Halogenated indigo dyes

A likely source of 1,3,6,8-tetrabromocarbazole and some other halogenated carbazoles in the environment

Robert Parette, Robert McCrindle, Katherine S. McMahon, Miren Pena-Abaurrea, Eric Reiner, Brock Chittim, Nicole Riddell, Gundula Voss, Franklin Lewis Dorman, Jr., Wendy N. Pearson

Research output: Contribution to journalReview article

26 Citations (Scopus)

Abstract

In recent years, a number of halogenated carbazoles have been detected in environmental samples. These emerging contaminants have been shown to be persistent and possess dioxin-like toxicological potential. The goal of this research was to examine the literature to determine likely anthropogenic origin(s) of halogenated carbazoles in the environment. The scientific literature indicated a number of pathways by which 1,3,6,8-tetrabromocarbazole could form in the manufacture of 5,5',7,7'-tetrabromoindigo. The U.S. production history of 5,5',7,7'-tetrabromoindigo correlates well with the concentration rise, decline, and disappearance of 1,3,6,8-tetrabromocarbazole in dated Lake Michigan sediments. Additionally, other halogenated carbazoles that have been found in environmental sediments can be explained by the production of other halogenated indigo dyes. 1,8-dibromo-3,6-dichlorocarbazole can be accounted for by the manufacture of 7,7'-dibromo-5,5'-dichloroindigo, while 1,3,6,8-tetrachlorocarbazole was found at relatively high concentration near the outfall of a U.S. manufacturer of 5,5',7,7'-tetrachloroindigo. Carbazoles containing an iodo-substituent can be explained by the use of iodine as a catalyst in the manufacture of halogenated indigo dyes. 3,6-Dichlorocarbazole measured in soils and dibromocarbazoles measured in more recently deposited sediments are not easily rationalized on the basis of an indigo related source and may be related to other anthropogenic sources or natural origins.

Original languageEnglish (US)
Pages (from-to)18-26
Number of pages9
JournalChemosphere
Volume127
DOIs
StatePublished - May 1 2015

Fingerprint

Carbazoles
Indigo Carmine
dye
Sediments
Coloring Agents
Dyes
anthropogenic source
iodine
dioxin
sediment
lacustrine deposit
Outfalls
catalyst
Iodine
Literature
Dioxins
Lakes
pollutant
history
Impurities

All Science Journal Classification (ASJC) codes

  • Environmental Engineering
  • Environmental Chemistry
  • Chemistry(all)
  • Pollution
  • Health, Toxicology and Mutagenesis

Cite this

Parette, R., McCrindle, R., McMahon, K. S., Pena-Abaurrea, M., Reiner, E., Chittim, B., ... Pearson, W. N. (2015). Halogenated indigo dyes: A likely source of 1,3,6,8-tetrabromocarbazole and some other halogenated carbazoles in the environment. Chemosphere, 127, 18-26. https://doi.org/10.1016/j.chemosphere.2015.01.001
Parette, Robert ; McCrindle, Robert ; McMahon, Katherine S. ; Pena-Abaurrea, Miren ; Reiner, Eric ; Chittim, Brock ; Riddell, Nicole ; Voss, Gundula ; Dorman, Jr., Franklin Lewis ; Pearson, Wendy N. / Halogenated indigo dyes : A likely source of 1,3,6,8-tetrabromocarbazole and some other halogenated carbazoles in the environment. In: Chemosphere. 2015 ; Vol. 127. pp. 18-26.
@article{11c5f0cf2b0b4dfbbd58363287592927,
title = "Halogenated indigo dyes: A likely source of 1,3,6,8-tetrabromocarbazole and some other halogenated carbazoles in the environment",
abstract = "In recent years, a number of halogenated carbazoles have been detected in environmental samples. These emerging contaminants have been shown to be persistent and possess dioxin-like toxicological potential. The goal of this research was to examine the literature to determine likely anthropogenic origin(s) of halogenated carbazoles in the environment. The scientific literature indicated a number of pathways by which 1,3,6,8-tetrabromocarbazole could form in the manufacture of 5,5',7,7'-tetrabromoindigo. The U.S. production history of 5,5',7,7'-tetrabromoindigo correlates well with the concentration rise, decline, and disappearance of 1,3,6,8-tetrabromocarbazole in dated Lake Michigan sediments. Additionally, other halogenated carbazoles that have been found in environmental sediments can be explained by the production of other halogenated indigo dyes. 1,8-dibromo-3,6-dichlorocarbazole can be accounted for by the manufacture of 7,7'-dibromo-5,5'-dichloroindigo, while 1,3,6,8-tetrachlorocarbazole was found at relatively high concentration near the outfall of a U.S. manufacturer of 5,5',7,7'-tetrachloroindigo. Carbazoles containing an iodo-substituent can be explained by the use of iodine as a catalyst in the manufacture of halogenated indigo dyes. 3,6-Dichlorocarbazole measured in soils and dibromocarbazoles measured in more recently deposited sediments are not easily rationalized on the basis of an indigo related source and may be related to other anthropogenic sources or natural origins.",
author = "Robert Parette and Robert McCrindle and McMahon, {Katherine S.} and Miren Pena-Abaurrea and Eric Reiner and Brock Chittim and Nicole Riddell and Gundula Voss and {Dorman, Jr.}, {Franklin Lewis} and Pearson, {Wendy N.}",
year = "2015",
month = "5",
day = "1",
doi = "10.1016/j.chemosphere.2015.01.001",
language = "English (US)",
volume = "127",
pages = "18--26",
journal = "Chemosphere",
issn = "0045-6535",
publisher = "Elsevier Limited",

