Abstract
Aromatic amines are widely used industrial chemicals as their major sources in the environment include several chemical industry sectors such as oil refining, synthetic polymers, dyes, adhesives, rubbers, perfume, pharmaceuticals, pesticides and explosives. They result also from diesel exhaust, combustion of wood chips and rubber and tobacco smoke. Some types of aromatic amines are generated during cooking, special grilled meat and fish, as well. The intensive use and production of these compounds explains its occurrence in the environment such as in air, water and soil, thereby creating a potential for human exposure. Since aromatic amines are potential carcinogenic and toxic agents, they constitute an important class of environmental pollutants of enormous concern, which efficient removal is a crucial task for researchers, so several methods have been investigated and applied.
In this chapter the types and general properties of aromatic amine compounds are reviewed. As aromatic amines are continuously entering the environment from various sources and have been designated as high priority pollutants, their presence in the environment must be monitored at concentration levels lower than 30 mg Lā1, compatible with the limits allowed by the regulations. Consequently, most relevant analytical methods to detect the aromatic amines composition in environmental matrices, and for monitoring their degradation, are essential and will be presented. Those include Spectroscopy, namely UV/visible and Fourier Transform Infrared Spectroscopy (FTIR); Chromatography, in particular Thin Layer (TLC), High Performance Liquid (HPLC) and Gas chromatography (GC); Capillary electrophoresis (CE); Mass spectrometry (MS) and combination of different methods including GC-MS, HPLC-MS and CE-MS. Choosing the best methods depend on their availability, costs, detection limit and sample concentration, which sometimes need to be concentrate or pretreated. However, combined methods may give more complete results based on the complementary information. The environmental impact, toxicity and carcinogenicity of many aromatic amines have been reported and are emphasized in this chapter too.
Lately, the conventional aromatic amines degradation and the alternative biodegradation processes are highlighted. Parameters affecting biodegradation, role of different electron acceptors in aerobic and anaerobic biodegradation and kinetics are discussed. Conventional processes including extraction, adsorption onto activated carbon, chemical oxidation, advanced oxidation, electrochemical techniques and irradiation suffer from drawbacks including high costs, formation of hazardous by-products and low efficiency. Biological processes, taking advantage of the naturally processes occurring in environment, have been developed and tested, proved as an economic, energy efficient and environmentally feasible alternative. Aerobic biodegradation is one of the most promising techniques for aromatic amines remediation, but has the drawback of aromatic amines autooxidation once they are exposed to oxygen, instead of their degradation. Higher costs, especially due to power consumption for aeration, can also limit its application. Anaerobic degradation technology is the novel path for treatment of a wide variety of aromatic amines, including industrial wastewater, and will be discussed. However, some are difficult to degrade under anaerobic conditions and, thus, other electron acceptors such as nitrate, iron, sulphate, manganese and carbonate have, alternatively, been tested.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Acquawell JF, Wilson JD, Conner P, Bannister R (1991) An alternative hypothesis for bladder cancer among workers exposed to o-toluidine and aniline. J Nat Cancer Inst 83:1686ā1697. doi:10.1093/jnci/83.22.1686
AkyĆ¼z M, Ata S (2004) Ion-Par extraction and GC-MS determination of aliphatic and Aromatic amines in water and sediment samples. In: 4th AACD congress, 29 Septā3 Oct 2004, Adnan Menderes University, KuÅadası-Aydin,Turkey, Proceedings Book 341, 623ā628. http://www.srcosmos.gr/srcosmos/showpub.aspx?aa=5641
Alaejos MS, Ayala JH, Gonzalez V, Afonso AM (2008) Analytical methods applied to the determination of heterocyclic aromatic amines in foods. J Chromatogr B 862:15ā42. doi:10.1016/j.jchromb.2007.11.040
Al-Johani H, Salam MA (2011) Kinetics and thermodynamic study of aniline adsorption by multi-walled carbon nanotubes from aqueous solution. J Colloid Interface Sci 360:760ā767. doi:10.1016/j.jcis.2011.04.097
Aoki K, Ohtsuka K, Shinke R, Nishira H (1983) Isolation of aniline assimilation bacteria and physiological characterization of aniline biodegradation in Rhodococcus erythropolis AN13. Agric Biol Chem 47:2569ā2575. http://www.doi.org/10.1271/bbb1961.47.2569
