2,4-Dichlorophenol (2,4-DCP) is a chlorinated derivative of phenol with the molecular formula Cl2C6H3OH. It is a white solid that is mildly acidic (pKa = 7.9). It is produced on a large scale as a precursor to the herbicide 2,4-dichlorophenoxyacetic acid (2,4-D).[4]
Production and use
2,4-DCP is produced by chlorination of phenol.[4]
Annual worldwide production is estimated at 88 million pounds.[5] It is also a photo-degradation product of the common antibacterial and antifungal agent triclosan along with the dioxin 2,8-dichlorodibenzo-p-dioxin.[6][7]
Safety
The LD50 is 580 mg/kg (rats, oral). Liquid (molten) 2,4-DCP is readily absorbed through the skin.[8] Solid 2,4-DCP does not readily absorb through skin and has a lower NFPA H=3 rating (versus H=4 for molten 2,4-DCP). This is primarily caused by instantaneous kidney failure, liver failure, and failure of various other organs.[dubious – discuss]
See also
References
- ^ a b Haynes, p. 3.166
- ^ Haynes, p. 5.12
- ^ Haynes, p. 16.20
- ^ a b François Muller, Liliane Caillard (2011). "Chlorophenols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a07_001.pub2. ISBN 978-3-527-30673-2.
- ^ Desmurs J, Ratton S. Chlorophenols. In: Kirk-Othmer Encyclopedia of Chemical Technology, 4th Edition. Kroschwitz JI, Howe-Grant M, eds. New York: John Wiley and Sons, 1993;6:156–168
- ^ Singer H, Muller S, Tixier C, Pillonel L (2002). "Triclosan: occurrence and fate of a widely used biocide in the aquatic environment: field measurements in wastewater treatment plants, surface waters, and lake sediments". Environ Sci Technol. 36 (23): 4998–5004. Bibcode:2002EnST...36.4998S. doi:10.1021/es025750i. PMID 12523412.
- ^ Latch DE, Packer JL, Stender BL, VanOverbeke J, Arnold WA, McNeill K (2005). "Aqueous photochemistry of triclosan: formation of 2,4-dichlorophenol, 2,8-dichlorodibenzo-p-dioxin, and oligomerization products". Environ. Toxicol. Chem. 24 (3): 517–25. doi:10.1897/04-243R.1. PMID 15779749. S2CID 19322739.
- ^ Kintz P, Tracqui A, Mangin P (1992). "Accidental death caused by the absorption of 2,4-dichlorophenol through the skin". Arch. Toxicol. 66 (4): 298–9. doi:10.1007/BF02307178. PMID 1514931. S2CID 23764834.