Critical Review of Anaerobic Biodegradation of Benzenediols: Catechol, Resorcinol, and Hydroquinone
Publication: Journal of Hazardous, Toxic, and Radioactive Waste
Volume 17, Issue 3
Abstract
Dihydroxybenzenes (DHBs) are widely used to manufacture a variety of chemicals. Because of their broad array of uses, they are found in the effluents of many industries and cause environmental contamination of aquifers and soils. Among various techniques for DHB removal, anaerobic biodegradation can achieve complete and cost-effective elimination of aromatic pollutants through diverse microbial metabolic processes. Successful application of microorganisms to biodegradation requires a deeper understanding of how microbial degradation proceeds under different environmental conditions in batch/continuous processes. In the degradation of a multicomponent feed, the initial acclimation of biomass to a specific component plays an important role in the subsequent biodegradation of the feed. Biodegradation of single and multiple components of DHBs in aqueous environments has not been adequately addressed. In the context of the available literature, the writers’ paper reviews the metabolic pathways of anaerobic degradability under methanogenic, denitrifying, sulfate-reducing, and fermentation conditions. In addition, the writers also critically review anaerobic degradation of DHBs in batch tests and in continuous reactors, such as upflow anaerobic fixed film-fixed bed reactors and upflow anaerobic sludge blanket reactors.
Get full access to this article
View all available purchase options and get full access to this article.
References
Balba, M. T., and Evans, W. C. (1980). “The methanogenic biodegradation of catechol by a microbial consortium: Evidence for the production of phenol through cis-benzenediol.” Biochem. Soc. Trans., 8(4), 452–453.
Battersby, N. S., and Wilson, V. (1989). “Survey of the anaerobic biodegradation potential of organic chemicals in digesting sludge.” Appl. Environ. Microbiol., 55(2), 433–439.
Bukowska, B., and Kowalska, S. (2004). “Phenol and catechol induce prehemalytic and hemolytic changes in human erythrocytes.” Toxicol. Lett., 152(1), 73–84.
Bureau of Indian Standards. (1974a). “Tolerance limits for industrial effluents discharged into inland surface waters.”, New Delhi, India.
Bureau of Indian Standards. (1974b). “Tolerance limits for industrial effluents discharged into public sewers.”, New Delhi, India.
Castro, H. F., Williams, N. H., and Ogram, A. (2000). “Phylogeny of sulfate-reducing bacteria.” FEMS Microbiol. Ecol., 31(1), 1–9.
Chemielowski, J., Grossman, A., and Wegrzynowska, T. (1964). “The anaerobic decomposition of phenol during methane fermentation.” Zesz. Nauk. Politech. Slask. Inz. Sanit., 8(1), 97–122.
Çınar, Ö. (2004). “Biodegradation of central intermediate compounds produced from biodegradation of aromatic compounds.” Bioprocess Biosyst. Eng., 26(5), 341–345.
Clark, F. M., and Fina, L. R. (1952). “The anaerobic decomposition of benzoic acid during methane fermentation.” Arch. Biochem. Biophys., 36(1), 26–32.
Deshpande, S. D., Chakraborti, T., and Subrahmanyam, P. V. R. (1987). “Mixed substrate utilization by acclimated sludge in batch and continuous flow stirred tank reactor.” Environ. Sci. Technol., 21(10), 1003–1008.
Ding, B., Schmeling, S., and Fuchs, G. (2008). “Anaerobic metabolism of catechol by the denitrifying bacterium Thauera aromatica—A result of promiscuous enzymes and regulators?” J. Bacteriol., 190(5), 1620–1630.
Godbole, A., and Chakrabarti, T. (1991). “Biodegradation in upflow anoxic fixed film-fixed bed reactors of resorcinol, catechol and phenol in mono and binary substrate matrices.” Water Res., 25(9), 1113–1120.
Gorny, N., and Schink, B. (1994a). “Anaerobic degradation of catechol by Desulfobacterium sp. strain Cat2 proceeds via carboxylation to protocatechuate.” Appl. Environ. Microbiol., 60(9), 3396–3400.
Gorny, N., and Schink, B. (1994b). “Complete anaerobic oxidation of hydroquinone by Desulfococcus sp. strain Hy5: Indications of hydroquinone carboxylation to gentistate.” Arch. Microbiol., 162(1–2), 131–135.
Gorny, N., and Schink, B. (1994c). “Hydroquinone degradation via reductive dehydroxylation of gentisyl-CoA by a strictly anaerobic fermenting bacterium.” Arch. Microbiol., 161(1), 25–32.
Hazardous Substances Data Bank (HSDB). (1993). National library of medicine, National Institutes of Health, Bethesda, MD.
Healy, J. B., and Young, L. Y. (1978). “Catechol and phenol degradation by a methanogenic population of bacteria.” Appl. Environ. Microbiol., 35(1), 216–218.