Asthana A, Bose D, Durgbanshi A, Sanghi SK, Kok WT (2000) Determination of aromatic amines in water samples by capillary electrophoresis with electrochemical and fluorescence detection. J Chromatogr A 895:197ā203. doi:10.1016/S0021-9673(00)00522-7, PII: S0021-9673(00)00522-7
Aust SD, Bourquin A, Loper JC, Salanitro JR, Suk WA, Tiedjet J (1994) Biodegradation of hazardous wastes. Environ Health Perspect Suppl 102:245ā252
Bachofer R, Lingens F, Schafer W (1975) Conversion of aniline into pyro-catechol by a Nocardia sp: incorporation of oxygen-18. FEBS Lett 50:288ā290. http://www.doi.org/10.1016/0014-5793(75)80510-2
Barsing P, Tiwari A, Joshi T, Garg S (2011) Application of a novel bacterial consortium for mineralization of sulphonated aromatic amines. Bioresour Technol 102:765ā771. http://www.doi.org/10.1016/j.biortech.2010.08.098
Bomhard EM, Herbold BA (2005) Genotoxic activities of aniline and its metabolites and their relationship to the carcinogenicity of aniline in the spleen of rats. Crit Rev Toxicol 35:783ā835. doi:10.1080/10408440500442384
Bƶrnick H, Eppinger P, Grischek T, Worch E (2001) Simulation of biological degradation of aromatic amines in river bed sediments. Water Res 35:619ā624. http://www.doi.org/10.1016/S0043-1354(00)00314-6
BrĆ”s R, Ferra MIA, Pinheiro HM, GonƧalves IC (2001) Batch tests for assessing decolourisation of azo dyes by methanogenic and mixed cultures. J Biotechnol 89:155ā162. http://www.doi.org/10.1016/S0168-1656(01)00312-1
Brown MA, De Vito SC (1993) Predicting azo dye toxicity. Crit Rev Environ Sci Technol 23(3):249ā324. doi:10.1080/10643389309388453
Brown D, Laboureur P (1983) The aerobic biodegradability of primary aromatic amines. Chemosphere 12:405ā414. http://www.doi.org/10.1016/S0045-6535(01)00074-1
Bull RJ, Reckhow DA, Li X, Humpaged AR, Joll C, Hrudey SE (2011) Potential carcinogenic hazards of non-regulated disinfection by-products: haloquinones, halo-cyclopentene and cyclohexene derivatives, N-halamines, halonitriles, and heterocyclic amines. Toxicology 286:1ā19. doi:10.1016/j.tox.2011.05.004
Carmona M, Zamarro MT, BlĆ”zquez B, Durante-RodrĆguez G, JuĆ”rez JF, Valderrama JA, BarragĆ”n MJL, GarcĆa JL, DĆaz E (2009) Anaerobic catabolism of aromatic compounds: a genetic and genomic view. Microbiol Mol Biol Rev 73(1):71ā133. doi:10.1128/MMBR.00021-08
Carvalho C, Fernandes A, Lopes A, Pinheiro H, GonƧalves I (2006) Electrochemical degradation applied to the metabolites of Acid Orange 7 anaerobic biotreatment. Chemosphere 67:1316ā1324
Carvalho MC, Pereira C, Goncalves IC, Pinheiro HM, Santos AR, Lopes A, Ferra MI (2008) Assessment of the biodegradability of a monosulfonated azo dye and aromatic amines. Int Biodeterior Biodegrad 62:96ā103. doi:10.1016/j.ibiod.2007.12.008
Carvalho CJ, Lizier TM, Zanoni MVB (2010) Highly ordered TiO2 nanotube arrays and photoelectrocatalytic oxidation of aromatic amine. Appl Catal Environ 99:96ā102. doi:10.1016/j.apcatb.2010.06.005
Casero I, Sicilia D, Rubio S, Bendito DP (1997) Chemical degradation of aromatic amines by Fentonās reagent. Water Res 31(8):1985ā1995. http://www.doi.org/10.1016/S0043-1354(96)00344-2
Cavallaro A, Piangerelli V, Nerini F, Cavalli S, Reshiotto C (1995) Selective determination of aromatic amines in water samples by capillary zone electrophoresis and solid-phase extraction. J Chromatogr A 709:361ā366. doi:10.1016/0021-9673(95)00435-P
Chen S, Sun D, Chung JS (2009) Simultaneous methanogenesis and denitrification of aniline wastewater by using anaerobicāaerobic biofilm system with recirculation. J Hazard Mater 169:575ā580. http://www.doi.org/10.1016/j.jhazmat.2009.03.132
Chey WM, Adams RN (1977) Anodic differential pulse voltammetry of aromatic amines and phenols at trace levels. J Electroanal Chem 75:731ā738. http://www.doi.org/10.1016/S0022-0728(77)80212-X
Chung KT (2000) Mutagenicity and carcinogenicity of aromatic amines metabolically produced from Azo Dyes. Environ Carcinog Ecotoxicol Rev C 18(l):51ā74. http://www.doi.org/10.1080/10590500009373515
Chung KT, Cerniglia CE (1992) Mutagenicity of azo dyes: structure activity relationships. Mutat Res 277:201ā220. http://www.doi.org/10.1016/0165-1110(92)90044-A
Chung K-T, Murdock CA, Stevens SE, Li Y-S, Wei C-I, Huang T-S, Chou MW (1995) Mutagenicity and toxicity studies of p-phenylenediamine and its derivatives. Toxicol Lett 81(1):23ā32. doi:10.1016/0378-4274(95)03404-8
Combes RD, Haveland-Smith RB (1982) A review of the genotoxicity of food, drug and cosmetic colours and other azo, triphenylmethane and xanthene dyes. Mutation Res/Rev Genetic Toxicol 98(2):101ā243. doi:10/1016/016511108290015X
Coughlin MF, Kinkle BK, Bishop PL (2002) Degradation of acid orange 7 in an aerobic biofilm. Chemosphere 46:11ā19. http://www.doi.org/10.1016/S0045-6535(01)00096-0
