liu.seSearch for publications in DiVA
Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • harvard1
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • oxford
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf
Phthalates in landfill leachates: a signature of their degradation: Analytical aspects & toxicological considerations
Linköping University, The Tema Institute, Department of Water and Environmental Studies. Linköping University, Faculty of Arts and Sciences.
2003 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Phthalic acid diesters comprise a large group of organic compounds that are used to manufacture a variety of products all over the world, and this has raised concerns about the fate of these compounds in the environment. The diester-containing products often end up in landfills, where they are degraded by various micro-organisms, which gives rise to transient intermediates such as phthalic acid monoesters and ortho-phthalic acid. These degradation products escape detection when applying the analytical protocols used to investigate the well-elucidated diesters, hence other methods are needed.

In the present work, the temporal pattern of degradation was scrutinised by studying leachates from both laboratory-scale Iandfill simulation reactors and newly established fullscale landfill cells. Leachate samples from a transect downstream of a landfill were also examined to highlight possible groundwater contamination from unlined landfills. In addition, extraction techniques were developed for simultaneous detection of diesters, monoesters of o-phthalic acid, and o-phthalic acid itself.

The degradation products of phthalate diesters (i.e. the monoesters and phthalic acid) were found in the landfill leachates, which demonstrates proves that phthalic acid diesters are degraded/transformed in situ in landfills. The monoesters and phthalic acid may accumulate in leachates during certain parts of landfill degradation development, for example, during establishment of the methanogenic micro-flora. The phthalates leached from landfills are potential groundwater contaminants, whereas breakdown of the diesters and monoesters was observed in the studied Iandfill plume. The monoesters and phthalic acid could be detected by proper acidification of the samples and derivatization of the extracts, followed by gas chromatography and mass spectrometry. Acute toxicity tests showed that the monoesters were generally less toxic than the corresponding diesters, and that phthalic acid was the least toxic. These results suggest that degradation of the diesters to monoesters and phthalic acidwill reduce the risk for acute toxic effects on the environment.

Place, publisher, year, edition, pages
Linköping: Linköpings universitet , 2003. , 66 p.
Series
Linköping Studies in Arts and Science, ISSN 0282-9800 ; 268
National Category
Social Sciences Interdisciplinary
Identifiers
URN: urn:nbn:se:liu:diva-29573Local ID: 14948ISBN: 91-7373-588-4 (print)OAI: oai:DiVA.org:liu-29573DiVA: diva2:250389
Public defence
2003-01-31, Sal Elysion, Hus-T, Universitetssjukhuset, Linköping, 10:00 (Swedish)
Supervisors
Available from: 2009-10-09 Created: 2009-10-09 Last updated: 2014-09-01Bibliographically approved
List of papers
1. Behaviour of mono- and diesters of o-phthalic acid in leachates released during digestion of municipal solid waste under landfill conditions
Open this publication in new window or tab >>Behaviour of mono- and diesters of o-phthalic acid in leachates released during digestion of municipal solid waste under landfill conditions
2003 (English)In: Advances in Environmental Research, ISSN 1093-0191, E-ISSN 1093-7927, Vol. 7, no 2, 429-440 p.Article in journal (Refereed) Published
Abstract [en]

In order to investigate phthalates in landfill leachates, four landfill simulation reactors, filled with municipal solid waste from a housing area, were studied. Plasticised polyvinyl chloride (PVC) was added to two of the reactors. Two reactors, one with and one without the additional PVC, were aerated for 3 months to achieve methanogenic conditions. The other two became acidogenic a few days after filling and closing. After approximately 3 years, the acidogenic waste became methanogenic. The leachates were analysed for phthalic acid diesters and their degradation products, phthalic acid monoesters and o-phthalic acid. The occurrence of monobenzyl phthalate (MbenzP) and mono(2-ethylhexyl) phthalate (MEHP) showed that the diesters, butylbenzyl phthalate (BBP) and di(2-ethylhexyl) phthalate (DEHP), released from the PVC products had been transformed, and that they were not completely sorbed to particles or to the waste material. Monoesters were observed once methanogenic conditions were established. The monoesters and phthalic acid were present in concentrations several orders of magnitude higher than the diesters themselves. Our results show that it is important to include monoesters in studies of the fate of diesters. To date, monoesters have been neglected in investigations of organic pollutants in landfill leachates.

