by Ion Mobility Spectrometry, Food Anal. Methods, 10: 3001–3008 (2017).
[16] Alonso R., Rodríguez-Estévez V., Domínguez-Vidal A., Ayora-Cañada MJ., Arce L., Valcárcel M., Ion Mobility Spectrometry of Volatile Compounds from Iberian Pig Fat for Fast Feeding Regime Authentication, Talanta, 76(3): 591–596 (2008).
[17] Zhao W.J., Wang Y., Li J., Li L.F., Wang Q., Han K., Zhang Y., Li X., Li P., Luo J., Wang X., Determination of Melamine in Milk and Dairy Products by Microchip-Based High-Field Asymmetric Ion Mobility Spectrometry Combined with Solid-Phase Extraction, Food Chem., 188: 489–495 (2015).
[18] Cohen G., Rudnik DD., Laloush M., Yakir D., Karpas Z., A Novel Method for Determination of Histamine in Tuna Fish by Ion Mobility Spectrometry, Food Anal. Methods, 8(9): 2376–2382 (2015).
[19] Kamalabadi M., Mohammadi A., Alizadeh N., Polypyrrole Nanowire as an Excellent Solid Phase Microextraction Fiber for Bisphenol an Analysis in Food Samples Followed by Ion Mobility Spectrometry, Talanta, 156: 147–153 (2016).
[20] Kalhor H., Hashemipour S., Yaftian M.R., Ultrasound-Assisted Emulsification-Microextraction/Ion Mobility Spectrometry Combination: Application for Analysis of Organophosphorus Pesticide Residues in Rice Samples, Food Anal. Methods, 9: 3006-3014 (2016).
[21] Sha M., Zhang Zh., Gui D., Wang Y., Fu L, Wang H., Data Fusion of Ion Mobility Spectrometry Combined with Hierarchical Clustering Analysis for the Quality Assessment of Apple Essence, Food Anal. Methods, 10: 3415–3423 (2017).
[22] Simpson NJ., ″Solid-Phase Extraction: Principles, Techniques, and Applications″, CRC Press, Florida, (2000).
[23] Aguilar M., Cortina JL., ″Solvent Extraction and Liquid Membranes″, CRC Press, Florida, (2010).
[24] Rezaee M., Assadi Y., Hosseini MR., Aghaee ME., Ahmadi F., Berijani S., Determination of Organic Compounds in Water using Dispersive Liquid–Liquid Microextraction, J. Chromatogr. A, 1116: 1–9 (2006).
[25] Serrano AB., Font G., Mañes J., Ferrer E., Dispersive Liquid-Liquid Microextraction for the Determination of Emerging Fusarium Mycotoxins in Water, Food Anal. Methods, 9(4): 856–862 (2016).
[26] Andraščíková M., Hrouzková S., Fast Preconcentration of Pesticide Residues in Oilseeds by Combination of Quechers with Dispersive Liquid–Liquid Microextraction Followed by Gas Chromatography-Mass Spectrometry, Food Anal. Methods, 9(8): 2182-2193 (2016).
[27] Sadrykia F., Shayanfar A., Valizadeh H., Nemati M., A Fast and Simple Method for Determination of Vitamin E in Infant Formula by Dispersive Liquid-Liquid Microextraction Combined with HPLC-UV, Food Anal. Methods, 12: 23-31 (2019).
[28] Mokhtari1 B., Dalali N., Pourabdollah K., Preconcentration and Determination of Methyl Methacrylate by Dispersive Liquid–Liquid Microextraction, J. Sep. Sci., 36(2): 356–361 (2013).
[29] Li J, Jia S., Yoon S.J., Lee S.J., Kwon S.W., Lee J., Ion-Pair Dispersive Liquid–Liquid Microextraction Solidification of Floating Organic Droplets Method for the Rapid and Sensitive Detection of Phenolic Acids in Wine Samples Using Liquid Chromatography Combined with a Core– Shell Particle Column,
J. Food Compos. Anal., 45: 73–79 (2016).
[30] Farajzadeh M.A., Sohrabi H., Mohebbi A., Combination of Modified Quechers Extraction Method and Dispersive Liquid–Liquid Microextraction as an Efficient Sample Preparation Approach for Extraction and Preconcentration of Pesticides from Fruit and Vegetable Samples, Food Anal. Methods, 12: 534-543 (2019).
[31] Bravo MA., Parra S., Vargas C., Quiroz W., Determination of Organotin Compounds in Sediment Samples by Dispersive Liquidliquid Microextraction Followed by Gas Chromatography–Pulsed Flame Photometric Detection (DLLME-GC-PFPD), Microchem. J., 134: 49−53 (2017).
[32] R. Karami-Osboo, M. Maham, Karami-Osboo R., Maham M., Pre-Concentration and Extraction of Aflatoxins from Rice Using Air-Assisted Dispersive Liquid–Liquid Microextraction, Food Anal. Methods, 11: 2816–2821 (2018).
[33] Jafari MT., Saraji M., Yousefi S., Negative Electrospray Ionization Ion Mobility Spectrometry Combined with Microextraction in Packed Syringe for Direct Analysis of Phenoxyacid Herbicides in Environmental Waters, J. Chromatogr. A, 1249: 41–47 (2012).
[34] Holopainen S., Luukkonen V., Nousiainen M., Sillanpää M., Determination of Chlorophenols in Water by Headspace Solid Phase Microextraction Ion Mobility Spectrometry (HS-SPME-IMS), Talanta, 114: 176–182 (2013).
