Advertisement

Chemical Behavior of Phthalates Under Abiotic Conditions in Landfills

  • Jingyu Huang
  • Philip N. NkrumahEmail author
  • Yi Li
  • Gloria Appiah-Sefah
Chapter
Part of the Reviews of Environmental Contamination and Toxicology book series (RECT, volume 224)

Abstract

Phthalates or phthalic acid esters (PAEs) are diesters of phthalic anhydride. They are synthesized from an esterification reaction between phthalic anhydride and oxo alcohols (ECOBILAN 2001). Phthalates are usually used as plasticizers to enhance the flexibility of materials and their technical properties. Mersiowsky et al. (2001) reported that the phthalates serve as plasticizers for approximately 93 % of the polyvinyl chloride (PVC) polymer that is produced. In addition, they are also used in cosmetics, in fragrances, as pesticide carriers, in insect repellants, and are found in vinyl floorings, wall coverings, cables, tubing, hoses, upholstery, films, paints, adhesives, and inks, among other products (ECPI 1994; Schierow and Lee 2008). The annual worldwide production of PAEs exceeds five million tons (Mackintosh et al. 2006).

Keywords

Phthalic Acid Phthalate Ester Phthalic Anhydride Catalytic Ozonation Butyl Benzyl Phthalate 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Notes

Acknowledgment

We are extremely grateful to Dr. Dave Whitacre, RECT Editor, for his excellent comments and editing of the manuscript. The authors appreciate the input made by Subhankar Chatterjee and other anonymous reviewers. We would also like to thank Jennifer Abena Kwofie for her contribution.

