Chemistry:2,4,6-Trichlorophenol

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2,4,6-Trichlorophenol, also known as TCP, phenaclor, Dowicide 2S, Dowcide 2S, omal, is a chlorinated phenol that has been used as a fungicide, herbicide, insecticide, antiseptic,[1] defoliant, and glue preservative.[2] It is a clear to yellowish crystalline solid with a strong, phenolic odor. It decomposes on heating to produce toxic and corrosive fumes including hydrogen chloride and chlorine.

Preparation

2,4,6-Trichlorophenol is produced industrially by the electrophilic chlorination of phenol:[3]

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Health effects

In animal models, consumption of 2,4,6-trichlorophenol leads to an increased incidence of lymphomas, leukemia, and liver cancer.[4][5] It is classified as Group B2 (probable human carcinogen) by the United States Environmental Protection Agency.[5] The technical grade of this substance may contain polychlorinated dibenzodioxins (PCDDs), polychlorinated dibenzofurans (PCDFs), and other contaminants.[6][7]

Environmental effects

2,4,6-Trichlorophenol is an environmental pollutant that has been found in fresh water lakes such as the Great Lakes.[8]

See also

References

  1. ↑ "Disinfectants/antiseptics in the management of guinea worm ulcers in the rural areas". Acta Tropica 74 (1): 33–38(6). 2000-01-05. doi:10.1016/S0001-706X(99)00057-1. PMID 10643905. 
  2. ↑ "Safety data for 2,4,6-trichlorophenol". University of Oxford. 2005-09-05. http://physchem.ox.ac.uk/MSDS/TR/2,4,6-trichlorophenol.html. 
  3. ↑ Muller, François; Caillard, Liliane (2011-10-15), Wiley-VCH Verlag GmbH & Co. KGaA, ed. (in en), Chlorophenols, Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, pp. a07_001.pub2, doi:10.1002/14356007.a07_001.pub2, ISBN 978-3-527-30673-2, https://onlinelibrary.wiley.com/doi/10.1002/14356007.a07_001.pub2, retrieved 2022-03-13 
  4. ↑ "2,4,6-Trichlorophenol". The Carcinogenic Potency Database Project, University of Berkeley. 2007-10-03. http://potency.berkeley.edu/chempages/2,4,6-TRICHLOROPHENOL.html. 
  5. ↑ 5.0 5.1 "2,4,6 Trichlorophenol". United States Environmental Protection Agency. Jan 2000. http://www.epa.gov/ttn/atw/hlthef/tri-phen.html. 
  6. ↑ Briois, C.; Ryan, S.; Tabor, D.; Touati, A.; Gullett, B. K. (2007). "Formation of polychlorinated dibenzo-p-dioxins and dibenzofurans from a mixture of chlorophenols over fly ash: Influence of water vapor". Environmental Science & Technology 41 (3): 850–856. doi:10.1021/es0613761. PMID 17328193. Bibcode: 2007EnST...41..850B. 
  7. ↑ "2,4,6-Trichlorophenol". IPCS. Nov 1998. http://www.oit.org/public/english/protection/safework/cis/products/icsc/dtasht/_icsc11/icsc1122.htm. [failed verification]
  8. ↑ TP Halappa Gowdal; John D Lock; Ruth G Kurtz (Feb 1985). "A comprehensive study of risk assessment for a hazardous compound of public health concern". Water, Air, & Soil Pollution 24 (2): 189. doi:10.1007/BF00285444. Bibcode: 1985WASP...24..189H. 

Cited sources



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