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Fate and biodegradability of sulfonated aromatic amines

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Abstract

Ten sulfonated aromatic amines were tested for their aerobic and anaerobic biodegradability and toxicity potential in a variety of environmental inocula. Of all the compounds tested, only two aminobenzenesulfonic acid (ABS) isomers, 2- and 4-ABS, were degraded. The observed degradation occurred only under aerobic conditions with inocula sources that were historically polluted with sulfonated aromatic amines. Bioreactor experiments, with non-sterile synthetic wastewater, confirmed the results from the aerobic batch degradation experiments. Both ABS isomers were degraded in long-term continuous experiment by a␣bioaugmented enrichment culture. The maximum degradation rate in the aerobic bioreactor was 1.6–1.8 gl−1 d−1 for 2-ABS and a somewhat lower value for 4-ABS at hydraulic retention times (HRT) of 2.8–3.3h. Evidence for extensive mineralization of 2- and 4-ABS was based on oxygen uptake and carbon dioxide production during the batch experiments and the high levels of chemical oxygen demand (COD) removal in the bioreactor. Furthermore, mineralization of the sulfonate group was demonstrated by high recovery of sulfate. The sulfonated aromatic amines did not show any toxic effects on the aerobic and anaerobic bacterial populations tested. The poor biodegradability of sulfonated aromatic amines indicated under the laboratory conditions of this study suggests that these compounds may not be adequately removed during biological wastewater treatment.

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References

  • APHA, Association AWW, Federation WE, Clesceri LS, Greenberg AE & Eaton AD (1995) Standard methods for the examination of water and wastewater. American Public Health Association, Washington DC, Denver, Alexandria

  • KT Chung CE Cerniglia (1992) ArticleTitleMutagenicity of azo dyes: structure-activity relationships Mutat. Res. 277 201–220

    Google Scholar 

  • AM Cook (1998) ArticleTitleSulfonated surfactants and related compounds: Facets of their desulfonation by aerobic and anaerobic bacteria Tenside surfact. Deterg. 35 52–56

    Google Scholar 

  • AM Cook H Laue F Junker (1998) ArticleTitleMicrobial desulfonation FEMS Microbiol. Rev. 22 399–419

    Google Scholar 

  • K Denger MA Kertesz EH Vock R Schoen A Magli AM Cook (1996) ArticleTitleAnaerobic desulfonation of 4-tolylsulfonate and 2-(4-sulfophenyl) butyrate by a Clostridium Sp Appl. Environ. Microbiol. 62 1526–1530

    Google Scholar 

  • P Ekici G Leupold H Parlar (2001) ArticleTitleDegradability of selected azo dye metabolite in activated sludge systems Chemosphere 44 721–728

    Google Scholar 

  • BJ Feigel HJ Knackmuss (1988) ArticleTitleBacterial catabolism of sulfanilic acid via catechol-4-sulfonic acid FEMS Microbiol. Lett. 55 113–118

    Google Scholar 

  • BJ Feigel HJ Knackmuss (1993) ArticleTitleSyntrophic interactions during degradation of 4-aminobenzenesulfonic acid by a two species bacterial culture Arch. Microbiol. 159 124–130

    Google Scholar 

  • SW Hooper (1991) Biodegradation of sulfonated aromatics GR Chaudhry (Eds) Biological Degradation and Bioremediation of Toxic Chemicals (pp 169–182) Chapman & Hall London

    Google Scholar 

  • J Jensen (1999) ArticleTitleFate and effects of linear alkylbenzene sulphonates (Las) in the terrestrial environment Sci. Total Environ. 226 93–111

    Google Scholar 

  • R Jung D Steinle R Anliker (1992) ArticleTitleA compilation of genotoxicity and carcinogenicity data on aromatic aminosulphonic acids Food Chem. Toxicol. 30 635–660

    Google Scholar 

  • MA Kertesz AM Cook T Leisinger (1994) ArticleTitlemicrobial metabolism of sulfur- and phosphorous-containing xenobiotics FEMS Microbiol. Rev. 15 195–215

    Google Scholar 

  • TP Knepper F Sacher FT Lange HJ Brauch F Karrenbrock O Roerden K Lindner (1999) ArticleTitleDetection of polar organic substances relevant for drinking water Waste Management 19 77–99

    Google Scholar 

  • P Kolbener U Baumann AM Cook T Leisinger (1994) ArticleTitle3-Nitrobenzenesulfonic acid and 3-aminobenzesulfonic acid in a laboratory trickling filter: biodegradability with different activated sludges Water Res. 28 1855–1860

    Google Scholar 

  • M Kudlich MJ Hetheridge HJ Knackmuss A Stolz (1999) ArticleTitleAutoxidation reactions of different aromatic o-aminohydroxynaphthalenes that are formed during the anaerobic reduction of sulfonated azo dyes Environ. Sci. Technol. 33 896–901

    Google Scholar 

  • EP Kuhn JM Suflita (1989) ArticleTitleAnaerobic biodegradation of nitrogen-substituted and sulfonated benzene aquifer contaminants Hazardous Waste Hazardous Mater. 6 121–134

    Google Scholar 

  • FT Lange C Redin HJ Brauch SH Eberle (1998) ArticleTitleOccurrence of aromatic sulfonates in industrial sewage, river water, bankside filterd water and in drinking water preparation Von Wasser 90 121–134

    Google Scholar 

  • FT Lange M Wenz HJ Brauch (1995a) ArticleTitleBehaviour of aromatic sulfonates in drinking water production from river rhine water and bank filtrate Anal. Methods Instr. 2 277–284

