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Phthalates biodegradation in the environment

  • Da-Wei Liang
  • Tong ZhangEmail author
  • Herbert H. P. Fang
  • Jianzhong He
Mini-Review

Abstract

Phthalates are synthesized in massive amounts to produce various plastics and have become widespread in environments following their release as a result of extensive usage and production. This has been of an environmental concern because phthalates are hepatotoxic, teratogenic, and carcinogenic by nature. Numerous studies indicated that phthalates can be degraded by bacteria and fungi under aerobic, anoxic, and anaerobic conditions. This paper gives a review on the biodegradation of phthalates and includes the following aspects: (1) the relationship between the chemical structure of phthalates and their biodegradability, (2) the biodegradation of phthalates by pure/mixed cultures, (3) the biodegradation of phthalates under various environments, and (4) the biodegradation pathways of phthalates.

Keywords

Phthalates Biodegradation Environment Pathway 

Notes

Acknowledgement

The authors wish to thank the Hong Kong Research Grants Council for the financial support of this study (HKU 7107/03E).

References

  1. Ahn JY, Kim YH, Min J, Lee J (2006) Accelerated degradation of dipentyl phthalate by Fusarium oxysporum f. sp pisi cutinase and toxicity evaluation of its degradation products using bioluminescent bacteria. Curr Microbiol 52:340–344Google Scholar
  2. Alatriste-Mondragon F, Iranpour R, Ahring BK (2003) Toxicity of di-(2-ethylhexyl) phthalate on the anaerobic digestion of wastewater sludge. Water Res 37:1260–1269Google Scholar
  3. Amir S, Hafidi M, Merlina G, Hamdi H, Jouraiphy A, El Gharous M, Revel JC (2005) Fate of phthalic acid esters during composting of both lagooning and activated sludges. Process Biochem 40:2183–2190Google Scholar
  4. Bago B, Martin Y, Mejia G, Broto-Puig F, Diaz-Ferrero J, Agut M, Comellas L (2005) Di-(2-ethylhexyl) phthalate in sewage sludge and post-treated sludge: quantitative determination by HRGC-MS and mass spectral characterization. Chemosphere 59:1191–1195Google Scholar
  5. Barnabé S, Beauchesne I, Cooper DG, Nicell JA (2008) Plasticizers and their degradation products in the process streams of a large urban physicochemical sewage treatment plant. Water Res 42:153–162Google Scholar
  6. Battersby NS, Wilson V (1989) Survey of the anaerobic biodegradation potential of organic-chemicals in digesting sludge. Appl Environ Microbiol 55:433-439Google Scholar
  7. Benckiser G, Ottow JCG (1982) Metabolism of the plasticizer di-normal-butylphthalate by Pseudomonas pseudoalcaligenes under anaerobic conditions, with nitrate as the only electron-acceptor. Appl Environ Microbiol 44:576–578Google Scholar
  8. Cartwright CD, Owen SA, Thompson IP, Burns RG (2000) Biodegradation of diethyl phthalate in soil by a novel pathway. FEMS Microbiol Lett 186:27–34Google Scholar
  9. Chang HK, Zylstra GJ (1998) Novel organization of the genes for phthalate degradation from Burkholderia cepacia DBO1. J Bacteriol 180:6529–6537Google Scholar
  10. Chang BV, Yang CM, Cheng CH, Yuan SY (2004) Biodegradation of phthalate esters by two bacteria strains. Chemosphere 55:533–538Google Scholar
  11. Chang BV, Liao CS, Yuan SY (2005a) Anaerobic degradation of diethyl phthalate, di-n-butyl phthalate, and di-(2-ethylhexyl) phthalate from river sediment in Taiwan. Chemosphere 58:1601–1607Google Scholar
