Aromatic amines from azo dye reduction: status review with emphasis on direct UV spectrophotometric detection in textile industry wastewaters

The present status of origins, known hazards, release restrictions and environmental fate of aromatic amines is reviewed. The specific case of aromatic amines arising from the reduction of the azo bond of azo colorants is addressed, with emphasis on the recalcitrance of azo dyes, their demonstrated vulnerability to azo bond reduction through different mechanisms and the lack of data on the biodegradability of the resulting amines. The evolution and present array of analysis methods for aromatic amines in water samples is reviewed, highlighting the increased sophistication and sensitivity attained, and referring a few efforts towards fast analysis methodologies. The case for the application of direct ultraviolet spectral analysis with advanced deconvolution techniques for the monitoring of aromatic amines in textile effluent treatment is presented.

[1]  Carolyn I. Pearce,et al.  The removal of colour from textile wastewater using whole bacterial cells: a review , 2003 .

[2]  D. Barceló,et al.  Determination of sulphonated azo dyes in water and wastewater , 1997 .

[3]  C. Cerniglia,et al.  Mutagenicity of azo dyes: structure-activity relationships. , 1992, Mutation research.

[4]  Romualdo Benigni,et al.  Carcinogenicity of the aromatic amines: from structure-activity relationships to mechanisms of action and risk assessment. , 2002, Mutation research.

[5]  T Robinson,et al.  Remediation of dyes in textile effluent: a critical review on current treatment technologies with a proposed alternative. , 2001, Bioresource technology.

[6]  R. Adams,et al.  Anodic differential pulse voltammetry of aromatic amines and phenols at trace levels , 1977 .

[7]  E. Benfenati,et al.  Determination of aromatic amines by solid-phase microextraction and gas chromatography-mass spectrometry in water samples , 1997 .

[8]  M. Lutz,et al.  Isolation of a Bacterial Strain with the Ability To Utilize the Sulfonated Azo Compound 4-Carboxy-4′-Sulfoazobenzene as the Sole Source of Carbon and Energy , 1998, Applied and Environmental Microbiology.

[9]  Olivier Thomas,et al.  Advanced UV Examination of Wastewater , 1996 .

[10]  S. Hawthorne,et al.  Solid-phase microextraction with pH adjustment for the determination of aromatic acids and bases in water. , 1998, Journal of chromatography. A.

[11]  F. Borrull,et al.  Solid-phase extraction coupling to capillary electrophoresis with emphasis on environmental analysis. , 2000, Journal of chromatography. A.

[12]  U. Pagga,et al.  The degradation of dyestuffs: Part II Behaviour of dyestuffs in aerobic biodegradation tests , 1986 .

[13]  M. G. Hutchings,et al.  A chemometric approach to understanding the bioelimination of anionic, water-soluble dyes by a biomass using empirical and semi-empirical molecular descriptors. , 2001, Water research.

[14]  M. Wimmerová,et al.  Sensitive amperometric biosensor for the determination of biogenic and synthetic amines using pea seedlings amine oxidase: a novel approach for enzyme immobilisation. , 1999, Biosensors & bioelectronics.

[15]  L. Fay,et al.  Determination of heterocyclic aromatic amines in food products: automation of the sample preparation method prior to HPLC and HPLC-MS quantification. , 1997, Mutation research.

[16]  Olivier Thomas,et al.  Wastewater quality monitoring , 1997 .

[17]  J. Weisburger A perspective on the history and significance of carcinogenic and mutagenic N-substituted aryl compounds in human health. , 1997, Mutation research.

[18]  H. Takeuchi,et al.  Determination of amines by flow-injection analysis based on aryl oxalate-Sulphorhodamine 101 chemiluminescence , 1993 .

[19]  Giovanna Marrazza,et al.  Electrochemical DNA biosensor for environmental monitoring , 2001 .

[20]  T. Sugimura,et al.  Overview of carcinogenic heterocyclic amines. , 1997, Mutation research.

[21]  B. Donlon,et al.  Biodegradation of selected azo dyes under methanogenic conditions , 1997 .

[22]  O. Thomas,et al.  An alternative method for the measurement of mineral sulphide in wastewater. , 1999, Talanta.

[23]  A. Włochowicz,et al.  Detection and determination of aromatic amines as products of reductive splitting from selected azo dyes. , 2002, Ecotoxicology and environmental safety.