[35] Karpas Z., Applications of Ion Mobility Spectrometry (IMS) in the Field of Foodomics, Food Res. Int., 54(1): 1146–1151 (2013).
[36] Kalhor H., Hashemipour S., Yaftian M.R., Shahdousti P., Determination of Carbamazepine in Formulation Samples Using Dispersive Liquid–Liquid Microextraction Method Followed by Ion Mobility Spectrometry, Int. J. Ion Mobility Spectrom., 19: 51-56 (2015).
[37] Allafchian AR., Majidian Z., Ielbeigi V., Tabrizchi M., A Novel Method for the Determination of Three Volatile Organic Compounds in Exhaled Breath by Solid-Phase Microextraction–Ion Mobility Spectrometry, Anal. Bioanal. Chem., 408: 839-847 (2016).
[38] Peñalver R., Ortiz A., Arroyo-Manzanares N., Campillo N., López-García I., Viñas P., Non-Targeted Analysis by DLLME-GC-MS for the Monitoring of Pollutants in the Mar Menor Lagoon, Chemosphere, 286: 131588 (2022).
[39] Chaikhan P., Udnan Y., Ampiah-Bonney R.J., Chaiyasith W.C.H., Air-Assisted Solvent Terminated Dispersive Liquid–Liquid Microextraction (AA-ST-DLLME) for the Determination of Lead in Water and Beverage Samples by Graphite Furnace Atomic Absorption Spectrometry, Microchem. J., 162: 105828 (2021).
[40] Gharanjik R., Nassiri M., Hashemi H., Spectrophotometric Determination of Copper and Nickel in Marine Brown Algae after Preconcentration with Surfactant Assisted Dispersive Liquid-Liquid Microextraction, Iran. J. Chem. Chem. Eng. (IJCCE), 39(3): 117-126 (2020).
[41] Wielens Becker R., Wilde M. L., Salmoria Araújo D., Seibert Lüdtke D., Sirtori C., Proposal of a New, Fast, Cheap, and Easy Method Using DLLME for Extraction and Preconcentration of Diazepam and its Transformation Products Generated by a Solar Photo-Fenton Process, Water Research, 184: 116183 (2020).
[42] Khani S., Mofazzeli F., Comparison of Directly Suspended Drop Microextraction with Dispersive Liquid-Liquid Microextraction Method for Extraction of Doxepin in Water and Biological Samples Prior to UV-Vis Spectrophotometer, Iran. J. Chem. Chem. Eng.(IJCCE), 39(3): 127-136 (2020).
[43] Nassiri M., Kaykhaii M., Hashemi S.H., Sepa M., Spectrophotometric Determination of Formaldehyde in Seawater Samples after In-Situ Derivatization and Dispersive Liquid-Liquid Microextraction, Iran. J. Chem. Chem. Eng.(IJCCE), 37(1): 89- 97 (2018).
[44] Farajzadeh MA., Sohrabi H., Mohebbi A., Combination of Modified Quechers Extraction Method and Dispersive Liquid–Liquid Microextraction as an Efficient Sample Preparation Approach for Extraction and Preconcentration of Pesticides from Fruit and Vegetable Samples, Food Anal. Methods, 12: 534-543 (2019).
[45] West C., Baron G., Minet J-J., Detection of Gunpowder Stabilizers with Ion Mobility Spectrometry, Forensic Sci. Int., 166(2-3): 91–101 (2007).
[46] Pankratov A.N., Shchavlev A.E., Protolytic, Redox, and Polar Properties of Diphenylamine and Related Reagents: Quantum-Chemical Evaluation, J. Anal. Chem., 56(2): 123-130 (2001).
[47] Aue D.H., Webb H. M., Bowers M.T., Quantitative Proton Affinities, Ionization Potentials, and Hydrogen Affinities of Alkylamines, J. Am. Chem. Soc., 98(2): 311–317 (1976).
[48] Jafari MT., Saraji M., Yousefi S., Negative Electrospray Ionization Ion Mobility Spectrometry Combined with Microextraction in Packed Syringe for Direct Analysis of Phenoxyacid Herbicides in Environmental Waters, J. Chromatogr. A, 1249: 41–47 (2012).
[49] Tong Y., Wu Z., Yang C., Yu J., Zhang X., Yang S., Determination of Diphenylamine Stabilizer and Its Nitrated Derivatives in Smokeless Gunpowder Using a Tandem MS Method, Analyst, 126(4): 480-484 (2001).
 [50] Nguyen TD., Yun MY., Lee GH., A Multiresidue Method for the Determination of 118 Pesticides in Vegetable Juice by Gas Chromatography-Mass Spectrometry and Liquid Chromatography-Tandem Mass Spectrometry, J. Agric. Food Chem., 57(21): 10095-10101 (2009).
[51] Gilbert-Lopez B., García-Reyes JF., Ortega-Barrales P., Molina-Díaz A., Fernández-Alba AR., Analyses of Pesticide Residues in Fruit-Based Baby Food by Liquid Chromatography/Electrospray Ionization Time-of-Flight Mass Spectrometry, Rapid Commun. Mass Spectrom., 21(13): 2059-2071 (2007).
Iranian Journal of Chemistry and Chemical Engineering
Volume 41, Issue 12 - Serial Number 122
December 2022
Pages 4122-4131

Files

Share

How to cite

Statistics