  12. Chang BV, Liao GS, Yuan SY (2005b) Anaerobic degradation of di-n-butyl phthalate and di-(2-ethylhexyl) phthalate in sludge. Bull Environ Contam Toxicol 75:775–782Google Scholar
  13. Chang BV, Wang TH, Yuan SY (2007) Biodegradation of four phthalate esters in sludge. Chemosphere 69:1116–1123Google Scholar
  14. Chao WL, Cheng CY (2007) Effect of introduced phthalate-degrading bacteria on the diversity of indigenous bacterial communities during di-(2-ethylhexyl) phthalate (DEHP) degradation in a soil microcosm. Chemosphere 67:482–488Google Scholar
  15. Chao WL, Lin CM, Shiung II, Kuo YL (2006) Degradation of di-butyl-phthalate by soil bacteria. Chemosphere 63:1377–1383Google Scholar
  16. Chatterjee S, Dutta TK (2003) Metabolism of butyl benzyl phthalate by Gordonia sp strain MTCC 4818. Biochem Biophy Res Commun 309:36–43Google Scholar
  17. Chatterjee S, Dutta TK (2008) Complete degradation of butyl benzyl phthalate by a defined bacterial consortium: role of individual isolates in the assimilation pathway. Chemosphere 70:933–941CrossRefGoogle Scholar
  18. Chen JA, Li X, Li J, Cao J, Qiu ZQ, Zhao Q, Xu C, Shu WQ (2007) Degradation of environmental endocrine disruptor di-2-ethylhexyl phthalate by a newly discovered bacterium, Microbacterium sp strain CQ0110Y. Appl Microbiol Biotechnol 74:676–682Google Scholar
  19. Cheng HF, Chen SY, Lin JG (2000) Biodegradation of di-(2-ethylhexyl) phthalate in sewage sludge. Water Sci Technol 41:1–6Google Scholar
  20. Cheung JKH, Lam RKW, Shi MY, Gu JD (2007) Environmental fate of endocrine-disrupting dimethyl phthalate esters (DMPE) under sulfate-reducing condition. Sci Total Envion 381:126–133Google Scholar
  21. Choi KY, Kim D, Sul WJ, Chae JC, Zylstra GJ, Kim YM, Kim E (2005) Molecular and biochemical analysis of phthalate and terephthalate degradation by Rhodococcus sp strain DK17. FEMS Microbiol Lett 252:207–213Google Scholar
  22. Dennis DA, Chapman PJ, Dagley S (1973) Degradation of protocatechuate in Pseudomonas testosteroni by a pathway involving oxidation of product of meta fission. J Bacteriol 113:521–523Google Scholar
  23. Di Gennaro P, Collina E, Franzetti A, Lasagni M, Luridiana A, Pitea D, Bestetti G (2005) Bioremediation of diethylhexyl phthalate contaminated soil: a feasibility study in slurry- and solid-phase reactors. Environ Sci Technol 39:325–330Google Scholar
  24. Eaton RW (2001) Plasmid-encoded phthalate catabolic pathway in Arthrobacter keyseri 12B. J Bacteriol 183:3689–3703Google Scholar
  25. Eaton RW, Ribbons DW (1982) Metabolism of dibutylphthalate and phthalate by Micrococcus sp strain 12b. J Bacteriol 151:48–57Google Scholar
  26. Ejlertsson J, Svensson BH (1997) Degradation of bis (2-ethylhexyl) phthalate constituents under methanogenic conditions. Biodegradation 7:501–506Google Scholar
  27. Ejlertsson J, Houwen FP, Svensson BH (1996a) Anaerobic degradation of diethyl phthalate and phthalic acid during incubation of municipal solid waste from a biogas digestor. Swed J Agri Res 26:53–59Google Scholar
  28. Ejlertsson J, Meyerson U, Svensson BH (1996b) Anaerobic degradation of phthalic acid esters during digestion of municipal solid waste under landfilling conditions. Biodegradation 7:345–352Google Scholar
  29. Ejlertsson J, Alnervik M, Jonsson S, Svensson BH (1997) Influence of water solubility, side-chain degradability, and side-chain structure on the degradation of phthalic acid esters under methanogenic conditions. Environ Sci Technol 31:2761–2764Google Scholar