Dados AE, Stalikas CD, Pilidis GA (2004) Determination of aromatic amines in textile after bromination, by gas chromatography coupled with electron capture detection. Chromatographia 59(5/6):335ā341. doi:10.1365/s10337-003-0156-x
DeBruin LS, Pawliszyn JB, Josephy PD (1999) Detection of monocyclic aromatic amines, possible mammary carcinogens, in human milk. Chem Res Toxicol 12:78ā82. doi:10.1021/tx980168m CCC
DĆaz E (2004) Bacterial degradation of aromatic pollutants: a paradigm of metabolic versatility. Int Microbiol 7:173ā180. http://www.im.microbios.org/0703/0703173.pdf
Fay LB, Ali S, Gross GA (1997) Determination of heterocyclic aromatic amines in food products: automation of the sample preparation method prior to HPLC and HPLCāMS quantification. Mutat Res 376:29ā35. http://www.doi.org/10.1016/S0027-5107(97)00022-5
Fekete A, Malik AK, Kumar A, Schmitt-Kopplin P (2010) Amines in the environment. Crit Rev Anal Chem 40:102ā121. doi:10.1080/10408340903517495
Franc J, KoudelkovĆ” V (1979) Thin-layer chromatography of aromatic amines and their derivatives after reactions with 1-fluoro-2,4-dinitrobenzene. J Chromatogr A 170:89ā97. doi:10.1016/S0021-9673(00)84241-7
Franciscon E, Zille A, Dias GF, Ragagnin MC, Durrant LR, Cavaco-Paulo A (2009) Biodegradation of textile azo dyes by a facultative Staphylococcus arlettae strain VN-11 using a sequential microaerophilic/aerobic process. Int Biodeter Biodegr 63:280ā288. doi:10.1016/j.ibiod.2008.10.003
Franciscon E, Piubeli F, Fantinatti-Garboggini F, Menezes CR, Silva IS, Cavaco-Paulo A, Grossman MJ, Durrant LR (2010) Polymerization study of the aromatic amines generated by the biodegradation of azo dyes using the laccase enzyme. Enzyme Microb Technol 46:360ā365. doi:10.1016/j.enzmictec.2009.12.014
Franciscon E, Grossman MJ, Paschoal JAR, Reyes FGR, Durrant LR (2012) Decolorization and biodegradation of reactive sulfonated azo dyes by a newly isolated Brevibacterium sp. strain VN-15. Springerplus 1(37):1ā10. doi:10.1186/2193-1801-1-37
Gan J, Skipper PL, Gago-Dominguez M, Arakawa K, Ross RK, Yu MC, Tannenbaum SR (2004) Alkylaniline-hemoglobin adducts and risk of non-smoking related bladder cancer. J Natl Cancer Inst 96(19):1425ā1431. doi:10.1093/jnci/djh274
Ganesh R, Pala S, Metiu H (2007) Modification of the oxidative power of ZnO(1010) surface by substituting some surface Zn atoms with other metals. J Phys Chem C 111(24):8617ā8622. doi:10.1021/jp071671n
Garrigue J-L, Ballantyne M, Kumaravel T, Lloyd M, Nohynek GJ, Kirkland D, Toutain H (2006) In vitro genotoxicity of para-phenylenediamine and its N-monoacetyl or N, N-diacetyl metabolites. Mutat Res 608:58ā71. doi:10.1016/j.mrgentox.2006.05.001
Ghafoor A, Bark LS (1982) Thin layer chromatography of aromatic amines. J Chem Soc Pak 4(3):147ā150
Gibson J, Harwood CS (2002) Metabolic diversity in aromatic compound utilization by anaerobic microbes. Annu Rev Microbiol 56:345ā369. doi:10.1146/annurev.micro.56.012302.160749
Gonzalez C, Touraud E, Spinelli S, Thomas O (2007) Organic constituents. In: Thomas O, Burgess C (eds) UV-visible spectrophotometry of water and wastewater. Elsevier Science, Amsterdam, The Netherlands, p 64. ISBN 9780080489841
Greaves AJ, Churchley JH, Hutchings MG, Phillips DAS, Taylor JA (2001) A chemometric approach to understanding the bioelimination of anionic, water-soluble dyes by a biomass using empirical and semi-empirical molecular descriptors. Water Res 35:1225ā1239. http://www.doi.org/10.1016/S0043-1354(00)00388-2
Guo K, Chen Y (2010) Simple and rapid detection of aromatic amines using a thin layer chromatography plate. Anal Methods 2:1156ā1159. doi:10.1039/C0AY00316F
Haas R, Schmidt TC, Steinbach K, Von Lƶw E (1997) Derivatization of aromatic amines for analysis in ammunition wastewater II: derivatization of methyl anilines by iodination with a Sandmeyer-like reaction. Fresenius J Anal Chem 359:497ā501
Han Y, Quan X, Chen S, Zhao H, Cui C, Zhao Y (2006) Electrochemically enhanced adsorption of aniline on activated carbon fibers. Sep Purif Technol 50:365ā372. doi:10.1016/j.seppur.2005.12.011
Hecht SS (2003) Carcinogen derived biomarkers: applications in studies of human exposure to secondhand tobacco smoke. Tob Control 13:48ā56. doi:10.1136/tc.2002.002816
Hinteregger C, Loidl M, Streichsbier F (1992) Characterization of isofunctional ring cleaving enzymes in aniline and 3-chloroaniline degradation by Pseudomonas acidovorans CA28. FEMS Microbiol Lett 97:261ā266. http://www.doi.org/10.1016/0378-1097(92)90346-P
Hocine O, Boufatit M, Khouider A (2004) Use of montmorillonite clays as adsorbents of hazardous pollutants. Desalination 167:141ā145
Hou L, Lee HK (2003) Dynamic three-phase microextraction as a sample preparation technique prior to capillary electrophoresis. Anal Chem 75:2784ā2789. doi:10.1021/ac020753z
Huang H, Sommerfeld D, Dunn BC, Lloyd CR, Eyring EM (2001) Ferrate(VI) oxidation of aniline. J Chem Soc Dalton Trans 1301ā1305. doi:10.1039/B008934F
