Mutagen chlorination

The Kraft process that is widely used in wood pulping leaves behind 5% to 8% by weight of residual modified lignin in the pulp. This residual is responsible for the characteristic brown color of the pulp and is commercially removed by the use of bleaching agents such as chlorine and chlorine oxides [32], Bleaching operations produce dark-brown effluents that contain toxic and mutagenic chlorinated products that constitute an environmental... 

The state of the art has been reviewed as has the incorporation of carbohydrates into macromolecular force fields <2006MI235>. 3-Chloro-4-(dichloromethyl)-5-hydroxyfuran-2(5//)-one 3, a mutagenic chlorinated-water pollutant, has been the subject of detailed molecular mechanics calculations <2004MI129>. 

Furylfuramide. a[(5-Nitro-2-furaiiyl)-2-methylene]-2-furaiiacetamide, withdrawn from the market in Japan in 1974 because of mutagenicity, is prepared by condensation of 5-nitro-2-furancarboxaldehyde with 2-furanacetic acid followed by chlorination and amination (30). The isomerization of cis to trans form of fudyfuramide has been shown to occur in the presence of a variety of biological reducing agents (31). 

Mere destruction of the original hazardous material is not, however, an adequate measure of the performance of an incinerator. Products of incomplete combustion can be as toxic as, or even more toxic than, the materials from which they evolve. Indeed, highly mutagenic PAHs are readily generated along with soot in fuel-rich regions of most hydrocarbon flames. Formation of dioxins in the combustion of chlorinated hydrocarbons has also been reported. We need to understand the entire sequence of reactions involved in incineration in order to assess the effectiveness and risks of hazardous waste incineration. 

Greim H, Bonse G, Radwan Z, et al. 1975. Mutagenicity in vitro and potential carcinogenicity of chlorinated ethylenes as a function of metabolic oxirane formation. Biochem Pharmacol 24 2013-2017. 

The use of chlorine for disinfecting wastewaters or drinking water has become widespread in this century. Recently, however, the increasing presence and variety of aquatic contaminants has raised the question of the chemical fate of these contaminants when subjected to aqueous chlorination [36]. In fact, the production of organochlorine compounds in chlorinated water, including mutagenic and carcinogenic substances, is well established [37,38], A number of alternatives to chlorination are used in many parts of the world, but the risks associated with their by-products are even less well established [39],... 

Schoeny RS, Smith CC, Loper JC. 1979. Non-mutagenicity for Salmonella of the chlorinated hydrocarbons aroclor 1254, 1,2,4-trichlorobenzene, mirex and Kepone. Mutat Res 68(2) 125-132. 

A. R. Jones, W. C. Mackrodt, Structure-Genotoxicity Relationship for Aliphatic Epoxides , Biochem. Pharmacol. 1983, 32, 2359 - 2362 A. R. Jones, W. C. Mackrodt, Structure-Mutagenicity Relationships of Chlorinated Ethylenes A Model Based on the Stability of the Metabolically Derived Epoxides , Biochem. Pharmacol. 1982, 31, 3710 -3712. 

Simmon VF, Tardiff RG. 1978. The mutagenic activity of halogenated compounds found in chlorinated drinking water. In Water chlorination Environmental impact and health effects. Vol. 2. Ann Arbor, Ml Ann Arbor Science, 417-431. 

Kitchin KT, Brown JE. 1989. Biochemical effects of three carcinogenic chlorinated methanes in rat liver. Teratogen Carcinogen Mutagen 9 61-69. 

Haloaldehydes are formed primarily with chlorine or chloramine disinfection, but they are increased in formation with preozonation. In the Nationwide Occurrence Study, haloaldehydes were the third largest DBP class by weight (behind THMs and HAAs) of all the DBPs studied. Dichloroacetaldehyde was the most abundant of these haloaldehydes, with a maximum concentration of 16 pg/L. Before this study, chloral hydrate (trichloroacetaldehyde) was the only commonly measured haloaldehyde, and it was included in the ICR. Chloral hydrate and monochloroacetaldehyde are mutagenic in vitro [1], and tribromoacetaldehyde and chloral hydrate were recently found to be genotoxic in human cells [72]. 

Two UV filters (used to block UV-rays in sunscreens and other products), octyl-p-methoxycinnamate and octyl-dimethyl-p-aminobenzoate, reacted with chlorine, producing chlorine-substituted compounds as intermediates that finally cleaved to smaller ester products [121]. Some of the identified octyl-p-methoxycinnamate DBPs showed weak mutagenic properties. Chlorinated and brominated intermediates were formed during chlorination of 2-ethylhexyl-4-(dimethylamine)benzoate and 2-hydroxy-4-methoxybenzophenone, with trichloromethoxyphenol the most abundant DBP [122]. 

Kronberg L, Vartiainen T (1988) Ames mutagenicity and concentration of the strong mutagen 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone and of its geometric isomer E-2-chloro-3-(dichloromethyl)-4-oxo-butenoic acid in chlorine-treated tap waters. Mutat Res 206 177-182... 

Nakajima M, Kawakami T, Niino T, Takahashi Y, Onodera S (2009) Aquatic fate of sunscreen agents octyl-4-methoxycinnamate and octyl-4-dimethylaminobenzoate in model swimming pools and the mutagenic assays of their chlorination byproducts. J Health Sci 55(3) 363-372... 

Richardson SD, DeMarini DM, Kogevinas M, Fernandez P, Marco E, Lourencetti C, Balleste C, Heederik D, Meliefste K, McKague AB, Marcos R, Font-Ribera L, Grimalt JO, Villanueva CM (2010) What s in the pool A comprehensive identification of disinfection by-products and assessment of mutagenicity of chlorinated and brominated swimming pool water. Environ Health Perspect 118(11) 1523-1530... 

Kringstad, K.P. Ljungquist, P.O. de Sousa, F. Stromberg, L.M. Identification and mutagenic properties of some chlorinated aliphatic compounds in the spent liquor from Kraft pulp chlorination. Environ. Sci. Technol. 1981, 15, 562-566. 

The Salmonella test is currently detecting about 90% of organic carcinogens as mutagens. A number of important carcinogens are not detected however, particularly many heavily chlorinated chemicals.(5,6) We hope that with further improvements in... 

Sycheva LP, Zholdakova ZI, Polyakova EE, et al Mutagenic activity of cyclohexene and products of its chlorination. Bull Exp Biol Med 129(6) 581-583,2000... 

Douglas GR, Nestmann ER, Betts JL, et al. 1980. Mutagenic activity in pulpmill effluents. Water Chlorination Environ Impact Health Eff 3 865- 880. 

Kim J, Marshall MR, Du WX, et al. 1999. Determination of chlorate and chlorite and mutagenicity of seafood treated with aqueous chlorine dioxide. J Agric Food Chem 47 3586-3591. 

Rapson WH, Nazar MA, Butsky VV. 1980. Mutagenicity produced by aqueous chlorination of organic compounds. Bull Environ Contam Toxicol 24 590-596. 

Zoeteman BCJ, Hmbec J, de Greef E, et al. 1982. Mutagenic activity associated with by-products of drinking water disinfection by chlorine, chlorine dioxide, ozone and UV-irradiation. Environ Health Perspect 46 197-205. 

Lag. M., Omichinski, J.G, Dybing, E., Nelson, S.D. Soderlund, E.J. (1994) Mutagenic activity of halogenated propanes and propenes effect of bromine and chlorine positioning. Chem.-biol. Interact., 93, 73-84... 

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