  30. El-Hadj TB, Dosta J, Mata-Alvarez J (2006) Biodegradation of PAH and DEHP micro-pollutants in mesophilic and thermophilic anaerobic sewage sludge digestion. Water Sci Technol 53:99–107Google Scholar
  31. Elder DJE, Kelly DJ (1994) The bacterial degradation of benzoic-acid and benzenoid compounds under anaerobic conditions—unifying trends and new perspectives. FEMS Microbiol Rev 13:441–468Google Scholar
  32. Engelhardt G, Wallnofer PR (1978) Metabolism of di-normal-butyl phthalate and mono-normal-butyl phthalate by soil bacteria. Appl Environ Microbiol 35:243–246Google Scholar
  33. Engelhardt G, Tillmanns G, Wallnofer PR, Hutzinger O (1977) Biodegradation of di-iso-butyl phthalate and related dialkyl phthalates by Penicillium lilacinum. Chemosphere 6:347–354Google Scholar
  34. Fang HHP, Liang DW, Zhang T (2007) Aerobic degradation of diethyl phthalate by Sphingomonas sp. Bioresour Technol 98:717–720Google Scholar
  35. Fauser P, Vikelsøe J, Sorensen PB, Carlsen L (2003) Phthalates, nonylphenols and LAS in an alternately operated wastewater treatment plant—fate modelling based on measured concentrations in wastewater and sludge. Water Res 37:1288–1295Google Scholar
  36. Feng Z, Cui KY, Li XD, Fu JA, Sheng GY (2004) Biodegradation kinetics of phthalate esters by Pseudomonas fluoresences FS1. Process Biochem 39:1125–1129Google Scholar
  37. Ganji S, Karigar C, Pujar B (1995) Metabolism of dimethylterephthalate by Aspergillus niger. Biodegradation 6:61–66Google Scholar
  38. Gavala HN, Alatriste-Mondragon F, Iranpour R, Ahring BK (2003) Biodegradation of phthalate esters during the mesophilic anaerobic digestion of sludge. Chemosphere 52:673–682Google Scholar
  39. Grifoll M, Selifonov SA, Chapman PJ (1994) Evidence for a novel pathway in the degradation of fluorene by Pseudomonas sp strain F274. Appl Environ Microbiol 60:2438–2449Google Scholar
  40. Gu JD, Li J, Wang Y (2005) Biochemical pathway and degradation of phthalate ester isomers by bacteria. Water Sci Technol 52:241–248Google Scholar
  41. Hashizume K, Nanya J, Toda C, Yasui T, Nagano H, Kojima N (2002) Phthalate esters detected in various water samples and biodegradation of the phthalates by microbes isolated from river water. Biol Pharm Bull 25:209–214Google Scholar
  42. Horn O, Nalli S, Cooper D, Nicell J (2004) Plasticizer metabolites in the environment. Water Res 38:3693–3698Google Scholar
  43. Jackson MA, Labeda DP, Becker LA (1996) Isolation for bacteria and fungi for the hydrolysis of phthalate and terephthalate esters. J Ind Microbiol 16:301–304Google Scholar
  44. Jonsson S, Ejlertsson J, Svensson BH (2003a) Behaviour of mono- and diesters of o-phthalic acid in leachates released during digestion of municipal solid waste under landfill conditions. Adv Environ Res 7:429–440Google Scholar
  45. Jonsson S, Ejlertsson J, Svensson BH (2003b) Transformation of phthalates in young landfill cells. Waste Manage 23:641–651Google Scholar
  46. Jonsson S, Ejlertsson M, Ledin A, Mersiowsky I, Svensson BH (2003c) Mono- and diesters from o-phthalic acid in leachates from different European landfills. Water Res 37:609–617Google Scholar
  47. Juneson C, Ward OP, Singh A (2001) Biodegradation of bis-(2-ethylhexyl) phthalate in a soil slurry-sequencing batch reactor. Process Biochem 37:305–313Google Scholar
  48. Juneson C, Ward OP, Singh A (2002) Biodegradation of dimethyl phthalate with high removal rates in a packed-bed reactor. World J Microbiol Biotechnol 18:7–10Google Scholar