Janghel EK, Rai JK, Rai MK, Gupta VK (2005) New analytical technique for the simultaneous determination of aromatic amines in environmental samples. J Sci Ind Res 64:594ā597
Jianguo C, Aimin L, Hongyan S, Zhenghao F, Chao L, Quanxing Z (2005) Equilibrium and kinetic studies on the adsorption of aniline compounds from aqueous phase onto bifunctional polymeric adsorbent with sulfonic groups. Chemosphere 61(4):502ā509. http://www.doi.org/10.1016/j.chemosphere.2005.03.001
Jin Q, Hu Z, Jin Z, Qiu L, Zhong W, Pan Z (2012) Biodegradation of aniline in an alkaline environment by a novel strain of the halophilic bacterium, Dietzia natronolimnaea JQ-AN. Bioresour Technol 117:148ā154. http://www.doi.org/10.1016/j.biortech.2012.04.068
Kahng HY, Kukor Jerome J, Oh KH (2000) Characterization of strain HY99, a novel microorganism capable of aerobic and anaerobic degradation of aniline. FEMS Microbiol Lett 190:215ā221 PII: S 0378ā1097 (00) 00338ā4
Kalyuzhnyi S, Sklyar V, Mosolova T, Kucherenko I, Russkova J, Degtyaryova N (2000) Methanogenic biodegradation of aromatic amines. Water Sci Technol 42(5ā6):363ā370
Kataoka H (1996) Derivatization reactions for the determination of amines by gas chromatography and their applications in environmental analysis. J Chromatogr A 733:19ā34. SSDI 0021-9673(95)00726-1
Khalid A, Arshad M, Crowley DE (2009) Biodegradation potential of pure and mixed bacterial cultures for removal of 4-nitroaniline from textile dye wastewater. Water Res 43:1110ā1116. doi:10.1016/j.watres.2008.11.045
Kim D, Guengerich FP (2005) Cytochrome P450 activation of arylamines and heterocyclic amines. Annu Rev Pharmacol Toxicol 45:27ā49. doi:10.1146/annurev.pharmtox.45.120403.100010
Kim SI, Leem SH, Choi JS, Chung YH, Kim S, Park YM, Lee YN, Ha KS (1997) Cloning and characterization of two cat-A genes in Acinetobacter lwoffii K24. J Bacteriol 179:5226ā5231. http://www.jb.asm.org/content/179/16/5226
Konopka A, Knight D, Turco RF (1989) Characterization of a Pseudomonas sp. capable of aniline degradation in the presence of secondary carbon sources. Appl Environ Microbiol 55:385ā389. http://www.aem.asm.org/content/55/2/385
KostelnĆkovĆ” H, Praus P, TuricovĆ” M (2008) Adsorption of phenol and aniline by original and quaternary ammonium salts-modified montmorillonite. Acta Geodyn Geomater 5(149):83ā88
Kudlich M, Hetheridge MJ, Knackmuss HJ, Stolz A (1999) Autoxidation reactions of different aromatic o-aminohydroxynaphthalenes that are formed during the anaerobic reduction of sulfonated azo dyes. Environ Sci Tech 33:896ā901. doi:10.1021/es9808346
Lewtas J (2007) Air pollution combustion emissions: characterization of causative agents and mechanisms associated with cancer, reproductive, and cardiovascular effects. Rev Mutat Res 636(1ā3):95ā133. doi:10.1016/j.mrrev.2007.08.003
Linākova YV, Dyakonova AT, Gladchenko MA, Kalyuzhnyi SV, Kotova IB, Stams A, Netrusov AI (2011) Methanogenic degradation of (Amino) aromatic compounds by anaerobic microbial communities. Appl Biochem Microbiol 47(5):507ā514. doi:10.1134/S0003683811050085
Liu Z, Yang H, Huang Z, Zhou P, Liu SJ (2002) Degradation of aniline by newly isolated, extremely aniline-tolerant Delftia sp. AN3. Appl Microbiol Biotechnol 58:679ā682. doi:10.1007/s00253-002-0933-8
Lizier TM, Zanoni MVB (2012) Effect of ionic liquid on the determination of aromatic amines as contaminants in hair dyes by liquid chromatography coupled to electrochemical detection. Molecules 17:7961ā7979. doi:10.3390/molecules17077961
Lovley DR (2001) Bioremediation anaerobes to the rescue. Science 293:1444ā1446. doi:10.1126/science.1063294
Lovley DR (2003) Cleaning up with genomics: applying molecular biology to bioremediation. Nat Rev Microbiol 1:35ā44. doi:10.1038/nrmicro731
Marques MM, Mourato LL, Amorim MT, Santos MA, Melchior WB Jr, Beland FA (1997) Effect of substitution site upon the oxidation potentials of alkylanilines, the mutagenicities of N-hydroxyalkylanilines, and the conformations of alkylaniline-DNA adducts. Chem Res Toxicol 10:1266ā1274. doi:10.1021/tx970104w
MartĆnez D, Cugat MJ, Borrull F, Calull M (2000) Solid-phase extraction coupling to capillary electrophoresis with emphasis on environmental analysis. J Chromatogr A 902:65ā89. PII: S0021-9673(00)00839-6
Masomboon N, Ratanatamskul C, Lu MC (2011) Kinetics of 2,6-dimethylaniline oxidation by various Fenton processes. J Hazard Mater 192:347ā353. doi:10.1016/j.jhazmat.2011.05.034
McLeod MP, Eltis LD (2008) Genomic insights into the aerobic pathways for degradation of organic pollutants. In: DĆaz E (ed) Microbial biodegradation: genomics and molecular biology. Caister Academic Press, Norfolk, pp 1ā23