References

  1. Amend WJ (1935) Hydrogenation of alkyl phthalates. United States Patent Office. http://ip.com/patent/US2070770. Accessed 21 May 2012
  2. Atkinson R (1988) Estimation of Gas-Phase hydroxyl radical rate constants for organic chemicals. Environ Toxicol Chem 7(6):435–442CrossRefGoogle Scholar
  3. Bauer MJ, Herrmann R, Martin A, Zellmann H (1998) Chemodynamics, transport behavior and treatment of phthalic acid esters in municipal landfill leachates. Water Sci Technol 38:185–192Google Scholar
  4. Chang BV, Yang CM, Cheng CH, Yuan SY (2004) Biodegradation of phthalate esters by two bacteria strains. Chemosphere 55:533–538CrossRefGoogle Scholar
  5. 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 67:482–488CrossRefGoogle Scholar
  6. Chatterjee S, Karlovsky P (2010) Removal of the endocrine disrupter butyl benzyl phthalate from the environment. Appl Microbiol Biotechnol 87(1):61–73CrossRefGoogle Scholar
  7. Chen Y, Hsieh D, Shang N (2011) Efficient mineralization of dimethyl phthalate by catalytic ozonation using TiO2/Al2O3 catalyst. J Hazard Mater 192:1017–1025CrossRefGoogle Scholar
  8. Christensen TH, Kjeldsen P, Bjerg PL, Jensen DL, Christensen JB, Baun A, Albrechtsen H, Heron G (2001) Biogeochemistry of landfill leachate plumes. Appl Geochem 16:659–718CrossRefGoogle Scholar
  9. Chung Y, Chen C (2009) Degradation of Di-(2-ethylhexyl)phthalate (DEHP) by TiO2 photocatalysis. Water Air Soil Pollut 200:191–198CrossRefGoogle Scholar
  10. Cousins IT, Mackay D, Parkerton TF (2003) Physical-chemical properties and evaluative fate modelling of phthalate esters. In: Charles AS (ed) The handbook of environmental chemistry, Vol. 3, Part Q. Springer, New York, pp 57–84Google Scholar
  11. Di Gennaro P, Collina E, Franzetti A, Lasagni M, Luridiana A, Pitea D (2005) Bioremediation of diethylhexyl phthalate contaminated soil: a feasibility study in slurry-and solid-phase reactors. Environ Sci Technol 39:325–330CrossRefGoogle Scholar
  12. Dohmann T (1997) Emission behaviour of pollutants. Report to the German Ministry of Research (BMBF) by Institut für Siedlungswasserwirtschaft, Rheinisch-Westfä -lische Technische Hochschule AachenGoogle Scholar
  13. Domininghaus H (1998) Plastics and their properties. Int J ChemTech Res 2:1Google Scholar
  14. ECOBILAN (2001) Eco-profile of high volume commodity phthalate esters (DEHP/DINP/DIDP). European Council for Plasticisers & Intermediates (ECPI), BrusselsGoogle Scholar
  15. ECPI (European Council for Plasticisers and Intermediates) (1994) Phthalate esters used in PVC—assessment of the release, occurrence and possible effects of plasticizers in the environment. ECPI, BrusselsGoogle Scholar
  16. Ejlertsson J, Meyerson U, Svensson BH (1996) Anaerobic degradation of phthalic acid esters during digestion of municipal solid waste under landfilling conditions. Biodegradation 7:345–352CrossRefGoogle Scholar
  17. 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 13:441–468CrossRefGoogle Scholar
  18. Fernandez MP, Ikonomou MG, Buchanan I (2007) An assessment of estrogenic organic contaminants in Canadian wastewaters. Sci Total Environ 373:250–269CrossRefGoogle Scholar
  19. Foster PM (2006) Disruption of reproductive development in male rat offspring following in utero exposure to phthalate esters. Int J Androl 29:140–147, discussion 181–185CrossRefGoogle Scholar
  20. Fromme H, Kücher T, Otto T, Pilz K, Müller J, Wenzel A (2002) Occurrence of phthalates and bisphenol A and F in the environment. Water Res 36:1429–1438CrossRefGoogle Scholar
  21. Furtmann K (1996) Phthalates in the aquatic environment. European Council for Plasticisers & Intermediates (ECPI), BrusselsGoogle Scholar
  22. Gächter R, Müller H (1990) Handbook of plastics additives, 3rd edn. Carl Hanser, Munich. ISBN 3-446-15627-5Google Scholar