  49. Kapanen A, Stephen JR, Bruggemann J, Kiviranta A, White DC, Itavaara M (2007) Diethyl phthalate in compost: ecotoxicological effects and response of the microbial community. Chemosphere 67:2201–2209Google Scholar
  50. Karegoudar TB, Pujar BG (1984) Metabolism of diethylphthalate by a soil bacterium. Curr Microbiol 11:321–324Google Scholar
  51. Keyser P, Pujar BG, Eaton RW, Ribbons DW (1976) Biodegradation of phthalates and their esters by bacteria. Environ Health Perspect 18:159–166Google Scholar
  52. Kido Y, Tanaka T, Yamadaa K, Hachiyanagi H, Baba H, Iriguchi T, Uyeda M (2007) Complete degradation of the endocrine-disrupting chemical dimethyl phthalate ester by Flavobacterium sp. J Health Sci 53:740–744Google Scholar
  53. Kim YH, Lee J (2005) Enzymatic degradation of dibutyl phthalate and toxicity of its degradation products. Biotechnol Lett 27:635–639Google Scholar
  54. Kim YH, Lee JW, Ahn JY, Gu MB, Moon SH (2002) Enhanced degradation of an endocrine-disrupting chemical, butyl benzyl phthalate, by Fusarium oxysporum f. sp pisi cutinase. Appl Environ Microbiol 68:4684–4688Google Scholar
  55. Kim YH, Lee J, Moon SH (2003) Degradation of an endocrine disrupting chemical, DEHP [di-(2-ethylhexyl)-phthalate], by Fusarium oxysporum f. sp pisi cutinase. Appl Microbiol Biotechnol 63:75–80Google Scholar
  56. Kim YH, Min JH, Bae KD, Gu MB, Lee J (2005) Biodegradation of dipropyl phthalate and toxicity of its degradation products: a comparison of Fusarium oxysporum f. sp pisi cutinase and Candida cylindracea esterase. Archives of Microbiol 184:25–31Google Scholar
  57. Kim YH, Seo HS, Min J, Kim YC, Ban YH, Han KY, Park JS, Bae KD, Gu MB, Lee J (2007) Enhanced degradation and toxicity reduction of dihexyl phthalate by Fusarium oxysporum f. sp pisi cutinase. J Appl Microbiol 102:221–228Google Scholar
  58. Kim DS, Um H-J, Lim E-S, Min J, Kim YH (2008) Degradation of diphenyl phthalate by Sphingomonas chungbukensis. Biotechnol Lett 30:93–96Google Scholar
  59. Kiyohara H, Nagao K (1978) Catabolism of phenanthrene and naphthalene by bacteria. J Gen Microbiol 105:69–75Google Scholar
  60. Kleerebezem R, Mortier J, Pol LWH, Lettinga G (1997) Anaerobic pre-treatment of petrochemical effluents: terephthalic acid wastewater. Water Sci Technol 36:237–248Google Scholar
  61. Kleerebezem R, Ivalo M, Pol LWH, Lettinga G (1999a) High-rate treatment of terephthalate in anaerobic hybrid reactors. Biotechnol Prog 15:347–357Google Scholar
  62. Kleerebezem R, Pol LWH, Lettinga G (1999b) Anaerobic biodegradability of phthalic acid isomers and related compounds. Biodegradation 10:63–73Google Scholar
  63. Kleerebezem R, Pol LWH, Lettinga G (1999c) Energetics of product formation during anaerobic degradation of phthalate isomers and benzoate. FEMS Microbiol Ecology 29:273–282Google Scholar
  64. Kleerebezem R, Beckers J, Pol LWH, Lettinga G (2005) High rate treatment of terephthalic acid production wastewater in a two-stage anaerobic bioreactor. Biotechnol Bioeng 91:169–179Google Scholar
  65. Kurane R (1997) Microbial degradation and treatment of polycyclic aromatic hydrocarbons and plasticizers. Ann NY Acad Sci 829:118–134Google Scholar
  66. Lee SM, Koo BW, Lee SS, Kim MK, Choi DH, Hong EJ, Jeung EB, Choi IG (2004) Biodegradation of dibutylphthalate by white rot fungi and evaluation on its estrogenic activity. Enzyme Microb Technol 35:417–423Google Scholar