}

Parette, R, McCrindle, R, McMahon, KS, Pena-Abaurrea, M, Reiner, E, Chittim, B, Riddell, N, Voss, G, Dorman, Jr., FL & Pearson, WN 2015, 'Halogenated indigo dyes: A likely source of 1,3,6,8-tetrabromocarbazole and some other halogenated carbazoles in the environment', Chemosphere, vol. 127, pp. 18-26. https://doi.org/10.1016/j.chemosphere.2015.01.001

Halogenated indigo dyes : A likely source of 1,3,6,8-tetrabromocarbazole and some other halogenated carbazoles in the environment. / Parette, Robert; McCrindle, Robert; McMahon, Katherine S.; Pena-Abaurrea, Miren; Reiner, Eric; Chittim, Brock; Riddell, Nicole; Voss, Gundula; Dorman, Jr., Franklin Lewis; Pearson, Wendy N.

In: Chemosphere, Vol. 127, 01.05.2015, p. 18-26.

Research output: Contribution to journalReview article

TY - JOUR

T1 - Halogenated indigo dyes

T2 - A likely source of 1,3,6,8-tetrabromocarbazole and some other halogenated carbazoles in the environment

AU - Parette, Robert

AU - McCrindle, Robert

AU - McMahon, Katherine S.

AU - Pena-Abaurrea, Miren

AU - Reiner, Eric

AU - Chittim, Brock

AU - Riddell, Nicole

AU - Voss, Gundula

AU - Dorman, Jr., Franklin Lewis

AU - Pearson, Wendy N.

PY - 2015/5/1

Y1 - 2015/5/1

N2 - In recent years, a number of halogenated carbazoles have been detected in environmental samples. These emerging contaminants have been shown to be persistent and possess dioxin-like toxicological potential. The goal of this research was to examine the literature to determine likely anthropogenic origin(s) of halogenated carbazoles in the environment. The scientific literature indicated a number of pathways by which 1,3,6,8-tetrabromocarbazole could form in the manufacture of 5,5',7,7'-tetrabromoindigo. The U.S. production history of 5,5',7,7'-tetrabromoindigo correlates well with the concentration rise, decline, and disappearance of 1,3,6,8-tetrabromocarbazole in dated Lake Michigan sediments. Additionally, other halogenated carbazoles that have been found in environmental sediments can be explained by the production of other halogenated indigo dyes. 1,8-dibromo-3,6-dichlorocarbazole can be accounted for by the manufacture of 7,7'-dibromo-5,5'-dichloroindigo, while 1,3,6,8-tetrachlorocarbazole was found at relatively high concentration near the outfall of a U.S. manufacturer of 5,5',7,7'-tetrachloroindigo. Carbazoles containing an iodo-substituent can be explained by the use of iodine as a catalyst in the manufacture of halogenated indigo dyes. 3,6-Dichlorocarbazole measured in soils and dibromocarbazoles measured in more recently deposited sediments are not easily rationalized on the basis of an indigo related source and may be related to other anthropogenic sources or natural origins.

AB - In recent years, a number of halogenated carbazoles have been detected in environmental samples. These emerging contaminants have been shown to be persistent and possess dioxin-like toxicological potential. The goal of this research was to examine the literature to determine likely anthropogenic origin(s) of halogenated carbazoles in the environment. The scientific literature indicated a number of pathways by which 1,3,6,8-tetrabromocarbazole could form in the manufacture of 5,5',7,7'-tetrabromoindigo. The U.S. production history of 5,5',7,7'-tetrabromoindigo correlates well with the concentration rise, decline, and disappearance of 1,3,6,8-tetrabromocarbazole in dated Lake Michigan sediments. Additionally, other halogenated carbazoles that have been found in environmental sediments can be explained by the production of other halogenated indigo dyes. 1,8-dibromo-3,6-dichlorocarbazole can be accounted for by the manufacture of 7,7'-dibromo-5,5'-dichloroindigo, while 1,3,6,8-tetrachlorocarbazole was found at relatively high concentration near the outfall of a U.S. manufacturer of 5,5',7,7'-tetrachloroindigo. Carbazoles containing an iodo-substituent can be explained by the use of iodine as a catalyst in the manufacture of halogenated indigo dyes. 3,6-Dichlorocarbazole measured in soils and dibromocarbazoles measured in more recently deposited sediments are not easily rationalized on the basis of an indigo related source and may be related to other anthropogenic sources or natural origins.

UR - http://www.scopus.com/inward/record.url?scp=84924804679&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84924804679&partnerID=8YFLogxK

U2 - 10.1016/j.chemosphere.2015.01.001

DO - 10.1016/j.chemosphere.2015.01.001

M3 - Review article

VL - 127

SP - 18

EP - 26

JO - Chemosphere

JF - Chemosphere

SN - 0045-6535

ER -