Melo A, Viegas O, EƧa R, Petisca C, Pinho O, Ferreira IMPLVO (2008) Extraction, detection, and quantification of heterocyclic aromatic amines in Portuguese meat dishes by HPLC/Diode array. J Liq Chromatogr Relat Technol 31:772ā787. doi:10.1080/10826070701855987
Mendes S, Pereira L, Batista C, Martins LO (2011) Molecular determinants of azo reduction activity in the strain Pseudomonas putida MET94. Appl Microbiol Biotechnol 92:393ā405. doi:10.1007/s00253-011-3366-4
Mondal PK, Ahmad R, Usmani SQ (2010) Anaerobic biodegradation of triphenylmethane dyes in a hybrid UASFB reactor for wastewater remediation. Biodegradation 21:1041ā1047. doi:10.1007/s10532-010-9364-x
Moradi M, Yamini Y, Esrafili A, Seidi S (2010) Application of surfactant assisted dispersive liquid-liquid microextraction for sample preparation of chlorophenols in water samples. Talanta 82:1864ā1869. doi:10.1016/j.talanta.2010.08.002, ISSN: 0039ā9140
Moriwakia H, Harino H, Hashimoto H, Arakawa R, Ohe T, Yoshikura T (2003) Determination of aromatic amine mutagens, PBTA-1 and PBTA-2, in river water by solid-phase extraction followed by liquid chromatographyātandem mass spectrometry. J Chromatogr A 995:239ā243. doi:10.1016/S0021-9673(03)00514-4
Mortensen SK, Trier XT, Foverskov A, Petersen JH (2005) Specific determination of 20 primary aromatic amines in aqueous food simulants by liquid chromatographyāelectrospray ionization-tandem mass spectrometry. J Chromatogr A 1091:40ā50. doi:10.1016/j.chroma.2005.07.026
Mucha K, Kwapisz E, Kucharska U, Okruszek A (2010) Mechanism of aniline degradation by yeast strain candida methanosorbosa BP-6. Pol J Microbiol 59(4):311ā315
Murakumi S, Takashima A, Takemoto J, Takenaka S, Shinke R, Aoki K (1999) Cloning and sequence analysis of two catechol-degrading gene clusters from the aniline assimilating bacterium Frateuria species ANA-18. Gene 226:189ā198. http://www.doi.org/10.1016/S0378-1119(98)00560-5
MƤlzer HJ, Gerlach M, Gimbel R (1993) Effects of shock loads on bank filtration and their prediction by control filters. Water Supply 11:165ā177
Narayana B, Sunil K (2009) A spectrophotometric method for the determination of nitrite and nitrate. Eurasian J Anal Chem 4(2):204ā214. ISSN: 1306ā3057
Neyens E, Baeyens J (2003) A review of classic Fentonās peroxidation as an advanced oxidation technique. J Hazard Mater 98(1ā3):33ā50. PII: S0304-3894(02)00282-0
Nohynek GJ, Antignac E, Re T, Toutain H (2010) Safety assessment of personal care products/cosmetics and their ingredients. Toxicol Appl Pharmacol 243:239ā259. doi:10.1016/j.taap.2009.12.001
OāNeill FJ, Brimley-Challenor KCA, Greenwood RJ, Knapp JS (2000) Bacterial growth of aniline: implications for the biotreatment of industrial wastewater. Water Res 34(18):4397ā4409. doi:10.1016/S0043-1354(00)00215-3
Oda H, Yokokawa C (1983) Adsorption of aromatic amines and o-substituted derivatives of phenol from organic solutions by activated carbons-effect of surface acidity. Carbon 21(5):485ā489. http://www.doi.org/10.1016/0008-6223(83)90141-0
Oguri S (2000) Electromigration methods for amino acids, biogenic amines and aromatic amines. J Chromatogr B 747:1ā19. http://www.doi.org/10.1016/S0378-4347(00)00092-X
Osterloh FE (2008) Inorganic materials as catalysts for photochemical splitting of water. Chem Mater 20:35ā54. doi:10.1021/cm7024203
Oturan MA, Brillas E (2007) Electrochemical Advanced Oxidation Processes (EAOPs) for environmental applications. Port Electrochim Acta 25:1ā18
Pacheco MJ, Santos V, CirĆaco L, Lopes A (2011) Electrochemical degradation of aromatic amines on BDD electrodes. J Hazard Mater 186(2ā3):1033ā1041. doi:10.1016/j.jhazmat.2010.11.108
Palmiotto G, Pieraccini G, Moneti G, Dolara P (2001) Determination of the levels of aromatic amines in indoor and outdoor air in Italy. Chemosphere 433:355ā361, PII:S0045-6535(00)00109-0
Panizza M, Zolezzi M, Nicolella C (2006) Biological and electrochemical oxidation of naphthalenesulfonates. J Chem Technol Biotechnol 81:225ā232
Panizza M, Brillas E, Comninellis C (2008) Application of boron-doped diamond electrodes for wastewater treatment. J Environ Eng Manag 18:139ā153
Parales RE, Resnick SM (2006) Aromatic ring hydroxylating dioxygenases. In: Ramos JL, Levesque RC (eds) Pseudomonas, vol 4, Molecular biology of emerging issues. Springer, New York, pp 287ā340
Parales RE, Ontl TA, Gibson DT (1997) Cloning and sequence analysis of a catechol 2,3-dioxygenase gene from the nitrobenzene degrading strain Comamonas sp. JS765. J Ind Microbiol Biotechnol 19:385ā391. doi:10.1038/sj.jim.2900420
Pereira R, Pereira L, Van der Zee FP, Alves MM (2011) Fate of aniline and sulfanilic acid in UASB bioreactors under denitrifying conditions. Water Res 45:191ā200. doi:10.1016/j.watres.2010.08.027
Pereira L, Pereira R, Oliveira CS, Alves MM (2013) UV/TiO2 photocatalytic degradation of xanthene dyes. Photochem Photobiol, 2013, 89:33ā50. doi:10.1111/j.1751-1097.2012.01208.x
