Anaerobic degradation pathway of linear alkylbenzene sulfonates (IAS) in sulfate-reducing marine sediments

Environmental Science and Technology

Volumn 44, Issue 5, 2010, Pages 1670-1676

  Lara Martín, Pablo A ^a   Gómez Parra, Abelardo ^a   Sanz, José Luis ^b   González Mazo, Eduardo ^a  

^a UNIVERSITY OF CÁDIZ   (Spain)

^b UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ANAEROBIC DEGRADATION; ANOXIC ENVIRONMENT; FUMARATES; LABORATORY EXPERIMENTS; LINEAR ALKYLBENZENE SULFONATES; MARINE SEDIMENTS; OXIDATION REACTIONS; SULFATE REDUCING; SULFOPHENYL; SYNTHETIC SURFACTANTS;

CARBOXYLIC ACIDS; DEGRADATION; MASS SPECTROMETRY; ORGANIC ACIDS; OXYGEN; SEDIMENTOLOGY; SUBMARINE GEOLOGY; SURFACE ACTIVE AGENTS;

LITHIUM ALLOYS;

ALKYLBENZENESULFONIC ACID; CARBOXYLIC ACID; FUMARIC ACID; SULFATE;

ANOXIC CONDITIONS; BIOTRANSFORMATION; CARBOXYLIC ACID; ENVIRONMENTAL FATE; LABORATORY METHOD; MARINE SEDIMENT; METABOLITE; SEDIMENT CHEMISTRY; SULFONATE (ESTER); SURFACTANT;

ANAEROBIC METABOLISM; ARTICLE; BIOTRANSFORMATION; DEGRADATION; MASS SPECTROMETRY; METABOLITE; SEDIMENT; WATER POLLUTION;

ALKANESULFONIC ACIDS; ANAEROBIOSIS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GEOLOGIC SEDIMENTS; ISOMERISM; MASS SPECTROMETRY; OXIDATION-REDUCTION; SOLVENTS; SPAIN; SULFATES; WATER;

EID: 77749258519     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es9032887     Document Type: Article

References (36)