  23. Ghisari M, Bonefeld-Jorgensen EC (2009) Effects of plasticizers and their mixtures on estrogen receptor and thyroid hormone functions. Toxicol Lett 189:67–77CrossRefGoogle Scholar
  24. Gomez-Hens A, Aguilar-Caballos MP (2003) Social and economic interest in the control of phthalic acid esters. Trends Anal Chem 22:847–857CrossRefGoogle Scholar
  25. Gray LE, Barlow NJ, Howdeshell KL, Ostby JS, Furr JR, Gray CL (2009) Transgenerational effects of di (2-ethylhexyl) phthalate in the male CRL:CD(SD) rat: added value of assessing multiple offspring per litter. Toxicol Sci 110:411–425CrossRefGoogle Scholar
  26. Gültekin I, Ince NH (2007) Synthetic endocrine disruptors in the environment and water remediation by advanced oxidation processes. J Environ Manage 85(4):816–832CrossRefGoogle Scholar
  27. Gurol MD, Singer PC (1982) Kinetic of ozone decomposition: a dynamic approach. Environ Sci Technol 16:377–383CrossRefGoogle Scholar
  28. Harris JC (1982) Rate of hydrolysis. In: Lyman WJ, Reehl WF, Rosenblart DH (eds) Handbook of chemical property estimation methods, chapter 7. McGraw-Hill, New YorkGoogle Scholar
  29. Harris CA, Sumpter JP (2001) The endocrine disrupting potential of phthalates. In: Metzler M (ed) Endocrine disruptors, Part I, vol 3, The handbook of environmental chemistry, Part L. Springer, Heidelberg, Germany, pp 169–201Google Scholar
  30. Hilal SH (2006) Estimation of hydrolysis rate constants of carboxylic acid ester and phosphate ester compounds in aqueous systems from molecular structure by SPARC. U.S. Environmental Protection Agency. EPA/600/R-06/105Google Scholar
  31. Hilal SH, Karickhoff SW, Carreira LA (2003) Prediction of chemical reactivity parameters and physical properties of organic compounds from molecular structure using SPARC. EPA/600/R-03/030Google Scholar
  32. Hoffmann MR, Martin ST, Choi W, Bahnemann DW (1995) Environmental applications of semiconductor photocatalysis. Chem Rev 95:69–96CrossRefGoogle Scholar
  33. Huang PC, Kuo PL, Chou YY, Lin SJ, Lee CC (2009) Association between prenatal exposure to phthalates and the health outcome of newborns. Environ Int 35(1):14–20CrossRefGoogle Scholar
  34. IHCP (2008) Bis (2-ethylhexyl) Phthalate (DEHP) Summary Risk Assessment Report. Institute for Health and Consumer Protection (IHCP). European Commission. European Communities, 2008. Available: http://cerhr.niehs.nih.gov/chemicals/dehp/DEHPMonograph.pdf. Accessed Aug 2012
  35. Jianlong W, Lujun C, Hanchang S, Yi Q (2000) Microbial degradation of phthalic acid esters under anaerobic digestion of sludge. Chemosphere 41:1245–1248CrossRefGoogle Scholar
  36. Jonsson S, Ejlertsson J, Svensson BH (2003) Behaviour of mono- and diesters of o-phthalic acid in leachates released during digestion of municipal solid waste under landfill conditions. Adv Environ Res 7:429–440CrossRefGoogle Scholar
  37. Juneson C, Ward OP, Singh A (2001) Biodegradation of bis(2-ethylhexyl) phthalate in a soil slurry-sequencing batch reactor. Process Biochem 37:305–313CrossRefGoogle Scholar
  38. Kelly TJ, Mukund R, Spicer CW, Pollack AJ (1994) Concentrations and transformations of hazardous air pollutants. Environ Sci Technol 28(8):379A–387ACrossRefGoogle Scholar
  39. Kirby AJ (1972) Hydrolysis and formation of esters of organic acids. In: Bamford CH, Tipper CFH (eds) Comprehensive chemical kinetics, vol 10. Elsevier, Amsterdam, pp 57–202Google Scholar
  40. Kleerebezem R, Pol LWH, Lettinga G (1999) Anaerobic biodegradability of phthalic acid isomers and related compounds. Biodegradation 10:63–73CrossRefGoogle Scholar
  41. Lertsirisopon R, Soda S, Sei K, Ike M (2009) Abiotic degradation of four phthalic acid esters in aqueous phase under natural sunlight irradiation. J Environ Sci 21:285–290CrossRefGoogle Scholar
