تعداد نشریات | 161 |
تعداد شمارهها | 6,532 |
تعداد مقالات | 70,500 |
تعداد مشاهده مقاله | 124,091,056 |
تعداد دریافت فایل اصل مقاله | 97,194,990 |
Review on Naphthenic Acids: An Important Environmental Pollutants Caused by Oil Extraction and Industries | ||
Pollution | ||
دوره 9، شماره 1، فروردین 2023، صفحه 254-270 اصل مقاله (589.14 K) | ||
نوع مقاله: Review Paper | ||
شناسه دیجیتال (DOI): 10.22059/poll.2022.344876.1532 | ||
نویسندگان | ||
Yaser Sotoudeh1؛ Mohammad Hossein Niksokhan* 2؛ Abdolreza Karbassi2؛ Mohammad Reza Sarafrazi3 | ||
1PhD Candidate, Department of Environmental Engineering, University of Tehran, Iran | ||
2Department of Environmental Engineering, Faculty of Environment, University of Tehran, Iran | ||
3Connoisseur in charge of HSE petrochemical projects of National Iranian Petrochemical Company, Iran | ||
چکیده | ||
Naphthenic acids are a group of polar organic carboxylic acids that are present in crude oil naturally. They are cycloaliphatic carboxylic acids which have 10 to 16 carbons, which gained importance since the early twentieth century because of corrosion in oil refineries. Moreover, they are the most important environmental pollutants caused by oil extraction from oil sand reserves. Heavy crude oils which have high concentration of naphthenic acids are usually considered as poor-quality oil and sold at a lower price. Often, the high concentration of naphthenic acids in crude oil reduces the life of the equipment which are used in the exploration and refining process because of corrosion. Hence, researchers are increasingly interested in the chemical properties of naphthenic acids and the acidic components of the crude oils. The most popular methods for the identification and analysis of naphthenic acids are liquid and gas chromatography (GC), liquid-liquid extraction, Fourier transform infrared spectroscopy (FTIR), and solid-phase extraction (SPE). Naphthenic acids are the most important environmental pollutants caused by oil extraction from oil sand reserves. Previous studies have revealed that naphthenic acids can be absorbed by fish, but their distribution in different tissues of fish has not been specified. Experimental samples showed the highest toxicity to fish, while there was less toxicity to invertebrates and algae. Moreover, naphthenates have various industrial utilizations; they are used in synthetic detergents, corrosion inhibitors, lubricants, fuel and oil additives, wood preservatives, insecticides, fungicides, pesticides, wetting agents, napalm thickening agents, and oil desiccants that are utilized in painting and treating wood surfaces. | ||
کلیدواژهها | ||
Naphthenic acids؛ Crude oil؛ Pollutant؛ Environment؛ Petroleum | ||
مراجع | ||
ABC Laboratories Inc. (2009). Validation of test solution preparations and analytical methods for use in the determination of naphthenic acids in various media used in environmental toxicity studies. ABC study no. 64403, Analytical Bio-Chemistry Laboratories, Columbia, Missouri. Adams, F.V., Chukwuneke, C.E. and Agboola, B.O. (2019). Recent Techniques for the Removal of Naphthenic Acid from Heavy Crude Oils. )In: Processing of Heavy Crude Oils - Challenges and Opportunities( DOI: 10.5772/intechopen.89585. Aguiar Porto, N., Crucello, J., Facanali, R., Junior, I.M., Carvalho, R.M., Hantao, and L.W. (2021). Profiling naphthenic acids in produced water using hollow fiber liquid-phase microextraction combined with gas chromatography coupled to Fourier transform Orbitrap mass spectrometry. Journal of Chromatography A, 1655; 462485. Ahad, J.M.E., Pakdel, H., Gammon, P.R., Mayer, B., Savard, M.M., Peru, K.M., Headley, J.V. (2020). Distinguishing natural from anthropogenic sources of acid extractable organics in groundwater near oil sands tailings ponds. Environmental Science and Technology, 54(4); 2790-2799. Allen, E.W. (2008). Process water treatment in Canada’s oil sands industry: I. Target pollutants and treatment objectives. Journal of Environmental Engineering and Science, 7; 123–138. Balaberda, A. and Ulrich, A.C. (2021). Persulfate Oxidation Coupled with Biodegradation by Pseudomonas fluorescens Enhances Naphthenic Acid Remediation and Toxicity Reduction. Microorganisms, 9(7); 1502. Brient, J.A., Wessner, P.J. and Doly, M.N. (1995) Naphthenic acids. (In J. I. Kroschwitz (Ed.), Encyclopedia of Chemical Technology. New York: Wiley.) Brient, J.A., Wessner, P.J. and Doyle, M.N. (2000). Naphthenic acids. In: Kirk-Othmer encyclopedia of chemical technology. (New York: Wiley(. DOI:10.1002/0471238961.1401160802180905.a01. Brown, L.D. and Ulrich, A.C. (2015a). Protocols for Measurement of Naphthenic Acids in Aqueous Samples. Springer. DOI: 10.1007/8623_2015_88. Brown, L.D. and Ulrich, A.C. (2015b). Oil sands naphthenic acids: A review of properties, measurement, and treatment. Chemosphere, 127; 276-290. Campos, M.C., Oliveira, E.C., Sanches Filho, P.J., Sartori Piatnicki, C.M. and Caramão, E.B. (2006). Analysis of tert-butyldimethylsilyl derivatives in heavy gas oil from Brazilian naphthenic acids by gas chromatography coupled to mass spectrometry with electron impact ionization. Journal of Chromatography A, 1105(1-2); 95-105. Chakravarthy, R., Naik, G.N., Savalia, A., Sridharan, U., Saravanan, C., Kumar, A. and Gudasi, K.B. (2016). Determination of Naphthenic Acid Number in Petroleum Crude Oils and Their Fractions by Mid-Fourier Transform Infrared Spectroscopy. Energy and Fuels, 30(10); 8579-8586. DOI: 10.1021/acs.energyfuels.6b01766. Clemente, J.S. and Fedorak, P.M. (2004). Evaluation of the analyses of tert-butyldimethylsilyl derivatives of naphthenic acids by gas chromatography–electron impact mass spectrometry. Journal of Chromatography, 1047(1); 117-128. Clemente, J.S. and Fedorak, P.M. (2005). A review of the occurrence، analyses, toxicity and biodegradation of naphthenic acids. Chemosphere, 60(5); 585-600. Clemente, J.S., Prasad, N.G.N., MacKinnon, M.D. and Fedorak, P.M. (2003). A statistical comparison of naphthenic acids characterized by gas chromatography-mass spectrometry. Chemosphere 50, 1265-1274. Colati, K.A., Dalmaschio, J.P., Castro, E.V., Gomes, A.O. and Vaz, B.G. (2013). Romão, W.; Monitoring the liquid/liquid extraction of naphthenic acids in brazilian crude oil using electrospray ionization FT-ICR mass spectrometry (ESI FT-ICR MS). Fuel, 108; 647-655. DOI: 10.1016/j.fuel.2013.02.007. Crawford, K.E., Campbell, J.L., Fiddler, M.N., Duan, P., Qian, K., Gorbaty, M.L. and Kenttämaa, H.L. (2005). Laser-Induced Acoustic Desorption/Fourier Transform Ion Cyclotron Resonance Mass Spectrometry for Petroleum Distillate Analysis. Analytical Chemistry, 77(24), 7916–7923. DOI: 10.1021/ac0511501 Damasceno, F.C., Gruber, L.D.A., Geller, A.M., Vaz de Campos, M.C., Gomes, A.O., Guimaraes, R.C.L., et al. (2014). Characterization of naphthenic acids using mass spectroscopy and chromatographic techniques: study of technical mixtures. Analytical Methods 6(3); 807. DOI: 10.1039/c3ay40851e. Dias, H.P., Gonçalvesa, G.R., Alexandre, J.C.C., Eustáquio, O.G., Boniek, V.R.C., Glória, G.V. and Romãoae, W. (2015). Catalytic decarboxylation of naphthenic acids in crude oils. Fuel, 158; 113-121. Fields, M.C.V. (2005). Study of naphthenic acids from diesel petroleum-derived heavy Marlin. Dissertation, Universidade Federal do Rio Grande do Sul. Institute of chemistry. Graduate program in materials science. Galimberti, R., Ghiselli, C. and Chiaramonte, M.A. (2000). Acidic polar compounds in petroleum: a new analytical methodology and applications as molecular migration indices. Organic Geochemistry, 31(12); 1375-1386. Geng, F., Zhang, R., Wu, L., Tang, T., Liu, H., Liu, H., et al. (2022). High-efficiency separation and extraction of naphthenic acid from high acid oils using imidazolium carbonate ionic liquids. Chinese Journal of Chemical Engineering, 