Healy, J. B., and Young, L. Y. (1979). “Anaerobic biodegradation of eleven aromatic compounds of methane.” Appl. Environ. Microbiol., 38(1), 84–89.
Heider, J., and Fuchs, G. (1997). “Anaerobic metabolism of aromatic compounds.” Eur. J. Biochem., 243(3), 577–596.
Hwang, P. C., and Cheng, S. S. (1991). “The influence of glucose supplement on the degradation of catechol.” Water Sci. Technol., 23(7–9), 1201–1209.
Jørgensen, B. B. (1982). “Mineralization of organic matter in the sea bed—The role of sulphate reduction.” Nature, 296(5858), 643–645.
Keith, L. H., and Telliard, W. A. (1979). “Priority pollutants: I—A perspective view.” Environ. Sci. Technol., 13(4), 416–423.
Klopman, G., Saiakhov, R., Tu, M., Pusca, F., and Rorije, E. (1998). “Computer-assisted evaluation of anaerobic biodegradation products.” Pure Appl. Chem., 70(7), 1385–1394.
Kluge, C., Tschech, A., and Fuchs, G. (1990). “Anaerobic metabolism of resorcicyclic acids (-dyhroxy benzoylic acids) and resorcinol (1,3-benzendiol) and in a fermenting and denitrifying bacterium.” Arch. Microbiol., 155(1), 68–74.
Kuever, J., Kulmer, J., Jannsen, S., Fischer, U., and Blotevogel, K. H. (1993). “Isolation and characterization of a new spore-forming sulfate-reducing bacterium growing by complete oxidation of catechol.” Arch. Microbiol., 159(3), 282–288.
Kuever, J., Rainey, F. A., and Widdel, F. (2005). “Class IV. Deltaproteobacteria class nov.” Bergey’s manual of systematic bacteriology, D. J. Brenner, N. R. Krieg, J. T. Staley, and G. M. Garrity, 2nd Ed., Part C, Springer, New York, 922.
Kumaran, P., and Paruchuri, Y. L. (1997). “Kinetics of phenol biotransformation.” Water Res., 31(1), 11–22.
Kuschk, P., Stottmeister, U., Liu, Y. J., Wiessner, A., Kästner, M., and Müller, R. A. (2010). “Batch methanogenic fermentation experiments of wastewater from a brown coal low-temperature coke plant.” J. Environ. Sci., 22(2), 192–197.
Latkar, M., and Chakrabarti, T. (1994). “Resorcinol, catechol and hydroquinone biodegradation in mono and binary substrate matrices in upflow anaerobic fixed film-fixed bed reactors.” Water Res., 28(3), 599–607.
Latkar, M., Swaminathan, K., and Chakrabarti, T. (2003). “Kinetics of anaerobic biodegradation of resorcinol, catechol and hydroquinone in upflow fixed film-fixed bed reactors.” Bioresour. Technol., 88(1), 69–74.
Levén, L., and Schnürer, A. (2005). “Effects of temperature on biological degradation of phenols, benzoates and phthalates under methanogenic conditions.” Int. Biodeterioration Biodegradation, 55(2), 153–160.
Lewis, R. J., Sr. (2004). Sax’s dangerous properties of industrial materials, 11th Ed., Wiley, Hoboken, NJ, 728.
MSDS. (2006). Material safety data sheet of Environmental Health and Safety.
Michalowicz, J., and Duda, W. (2007). “Phenols—Sources and toxicity.” Polish J. Environ. Stud., 16(3), 347–362.
Milligan, P. W., and Häggblom, M. M. (1998). “Biodegradation of resorcinol and catechol by denitrifying enrichment cultures.” Environ. Toxicol. Chem., 17(8), 1456–1461.
O’Connor, O. A., and Young, L. Y. (1996). “Effects of six different functional groups and their position on the bacterial metabolism of monosubstituted phenols under anaerobic conditions.” Environ. Sci. Tech., 30(5), 1419–1428.
Owen, W. F., Stuckey, D. C., Healy, J. B., Young, L. Y., and McCarty, P. L. (1979). “Bioassay for monitoring biochemical methane potential and anaerobic toxicity.” Water Res., 13(6), 485–492.
Philipp, B., and Schink, B. (1998). “Evidence of two oxidative reaction steps initiating anaerobic degradation of resorcinol (1,3-dihydroxybenzene) by the denitrifying bacterium Azoarcus anaerobius.” J. Bacteriol., 180(14), 3644–3649.
Prager, J. C. (1997). Environmental contaminant reference data book, Van Nostrand Reinhold, New York, 190–193.
Raff, R., and Etlling, B. V. (1966). Kirk-Othmer encyclopedia of chemical technology, 2nd Ed., Wiley, New York, 462–483.
Schink, B., Philipp, B., and Müller, J. (2000). “Anaerobic degradation of phenolic compounds.” Naturwissenschaften, 87(1), 12–23.