  67. Lee SM, Lee JW, Koo BW, Kim MK, Choi DH, Choi IG (2007) Dibutyl phthalate biodegradation by the white rot fungus, Polyporus brumalis. Biotechnol Bioeng 97:1516–1522Google Scholar
  68. Li H, Gu JD (2007) Complete degradation of dimethyl isoplithalate requires the biochemical cooperation between Klebsiella oxytoca Sc and Methylobacterium mesophilicum Sr Isolated from Wetland sediment. Sci Total Environ 380:181–187Google Scholar
  69. Li JX, Gu JD, Pan L (2005a) Transformation of dimethyl phthalate, dimethyl isophthalate and dimethyl terephthalate by Rhodococcus rubber Sa and modeling the processes using the modified Gompertz model. Int Biodeter Biodegr 55:223–232Google Scholar
  70. Li JX, Gu JD, Yao JH (2005b) Degradation of dimethyl terephthalate by Pasteurella multocida Sa and Sphingomonas paucimobilis Sy isolated from mangrove sediment. Int Biodeter Biodegr 56:158–165Google Scholar
  71. Li J, Chen JA, Zhao Q, Li X, Shu WQ (2006) Bioremediation of environmental endocrine disruptor di-n-butyl phthalate ester by Rhodococcus ruber. Chemosphere 65:1627–1633Google Scholar
  72. Li B, Chi J, Wu WX, Wang ZK (2007) Effect of nutrients and light on biodegradation of dibutyl phthalate and di-2-ethylexyl phthalate in haihe estuary. Bull Environ Contam Toxicol 79:80–83Google Scholar
  73. Liang DW, Zhang T, Fang HHP (2007) Anaerobic degradation of dimethyl phthalate in wastewater in a UASB reactor. Water Res 41:2879–2884Google Scholar
  74. Liu SM, Chi WC (2003) CO2-H2 dependent anaerobic biotransformation of phthalic acid isomers in sediment slurries. Chemosphere 52:951–958Google Scholar
  75. Madsen PL, Thyme JB, Henriksen K, Moldrup P, Roslev P (1999) Kinetics of di-(2-ethylhexyl) phthalate mineralization in sludge amended soil. Environ Sci Technol 33:2601–2606Google Scholar
  76. Marttinen SK, Kettunen RH, Rintala JA (2003a) Occurrence and removal of organic pollutants in sewages and landfill leachates. Sci Total Environ 301:1–12Google Scholar
  77. Marttinen SK, Kettunen RH, Sormunen KM, Rintala JA (2003b) Removal of bis(2-ethylhexyl) phthalate at a sewage treatment plant. Water Res 37:1385–1393Google Scholar
  78. Marttinen SK, Hanninen K, Rintala JA (2004a) Removal of DEHP in composting and aeration of sewage sludge. Chemosphere 54:265–272Google Scholar
  79. Marttinen SK, Ruissalo M, Rintala JA (2004b) Removal of bis-(2-ethylhexyl) phthalate from reject water in a nitrogen-removing sequencing batch reactor. J Environ Manage 73:103–109Google Scholar
  80. Maruyama K, Akita K, Naitou C, Yoshida M, Kitamura T (2005) Purification and characterization of an esterase hydrolyzing monoalkyl phthalates from Micrococcus sp YGJ1. J Biochem 137:27–32Google Scholar
  81. Matsumoto M, Hirata-Koizumi M, Ema M (2008) Potential adverse effects of phthalic acid esters on human health: a review of recent studies on reproduction. Regul Toxicol Pharm 50:37–49Google Scholar
  82. Mohan SV, Shailaja S, Krishna MR, Reddy KB, Sarma PN (2006) Bioslurry phase degradation of di-ethyl phthalate (DEP) contaminated soil in periodic discontinuous mode operation: influence of bioaugmentation and substrate partition. Process Biochem 41:644–652Google Scholar
  83. Nakamiya K, Hashimoto S, Ito H, Edmonds JS, Yasuhara A, Morita M (2005) Microbial treatment of bis (2-ethylhexyl) phthalate in polyvinyl chloride with isolated bacteria. J Biosci Bioeng 99:115–119Google Scholar
  84. Nakazawa T, Hayashi E (1977) Phthalate metabolism in Pseudomonas testosterone—accumulation of 4,5-dihydroxyphthalate by a mutant strain. J Bacteriol 131:42–48Google Scholar