41; 252-259. Gruber, L.D.A., Dalli, F.C., Caramao, E.B. and Jacques, R.A. (2012). Naphthenic acids in the oil. Qiu. New, 35(7); 1423-1433. Gruber, L.D.A., Moraes, M.S.A., Santestevan, V.A., Geller, A.M., Bortoluzzi, J.H., Dalli, F.C., et al. (2009). Characterization of Naphthenic Acids in Heavy petroleum Fractions via Two-dimensional Chromatography. (Paper presented at the XII Colacro: Latin American Congress of chromatography and Related Techniques, Florianopolis). http://hdl.handle.net/10183/21693. Havre, T., Sjöblom, J. and Vindstad, J.E. (2007). Oil/Water‐Partitioning and Interfacial Behavior of Naphthenic Acids. Journal of Dispersion Science and Technology, 24(6); 789-801. DOI: 10.1081/DIS-120025547 Havre, T.E. (2002). Formation of Calcium Naphthenate in Water/Oil Systems, Naphthenic Acid Chemistry and Emulsion Stability. Dissertation, Department of Chemical Engineering Norwegian University of Science and Technology Trondheim. Headley, J.V. and McMartin, W. (2004). A Review of the Occurrence and Fate of Naphthenic Acids in Aquatic Environments. Journal of Environmental Science and Health, Part A: Toxic/Hazardous Substances and Environmental Engineering, 39(8); 1989-2010. Headley, J.V., Peru, K.M., Mohamed, M.H., Frank, R.M. Martin, J.W., Hazewinkel, R.R.O., et al. (2013). Chemical fingerprinting of naphthenic acids and oil sands process waters-A review of analytical methods for environmental samples. J Environ Sci Health A: Toxic/Hazardous Substances and Environmental Engineering, 48(10);1145-63. Herman, D., Fedorak, P. and Costerton, J. (1993). Biodegredation of cycloalkane carboxylic acids in oil sands tailings. Canadian Journal of Microbiology, 39(6); 576-80. Hindle, R., Noestheden, M., Peru, K. and Headley, J. (2013). Quantitative analysis of naphthenic acids in water by liquid chromatography-accurate mass time-offlight mass spectrometry. Journal of Chromatography A, 1286; 166–174. Hwang, G., Dong, T., Islam, M.S., Sheng, Z., Pérez-Estrada, L., Liu, Y. and Gamal El-Din, M. (2013). The impacts of ozonation on oil sands process-affected water biodegradability and biofilm formation characteristics in bioreactors. Bioresource Technology, 130; 269–277. Jalayer, M., Pirzadeh, M., Mokbari, A. and Nasrabadi, A.M. (2013). Investigation of the causes of corrosion in the distillation units of Bandar Abbas refinery and presenting a solution to reduce the corrosion rate. (Paper presented at the 14th National Corrosion Congress, Iran) Jivraj, M.N., MacKinnon, M.D. and Fung, B. (1991). Naphthenic acid extraction and quantitative analysis with FT-IR spectroscopy. Syncrude analytical methods manual. John, W.P., Rughania, J., Green, S.A. and McGinnisa, M.D. (1998). Analysis and characterization of naphthenic acids by gas chromatography–electron impact mass spectrometry of tert.-butyldimethylsilyl derivatives. Journal of Chromatography. 807(2); 241-251. Khan, M.K., Insyani, R., Lee, J., Yi, M., Lee, J.W. and Kim, J. (2016). Non-catalytic, supercritical methanol route for effective de-acidification of naphthenic acids. Fuel, 182; 650-659. DOI: 10.1016/j.fuel.2016.06.023. Kinley, C.M. (2015). Comparative aquatic toxicity of a commercial naphthenic acid and processes for mitigating risks. Dissertation, Clemson University. Le Roy, W.H. (1960). Removal of naphthenic acids by hydrogenation with a molybdenum oxidesilica alumina catalyst. US Patent. 