Transformations of pentachlorophenol

Engelhardt, G.; Wallnöfer, P. R.; Mücke, W.; Renner, Gerhard

doi:10.1080/02772248609357134

Cited by 31 publications

(8 citation statements)

References 39 publications

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“…Due to the use of pentachlorophenol as an antifungal compound coupled with the very poor information available concerning its degradation by fungi (Engelhardt et al, 1986), earlier results have motivated the initiation of a more detailed study with fungal strains belonging to different taxonomic groups. We have previously reported on the biodegradation of pentachlorophenol (PCP) by Micromycetes cultivated in liquid synthetic medium with high concentration of PCP (1 g L-I) .…”

Section: Introductionmentioning

confidence: 99%

Biodegradation of pentachlorophenol by micromycetes. II. Ascomycetes, basidiomycetes, and yeasts

Steiman

Benoit‐Guyod

Seigle‐Murandi

et al. 1994

Environ. Toxicol. Water Qual.

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Following a previous study on the biodegradation of pentachlorophenol (PCP) (100 mg L-') by Zygomycetes, other taxonomic groups (Ascomycetes, Basidiomycetes, and Yeasts) have been investigated in relation to their ability to produce extracellular phenoloxidases. Ascomycetes gave heterogeneous results since disappearance of PCP occurred both in phenoloxidases-producing and nonproducing strains. Basidiornycetes were high producers of phenoloxidases and showed a moderate depletion of PCP. Yeasts degraded PCP very poorly and did not produce phenoloxidases. No correlation was found between phenoloxidases production and PCP depletion. 0 7994 by John Wiley & Sons, Inc. Culture ConditionsStrains were cultivated in Galzy and Slonimski liquid synthetic medium (Galzy and Slonimski, 1957) adjusted

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Section: Introductionmentioning

confidence: 99%

Biodegradation of pentachlorophenol by micromycetes. II. Ascomycetes, basidiomycetes, and yeasts

Steiman

Benoit‐Guyod

Seigle‐Murandi

et al. 1994

Environ. Toxicol. Water Qual.

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“…Its biodegradation is slow, and thus it is not surprising that it is still observed in many drinking-water resources (for a review on the degradation of pentachlorophenol under environmental conditions, see ref. 1). This situation has led to studies regarding the biological, 2 photochemical, 3-7 sonolytic 8 and oxidative 9-13 degradation of halogenated phenols.…”

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confidence: 99%

The reaction of the OH radical with pentafluoro-, pentachloro-, pentabromo- and 2,4,6-triiodophenol in water: electron transfer vs. addition to the ring

Fang

Schuchmann

Sonntag

2000

J. Chem. Soc., Perkin Trans. 2

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The OH-radical-induced dehalogenation of pentafluorophenol (F 5 C 6 OH), pentachlorophenol (Cl 5 C 6 OH), pentabromophenol (Br 5 C 6 OH) and 2,4,6-triiodophenol (I 3 H 2 C 6 OH) in water has been studied by pulse radiolysis in basic solution where these compounds are deprotonated and hence slightly water soluble. Hydroxyl radicals react with these phenolates both by electron transfer and by addition. Electron transfer yields hydroxide ions and the corresponding phenoxyl radicals (X 5 C 6 O ؒ and I 3 H 2 C 6 O ؒ ); these were also generated independently, to the exclusion of OH-adduct radicals, by reacting the phenolates withHydroxyl radical addition to the pentahalophenolates is followed by rapid halide elimination, giving rise to hydroxytetrahalophenoxyl radical anions (X 4 O Ϫ C 6 O ؒ ). The latter exhibit absorption maxima near those of the pentahalophenoxyl radicals. This prevents a proper determination of the relative importance of the two processes by optical detection. However, these two processes distinguish themselves by their behaviour with respect to the stoichiometry and kinetics of the production of ionic conducting species. In basic solution, electron transfer causes a conductivity increase due to the formation of OH Ϫ whereas addition followed by HX elimination and deprotonation of the X 4 OHC 6 O ؒ radical results in a conductivity drop. The evaluation of the conductivity change at 8 µs after the radiolytic pulse has ended, reveals that about 27%, 53%, 73%, and 97% of the OH radicals react by electron transfer with F

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“…O-Methylation of chlorophenols (i.e. chloroanisole formation) is a common mechanism used by microorganisms to reduce the toxicity of these compounds (Engelhardt et al 1986), although the toxicity for higher life forms is increased by this conversion, largely because of the increased lipophilic nature of the methylated compound and the resulting accumulation in the fat reserves of animals. Some bacteria are capable of conducting O-methylation (Gee and Peel 1974) but not as rapidly or as efficiently as certain white-rot fungi (in particular, the Basidiomycetes -see below).…”

Section: Fate and Degradation Of Chlorophenols In The Environmentmentioning

confidence: 99%

Origin and fate of 2,4,6-trichloroanisole in cork bark and wine corks

Simpson

Sefton

2007

Aust J Grape Wine Res

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2,4,6‐Trichloroanisole (TCA), which is a major cause of cork taint in bottled wine, is already present in the bark of living cork trees to the extent that it can account for the majority of incidences of cork taint in bottled wine. Other post‐harvest sources of TCA are known and may add to the forest‐derived TCA in cork. Both the origin of TCA in the bark in the forest, and the means by which additional TCA can accumulate in the corks during manufacture, have been examined. TCA can originate from 2,4,6‐trichlorophenol (TCP) produced from naturally‐occurring phenol and chlorine from sanitisers and cleaning products, and town water. Also, chlorophenol biocides have accumulated in the environment due to the large quantities used in previous times – TCP has been a minor impurity in pentachlorophenol biocides and a major ingredient in other preparations. There is some evidence that chlorophenols were used in pest management in the forest prior to restrictions on the use of these materials. The factors affecting the uptake and loss of TCA by the bark on the tree and by corks during production, and through to their use in the bottling of wine have been considered in this review.

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Transformations of pentachlorophenol

Cited by 31 publications

References 39 publications

Biodegradation of pentachlorophenol by micromycetes. II. Ascomycetes, basidiomycetes, and yeasts

Biodegradation of pentachlorophenol by micromycetes. II. Ascomycetes, basidiomycetes, and yeasts

The reaction of the OH radical with pentafluoro-, pentachloro-, pentabromo- and 2,4,6-triiodophenol in water: electron transfer vs. addition to the ring

Origin and fate of 2,4,6-trichloroanisole in cork bark and wine corks

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