[24]  G. Norwitz,et al.  Continued investigation of the diazotization and coupling spectrophotometric technique for the determination of aromatic amines with 8-amino-1-hydroxynaphthalene-3,6-disulphonic acid and N-(1-naphthyl)ethylenediamine as coupling agents. , 1984, Talanta.

[25]  H. Börnick,et al.  Laboratory tests for simulating attenuation processes of aromatic amines in riverbank filtration , 2002 .

[26]  N. Zatar,et al.  Spectrophotometric determination of some aromatic amines. , 1998, Talanta.

[27]  A. E. Greenberg,et al.  Standard methods for the examination of water and wastewater : supplement to the sixteenth edition , 1988 .

[28]  M. Gennaro,et al.  Determination of aromatic amines at trace levels by ion interaction reagent reversed-phase high-performance liquid chromatography : Analysis of hair dyes and other water-soluble dyes , 1990 .

[29]  M. Knize,et al.  Chromatographic and related techniques for the determination of aromatic heterocyclic amines in foods. , 2000, Journal of chromatography. B, Biomedical sciences and applications.

[30]  B. Donlon,et al.  Biotransformation and biodegradation of N‐substituted aromatics in methanogenic granular sludge , 1997 .

[31]  J. Biada,et al.  The use of capillary electrophoresis to study the formation of carcinogenic aryl amines in azo dyes , 1999 .

[32]  M. Dalene,et al.  Trace analysis of amines and isocyanates using glass capillary gas chromatography and selective detection , 1983 .

[33]  D. Barceló,et al.  Stability of sulfonated derivatives of benzene and naphthalene on disposable solid-phase extraction pre-columns and in an aqueous matrix. , 2000, Journal of chromatography. A.

[34]  R. Sinha,et al.  Highlights of the eighth international conference on carcinogenic/mutagenic N-substituted aryl compounds. , 2002, Mutation research.

[35]  J. L. Pérez-Pavón,et al.  Surfactant cloud point extraction and preconcentration of organic compounds prior to chromatography and capillary electrophoresis. , 2000, Journal of chromatography. A.

[36]  A. Stolz Degradation of substituted naphthalenesulfonic acids by Sphingomonas xenophaga BN6 , 1999, Journal of Industrial Microbiology and Biotechnology.

[37]  S. Oguri Electromigration methods for amino acids, biogenic amines and aromatic amines. , 2000, Journal of chromatography. B, Biomedical sciences and applications.

[38]  H. Kataoka,et al.  Determination of aromatic amines as their N-dimethylthiophosphoryl derivatives by gas chromatography with flame photometric detection , 1996 .

[39]  H. Börnick,et al.  Simulation of biological degradation of aromatic amines in river bed sediments. , 2001, Water research.

[40]  T. Schmidt,et al.  Gas chromatographic determination of aromatic amines in water samples after solid-phase extraction and derivatization with iodine. II. Enrichment. , 1998, Journal of chromatography. A.

[41]  K. Verma,et al.  Spectrophotometric determination of aromatic primary amines and nitrite by flow injection analysis , 1988 .

[42]  S. Cavalli,et al.  Selective determination of aromatic amines in water samples by capillary zone electrophoresis and solid-phase extraction☆ , 1995 .

[43]  L. Mathiasson,et al.  Harmful azo colorants in leather. Determination based on their cleavage and extraction of corresponding carcinogenic aromatic amines using modern extraction techniques. , 2002, Journal of chromatography. A.

[44]  Paul Gerhard Rieger,et al.  Xenobiotics in the environment: present and future strategies to obviate the problem of biological persistence. , 2002, Journal of biotechnology.

[45]  O. Fiehn,et al.  Analysis of phenolic compounds in industrial wastewater with high-performance liquid chromatography and post-column reaction detection , 1997 .

[46]  G. Chiavari,et al.  Gas chromatographic analysis of aromatic amines as N-permethylated derivatives , 1981 .

[47]  M. Hennion,et al.  New methodology for a selective on-line monitoring of some polar priority industrial chemicals in waste water , 1999 .

[48]  I. Skjevrak,et al.  Determination of primary aromatic amines in water food simulant using solid-phase analytical derivatization followed by gas chromatography coupled with mass spectrometry. , 2003, Journal of chromatography. A.

[49]  Hian Kee Lee,et al.  Analysis of aromatic amines in water samples by liquid-liquid-liquid microextraction with hollow fibers and high-performance liquid chromatography. , 2002, Journal of chromatography. A.

[50]  Olivier Thomas,et al.  UV spectral deconvolution: A valuable tool for waste water quality determination , 1993 .