  85. Nalli S, Cooper DG, Nicell JA (2002) Biodegradation of plasticizers by Rhodococcus rhodochrous. Biodegradation 13:343–352Google Scholar
  86. Nalli S, Cooper DG, Nicell JA (2006) Metabolites from the biodegradation of di-ester plasticizers by Rhodococcus rhodochrous. Sci Total Environ 366:286–294Google Scholar
  87. Naumova RP, Zaripova SK, Usmanova LP (1986) Regulation of terephthalate catabolism in Rhodococcus rubropertinctus. Microbiology 55:729–734Google Scholar
  88. Niazi JH, Karegoudar TB (2001) Degradation of dimethylphthalate by cells of Bacillus sp immobilized in calcium alginate and polyurethane foam. J Environ Sci Health Part A 36:1135–1144Google Scholar
  89. Nomura Y, Nakagawa M, Ogawa N, Harashima S, Oshima Y (1992) Genes in pht plasmid encoding the initial degradation pathway of phthalate in Pseudomonas putida. J Ferm Bioeng 74:333–344Google Scholar
  90. Nozawa T, Maruyama Y (1988) Anaerobic metabolism of phthalate and other aromatic-compounds by a denitrifying bacterium. J Bacteriol 170:5778–5784Google Scholar
  91. O’connor OA, Rivera MD, Young LY (1989) Toxicity and biodegradation of phthalic-acid esters under methanogenic conditions. Environ Toxicol Chem 8:569–576Google Scholar
  92. Oliver R, May E, Williams J (2005) The occurrence and removal of phthalates in a trickle filter STW. Water Res 39:4436–4444Google Scholar
  93. Oliver R, May E, Williams J (2007) Microcosm investigations of phthalate behaviour in sewage treatment biofilms. Sci Total Environ 372:605–614Google Scholar
  94. Patil N, Karegoudar T (2005) Parametric studies on batch degradation of a plasticizer di-n-butylphthalate by immobilized Bacillus sp. World J Microbiol Biotechnol 21:1493–1498Google Scholar
  95. Patil NK, Kundapur R, Shouche YS, Karegoudar TB (2006) Degradation of a plasticizer, di-n-butylphthalate by Delftia sp TBKNP-05. Curr Microbiol 52:225–230Google Scholar
  96. Patrauchan MA, Florizone C, Dosanjh M, Molm WW, Davies J, Eltis LD (2005) Catabolism of benzoate and phthalate in Rhodococcus sp strain RHA1: redundancies and convergence. J Bacteriol 187:4050–4063Google Scholar
  97. Qiu YL, Sekiguchi Y, Imachi H, Kamagata Y, Tseng IC, Cheng SS, Ohashi A, Harada H (2004) Identification and isolation of anaerobic, syntrophic phthalate isomer-degrading microbes from methanogenic sludges treating wastewater from terephthalate manufacturing. Appl Environ Microbiol 70:1617–1626Google Scholar
  98. Qiu YL, Sekiguchi Y, Hanada S, Imachi H, Tseng IC, Cheng SS, Ohashi A, Harada H, Kamagata Y (2006) Pelotomaculum terephthalicum sp nov. and Pelotomaculum isophthalicum sp nov.: two anaerobic bacteria that degrade phthalate isomers in syntrophic association with hydrogenotrophic methanogens. Archives Microbiol 185:172–182Google Scholar
  99. Quan CS, Liu Q, Tian WJ, Kikuchi J, Fan SD (2005) Biodegradation of an endocrine-disrupting chemical, di-2-ethylhexyl phthalate, by Bacillus subtilis no. 66. Appl Microbiol Biotechnol 66:702–710Google Scholar
  100. Rani M, Prakash D, Sobti RC, Jain RK (1996) Plasmid-mediated degradation of o-phthalate and salicylate by a Moraxella sp.. Biochem Biophys Res Commun 220:377–381Google Scholar
  101. Roslev P, Vorkamp K, Aarup J, Frederiksen K, Nielsen PH (2007) Degradation of phthalate esters in an activated sludge wastewater treatment plant. Water Res 41:969-976Google Scholar