Schmiedel, K. W., and Decker, D. (2000). “Resorcinol.” Ullmann’s encyclopedia of industrial chemistry, Wiley, Weinheim, Germany, 1–14.
Schnell, S., Bak, F., and Pfennig, N. (1989). “Anaerobic degradation of aniline and dihydroxybenzenes by newly isolated sulfate-reducing bacteria and description of Desulfobacterium anilini.” Arch Microbiol., 152(6), 556–563.
Shivaraman, N., and Pandey, R. A. (2000). “Characterization and biodegradation of phenolic wastewater.” J. IAEM, 27(1), 12–15.
Subramanyam, R. (2007). “Performance of an UASB reactor for the treatment of catechol and resorcinol.” Ph.D. thesis, Indian Institute of Technology, Roorkee, India.
Subramanyam, R. (2013). “Physicochemical and morphological characteristics of granular sludge in upflow anaerobic sludge blanket (UASB) reactors.” Environ. Eng. Sci., in press.
Subramanyam, R., and Mishra, I. M. (2007). “Biodegradation of catechol (2-hydroxy phenol) bearing wastewater in an UASB reactor.” Chemosphere, 69(5), 816–824.
Subramanyam, R., and Mishra, I. M. (2008a). “Co-degradation of resorcinol and catechol in an UASB reactor.” Bioresour. Technol., 99(10), 4147–4157.
Subramanyam, R., and Mishra, I. M. (2008b). “Treatment of catechol bearing wastewater in an upflow anaerobic sludge blanket (UASB) reactor: Sludge characteristics.” Bioresour. Technol., 99(18), 8917–8925.
Subramanyam, R., and Mishra, I. M. (2011). “Chemical characteristics of the granular sludge from an UASB reactor treating binary mixture of catechol and resorcinol in an aqueous solution.” Proc., 2nd Int. Conf. on Environmental Engineering and Applications, IPCBEE, IACSIT Press, Singapore, 17(1), 128–133.
Subramanyam, R., and Mishra, I. M. (2013). “Characteristics of methanogenic granules grown on glucose in an upflow anaerobic sludge blanket reactor.” Biosyst. Eng., 114(2), 113–123.
Suidan, M. T., Cross, W. H., and Fong, M. (1980). “Continuous bioregeneration of granular activated carbon during the anaerobic degradation of catechol.” Prog. Water Technol., 12(6), 203–214.
Swaminathan, K., Chakrabarti, T., and Subrahmanyam, P. V. R. (1999). “Substrate-substrate interaction of resorcinol and catechol in upflow anaerobic fixed film-fixed bed reactors in mono and multi substrate matrices.” Bioprocess Eng., 20(4), 349–353.
Swaminathan, K., Swaminathan, T., and Subrahmanyam, P. V. R. (1991). “Degradation of resorcinol in upflow anaerobic filter” J. Environ. Sci. Health A, 26(5), 655–672.
Szewzyk, R., and Pfennig, N. (1987). “Complete oxidation of catechol by the strictly anaerobic sulfate-reducing Desulfobacterium catecholicum sp. nov.” Arch. Microbiol., 147(2), 163–168.
Travin, D., and Buswell, A. M. (1934). “The methane fermentation of organic acids and carbohydrates.” J. Am. Chem. Soc., 56(8), 1751–1755.
Tschech, A., and Schink, B. (1985). “Fermentative degradation of resorcinol and resorcylic acids.” Arch. Microbiol., 143(1), 52–59.
U.S. EPA. (2012). “EPA TRI explorer.” 〈http://iaspub.epa.gov/triexplorer/tri_release.chemical〉 (Dec. 14, 2012).
Welsch, F. (2008). “Routes and modes of administration of resorcinol and their relationship to potential manifestations of thyroid gland toxicity in animals and man.” Int. J. Toxicol., 27(1), 59–63.
Yang, H., Jiang, Z., and Shi, S. (2006). “Aromatic compounds biodegradation under anaerobic conditions and their QSBR models.” Sci. Total Environ., 358(1), 265–276.
Young, L. Y., and Rivera, M. D. (1985). “Methanogenic degradation of four phenolic compounds.” Water Res., 19(10), 1325–1332.
Zeyaullah, M., Abdelkafe, A. S., Zabya, W. B., and Ali, A. (2009). “Biodegradation of catechols by micro-organisms—A short review.” Afr. J. Biotechnol., 8(13), 2916–2922.
Information & Authors
Information
Published In
Journal of Hazardous, Toxic, and Radioactive Waste
Volume 17 • Issue 3 • July 2013
Pages: 218 - 229
Copyright
© 2013 American Society of Civil Engineers.
History
Received: Jun 23, 2012
Accepted: Dec 17, 2012
Published online: Dec 19, 2012
Published in print: Jul 1, 2013
Authors
Metrics & Citations
Metrics
Citations
Download citation
If you have the appropriate software installed, you can download article citation data to the citation manager of your choice. Simply select your manager software from the list below and click Download.