Chlorinated diphenyl ether

Colorless dyes of the chlorinated diphenyl ether—ureasulfonic acid type (Mitin [3567-25-7] (158)) and the (polychloro-2-chloromethylsulfonamido)-diphenyl ether type (Eulan (159)) appHed at 1—3% of the fabric weight are the most widely used during the fabrication of woolens. They cannot be removed by dry cleaning and provide protection from fabric pests over the lifetime of the product. 

Commercial PCP preparations often contain variable amounts of chlorophenols, hexachloroben-zene, phenoxyphenols, dioxins, dibenzofurans, chlorinated diphenyl ethers, dihydroxybiphenyls, anisoles, catechols, and other chlorinated dibenzodioxin and dibenzofuran isomers. These contaminants contribute to the toxicity of PCP — sometimes significantly — although the full extent of their interactions with PCP and with each other in PCP formulations are unknown. Unless these contaminants are removed or sharply reduced in existing technical- and commercial-grade PCP formulations, efforts to establish sound PCP criteria for protection of natural resources may be hindered. 

Villeneuve, J.Y. Niimi, A.J. Metcalfe, C.D. 2000, Distribution and bioaccumulation of chlorinated diphenyl ethers in a contaminated embayment of Lake Ontario. J. Great Lakes Res. 25 760-771. 

Choudhry GG, Sundstrom G, Ruzo LO, et al. 1977. Photochemistry of chlorinated diphenyl ethers. J Agnc Food Chem 25 1371-1376. 

Hargreaves J, Park J, Ghisalberti EL, Swasithamparam K, Skelton BW, White AH (2002) New Chlorinated Diphenyl Ethers from an Aspergillus Species. J Nat Prod 65 7... 

Niimi, A.J., Oliver, B. (1983) Biological half-lives of chlorinated diphenyl ethers in rainbow trout (Salmo gairdneri). Can. J. Fish Aquatic Sci. 40, 1388. 

Ryan JJ, Lizotte R, Newsome WH. 1984b. Study of chlorinated diphenyl ethers and chlorinated 2-phenoxyphenols as interferences in the determination of chlorinated dibenzo-p-dioxins and chlorinated dibenzofiirans in biological samples. J Chromatogr 303 351-360. 

Choudry GG, Sundstrom G, van der Wielen FWM, Hutzinger O (1977), Chemosphere 6 327-332. Synthesis of chlorinated dibenzofurans by photolysis of chlorinated diphenyl ethers in acetone solution"... 

Niimi, A.J., Metcalfe, C.D., Huestis, S.Y. (1994) Chlorinated diphenyl ethers in Great Lakes fish and their environmental implication. Environ. Toxicol. Chem. 13, 1133-1138. 

Zitko, V, Carson, W.G. (1977) Uptake and excretion of chlorinated diphenyl ethers and hrominated toluenes hy fish. Chemosphere 6, 293-301. 

Analytes. DBF, decabromobiphenyl HBCD, Hexabromocyclododecane PBCDE, polybrominated or chlorinated diphenyl ether PBDE, polybrominated diphenyl ether PCB, polychlorinated biphenyl PBDD, polybrominated dibenzo-p-dioxins PBB, polybrominated biphenyl PeBDE, pentabromodiphenyl ether. 

SYNONYMS benzene, l,l -oxybis, hexachloro, chlorinated diphenyl ether, hexaclorodi-phenyl ether, hexachlorodiphenyl oxide, hexachlorophenyl ether, trichlorodiphenyl ether, tri-chlorodiphenyl oxide. 

Pentachlorophenol (PCP, XIV) also could be considered to enter into the same photonucleophilic reaction in aqueous solution to give, among other products, tetrachlororesorcinol and chlorinated quinones (46). Further oxidation and condensation reactions then result in several unusual diphenyl ethers and aryloxyquinones (Figure 6). In alkaline solution, photonucleophilic attack of pentachlorophenoxide ion on an ortho chlorine of PCP could produce a chlorinated diphenyl ether which then goes on to form 1,2,3,4,6,7,8,9-octachlorodibenzo-p-dioxin (XV) (40). 

Pyrolysis of tri-, tetra-, and penta-chlorobenzenes affords mixtures of chlorinated dibenzofurans and dibenzo-p-dioxins, " and chlorinated diphenyl ethers cyclize in the presence of palladium acetate to polychloro-dibenzofurans/ The action of malononitrile on tetrahydroxy-p-benzoquinone leads to the benzo-difuran (79), contrary to a previous report/ The acid-catalysed condensation of quinones with phenols has been studied p-benzoquinone and resorcinol, for example, afford compound (80)/ Naphtho[2,3- >]furan-4,9-diones (81 R = Me or Ph R = Ac, Bz, C02Et, or CN) are obtained from 2,3-dichloronaphtho-1,4-quinone and compounds R COCHaR in DMF that contains potassium fluoride/ The action of mineral acids on p-benzoquinone produces a mixture of complex benzofurans, which includes (82) and (83)/ Bases convert the ben-zofuranone (84) into the tetrameric compound (85), contrary to an earlier... 

Commercial PCP preparations often contain variable amounts of chlorophenols, hexachlorobenzene, phenoxyphenols, dioxins, dibenzofurans, chlorinated diphenyl ethers,... 

When heated, PCP will form chlorinated diphenyl ethers which can further react to produce chlorinated choxins and furans. This is why wood treated with PCP should only be burned at controlled temperatures so that dioxins and furans are not produced. The reactions are illustrated in Figs. 38.2 to 38.5. 

Observations were reported on the following classes related to known antibacterials biguanides,chlorinated diphenyl ethers, and chlorophenoxycarbanllides. 

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