2,921,023. Lochte, H.L. and Littmann, E.R. (1955). The Petroleum Acids and Bases. Chemical Publishing Co. Inc., New York. Lu, W., Ewanchuk, A., Pérez-Estrada, L., Sego, D., Ulrich, A., 2013. Limitation of fluorescence spectrophotometry in the measurement of naphthenic acids in oil sands process water. Journal of Environmental Science and Health, Part A: Toxic/Hazardous Substances and Environmental Engineering, 48(4); 429–436. Marsh, P.W. (2006). Sorption of Naphthenic Acids to Soil Minerals. University of Alberta. http://www.worldcat.org/oclc/123192658 Martin, J.W., Barri, T., Han, X., Fedorak, P.M., Gamal El-Din, M., Pérez-Estrada, L., Scott, A.C. and Jiang, J.T. (2010). Ozonation of oil sands process-affected water accelerates microbial bioremediation. Environmental Science and Technology, 44(21), 8350–8356. Martin, J.W., Han, X. and Headley, J.V. (2008). Comparison of high- and low-resolution electrospray ionization mass spectrometry for the analysis of naphthenic acid mixtures in oil sands process water. Rapid Commun Mass Spectrom, 22(12); 1919–1924. McKay, J.F., Cogswell, T.E., Weber, J.H. and Latham, D.R. (1975). Analysis of acids in high-boiling petroleum distillates. Fuel, 54(1); 50-61. McKenzie, N., Yue, S., Liu, X., Ramsay, B.A. and Ramsay, J.A. (2014). Biodegradation of naphthenic acids in oils sands process waters in an immobilized soil/sediment bioreactor. Chemosphere, 109; 164-172. McQueen, A.D., Kinley, C.M., Kiekhaefer, R., Calomeni, A., Rodgers Jr, J. and Castle, J. (2016). Photocatalysis of a Commercial Naphthenic Acid in Water Using Fixed-Film TiO2. Water Air Soil Pollution, 227; 132. Merlin, M., Guigard, S.E. and Fedorak, P.M. (2007). Detecting naphthenic acids in waters by gas chromatography–mass spectrometry. Journal of Chromatography A, 1140(1-2); 225–229. Mokhtari, R. and Ayatollahi, S. (2019). Laboratory study of the effect of divalent ions of intelligent water on the surface interactions of the water-crude oil system. Journal of Applied Chemistry, 14(51); 147-162. Oliveira, G.E., Mansur, C.R.E., Pires, R.V., Passos, L.B., Lucas, E.F., Alvares, D.R.S. and Gonzalez, G. (2004). Influence of containing of asphaltenes and naphthenic acids over organic deposition inhibitor performance. osti.gov. Pasban, A.A. and Miran Beig, A.A. (2014). An Experimental Study on Decreasing Acidity of Iranian Crude oil. Journal of Petroleum Research, 24; 79-88. Pereira Rosa, A., Dias Jacques, C.E., Moraes, T.B., Wannmacher, C.M.D., Dutra, A.M. and Dutra-Filho, C.S. (2012). Phenylpyruvic Acid Decreases Glucose-6-Phosphate Dehydrogenase Activity in Rat Brain. Cellular and Molecular Neurobiology, 32; 1113–1118. Pinzón-Espinosa, A., Collins, T.J. and Kanda, R. (2021). Detoxification of oil refining effluents by oxidation of naphthenic acids using TAML catalysts. Science of the Total Environment, 784; 147148. Qian, K., Robbins, W.K., Huguey, C.A., Cooper, H.J., Rodgers, R.P. and Marshall, A.G. (2001). Resolution and identification of elemental with-positions for more than 3000 acids in heavy crude petroleum by negative-ion microelectrospray high field Fourier transform ion cyclotron resonance mass spectrometry. Energy Fuels, 15(6); 1505-1511. Rockhold, W. (1955). Toxicity of naphthenic acids and their metal salts. American Medical Association Archives of Industrial Health, 12(5); 477-82. Rogers, V., Liber, K. and MacKinnon, M. (2002b). Isolation and characterization of naphthenic acids from Athabasca oil sands tailings pond water. Chemosphere. 48(5); 519-27. DOI: 10.1016/s0045-6535(02)00133-9. Rogers, V.V., Wickstrom, M., Liber, K. and MacKinnon, M. D. (2002a). Acute and Subchronic Mammalian Toxicity of Naphthenic Acids from Oil Sands Tailings. Toxicological Sciences, 66(2); 347–355. Samanipour, S., Hooshyari, M., Baz-Lomba, J.A., Reid, M.J., Casale, M. and Thomas, K.V. (2019). The effect of extraction methodology on the recovery and distribution of naphthenic acids of oilfield produced water. Science of the Total Environment, 652; 1416-1423. DOI: 10.1016/j.scitotenv.2018.10.264. Samanipour, S., Reid, M.J., Rundberget, J.T., Frost, T.K. and Thomas, K.V. (2020). Concentration and Distribution of Naphthenic Acids in the Produced Water from Offshore Norwegian North Sea Oil fields. Environmental Science and Technology, 54(5); 2707–2714. DOI: 10.1021/acs.est.9b05784. Santesteavan, V., Gruber, L.D., Moraes, M.S., Geller, A., Bortoluzzi, J., Dalli, F., et al. (2008). Development of