[51]  M. Dalene,et al.  Trace analysis of amines and isocyanates using glass capillary gas chromatography and selective detection : I. Determination of aromatic amines as perfluoro fatty acid amides using electron-capture detection , 1983 .

[52]  Y. Slokar,et al.  Methods of decoloration of textile wastewaters , 1998 .

[53]  D. Hempel,et al.  Mineralization of the sulfonated azo dye Mordant Yellow 3 by a 6-aminonaphthalene-2-sulfonate-degrading bacterial consortium , 1991, Applied and environmental microbiology.

[54]  P. Bishop,et al.  Characterization of aerobic azo dye-degrading bacteria and their activity in biofilms , 1997 .

[55]  A. Damasiewicz-Bodzek,et al.  Clean-up procedures for the analysis of heterocyclic aromatic amines (aminoazaarenes) from heat-treated meat samples. , 2001, Journal of chromatography. A.

[56]  A. Asthana,et al.  Determination of aromatic amines in water samples by capillary electrophoresis with electrochemical and fluorescence detection. , 2000, Journal of chromatography. A.

[57]  A. Pielesz The process of the reduction of azo dyes used in dyeing textiles on the basis of infrared spectroscopy analysis , 1999 .

[58]  Ibrahim M. Banat,et al.  Microbial decolorization of textile-dye-containing effluents A review , 1996 .

[59]  G. Lettinga,et al.  Biodegradation of azo dyes in cocultures of anaerobic granular sludge with aerobic aromatic amine degrading enrichment cultures , 1999, Applied Microbiology and Biotechnology.

[60]  B. Björkqvist Separation adn determination of aliphatic and aromatic amines by high-performance liquid chromatography with ultraviolet detection , 1981 .

[61]  Olivier Thomas,et al.  A simple UV spectrophotometric procedure for the survey of industrial sewage system , 1999 .

[62]  H. Pinheiro,et al.  Batch tests for assessing decolourisation of azo dyes by methanogenic and mixed cultures. , 2001, Journal of Biotechnology.

[63]  Cliona O’Neill,et al.  Anaerobic treatment of textile effluents: A review , 1998 .

[64]  T. Schmidt,et al.  Derivatization of aromatic amines for analysis in ammunition wastewater I. Derivatization via bromination of the aromatic ring , 1997 .

[65]  H. Pinheiro,et al.  Effect of some operational parameters on textile dye biodegradation in a sequential batch reactor. , 2001, Journal of biotechnology.

[66]  M. Varney,et al.  Measurement of trace aromatic amines in seawater using high-performance liquid chromatography with electrochemical detection , 1985 .

[67]  P. Bishop,et al.  Degradation of acid orange 7 in an aerobic biofilm. , 2002, Chemosphere.

[68]  Shang-da Huang,et al.  Trace determination of aromatic amines or phenolic compounds in dyestuffs by high-performance liquid chromatography with on-line preconcentration , 1995 .

[69]  H. Parlar,et al.  Degradability of selected azo dye metabolites in activated sludge systems. , 2001, Chemosphere.

[70]  A. Jiménez,et al.  Determination of aromatic amines formed from azo colorants in toy products. , 2002, Journal of chromatography. A.

[71]  Olivier Thomas,et al.  Deterministic resolution of molecular absorption spectra of aqueous solutions: environmental applications , 1995 .

[72]  Hian Kee Lee,et al.  Liquid-liquid-liquid microextraction of aromatic amines from water samples combined with high-performance liquid chromatography. , 2002, Journal of chromatography. A.

[73]  A. Stolz,et al.  Autoxidation Reactions of Different Aromatic o-Aminohydroxynaphthalenes That Are Formed during the Anaerobic Reduction of Sulfonated Azo Dyes , 1999 .

[74]  J. Franc,et al.  Thin-layer chromatography of aromatic amines and their derivatives after reactions with 1-fluoro-2,4-dinitrobenzene , 1979 .

[75]  K. Vytras,et al.  Ion-selective electrodes in titrations involving azo-coupling reactions , 1984 .

[76]  K. Verma,et al.  Spectrophotometric determination of primary aromatic amines with 4-N-methylaminophenol and 2-iodylbenzoate. , 1988, Talanta.

[77]  D. Barceló,et al.  Solid-phase extraction of polar hydrophilic aromatic sulfonates followed by capillary zone electrophoresis-UV absorbance detection and ion-pair liquid chromatography-diode array UV detection and electrospray mass spectrometry. , 2000, Journal of chromatography. A.