Camphene polychlorinated

Toxaphene is a complex mixture of compounds prepared by chlorinating camphene, and contains several hundred polychlorinated bornanes. After incubation with Sulfurospirillum (Dehalospirillum) multivorans only the hexa- (B6-923) and the heptachlorinated (B7-1001) remained. The nonachlorinated congener B9-1679 could be transformed by preferential dechlorination of the em-dichloro groups with formation of the heptachlorinated B7-1001 (Ruppe et al. 2003). Further examination showed that this congener could be dechlorinated to penta- and hexachlorinated bornanes (Ruppe et al. 2004). 

Andersson, O. and A. Wartanian. 1992. Levels of polychlorinated camphenes (toxaphene), chlordane compounds and polybrominated diphenyl ethers in seals from Swedish waters. Ambio 21 550-552. 

Toxaphene (CioHio(- 18) is a mixture of polychlorinated camphenes (bicyclic terpenes). Currently in restricted use as an insecticide, it is toxic to fish, birds and wildlife and may be fatal to shrimp, and crab, etc. (ref. 103, p. 26). Its toxicity and routes of entry in mammals are typical of the cyclic chlorinated hydrocarbons as a class ... 

Often, many simultaneously occurring pollutants or contaminants determine an environmental problem. In industry, agriculture, and households, products are often mixtures of many compounds. The process of production and consumption is accompanied by emissions and consequently by contamination. One example is the use of toxaphene in the past, a very complex mixture of polychlorinated camphenes, as a pesticide. Technical toxaphene consists of more than 175 individual compounds. A second example is industrial and domestic emissions resulting from the combustion of fossil fuels. The emissions contain both a mixture of gases (SO2, NOx, CO2, etc.) and airborne particulate matter which itself contains a broad range of heavy metals and also polycyclic aromatic hydrocarbons (PAH). 

Higher-chlorinated camphenes are the most plausible side products. They may be formed together with other cyclic carbon skeletons if the Wagner-Meerwein rearrangement (to polychlorinated bornanes) is hindered [38, 39]. The ionic addition of chlorine to the primary olefinic carbon is always in competition with radical chlorination. Although the first mechanism is more likely, the second one may also take place. It was found that a gentle chlorination of... 

The formation of polychlorinated dihydro camphenes is not as straightforward as it might seem. Addition of HCl to the double bond of camphene [44] is unlikely since an ionic attack at the double bond is more favorable due to the... 

The complex composition of toxaphene also creates nomenclature problems. Initially, toxaphene was the trademark of the product manufactured by the Hercules Inc. However, due to the non-restricted use of the trademark, toxaphene has become a general term for this pesticide. Further frequently applied terms were camphechlor , polychlorinated bornanes , camphenes , and ter-penes , as well as chlorobornanes . The expression toxaphene is not the same as the trademark Toxaphene , since residues in the environment may also originate from other technical products (see Table 2). Toxaphene is the reaction product of the chlorination of technical camphene is a suitable definition of the expression used in the scientific language [27]. Owing to the problems with abbreviations as described below, toxaphene will be used in the following chapters as a synonym for the compounds of technical toxaphene. 

Due to the variable composition, no general abbreviation is used in the literature in contrast to the case for, e.g., polychlorinated biphenyls which are normally assigned as PCBs. Nevertheless, the following abbreviations are found in the literature PCCs (for polychlorinated camphenes) [74],CHBs [75],CBNs [2], and CB (for chlorinated bornanes or chlorobornanes) [76], and CTTs (compounds of technical toxaphene) [77]. The latter includes all substance classes of toxaphene but so far it has not found a broad application. 

The following year, Andrews and Vetter introduced a system which allowed a conversion of the structure into a code with a computer program [88]. These so-called AV-codes (Andrews and Vetter codes) start with a number and a letter representing the C-backbone and the degree of chlorination which are connected to a one to four-digit number by a hyphen. The latter is the isomer-specific assignment. So far, this system is restricted to polychlorinated bornanes since the IUPAC nomenclature for camphenes and dihydrocamphenes is still not completely clarified (see Sect. 1.2). 

The bulk of the toxaphene components detected in environmental samples are polychlorinated bornanes and a few camphenes or bornenes. Since reductive dechlorination of polychlorinated bornanes leads to bornanes with one less chlorine atom, at present it is not possible to distinguish unequivocally between components originating from technical toxaphene and dechlorinated metabolites. This question can only be solved with fate studies of single components in the laboratory [122,165],... 

Samples of seal blubber from the high-arctic archipelago Svalbard contained levels of polychlorinated camphenes comparable with those found in biota in the Baltic (Andersson et al. 1988), and the same group of compounds was dominant in samples of narwhal (Monodon monoceros) blubber from Pond Inlet, Baffin Island in the Canadian high arctic (Muir et al. 1992). 

POLYCHLORINATED CAMPHENE (8001-35-2) The solid bums with difficulty but is usually dissolved in xylene (solution flash point 84°F/29°C cc). Reacts with strong oxidizers, with a risk of fire or explosions. Decomposes on heating above 311°F/155°C on contact with strong bases, strong sunlight, and catalysts such as iron, forming hydrogen chloride. Attacks metals in the presence of moisture. 

Formula mixture of several compounds consisting of many terpene polychlorinates inclnding chlorinated camphene, pinene, and related componnds ( 65% Cl content) CAS [8001-50-1]... 

Technical toxaphene is a mixture of polychlorinated monoterpenes obtained by chlorination of camphene under UV irradiation. Introduced in 1945, toxaphene was mass-produced until the mid-1980s and widely used as an insecticide, especially in cotton cultures. Currently, toxaphene is considered a worldwide... 

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