  102. Roslev P, Madsen PL, Thyme JB, Henriksen K (1998) Degradation of phthalate and di-(2-ethylhexyl) phthalate by indigenous and inoculated microorganisms in sludge-amended soil. Appl Environ Microbiol 64:4711–4719Google Scholar
  103. Schlafli HR, Weiss MA, Leisinger T, Cook AM (1994) Terephthalate 1,2-dioxygenase system from comamonas-testosteroni-t-2—purification and some properties of the oxygenase component. J Bacteriol 176:6644–6652Google Scholar
  104. Schwarzbauer J, Heim S, Brinker S, Littke R (2002) Occurrence and alteration of organic contaminants in seepage and leakage water from a waste deposit landfill. Water Res 36:2275–2287Google Scholar
  105. Shailaja S, Ramakrishna M, Mohan SV, Sarma PN (2007) Biodegradation of di-n-butyl phthalate (DnBP) in bioaugmented bioslurry phase reactor. Bioresour Technol 98:1561–1566Google Scholar
  106. Shelton DR, Boyd SA, Tiedje JM (1984) Anaerobic biodegradation of phthalic-acid esters in sludge. Environ Sci Technol 18:93–97Google Scholar
  107. Sivamurthy K, Swamy BM, Pujar BG (1991) Transformation of dimethylterephthalate by the fungus Sclerotium rolfsii. FEMS Microbiol Lett 79:37–40Google Scholar
  108. Staples CA, Peterson DR, Parkerton TF, Adams WJ (1997) The environmental fate of phthalate esters: a literature review. Chemosphere 35:667–749Google Scholar
  109. Sugatt RH, Ogrady DP, Banerjee S, Howard PH, Gledhill WE (1984) Shake flask biodegradation of 14 commercial phthalate esters. Appl Environ Microbiol 47:601–606Google Scholar
  110. Tanaka T, Yamada K, Iijima T, Iriguchi T, Kido Y (2006) Complete degradation of the endocrine-disrupting chemical phthalic acid by Flavobacterium sp. J Health Sci 52:800–804Google Scholar
  111. Tur MY, Huang JC (1997) Treatment of phthalic waste by anaerobic hybrid reactor. J Environ Eng-ASCE 123:1093–1099Google Scholar
  112. Turner A, Rawling MC (2000) The behaviour of di-(2-ethylhexyl) phthalate in estuaries. Marine Chem 68:203–217Google Scholar
  113. Vamsee-Krishna C, Mohan Y, Phale PS (2006) Biodegradation of phthalate isomers by Pseudomonas aeruginosa PP4, Pseudomonas sp PPD and Acinetobacter lwoffii ISP4. Appl Microbiol Biotechnol 72:1263–1269Google Scholar
  114. Vega D, Bastide J (2003) Dimethylphthalate hydrolysis by specific microbial esterase. Chemosphere 51:663–668Google Scholar
  115. Wang YP, Gu JD (2006a) Degradability of dimethyl terephthalate by Variovorax paradoxus T4 and Sphingomonas yanoikuyae DOS01 isolated from deep-ocean sediments. Ecotoxicol 15:549–557Google Scholar
  116. Wang YP, Gu JD (2006b) Degradation of dimethyl isophthalate by Viarovorax paradoxus strain T4 isolated from deep-ocean sediment of the South China Sea. Human Ecol Risk Assess 12:236–247Google Scholar
  117. Wang YZ, Zhou YM, Zystra GJ (1995) Molecular analysis of isophthalate and terephthalate degradation by Comamonas testosteroni YZW-D. Environ Health Perspect 103:9–12Google Scholar
  118. Wang JL, Liu P, Shi HC, Qian Y (1997a) Biodegradation of phthalic acid ester in soil by indigenous and introduced microorganisms. Chemosphere 35:1747–1754Google Scholar
  119. Wang JL, Liu P, Shi HC, Qian Y (1997b) Kinetics of phthalic acid ester degradation by acclimated activated sludge. Process Biochem 32:567–571Google Scholar
  120. Wang JL, Chen LJ, Shi HC, Qian Y (2000) Microbial degradation of phthalic acid esters under anaerobic digestion of sludge. Chemosphere 41:1245–1248Google Scholar