Perez F (2001) Spectrophotometric study of industrial effluents ā application in parameters estimation. PhD thesis, Universiteā dāAix-Marseille; II
Pielesz A (1999) The process of the reduction of azo dyes used in dyeing textiles on the basis of infrared spectroscopy analysis. J Mol Struct 337ā344. http://www.doi.org/10.1016/S0022-2860(99)00176-3
Pielesz A, Baranowska I, Rybak A, WÅochowicz A (2002) Detection and determination of aromatic amines as products of reductive splitting from selected azo dyes. Ecotoxicol Environ Saf 53:42ā47. doi:10.1006/eesa.2002.2191
Pinheiro HM, Touraud E, Thomas O (2004) Aromatic amines from azo dye reduction: status review with emphasis on direct UV spectrophotometric detection in textile industry wastewaters. Dyes Pigments 61:121ā139. doi:10.1016/j.dyepig.2003.10.009
Ramalho PA, Helena CM, Cavaco-Paulo A, Teresa RM (2004) Characterization of azo reduction activity in a novel ascomycete yeast strain. Appl Environ Microbiol 70(4):2279ā2288. doi:10.1128/AEM.70.4.2279-2288.2004
Ramya M, Iyappan S, Manju A, Jiffe JS (2010) Biodegradation and decolorization of acid red by acinetobacter radioresistens. J Bioremediat Biodegrad 1(105):2ā6. doi:10.4172/2155-6199.1000105
Ratiu C, Manea F, Lazau C, Grozescu I, Radavon C, Schoonman J (2010) Electrochemical oxidation of p-aminophenol from water with boron-doped diamond anodes and assisted photocatalytically by TiO2-supported zeolite. Desalination 260(1ā3):51ā56. doi:10.1016/j.desal.2010.04.068
Razo-Flores E (1997) Biotransformation and biodegradation of N-substituted aromatics in methanogenic granular sludge. PhD thesis, Wageningen Agriculture University, The Netherlands. http://edepot.wur.nl/199864
Razo-Flores E, Donlon BA, Field JA, Lettinga G (1996) Biodegradability of N-substituted aromatics and alkylphenols under methanogenic conditions using granular sludge. Water Sci Technol 33(3):47ā57. http://www.doi.org/10.1016/0273-1223(96)00320-4
Razo-Flores E, Donlon B, Lettinga G, Field JA (1997a) Biotransformation and biodegradation of N-substituted aromatics in methanogenic granular sludge. FEMS Microbiol Rev 20:525ā538, PII S0168-6445(97)00031ā4
Razo-Flores E, Luijten M, Donlon BA, Lettinga G, Field JA (1997b) Complete biodegradation of the azo dye azodisalicylate under anaerobic conditions. Environ Sci Tech 31:2098ā2103
Razo-Flores E, Lettinga G, Field JA (1999) Biotransformation and biodegradation of selected nitroaromatics under anaerobic conditions. Biotechnol Prog 15:358ā365. doi:10.1021/bp9900413
Rieger P-G, Meier H-M, Gerle M, Vogtb U, Groth T, Knackmuss H-J (2002) Xenobiotics in the environment: present and future strategies to obviate the problem of biological persistence. J Biotechnol 94(1):101ā123. doi:10.1016/S0168-1656(01)00422-9
Robinson T, MacMullan G, Marchant R, Nigam P (2001) Remediation of dyes in textile effluents, current treatment technologies with a proposed alternative. Bioresour Technol 77:247ā255. http://www.doi.org/10.1016/S0960-8524(00)00080-8
SĆ”nchez L, Peral J, DomĆØnech X (1998) Aniline degradation by combined photocatalysis and ozonation. Appl Catal Environ 19:59ā65. PII: S0926- 3373(9 8)00058-7
Santos V, Diogo J, Pacheco MJ, CirĆaco L, MorĆ£o A, Lopes A (2010) Electrochemical degradation of sulfonated amines on SI/BDD electrodes. Chemosphere 79(6):637ā645. doi:10.1016/j.chemosphere.2010.02.031
Savelieva O, Kotova I, Roelofsen W, Stams AJM, Netrusov A (2004) Utilization of aminoaromatic acids by a methanogenic enrichment culture and by a novel Citrobacter freundii strain. Arch Microbiol 181:163ā170. doi:10.1007/s00203-003-0645-1
Schmidt TC, Haas R, Von Lƶw E, Steinbach K (1998) Derivatization of aromatic amines with bromine for improved gas chromatographic determination. Chromatographia 48(5ā6):436ā442. doi:10.1007/BF02467717
Sentellas S, Moyano E, Puignou L, Galceran MT (2003) Determination of heterocyclic aromatic amines by capillary electrophoresis coupled to mass spectrometry using in-line preconcentration. Electrophoresis 24:3075ā3082. doi:10.1002/elps.200305523
Sentellas S, Moyano E, Puignou L, Galceran MT (2004) Optimization of a clean-up procedure for the determination of heterocyclic aromatic amines in urine by field-amplified sample injectionācapillary electrophoresisāmass spectrometry. J Chromatogr A 1032:193ā201. doi:10.1016/j.chroma.2003.11.011
Seymour EH, Lawrence NS, Pandurangappa M, Compton RG (2002) Indirect electrochemical detection of nitrite via diazotization of aromatic amines. Microchim Acta 140:211ā217. doi:10.1007/s00604-002-0915-7
Sharma N, Jain A, Verma KK (2011) Headspace solid-phase microextraction and on-fibre derivatization of primary aromatic amines for their determination by pyrolysis to aryl isothiocyanates and gas chromatography-mass spectrometry. Anal Methods 3(4):970ā976. doi:10.1039/C0AY00745E