1. Field, J. A.; Iohnson, C. A.; Rose, J. B. What is "emerging. Environ. Sci Technol. 2006, 40, 7105.
2. Rodgers-Gray, T. P.; Jobling, S.; Morris, S.; Kelly, C.; Kirby, S.; Ianbakhsh, A.; Harries, J. E.; Waldock, M. J.; Sumpter, J. P.; Tyler, C. R. Long-term temporal changes in the estrogenic composition of treated sewage effluent and its biological effects on fish. Environ. Sci. Technol, 2000, 34, 1521-1528.
3. Human & Environmental Risk Assessment on Ingredients of European Household Cleaning Products, HERA Report on LAS v3.0; Human and Environmental Risk Assessment: Brussels, Belgium, 2007; p 9.
4. McAvoy, D. C.; Dyer, S. D.; Fendinger, N. J.; Eckhoff, W. S.; Lawrence, D. L.; Begley, W. M. Removal of alcohol ethoxylates, alkyl ethoxylate sulfates, and linear alkylbenzene sulfonates in wastewater treatment. Environ. Toxicol. Chem. 1998, 17, 1705-1711.
5. León,V. M.; Gómez-Parra, A.; González-Mazo, E. Biodegradation of linear alkylbenzene sulfonates and their degradation intermediates in seawater. Environ. Sci Technol. 2004, 38, 2359-2367. (Pubitemid 38488825)
6. María-Navas, J.; González-Mazo, E.; Wenzel, A.; Gómez-Parra, A; Segner, H. Linear alkylbenzene sulfonates and intermediate products from their degradation are not estrogenic. Mar. Pollut. Bull. 1999, 38, 880-884. (Pubitemid 29474005)
7. Bruno, R.; Curini, R.; Di Coreia, A.; Fochi, I.; Nazzari, M.; Samperi, R. Determination of surfactants and some of their metabolites in untreated and anaerobically digested sewage sludge by subcritical water extraction followed by liquid chromatography mass spectrometry. Environ. Sci. Technol. 2002, 36,4156-11161
8. González-Mazo, E.; Forja, J. M.; Gómez-Parra, A. Fate and distribution of linear alkylbenzene sulfonates in the littoral environment. Environ. Sci Technol. 1998, 32, 1636-1641.
9. Wagener, S.; Schink, B. Anaerobic degradation of nonionic and anionic surfactants in enrichment cultures and fixed-bed reactors. Water Res. 1987, 21, 615-622. (Pubitemid 17115263)
10. Federle, T. W.; Schwab, B. S. Mineralization of surfactants in anaerobic sediments of a laundromat wastewater pond. Water Res. 1992, 26, 123-127.
11. Garcia, M. T.; Campos, E.; Ribosa, I.; Latorre, A; Sánchez-Leal, J. Anaerobic digestion of linear alkylbenzene sulfonates: biodegradation kinetics and metabolite analysis. Chemosphere 2005, 60, 1636-1643. (Pubitemid 41096621)
12. Mogensen, A. S.; Haagensen, F.; Ahring, B. Anaerobic degradation of linear alkylbenzene sulfonate. Environ. Toxicol. Chem. 2003, 22, 706-711. (Pubitemid 36596727)
13. Sanz, J. L.; Culubret, E.; de Ferrer, J.; Moreno, A.; Berna, J. L. Anaerobic biodégradation of linear alkylbenzene sulfonate (IAS) in upflow anaerobic sludge blanket (UASB) reactors. Biodegradation 2003, 14, 57-64.
14. Angelidaki, I.; Toräng, I.; Waul, C. M.; Schmidt, J. E. Anaerobic bioprocessing of sewage sludge, focusing on degradation of linear alkylbenzene sulfonates (LAS). Water Sci. Technol. 2004, 49, 115-122. (Pubitemid 38967920)
15. León, V. M.; González-Mazo, E.; Forja Pajares, J. M.; GómezParra, A. Vertical distribution profiles of linear alkylbenzene sulfonates and their long-chain intermediate degradation products in coastal marine sediments. Environ. Toxicol Chem. 2001, 20, 2171-2178.
16. Lara-Martin, P. A.; Petrovic, M.; Gómez-Parra, A.; Barceló, D.; González-Mazo, E. Presence of surfactants and their degradation intermediates in sediment cores and grabs from the Cadiz Bay area. Environ. Pollut. 2006, 144, 483-491. (Pubitemid 44376618)
17. Lara-Martin, P. A.; Gómez-Parra, A.; Köchling, T.; Sanz, J. L.; Amils, R.; González-Mazo, E. Anaerobic degradation of linear alkylbenzene sulfonates in coastal marine sediments. Environ. Sci. Technol. 2007, 41, 3573-3579. (Pubitemid 350067202)
18. Lara-Martin, P. A.; Gómez-Parra, A.; Köchling, T.; Sanz, J. L.; González-Mazo, E. Monitoring the primary biodégradation of linear alkylbenzene sulfonates and their coproducts in anoxic sediments using liquid chromatography-mass spectrometry. Environ. Sci. Technol. 2007, 41, 3580-3586. (Pubitemid 350067203)