  121. Wang YY, Fan YZ, Gu JD (2003) Aerobic degradation of phthalic acid by Comamonas acidovoran Fy-1 and dimethyl phthalate ester by two reconstituted consortia from sewage sludge at high concentrations. World J Microbiol Biotechnol 19:811–815Google Scholar
  122. Wang JL, Xuan Z, Wu WZ (2004a) Biodegradation of phthalic acid esters (PAEs) in soil bioaugmented with acclimated activated sludge. Process Biochem 39:1837–1841Google Scholar
  123. Wang SG, Lin XG, Yin R, Hou YL (2004b) Effect of inoculation with arbuscular mycorrhizal fungi on the degradation of DEHP in soil. J Environ Sci China 16:458–461Google Scholar
  124. Wang YY, Fan YZ, Gu JD (2004c) Dimethyl phthalate ester degradation by two planktonic and immobilized bacterial consortia. Int Biodeter Biodegr 53:93–101Google Scholar
  125. Wensing M, Uhde E, Salthammer T (2005) Plastics additives in the indoor environment—flame retardants and plasticizers. Sci Total Envion 339:19–40Google Scholar
  126. Wolfe NL, Steen WC, Burns LA (1980) Phthalate ester hydrolysis—linear free energy relationships. Chemosphere 9:403–408Google Scholar
  127. Wu JH, Liu WT, Tseng IC, Cheng SS (2001) Characterization of microbial consortia in a terephthalate-degrading anaerobic granular sludge system. Microbiology 147:373–382Google Scholar
  128. Wu DL, Mahmood Q, Zheng P, Hassan MJ (2007) Isolation and physiology of a dimethyl phthalate degrading bacterial strain YZ2. Environ Prog 26:384–390Google Scholar
  129. Xia F, Zheng PZQ, Feng X (2004) Relationship between quantitative structure and biodegradability for phthalic acid ester compounds. J Zhejiang Univ (Agri Life Sci) 30:141–146Google Scholar
  130. Xu XR, Li HB, Gu JD (2005) Biodegradation of an endocrine-disrupting chemical di-n-butyl phthalate ester by Pseudomonas fluorescens B-1. Int Biodeter Biodegr 55:9–15Google Scholar
  131. Xu XR, Li HB, Gu JD (2007) Metabolism and biochemical pathway of n-butyl benzyl phthalate by Pseudomonas fluorescens B-1 isolated from a mangrove sediment. Ecotoxicol Environ Safety 68:379–385Google Scholar
  132. Yan H, Pan G (2004) Increase in biodegradation of dimethyl phthalate by Closterium lunula using inorganic carbon. Chemosphere 55:1281–1285Google Scholar
  133. Yan H, Pan G, Liang PL (2002) Effect and mechanism of inorganic carbon on the biodegradation of dimethyl phthalate by Chlorella pyrenoidosa. J Environ Sci Health Part A 37:553–562Google Scholar
  134. Yuan SY, Liu C, Liao CS, Chang BV (2002) Occurrence and microbial degradation of phthalate esters in Taiwan river sediments. Chemosphere 49:1295–1299Google Scholar
  135. Yuwatini E, Hata N, Taguchi S (2006) Behavior of di-(2-ethylhexyl) phthalate discharged from domestic waste water into aquatic environment. J Environ Monitor 8:191–196Google Scholar
  136. Zheng Z, He P-J, Shao L-M, Lee D-J (2007) Phthalic acid esters in dissolved fractions of landfill leachates. Water Res 41:4696–4702Google Scholar
  137. Zhou QH, Wu ZB, Cheng SP, He F, Fu GP (2005) Enzymatic activities in constructed wetlands and di-n-butyl phthalate (DBP) biodegradation. Soil Biol Biochem 37:1454–1459Google Scholar

Copyright information

© Springer-Verlag 2008

Authors and Affiliations

  • Da-Wei Liang
    • 1
  • Tong Zhang
    • 2
    Email author
  • Herbert H. P. Fang
    • 2
  • Jianzhong He
    • 1
  1. 1.Division of Environmental Science and EngineeringNational University of SingaporeSingaporeSingapore
  2. 2.Department of Civil EngineeringThe University of Hong KongHong KongPeople’s Republic of China

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