    Google Scholar 

  • FT Lange M Wenz HJ Brauch (1995b) ArticleTitleTrace-level determination of aromatic sulfonates in water by on-line ion-pair extraction/ion-pair chromatography and their behavior in the aquatic environment J. High Resol. Chrom. 18 243–252

    Google Scholar 

  • KG Malle (1978) ArticleTitleWie schmutzig Ist der rhein Chemie Unserer Zeit 12 111–122

    Google Scholar 

  • SW Oh MN Kang MW Cho MW Lee (1997) ArticleTitleDetection of carcinogenic amines from dyestuffs or dyed substrates Dyes Pigments 33 119–135

    Google Scholar 

  • C O’Neill FR Hawkes DL Hawkes ND Lourenco HM Pinheiro W Delee (1999) ArticleTitleColour in textile effluents - sources, measurments, discharge, contents and simulation: a review J. Chem. Technol. Biotechenol. 74 1009–1018

    Google Scholar 

  • K Perei G Rakhely I Kiss B Polyak KL Kovacs (2001) ArticleTitleBiodegradation of sulfanilic acid by Pseudomonas Paucimobilis Appl. Microbiol. Biotechnol. 55 101–107

    Google Scholar 

  • HM Pinheiro E Touraud O Thomas (2004) ArticleTitleAromatic amines from azo dye reduction: status review with emphasis on direct UV spectrophotometric detection in textile industry wastewaters Dyes Pigments 61 121–139

    Google Scholar 

  • D Prats M Rodriguez MA Muela JM Llamas A Moreno J Ferrer ParticleDe JL Berna (1999) ArticleTitleElimination of xenobiotics during composting–a case study: Las (Linear Alkylbenzene Sulfonate) Tenside Surfactants Deterg. 36 294–298

    Google Scholar 

  • E Razo-Flores BA Donlon JA Field G Lettinga (1996) ArticleTitleBiodegradability of N-substituted aromatics and alkylphenols under methanogenic conditions using granular sludge Water Sci. Technol. 33 47–57

    Google Scholar 

  • T Reemtsma (1996) ArticleTitleMethods of analysis of polar aromatic sulfonates from aquatic environments J. of chromatog. A 733 473–489

    Google Scholar 

  • T Reemtsma J Jakobs (2001) ArticleTitleConcerted chemical and microbial degradation of sulfophthalimides formed from sulfophthalocyanine dyes by white-rot fungi Environ. Sci. Technol. 35 4655–4659

    Google Scholar 

  • J Ruff T Hitzler U Rein A Ritter AM Cook (1999) ArticleTitleBioavailability of water-polluting sulfonoaromatic compounds Appl. Microbiol. Biotechnol. 52 446–450

    Google Scholar 

  • A Stolz (2001) ArticleTitleBasic and applied aspects in the microbial degradation of azo dyes Appl. Microbiol. Biotechnol. 56 69–80

    Google Scholar 

  • NCG Tan A Borger P Slender AV Svitelskaya G Lettinga JA Field (2000) ArticleTitleDegradation of azo dye mordant yellow 10 in a sequential anaerobic and bioaugmented aerobic bioreactor Water Sci. Technol. 42 337–344

    Google Scholar 

  • NCG Tan JA Field (2000) Biodegradation of sulfonated aromatic compounds P Lens L Hulshoff Pol (Eds) Environmental Technologies to Treat Sulfur Pollution Principles and Engineering IWA Publishing London 377–392

    Google Scholar 

  • NCG Tan G Lettinga JA Field (1999a) ArticleTitleReduction of the azo dye mordant orange 1 by methanogenic granular sludge exposed to oxygen Biores. Technol. 67 35–42

    Google Scholar 

  • NCG Tan FX Boldu Prenafeta JL Opsteeg G Lettinga JA Field (1999b) ArticleTitleBiodegradation of azo dyes in cocultures of anaerobic granular sludge with aerobic aromatic amine degrading enrichment cultures Appl. Microbiol. Biotechnol. 51 865–871

    Google Scholar 

  • G Tchobanoglus F Burton (1991) Wastewater Engineering. Treatment Disposal and Reuse EditionNumber3 Metclaf & Eddy Inc. McGraw-Hill, In. New York

    Google Scholar 

  • T Thurnheer M Alasdiar T Leisinger (1988) ArticleTitleCo-culture of defined bacteria to degrade seven sulfonated aromatic compounds: efficiency, rates and phenotypic variations Appl. Microbiol. Biotechnol. 29 605–609

    Google Scholar 

  • T Thurnheer T Koehler AM Cook T Leisinger (1986) ArticleTitleOrthanilic acid and analogs as carbon sources for bacteria: growth physiology and enzymatic desulphonation J. Gen. Microbiol. 132 1215–1220

    Google Scholar 

  • O Zerbinati S Salomone G Ostacoli (1994) ArticleTitleSulfonated derivatives of naphthalene in water samples of an Italian River Chemosphere 29 2639–2643

    Google Scholar 

  • O Zerbinati M Vincenti S Pittavino MC Gennaro (1997) ArticleTitleFate of aromatic sulfonates in fluvial environment Chemosphere 35 2295–2305

    Google Scholar 

  • D Zurrer AM Cook T Leisinger (1987) ArticleTitleMicrobial desulfonation of substituted naphthalenesulfonic acids and bezenensulfonic acids Appl. Environ. Microbiol. 53 1459–1463

    Google Scholar 

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Correspondence to Nico C. G. Tan.

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Tan, N.C.G., Leeuwen, A.v., Voorthuizen, E.M.v. et al. Fate and biodegradability of sulfonated aromatic amines. Biodegradation 16, 527–537 (2005). https://doi.org/10.1007/s10532-004-6593-x

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