Skarping G, Renman L, Dalene M (1983) Trace analysis of amines and isocyanates using glass capillary gas chromatography and selective detection. II Determination of aromatic amines as perfluoro fatty acid amides using nitrogen-selective detection. J Chromatogr A 270:207ā218
Skipper PL, Kim MY, Sun H-LP, Wogan GN, Tannenbaum SR (2010) Monocyclic aromatic amines as potential human carcinogens: old is new again. Carcinogenesis 31(1):50ā58. doi:10.1093/carcin/bgp267
Srivastava SP, Dua VK (1975) TLC separation of closely related amines. J Anal Chem 276:382
Stolz A (1999) Degradation of substituted naphthalene sulfonic acids by Sphingomonas xenophaga BN6. J Ind Microbiol Biotechnol 23:391ā399. doi:10.1038/sj.jim.2900725
Sun Y, Liang L, Zhao X, Yu L, Zhana J, Shi G, Zhou T (2009) Determination of aromatic amines in water samples by capillary electrophoresis with amperometric detection. Water Res 43:41ā46. doi:10.1016/j.watres.2008.10.004
Sun X-M, Sun Y, Wu L-W, Jiang C-Z, Yu X, Gao Y, Wang L-Y, Song D-Q (2012a) Determination of aromatic amines in environmental water samples. Anal Methods 4(7):2074ā2080. doi:10.1039/C2AY25056J
Sun XM, Sun Y, Wu LW, Jiang CZ, Yu X, Gao Y, Wang LY, Song DQ (2012b) Development of a vortex-assisted ionic liquid microextraction method for the determination of aromatic amines in environmental water samples. Anal Methods 4:2074ā2080. doi:10.1039/C2AY25056J
Szterk A, Roszko M, MaÅek K, Kurek M, ZbieƦ M, Waszkiewicz-Robak B (2012) Profiles and concentrations of heterocyclic aromatic amines formed in beef during various heat treatments depend on the time of ripening and muscle type. Meat Sci 92:587ā595. doi:10.1016/j.meatsci.2012.06.004
Tan NCG, Prenafeta-Boldu FX, Opsteeg J, Lettinga G, Field JA (1999) Biodegradation of azo dyes in cocultures of anaerobic granular sludge with aerobic aromatic amine degrading enrichment cultures. Appl Microbiol Biotechnol 51:865ā871. doi:10.1007/s002530051475
Tan NCG, Van Leeuwen A, Van Voorthuizen EM, Slenders P, Prenafeta-BoldĆŗ FX, Temmink H, Lettinga G, Field JA (2005) Fate and biodegradability of sulfonated aromatic amines. Biodegradation 16:527ā537
Tannenbaum SR (1991) Bladder cancer in workers exposed in aniline. J Nat Cancer Inst 83:1507ā1508
Tao Y, Liu JF, Wang T, Jiang GB (2009) Simultaneous conduction of two- and three-phase hollow-fiber-based liquid-phase microextraction for the determination of aromatic amines in environmental water samples. J Chromatogr A 1216(5):756ā762. doi:10.1016/j.chroma.2008.11.094
TorƤng L, Reuschenbach P, MĆ¼ller B, Nyholm N (2002) Laboratory shake flask batch tests can predict field biodegradation of aniline in the Rhine. Chemosphere 49:1257ā1265. http://www.doi.org/10.1016/S0045-6535(02)00605-7
Toribio F, Moyano E, Puignou L, Galceran MT (2002) Ion-trap tandem mass-spectrometry for the determination of heterocyclic amines in food. J Chromatogr A 948:267ā281. PII: S0021-9673(01)01476-5
Torres RA, Sarria V, Torres W, Peringer P, Pulgarin C (2003) Electrochemical treatment of industrial wastewater containing 5-amino-6-methyl-2-benzimidazolone: toward an electrochemicalābiological coupling. Water Res 37:3118ā3124. doi:10.1016/S0043-1354(03)00179-9
USA National Toxicology Program (2005) 11th report on carcinogens. U.S. Department of Health and Human Services
Vaillancourt FH, Bolin JT, Eltis LD (2006) The ins and outs of ring-cleaving dioxygenases. Crit Rev Biochem Mol Biol 41:241ā267. doi:10.1080/10409230600817422
Van der Plas SE, De Clercq PJ, Madder A (2007) Fast and easy detection of aromatic amines on solid support. Tetrahedron Lett 48:2587ā2589. doi:10.1016/j.tetlet.2007.02.023
Van der Zee FP, Villaverde S (2005) Combined anaerobicāaerobic treatment of azo dyes ā A short review of bioreactor studies. Water Res 39:1425ā1440. doi:10.1016/j.watres.2005.03.007
VĆ”zquez-RodrĆguez GA, BeltrĆ”n-HernĆ”ndez RI, Lucho-Constantino CA, Blasco JL (2008) A method for measuring the anoxic biodegradability under denitrifying conditions. Chemosphere 71:1363ā1368. doi:10.1016/j.chemosphere.2007.11.012
Verma KK, Sanghi SK, Jain A (1988) Spectrophotometric determination of primary aromatic amines with 4-N methylaminophenol and 2-iodylbenzoate. Talanta 35:409ā411. http://www.doi.org/10.1016/0039-9140(88)80037-7
Vytras K, Kalous J, KalaĀ“bovaĀ“ Z, Remes M (1982) Ion-selective electrodes in titrations involving azo-coupling reactions. Anal Chem Acta 141:163ā171
Wang L, Barrington S, Kim JW (2007) Biodegradation of pentyl amine and aniline from petrochemical wastewater. J Environ Manage 83:191ā197. http://www.doi.org/10.1016/j.jenvman.2006.02.009
Wang X, Fu L, Wei G, Hu J, Zhao X, Liu X, Li Y (2008) Determination of four aromatic amines in water samples using dispersive liquidāliquid microextraction combined with HPLC. J Sep Sci 31:2932ā2938. doi:10.1002/jssc.200800273