  42. Liang D, Zhang T, Fang HHP, He J (2008) Phthalates biodegradation in the environment. Appl Microbiol Biotechnol 80:183–198CrossRefGoogle Scholar
  43. Liu SM, Chi WC (2003) Effects of the Headspace gas composition on anaerobic biotransformation of o-, m-, and p-toluic acid in sediment slurries. J Environ Sci Health A Tox Hazard Subst Environ Eng 38(6):1099–1113CrossRefGoogle Scholar
  44. Mabey W, Mill T (1978) Critical review of hydrolysis of organic compounds in water under environmental conditions. J Phys Chem 7(2):383–415Google Scholar
  45. Mabey WR, Smith JH, Podoll RT, Jonson HL, Moll T, Chou TW, Gates J, Partridge IW, Vandenberg D (1982) Aquatic fate process data for organic priority pollutants. U.S. Environmental Protection Agency Report. EPA 440/4-81-014Google Scholar
  46. Mackintosh CE, Maldonado JA, Ikonomou MG, Gobas FAPC (2006) Sorption of phthalate esters and PCBs in a marine ecosystem. Environ Sci Technol 40(11):3481–3488CrossRefGoogle Scholar
  47. 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 Pharmacol 50:37–49CrossRefGoogle Scholar
  48. Mersiowsky I, Ejlertsson J, Stegmann R, Svensson BH (1999) Long-term behaviour of PVC products under soil-buried and landfill conditions. Report for Norsk Hydro ASA, ECVM, ECPI, ESPA and ORTEP, Hamburg, GermanyGoogle Scholar
  49. Mersiowsky I, Weller M, Ejlertsson J (2001) Fate of plasticised PVC products under landfill conditions: a laboratory-scale landfill simulation reactor study. Water Res 35(13):3063–3070CrossRefGoogle Scholar
  50. Miller FC (1992) Composting as a process based on the control of ecologically selective factors. In: Blaine-Metting F (ed) Soil microbial ecology: applications in agriculture environment management. Marcel Dekker, New York, p 646Google Scholar
  51. Nagao T, Ohta R, Marumo H, Shindo T, Yoshimura S, Ono H (2000) Effect of butyl benzyl phthalate in Sprague-Dawley rats after gavage administration: a two-generation reproductive study. Reprod Toxicol 14:513–532CrossRefGoogle Scholar
  52. OECD (1981) Hydrolysis as a function of pH. OECD GUIDELINE FOR TESTING OF CHEMICALS. http://www.oecd.org/dataoecd. Accessed on 7 May 2012
  53. Oh BS, Jung YJ, Oh YJ, Yoo YS, Kang JW (2006) Application of ozone, UV and ozone/UV processes to reduce diethyl phthalate and its estrogenic activity. Sci Total Environ 367:681–693CrossRefGoogle Scholar
  54. Patnaik P, Yang M, Powers E (2001) Kinetics of phthalate reactions with ammonium hydroxide in aqueous matrix. Water Res 35(6):1587–1591CrossRefGoogle Scholar
  55. Peterson DR, Staples CA (2003) Degradation of phthalate esters in the environment. In: Staples CA (ed) The handbook of environmental chemistry, Vol. 3, Part Q. Springer, New York, pp 85–124Google Scholar
  56. Sayyed HS, Mazhar FN, Gaikwad DD (2010) Kinetic and mechanistic study of oxidation of ester by KMnO4. Int J ChemTech Res 2(1):242–249Google Scholar
  57. Schierow L, Lee MM (2008) Congressional Research Service Report RL34572: Phthalates in Plastics and Possible Human Health Effects. Available at www.policyarchive.org/handle/10207/bitstreams/19121.pdf. Accessed Aug 2012
  58. Schwartzenbach RP, Gschwend PM, Imboden DM (1992) Environmental organic chemistry. Wiley, New YorkGoogle Scholar
  59. 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 36:2275–2287CrossRefGoogle Scholar
  60. Schwarzbauer J, Heim S, Krooss B, Littke R (2006) Analysis of undisturbed layers of a waste deposit landfill—insights into the transformation and transport of organic contaminants. Org Geochem 37:2026–2045CrossRefGoogle Scholar
  61. Sharpe RM, Shakkebaek NE (1993) Are estrogens involved in falling sperm counts and disorder of the male reproductive tract? Lancet 341:1392–1395CrossRefGoogle Scholar
  62. Shen OX, Du GZ, Sun H, Jiang Y, Wu W, Song L, Wang XR (2009) Comparison of in vitro hormone activities of selected phthalates using reporter gene assays. Toxicol Lett 191:9–14CrossRefGoogle Scholar
  63. Shibata K, Fukuwatari T, Sasak R (2007) Phthalate esters enhance quinolinate production by inhibiting amino-carboxymuconate-semialdehyde decarboxylase (ACMSD), a key enzyme of the tryptophan-niacin pathway. Int Congr Series 1304:184–194CrossRefGoogle Scholar
  64. Skrzypek J, Lachowska M, Kulawska M, Moroz H (2008) Synthesis Of Bis(2-Ethylhexyl) phthalate over methane sulfonic acid catalyst, kinetic investigations. React Kinet Catal Lett 93(2):281–286CrossRefGoogle Scholar
  65. Stanley MK, Robillard KA, Staples CA (2003) Introduction. In: Staples CA (ed) The handbook of environmental chemistry, Vol. 3, Part Q. Springer, Berlin, pp 1–7Google Scholar
  66. Staples CA, Peterson DR, Parkerton TF, Adams WJ (1997) The environmental fate of phthalate esters: a literature review. Chemosphere 35(4):667–749CrossRefGoogle Scholar
  67. Staples CA, Parkerton TF, Peterson DR (2000) A risk assessment of selected phthalate esters in North American and Western European surface waters. Chemosphere 40:885–891CrossRefGoogle Scholar
  68. Strac IV (2009) Migration of Di-(2-ethylhexyl) phthalate in normal saline during one year. Toxicol Lett 189:S259–S259CrossRefGoogle Scholar
  69. Sykes P (1975) A guidebook to mechanism in organic chemistry, 4th edn. Longman Group Ltd, London, pp 232–239Google Scholar
  70. US EPA (1996) Method 8061A—Phthalate esters by Gas Chromatography with Electron Capture detection (GC/ECD). Available: http://www.epa.gov/epawaste/hazard/testmethods/sw846/pdfs/8061a.pdf. Accessed Aug 2012
  71. US EPA (2001) Removal of endocrine disrupter chemicals using water treatment processes. 625/R-00/015, Washington DCGoogle Scholar
  72. Wensing M, Uhde E, Salthammer T (2005) Plastics additives in the indoor environment-flame retardants and plasticizers. Sci Total Envion 339:19–40CrossRefGoogle Scholar
  73. Wolfe NL, Steen WC, Bums LA (1980) Phthalate ester hydrolysis: linear free energy relationships. Chemosphere 9:403–408CrossRefGoogle Scholar
  74. Woodward KN (1988) Phthalate esters: toxicity and metabolism, vol I. CRC, Boca Raton, FLGoogle Scholar
  75. Xu G, Li F, Wang Q (2008) Occurrence and degradation characteristics of dibutyl phthalate (DBP) and di-(2-ethylhexyl) phthalate (DEHP) in typical agricultural soils of China. Sci Tot Environ 393:333–340CrossRefGoogle Scholar
  76. Yan H, Ye C, Yin C (1995) Kinetics of phthalate ester biodegradation by Chlorella pyrenoidosa. Environ Toxicol Chem 6:931–938Google Scholar
  77. Zeng F, Cui K, Xie Z, Wu L, Luo D, Chen L, Lin Y, Liu M, Sun G (2009) Distribution of phthalate esters in urban soils of subtropical city, Guangzhou, China. J Hazard Mater 164:1171–1178CrossRefGoogle Scholar
  78. Zhang W, Li Y, Wang C, Wang P (2011a) Kinetics of heterogeneous photocatalytic degradation of rhodamine B by TiO2-coated activated carbon: roles of TiO2 content and light intensity. Desalination 266:40–45CrossRefGoogle Scholar
  79. Zhang Z, Hu Y, Zhao L, Li J, Bai H, Zhu D, Hu J (2011b) Estrogen agonist/antagonist properties of dibenzyl phthalate (DBzP) based on in vitro and in vivo assays. Toxicol Lett 207:7–11CrossRefGoogle Scholar
  80. Zheng Z, He PJ, Shao LM, Lee DJ (2007) Phthalic acid esters in dissolved fractions of landfill leachates. Water Res 41:4696–4702CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • Jingyu Huang
    • 1
  • Philip N. Nkrumah
    • 1
    Email author
  • Yi Li
    • 1
  • Gloria Appiah-Sefah
    • 1
  1. 1.Ministry of Education, Key Laboratory of Integrated Regulation and Resource Development on Shallow Lakes, College of EnvironmentHohai UniversityNanjingChina

Personalised recommendations