Keyword
acidogenic, anaerobic, analysis, degradation, leachate, methanogenic, phthalic acid diester, phthalic acid monoester
National Category
Social Sciences Interdisciplinary
Identifiers
urn:nbn:se:liu:diva-29647 (URN)10.1016/S1093-0191(02)00015-1 (DOI)15027 (Local ID)15027 (Archive number)15027 (OAI)
Available from: 2009-10-09 Created: 2009-10-09 Last updated: 2017-12-13Bibliographically approved
2. Mono- and diesters of o-phthalic acid esters in leachates from young landfills
Open this publication in new window or tab >>Mono- and diesters of o-phthalic acid esters in leachates from young landfills
(English)Manuscript (preprint) (Other academic)
Abstract [en]

Phthalic acid diesters are additives in a variety of materials that can end up in landfills. ln a previous laboratory landfill simulation study, it was fouod that degradation intermediates such as phthalic acid monoesters and phthalic acid accumulate during the change from acidic to methanogenic conditions in municipal solid waste. In the present investigation, leachates from a series of fullscale youog landfill cells were analysed over time for dimethyl, diethyl, dibutyl, butylbenzyl, and di(2-ethylheliyl) phthalate (respectively designated DMP, DEP, DBP, BBP, and DEHP), and their corresponding monoesters monomethyl, monoethyl, monobutyl, monobenzyl, and mono(2 ethylhexyl) phthalate (MMP, MEP, MbutP, MbenzP, and MEHP, respectively), as well as ophthalic acid. One landfill cell was created in each of three consecutive years by deposition of the same type of waste in July and August. The pH, volatile fatty acids (VF As), and total orgaulc carbon (TOC) were measured to characterise development of the degradation phases in three landfill cells, which revealed early acidogenic to initial methanogenic stages. Analysis of the phthalate compounds showed that levels of the degradation products were below the detection limit in the acidogenic leachates but exceeded concentrations of their corresponding diesters in leachates from cells in the initial methanogenic phase. Maximmn and average concentrations of phthalic acid were 50 and 23 mg/L, respectively, and the corresponding values for the other phthalates were 430 and 27 µg/L. The concentrations of all phthalates decreased during the evolution of stable methanogenic conditions. The results were in aggrement with the landfill simulation reactor study.

National Category
Social Sciences Interdisciplinary
Identifiers
urn:nbn:se:liu:diva-80182 (URN)
Available from: 2012-08-22 Created: 2012-08-22 Last updated: 2012-08-22Bibliographically approved
3. Mono- and diesters from o-phthalic acid in leachates from different European landfills
Open this publication in new window or tab >>Mono- and diesters from o-phthalic acid in leachates from different European landfills
Show others...
2003 (English)In: Water Research, ISSN 0043-1354, E-ISSN 1879-2448, Vol. 37, no 3, 609-617 p.Article in journal (Refereed) Published
Abstract [en]

Leachates from 17 different landfills in Europe were analysed with respect to phthalates, i.e. phthalic acid diesters (PAEs) and their degradation products phthalic acid monoesters (PMEs) and ortho-phthalic acid (PA). Diesters are ubiquitous and the human possible exposure and potential to human health and environment has put them in focus. The aim of this study was to elucidate whether monoesters and phthalic acid could be traced in landfill leachates and in what concentrations they may be found. The results showed that phthalates were present in the majority of the leachates investigated. The monoesters appeared from 1 to 20 μg/L and phthalic acid 2–880 μg/L (one divergent value of 19 mg phthalic acid/L). Their parental diesters were observed from 1 to 460 μg/L. These observed occurrences of degradation products, of all diesters studied, support that they are degraded under the landfill conditions covered by this study. Thus, we have presented strong evidences to conclude that microorganisms in landfills degrade diesters released from formulations in a variety of products, including polyvinyl chloride (PVC) species.

Keyword
Biodegradation, Landfill, Leachate, Phthalate, Diester, Monoester
National Category
Social Sciences Interdisciplinary
Identifiers
urn:nbn:se:liu:diva-29668 (URN)10.1016/S0043-1354(02)00304-4 (DOI)15050 (Local ID)15050 (Archive number)15050 (OAI)
Available from: 2009-10-09 Created: 2009-10-09 Last updated: 2017-12-13Bibliographically approved
4. In situ degradation of monoethyl-, diethyl phthalate and o-phthalic acid in a landfil leachate plume (Grindsted, Denmark)
Open this publication in new window or tab >>In situ degradation of monoethyl-, diethyl phthalate and o-phthalic acid in a landfil leachate plume (Grindsted, Denmark)
(English)Manuscript (preprint) (Other academic)
Abstract [en]

The distribution of a-phthalic acid and ten of its mono- and diesters in the leachate plume downgradient of an unlined landfill (Grindsted, Denmark) was mapped along an 80 m transect. A total of 27 groundwater samples were concentrated by solid-phase extraction (SPE) using a polystyrene divinylbenzene (PS-DVB) polymer. Elevated concentrations of DEP, MEP and phthalic acid were observed, with maxima of 1260, 231 and 51 µg/L, respectively. Generally, high concentrations were observed close to the landfill border and in the lower parts of the aquifer. At a distance of 50m from the landfill border, the concentrations of all the studied phthalates, including DEP, MEP and PA, had decreased to below the detection limits (1 µg/L ). The presence of the specific metabolite MEP and PA, at the landfill border and in the plume, indicates that in situ anaerobic degradation/transformation of DEP occurred both in and beneath the landfill, as well as in the leachate-contarninated soil profile. Our findings suggest that anaerobic degradation is a key process also in the aquifer at the Grindsted landfill site. Tills study emphasises that phthalates should be regarded as potential contaminants in aquifers.