methodology for the fractionation of Heavy Brazilian oil Samples via HPLC for characterization of Naphthenic Acids by gas chromatography. (Paper presented at XII Colacro: Latin American Congress of chromatography and Related Techniques, Florianopolis) Santos, D.F., Chaves, A.R. and Ostroski, I.C. (2020). Naphthenic acid removal in model and real aviation kerosene mixture. Chemical Engineering Communications, 208(10); 1405-1418. Scott, A.C., MacKinnon, M.D. and Fedorak, P.M. (2005). Naphthenic acids in Athabasca oil sands tailings waters are less biodegradable than commercial naphthenic acids. Environmental Science and Technology, 39; 8388–8394. Scott, A.C., Young, R.F. and Fedorak, P.M. (2008). Comparison of GC-MS and FTIR methods for quantifying naphthenic acids in water samples. Chemosphere, 73; 1258–1264. Seifert, W.K and Teeter, R.M. (1969). Preparative thin-layer chromatography and high-resolution mass spectrometry of crude oil carboxylic acids. Analytical Chemistry, 41(6); 786-795. Shah, S.N., Abdul Mutalib, M.I., Mohd Pilus, R.B. and Lethesh, K.C. (2014). Separation of Naphthenic Acid Using Hydroxide Based Ionic Liquids. Applied Mechanics and Materials, 625; 570-573. Shah, S.N., Ibrahim, M., Mutalib, A., Mohd Pilus, R.B. and Lethesh, K.C. (2019). Extraction of Naphthenic Acid from Highly Acidic Oil Using Hydroxide-Based Ionic Liquids. Energy and Fuels, 29(1); 106–111. Simair, M.C., Parrott, J.L., Roux, M., Gupta, V., Frank, R.A., Peru, K.M., et al. (2021). Treatment of oil sands process affected waters by constructed wetlands: Evaluation of designs and plant types. Science of The Total Environment, 772; 145508. Simonsen, G., Strand, M., Norrman, J. and Øye, G. (2019). Amino-functionalized iron oxide nanoparticles designed for adsorption of naphthenic acids. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 568; 147-156. Swigert, J.P., Lee, C., Wong, D.C.L., Russell, W., Scarlett, A.G., West, C.E. and Rowlande, S.J. (2015). Aquatic hazard assessment of a commercial sample of naphthenic acids. Chemosphere, 124; 1-9. DOI: 10.1016/j.chemosphere.2014.10.052 Tomczyk, N.A. and Winans, R.E. (2001). On the Nature and Origin of Acidic Species in Petroleum. 1. Detailed Acid Type Distribution in a California Crude Oil. Energy and Fuels, 15(6); 1498-1504. DOI: 10.1021/ef010106v. United States Environmental Protection Agency (USEPA) (2012). Screening-level hazard characterization: reclaimed substances (Naphthenic acids category). Washington DC. EPA-821-R-02-12. Wang, N., Chelme-Ayala, P., Pérez-Estrada, L., Garcia-Garcia, E., Pun, J., Martin, J.W., et al. (2013). Impact of ozonation on naphthenic acids speciation and toxicity of oil sands process-affected water to Vibrio fischeri and mammalian immune system. Environmental Science and Technology, 47; 6518–6526. Wang, X. and Kasperski, K. L. (2010). Analysis of naphthenic acids in aqueous solution using HPLC-MS/MS. Analytical Methods, 11(2); 1715-1722. Woo, O.T., Chung, W.K., Wong, K.H., Chow, A.T. and Wong, P.K. (2009). Photocatalytic oxidation of polycyclic aromatic hydrocarbons: Intermediates identification and toxicity testing. Journal of Hazardous Materials, 168(2–3); 1192–1199. Wu, C., Visscher, A.D. and Gates, I.D. (2019). On naphthenic acids removal from crude oil and oil sands process-affected water. Fuel, 253(1); 1229-1246. Young, R.F., Michel, L.M. and Phillip, P.M. (2011). Distribution of naphthenic acids in tissues of laboratory-exposed fish and in wild fishes from near the Athabasca oil sands in Alberta, Canada. Ecotoxicology and Environmental Safety, 74(4); 889-896. Zanin, R.D., Schutz, P., Campos, M.C.V. and Caramao, E.B. (2002). Extraction of carboxylic acids with Petróleo Brasileiro. In: XIV Salão de Iniciação Científica of UFRGS, Porto Alegre. Book of abstracts of the 13th Century Hall of Ufrgs de Iniciação Científica. | ||
آمار تعداد مشاهده مقاله: 614 تعداد دریافت فایل اصل مقاله: 1,295 |