Of chlorophenols

Uses. Uses of sulfuryl chloride include the manufacture of chlorophenols, eg, chlorothymol for use as disinfectants. It is also used in the manufacture of alpha-chlorinated acetoacetic derivatives, eg, CH2COCHCICOOC2H3, which ate precursors for important substituted imidazole dmgs,... 

The main characteristics and physical properties of the chlorophenols are brought together in Table 1. With the exception of o-chlorophenol, they are all sohds at room temperature. The refractive indexes of the monochlorophenols, C H CIO, are as follows ortho, 1.5524 meta, 1.5565 para, 1.5579. The piC values of chlorophenols depend on the number and the position of the substituents. 

Effects in Humans. In chlorophenol production, irritation symptoms of the nose, eyes, respiratory tract, and skin resulting ia chloroacne have been observed. The results of epidemiology studies on the long-term effects of chlorophenols are quite contradictory and have not allowed the experts to reach any firm conclusions (54). 

Pera-Titus M, Garcia-Molina V, Banos MA et al (2004) Degradation of chlorophenols by means of advanced oxidation processes a general review. Appl Catal B 47 219-256... 

PCDDs have been released into the environment in a number of different ways. Sometimes this has been due to the use of a pesticide that is contaminated with them. 2,4,5-T and related phenoxyalkanoic herbicides have been contaminated with them as a consequence of the interaction of chlorophenols used in the manufacturing... 

PCDFs are similar in many respects to PCDDs but have been less well studied, and will be mentioned only briefly here. Their chemical structure is shown in Figure 7.1. Like PCDDs, they can be formed by the interaction of chlorophenols, and are found in commercial preparations of chlorinated phenols and in products derived from phenols (e.g., 2,4,5-T and related phenoxyalkanoic herbicides). They are also present in commercial polychlorinated biphenyl (PCB) mixtures, and can be formed... 

Both PCDDs and PCDEs are refractory lipophilic pollutants formed by the interaction of chlorophenols. They enter the environment as a consequence of their presence as impurities in pesticides, following certain industrial accidents, in effluents from pulp mills, and because of the incomplete combustion of PCB residues in furnaces. Although present at very low levels in the environment, some of them (e.g., 2,3,7,8-TCDD) are highly toxic and undergo biomagnification in food chains. 

It has been shown that a combination of photolytic and biotic reactions can result in enhanced degradation of xenobiotics in municipal treatment systems, for example, of chlorophenols (Miller et al. 1988a) and benzo[a]pyrene (Miller et al. 1988b). Two examples illustrate the success of a combination of microbial and photochemical reactions in accomplishing the degradation of widely different xenobiotics in natural ecosystems. Both of them involved marine bacteria, and it therefore seems plausible to assume that such processes might be especially important in warm-water marine enviromnents. 

Miller RM, GM Singer, JD Rosen, R Bartha (1988a) Sequential degradation of chlorophenols by photolytic and microbial treatment. Environ Sci Technol 22 1215-1219. 

Considerable interest has been expressed in the chlorophenol-degrading organism Mycobacterium chlorophenolicum (R. chlorophenolicus) (Apajalahti et al. 1986), partly motivated by its potential for application to bioremediation of chlorophenol-contaminated industrial sites (Haggblom and Valo 1995). 

Haggblom MM, RJ Valo (1995) Bioremedation of chlorophenol wastes. In Microbial Transformation and Degradation of Toxic Organic Chemicals (Eds LY Young and CE Cerniglia), pp. 389-434. Wiley-Liss, New York, USA. 

Walker N (1973) Metabolism of chlorophenols by Rhodotorula glutinis. Soil Biol Biochem 5 525-530. 

A range of mechanisms operates for the degradation of chlorophenols with three or more... 

Gisi MR, L Xun (2003) Characterization of chlorophenol 4-monooxygenase (TftD) and NADH flavin adenine dinucleotide oxidoreductase (TftC) of Burkholderia cepacia ACllOO. J Bacteriol 185 2786-2792. 

Xun L (1996) Purification and characterization of chlorophenol 4-monooxygenase from Burkholderia cepacia ACnOO. J Bacterial 178 2645-2649. 

Experiments using a fluidized-bed reactor showed that the removal of chlorophenols could be accomplished by organisms adapted to a temperature of 5-7°C (Jarvinen et al. 1994). 

Jarvinen KT, ES Melin, K A Puhakka (1994) High-rate bioremediation of chlorophenol-contaminated ground-water at low temperatures. Environ Sci Technol 28 2387-2392. 

Kiyohara H, T Hatta, Y Ogawa, T Kakuda, H Yokoyama, N Takizawa (1992) Isolation of Pseudomonas pick-ettii strains that degrade 2,4,6-trichlorophenol and their dechlorination of chlorophenols. Appl Environ Microbiol 58 1276-1283. 

Mohn WW, KJ Kennedy (1992) Reductive dehalogenation of chlorophenols by Desulfomonile tiedjei DCB-1. Appl Environ Microbiol 58 1367-1370. 

Naturally occurring oxaarenes based on polycyclic pyrans encompass a plethora of structures including the plant polyphenols such as anthocyanins and a-tocopherol (vitamin E). Halogenated dibenzo-p-dioxins and dibenzofurans are formed both as by-products during the manufacture of chlorophenols, and from the incineration of organic matter in the presence of inorganic halides. 

The tolerance of the strains to high concentrations of pentachlorophenol—S. chlorophenolica appears to be less sensitive than M. chlorophenolicus (Miethling and Karlson 1996). This may be attribnted to the ability of the cells to adapt their metabolism to avoid synthesis of toxic concentrations of chlorinated hydroquinones, and is consistent with the low levels of these metabolites measnred in the cytoplasm of cells metabolizing pentachlorophenol (McCarthy et al. 1997). Inocnla have also been immobilized on polyurethane that, in addition, ameliorates the toxicity of chlorophenols (Valo et al. 1990). 

Laine MM, KS Jorgensen (1996) Straw compost and bioremediated soil as inocula for the bioremediation of chlorophenol contaminated soil. Appl Environ Microbiol 62 1507-1513. 

Laine MM, KS Jorgensen (1997) Effective and safe composting of chlorophenol contaminated soil in pilot scale. Environ Sci Technol 30 371-378. 

Valo RJ, MM Haggblom, MS SaUdnoja-Salonen (1990) Bioremediation of chlorophenol containing simulated ground water by immobilized bacteria. Water Res 24 253-258. 

Sedarati, M.R., Keshavarz, T., Leontievsky, A.A., and Evans, C.S., Transformation of high concentrations of chlorophenols by the white-rot basidiomycete Trametes versicolor immobilized on nylon mesh. Electronic J. Biotechnol. [online], 6(2), August 15, 2003. 

Tatsumi, K., Wada, S., and Ichikawa, H., Removal of chlorophenols from wastewater by immobilized horseradish peroxidase, Biotechnol. Bioeng., 51, 126-130, 1996. 

Cho, N.S., Rogalski, J., Jaszek, M., Luterek, J., Wojtas-Wasilewska, M., Malarczyk, E., Fink-Boots, M., and Leonowicz, A., Effect of coniferyl alcohol addition on removal of chlorophenols from water effluent by fungal laccase, J. Wood Sci., 45, 174-178, 1999. 

Choi, S.H., Moon, S.H., and Gu, M.B., Biodegradation of chlorophenols using the cell-free culture broth of Phanerochaete chrysosporium immobilized in polyurethane foam, J. Chem. Technol. Biotechnol., 77, 999-1004, 2002. 

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