19. Lara-Martin, P. A.; Gómez-Parra, A.; González-Mazo, E. Development of a method for the simultaneous analysis of surfactants and their carboxylatedintermediates by pressurized liquid extraction and mixed-modeliquid chromatography-mass spectrometry. J. Chromatogr., A 2006, 1137, 188-197. (Pubitemid 44834520)
20. Callaghan, A. V.; Gieg, L. M.; Kropp, K. G.; Suflita, J. M.; Young, L. Y. Comparison of mechanisms of alkane metabolism under sulfate-reducing conditions among two bacterial isolates and a bacterial consortium. Appl Environ. Microbiol. 2006, 72,4274-4282.
21. Kropp, K. G.; Davidova, I. A.; Suflita, J. M. Anaerobic oxidation of n-dodecane by an addition reaction in a sulfate-reducing bacterial enrichment culture. Appl Environ. Microbiol. 2000, 66, 5393-5398.
22. Reiser, R.; Toljander, H. O.; Giger, W. Determination of alkylbenzenesulfonates in recent sediments by gas chromatography/mass spectrometry. Anal. Chem. 1997, 69, 4923-4930.
23. González-Mazo, E.; Honing, M.; Barceló, D.; Gómez-Parra, A. Monitoring long-chain intermediate products from the degradation of linear alkylbenzene sulfonates in the marine environment by solid-phase extraction followed by liquid chromatography/ion mass spectrometry. Environ. Sci. Technol. 1997, 31, 504-510.
24. DiCoreia, A.; Casassa, F.; Crescenzi, C.; Marcomini,A.; Samperi, R. Investigation of the fate of linear alkyl benzenesulfonates and coproducts in a laboratory biodégradation test by using liquid chromatography/mass spectrometry. Environ. Sci. Technol. 1999, 33, 4112-4118.
25. So, C. M.; Young, L. Y. Initial reactions in anaerobic alkane degradation by a sulphate reducer, strain AK-0l. Appl. Environ. Microbiol. 1999, 65, 5532-5540.
26. Rabus, R.; Wilkes, H.; Behrends, A.; Armstroff, A; Fischer, T.; Pierik, A. J.; Widdel, F. Anaerobic initial reaction of n-alkanes in a denitrifying bacterium: evidence for (l-methylpentyl)succinate as initial product and for involvement of an organic radical in n-hexane metabolism. J. Bacteriol 2001, 183, 1707-1715.
27. Cravo-Laureau, C.; Grossi, V.; Raphel, D.; Matheron, R.; Hirschler-Réa, A. Anaerobic n-alkane metabolism by a sulfatereducing bacterium Desulfatibacillum aliphaticivorans strain CV2803. Appl. Environ. Microbiol. 2005, 71, 3458-3467.
28. Rabus, R.; Heider, J. Initial reactions of anaerobic metabolism of alkylbenzenes in denitrifying and sulfate-reducing bacteria. Arch. Microbiol. 1998, 170, 377-384.
29. Annweiler, E.; Materna, A.; Safinowski, M.; Kappler, A; Richnow, H. H.; Michaelis, W.; Meckenstock, R. U. Anaerobic degradation of 2-methylnaphthalene by a sulfate-reducing enrichment culture. Appl Environ. Microbiol, 2000, 66, 5329-5333. (Pubitemid 32217138)
30. Kniemeyer, O.; Fischer, T.; Wilkes, H.; Glöckner, F. O.; Widdel, F. Anaerobic degradation of ethylbenzene by a new type of marine sulfate-reducing bacterium. Appl Environ. Microbiol. 2003, 69, 760-768. (Pubitemid 36204801)
31. Mavrovouniotis, M. L. Estimation of standard Gibbs energy changes of biotransformations. J. Biol. Chem. 1991, 266, 14440-14445.
32. Wilkes, H.; Rabus, R.; Fischer, T.; Armstroff, A; Behrends, A.; Widdel, F. Anaerobic degradation of n-hexane in a denitrifying bacterium: further degradation of the initial intermediate (1methylpentyl) succinate via C-skeleton rearrangement. Arch. Microbiol. 2002, 177, 235-243. (Pubitemid 34185546)
33. Davidova, I. A; Gieg, L. M.; Nanny, M.; Kropp, K. G.; Suflita, L M. Stable isotopic studies of n-alkane metabolism by asulfatereducing bacterial enrichment culture. Appl. Environ. Microbiol 2005, 71, 8174-8182.
34. Denger, K.; Cook, A. M. Linear alkylbenzenesulphonate (LAS) bioavailable to anaerobic bacteria as a source of sulphur. ¿Appl Microbiol. 1999, 86, 165-168.
35. Lie, T. J.; Godchaux, W.; Leadbetter, E. R. Sulfonates as terminal electron acceptors for growth of sulfite-reducing bacteria (Desulfitobacterium spp.) and sulfate-reducing bacteria: effects of inhibitors of sulfidogenesis. Appl Environ. Microbiol. 1999, 65, 4611-4617.
36. Rontani, J. F.; Bonin, P. C.;Volkman,L K. Biodegradation of free phytol by bacterial communities isolated from marine sediments under aerobic and denitrifying conditions. Appl Environ. Microbiol. 1999, 65, 5484-5492.