Weisburger JH (1997) A perspective on the history and mutagenic, N-substituted aryle compounds in human health. Mutat Res 376:61ā266
Wilmer JL, Rosenkranz HS, Pet-Edwards J, Chankong V, Haimes YY (1984) On the carcinogenicity of aniline. Environ Mutagen 6(5):629ā632. doi:10.1002/em.2860060502
Worch E, Grischek T, Bƶrnick H, Eppinger P (2002) Laboratory tests for simulating attenuation processes of aromatic amines in riverbank filtration. J Hydrol 266:259ā268. http://www.doi.org/10.1016/S0022-1694(02)00169-5
Wu YG, Hui L, Li X, Zhang YZ, Zhang WC (2007) Degradation of aniline in weihe riverbed sediments under denitrification conditions. J Environ Sci Health, Part A: Tox Hazard Subst Environ Eng 42(4):413ā419. doi;org/10.1080/10934520601187302
Yadav S, Tyagi DK, Yadav OP (2011) Equilibrium and kinetics studies on adsorption of aniline blue from aqueous solution onto rice husk carbon. Int J Chem Res 2(3):59ā64
Yang J, Tsai FP (2001) Development of a solid-phase microextraction/reflection-absorption infrared spectroscopic method for the detection of chlorinated aromatic amines in aqueous solutions. Anal Sci 17:751ā756
Yang K, Wu W, Jing Q, Zhu L (2008) Aqueous adsorption of aniline, phenol, and their substitutes by multi-walled carbon nanotubes. Environ Sci Tech 42:7931ā7936. doi:10.1021/es801463v
Ye S, Huang F (2007) Separation of carcinogenic aromatic amines in the dyestuff plant wastewater treatment. Desalination 206:78ā85. doi:10.1016/j.desal.2006.03.562
Yemashova N, Kalyuzhnyi S (2006) Microbial conversion of selected azo dyes and their breakdown products. Water Sci Technol 53(11):163ā171. http://www.ukpmc.ac.uk/abstract/MED/16862786
Yu MC, Ross RK (1998) Epidemiology of bladder cancer. In: Petrovich Z, Baert L, Brady LW (eds) Carcinoma of the bladder. Innovations in management. Springer, Berlin, pp 1ā13
Yu MC, Skipper PL, Tannenbaum SR, Chan KK, Ross RK (2002) Arylamine exposures and bladder cancer risk. Mutat Res/Fundam Mol Mech Mutagen 506ā507:21ā28. http://www.doi.org/10.1016/S0027-5107(02)00148-3
Zatar NA, Abu-Zuhri AZ, Abu-Shaweesh AA (1998) Spectrophotometric determination of some aromatic amines. Talanta 47:883ā890. http://www.doi.org/10.1016/S0039-9140(98)00177-5
Zeng Z, Qiu W, Yang M, Wei X, Huang Z, Li F (2001) Solid-phase microextraction of monocyclic aromatic amines using novel fibers coated with crown ether. J Chromatogr A 934:51ā57, PII: S0021-9673(01)01303-6
Zeyer J, Wasserfallen A, Timmis KN (1985) Microbial mineralization of ring-substituted anilines through an ortho-cleavage pathway. Appl Environ Microbiol 50(2):447ā453. http://www.ncbi.nlm.nih.gov/pmc/articles/PMC239144/pdf/aem00133-0350.pdf
Zhang Q, Wang C, Bai H, Wang X, Wu T, Ma Q (2009) Determination of aromatic amines from azo dyes reduction by liquid-phase sorbent trapping and thermal desorption-gas chromatography-mass spectrometry. J Sep Sci 32(14):2434ā2441. doi:10.1002/jssc.200900089
Zhang S, Li A, Cui D, Yang JX, Ma F (2011) Performance of enhanced biological SBR process for aniline treatment by mycelial pellet as biomass carrier. Bioresour Technol 102(6):4360ā4365. http://www.doi.org/10.1016/j.biortech.2010.12.079
Zhao X, Suo Y (2008) Analysis of primary aromatic amines using precolumn derivatization by HPLC fluorescence detection and online MS identification. J Sep Sci 31:646ā658. doi:10.1002/jssc.200700400
Zhou QX, Ye CL (2008) Ionic liquid for improved single-drop microextraction of aromatic amines in water samples. Microchim Acta 162(1ā2):153ā159. doi:10.1007/s00604-007-0857-1
Zwirner-Baier I, Deckart K, JƤckh R, Neumann HG (2003) Biomonitoring of aromatic amines VI: determination of hemoglobin adducts after feeding aniline hydrochloride in the diet of rats for 4 weeks. Arch Toxicol 77:672ā677. doi:10.1007/s00204-003-0473-8
Acknowledgement
The authors thank the FCT exploratory EXPL/AAG-TEC/0898/2013 and Strategic Project of UID/BIO/04469/2013 unit. Acknowledgements also to the project RECI/BBB-EBI/0179/2012 (FCOMP-01-0124-FEDER-027462) and the Project āBioEnv - Biotechnology and Bioengineering for a sustainable worldā, REF. NORTE-07-0124-FEDER-000048, co-funded by the Programa Operacional Regional do Norte (ON.2 ā O Novo Norte), QREN, FEDER.
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
Ā© 2015 Springer International Publishing Switzerland
About this chapter
Cite this chapter
Pereira, L., Mondal, P.K., Alves, M. (2015). Aromatic Amines Sources, Environmental Impact and Remediation. In: Lichtfouse, E., Schwarzbauer, J., Robert, D. (eds) Pollutants in Buildings, Water and Living Organisms. Environmental Chemistry for a Sustainable World, vol 7. Springer, Cham. https://doi.org/10.1007/978-3-319-19276-5_7
Download citation
DOI: https://doi.org/10.1007/978-3-319-19276-5_7
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-19275-8
Online ISBN: 978-3-319-19276-5
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)