The occurence of trichloroacetic acid (tcaa) - indications of a natural production?

Haiber, G.; Jacob, George; Niedan, V.; Nkusi, G.; Schöler, H. F.

doi:10.1016/0045-6535(96)00239-1

Cited by 65 publications

(50 citation statements)

References 16 publications

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“…A firn core from Antarctica with snow accumulated from the past 200 years exhibits haloacetic acids even in Chemosphere 52 (2003) [513][514][515][516][517][518][519][520] www.elsevier.com/locate/chemosphere preindustrial layers (von Sydow et al, 2000). Moreover, TCA is also present in glacier ice of preindustrial origin from Northern Sweden (von Sydow et al, 1998) and in glacier ice samples from Monte Rosa, Switzerland (Haiber et al, 1996), dated around 1900, from the time before the mass production of chlorinated solvents, indicating that natural sources must also exist. Indeed, in recent years it has been argued that mass balances and experiments suggest a natural formation of haloacetates in soil (Hoekstra, 1999, Sch€ o oler et al, 2003.…”

Section: Introductionmentioning

confidence: 99%

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Formation of chloroacetic acids from soil, humic acid and phenolic moieties

2003

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The mechanism of formation of chloroacetates, which are important toxic environmental substances, has been controversial. Whereas the anthropogenic production has been well established, a natural formation has also been suggested. In this study the natural formation of chloroacetic acids from soil, as well as from humic material which is present in soil and from phenolic model substances has been investigated. It is shown that chloroacetates are formed from humic material with a linear relationship between the amount of humic acid used and chloroacetates found. More dichloroacetate (DCA) than trichloroacetate (TCA) is produced. The addition of Fe 2þ , Fe 3þ and H 2 O 2 leads to an increased yield. NaCl was added as a source of chloride. We further examined the relationship between the structure and reactivity of phenolic substances, which can be considered as monomeric units of humic acids. Ethoxyphenol with built-in ethyl groups forms large amounts of DCA and TCA. The experiments with phenoxyacetic acid yielded large amounts of monochloroacetate (MCA). With other phenolic substances a ring cleavage was observed. Our investigations indicate that chloroacetates are formed abiotically from humic material and soils in addition to their known biotic mode of formation.

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Section: Introductionmentioning

confidence: 99%

“…The necessity of CPO for the formation of TCA was questioned by Haiber et al (1996), who found TCA formation in experiments using only H 2 O 2 and humic acid. The TCA production in absence of CPO suggests that an abiotic formation might also occur.…”

Section: Introductionmentioning

confidence: 99%

Formation of chloroacetic acids from soil, humic acid and phenolic moieties

2003

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“…It is evident that we meet chlorination of SOM, of lignin (Johansson et al 2000), humic and of fulvic acids (FA) , and its products -chlorocarbons, CAAs, chlorinated aromatic compounds (Harper 1985, Haiber et al 1996, de Jong and Field 1997, Pracht et al 2001, Fahimi et al 2003, Matucha et al 2003b, 2007a,b, Laturnus et al 2005 etc. -are expected or present in the forest ecosystems, where haloperoxidases are present at the same time (Asplund et al 1993, Laturnus et al 1995.…”

Section: Biogeochemical Cycling Of Chlorine and Chlorination In The Fmentioning

confidence: 99%

Biogeochemical cycles of chlorine in the coniferous forest ecosystem: practical implications

Matucha¹,

Clarke²,

Lachmanová³

et al. 2010

PLANT SOIL ENVIRON

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Chlorine -one of the most widespread elements on the Earth -is present in the environment as chloride ion or bound to organic substances. The main source of chloride ions is the oceans while organically bound chlorine (OCl) comes from various sources, including anthropogenic ones. Chlorinated organic compounds were long considered to be only industrial products; nevertheless, organochlorines occur plentifully in natural ecosystems. However, recent investigations in temperate and boreal forest ecosystems have shown them to be products of biodegradation of soil organic matter under participation of chlorine. It is important to understand both the inorganic and organic biogeochemical cycling of chlorine in order to understand processes in the forest ecosystem and dangers as a result of human activities, i.e. emission and deposition of anthropogenic chlorinated compounds as well as those from natural processes. The minireview presented below provides a survey of contemporary knowledge of the state of the art and a basis for investigations of formation and degradation of organochlorines and monitoring of chloride and organochlorines in forest ecosystems, which has not been carried out in the Czech Republic yet.

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“…[11] Laboratory studies suggest that TCAA is produced when humic or fulvic acids are incubated with chloroperoxidase (CPO) in the presence of chloride and H 2 O 2 . [12,13] Compound-specific isotope analysis (CSIA) is increasingly used to evaluate the source and fate of different classes of organic compounds such as chlorinated solvents (e.g. PCE, TCE and DCE), PCBs and aromatic compounds (e.g.…”

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confidence: 99%

Position‐specific carbon isotope analysis of trichloroacetic acid by gas chromatography/isotope ratio mass spectrometry

Breider

Hunkeler

2011

Rapid Comm Mass Spectrometry

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Trichloroacetic acid (TCAA) is an important environmental contaminant present in soils, water and plants. A method for determining the carbon isotope signature of the trichloromethyl position in TCAA using gas chromatography/ combustion/isotope ratio mass spectrometry (GC/C/IRMS) was developed and tested with TCAA from different origins. Position-specific isotope analysis (PSIA) can provide direct information on the kinetic isotope effect for isotope substitution at a specific position in the molecule and/or help to distinguish different sources of a compound. The method is based on the degradation of TCAA into chloroform (CF) and CO2 by thermal decarboxylation. Since thermal decarboxylation is associated with strong carbon isotope fractionation (« = 34.6 0.2%) the reaction conditions were optimized to ensure full conversion. The combined isotope ratio of CF and CO2 at the end of the reaction corresponded well to the isotope ratio of TCAA, confirming the reliability of the method. A method quantification limit (MQL) for TCAA of 18.6 mg/L was determined. Samples of TCAA produced by enzymatic and non-enzymatic chlorination of natural organic matter (NOM) and some industrially produced TCAA were used as exemplary sources. Significant different PSIA isotope ratios were observed between industrial TCAA and TCAA samples produced by chlorination of NOM. This highlights the potential of the method to study the origin and the fate of TCAA in the environment.

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The occurence of trichloroacetic acid (tcaa) - indications of a natural production?

Cited by 65 publications

References 16 publications

Formation of chloroacetic acids from soil, humic acid and phenolic moieties

Formation of chloroacetic acids from soil, humic acid and phenolic moieties

Biogeochemical cycles of chlorine in the coniferous forest ecosystem: practical implications

Position‐specific carbon isotope analysis of trichloroacetic acid by gas chromatography/isotope ratio mass spectrometry

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