Keyword
diethyl phthalate, monoethyl phthalate, phthalic acid, redox, biotic degradation
National Category
Social Sciences Interdisciplinary
Identifiers
urn:nbn:se:liu:diva-80183 (URN)
Available from: 2012-08-22 Created: 2012-08-22 Last updated: 2012-08-22Bibliographically approved
5. Analysis of mono- and diesters of o-phthalic acid by solid-phase extractions with polystyrene–divinylbenzene-based polymers
Open this publication in new window or tab >>Analysis of mono- and diesters of o-phthalic acid by solid-phase extractions with polystyrene–divinylbenzene-based polymers
2002 (English)In: Journal of Chromatography A, ISSN 0021-9673, E-ISSN 1873-3778, Vol. 963, no 1-2, 393-400 p.Article in journal (Refereed) Published
Abstract [en]

Retention mechanisms of an unmodified and a hydroxylated polystyrene–divinylbenzene polymer were studied by solid-phase extraction of o-phthalic acid and some of its mono- and diesters from purified water and then analysing by GC–MS. The monoesters and phthalic acid were retained only when protonated (i.e. acidified with HCl to pH 0.9). Of all elution solvents tested, ethyl acetate gave the best overall recoveries (61–89%) with both polymers. Applicability to complex matrixes (e.g. acidogenic landfill leachates) was examined by introducing a washing step with acetone in acidified water (pH 0.9) to eliminate volatile fatty acids (C2–C6) from the cartridge. Finally, the method was tested on real samples.

Keyword
retention mechanisms, poly(sturenedivinylbenzene), phthalates, fatty acids
National Category
Social Sciences Interdisciplinary
Identifiers
urn:nbn:se:liu:diva-29634 (URN)10.1016/S0021-9673(02)00647-7 (DOI)15013 (Local ID)15013 (Archive number)15013 (OAI)
Note

The original title of this article was: Analysis of mono- and diesters of o-phthalic acid by solid-phase extractions with styrene–divinylbenzene polymers.

Available from: 2009-10-09 Created: 2009-10-09 Last updated: 2017-12-13Bibliographically approved
6. Aquatic toxicity of mono- and diesters of o-phthalic acid
Open this publication in new window or tab >>Aquatic toxicity of mono- and diesters of o-phthalic acid
(English)Manuscript (preprint) (Other academic)
Abstract [en]

The degradation of phthalic acid diesters may lead to formation of a-phthalic acid and phthalic acid monoesters. The ecotoxic properties of the monoesters have never been systematically investigated and concern has been raised that these degradation products may be more toxic than the diesters. Therefore, the aquatic toxicity of phthalic acid, 6 monoesters, and 5 diesters of a-phthalic acid was tested in three standardized toxicity tests using the bacteria Vibrio fischeri, the green algae Pseudokirchneriella subcapitata, and the crustacean Daphnia magna. The monoesters tested were monomethyl-, monoethyl-, monobutyl-, monobenzyl-, mono(2-ethylhexyl)-and monodecyl phthalate; while the diesters tested were dimethyl-, diethyl-, dibutyl-, butylbenzyl-, and di(2-ethylhexyl) phthalate. The compounds were tested in concentrations below the water solubility and concentrations were confirmed by chemical analyses. The EC50-values for the three organisms ranged from 103 mg/L to >4710 mg/L for phthalic acid, and corresponding values for the monoesters ranged from 2.3 mg/L (monodecyl phthalate in bacteria test) to 4130 mg!L (monomethyl phtalate in bacteria test). Dhnethyl- and diethyl- phthalate were found to be the least toxic of the diesters (EC50 from 26.2-377 mg/L) and the toxicity of the other diesters (butylbenzyland dibutyl phthalate) ranged from 0.96 mg/L to 7.74 mg/L. In general, the phthalate monoesters (degradation products) were less toxic than the corresponding diesters (mother compounds).

Keyword
Phthalates, phthalic acid monoesters, Daphnia magna, Pseudokirclmeriella subcapitata, Vibrio fischeri
National Category
Social Sciences Interdisciplinary
Identifiers
urn:nbn:se:liu:diva-80184 (URN)
Available from: 2012-08-22 Created: 2012-08-22 Last updated: 2012-08-22Bibliographically approved

Open Access in DiVA

No full text

Authority records BETA

Jonsson, Susanne

Search in DiVA

By author/editor
Jonsson, Susanne
By organisation
Department of Water and Environmental StudiesFaculty of Arts and Sciences
Social Sciences Interdisciplinary

Search outside of DiVA

GoogleGoogle Scholar

isbn
urn-nbn

Altmetric score

isbn
urn-nbn
Total: 909 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • harvard1
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • oxford
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf