Naphthalene chlorinated

Other chlorinated naphthalenes. The other monochloronaphthalene (2-), the ten theoretically possible dichloronaphthalenes, and the fourteen trichloronaphthalenes have all been prepared, generally from the corresponding amino-derivatives by diazotization and treatment with CuCl. They are of little industrial importance. 

The toxicity of chloronaphthalenes requires that special attention and caution be used during their manufacture and use acne is the most common result of excessive skin exposure to them and the most frequendy affected areas are the face and neck (16). Liver damage has occurred in workers who have been exposed repeatedly to vapors, particulady to those of penta- and hexachloronaphthalene [1335-87-1] (17,18). Uses for the chlorinated naphthalenes include solvents, gauge and instmment duids, capacitor impregnants, components in electric insulating compounds, and electroplating stop-off compounds. 

Miscellaneous uses include several organic compounds and intermediates, eg, 1-naphthalenol, 1-naphthylamine [134-32-7] 1,2,3,4-tetrahydronaphthalene, decahydronaphthalene, and chlorinated naphthalenes. 

In earlier editions of the Eniyclopedia there have been articles covering the properties, manufacture, capacities, etc, of polychlorinated biphenyls (PCBs), chlorinated naphthalenes, benzene hexachloride, and chlorinated derivatives of cyclopentadiene. These materials are no longer in commercial use because of their toxicity. However, they stiU impact on the chemical industry because of residual environmental problems. Their toxicity and environmental impact are discussed (see Cm.OROCARBONSANDCm.OROHYDROCARBONS, TOXIC aromatics). 

Uses Chlorinated naphthalenes were formerly used in the production of electric condensers, insulating electric condensers, electric cables, and wires additive for high pressure lubricants. 

Uses Chemical research organic synthesis. According to HSDB (1005), U.S. has discontinued manufacturing of chlorinated naphthalenes since 1977. Chlorinated naphthalenes were formerly used as a wood preservative, additives in cutting oils, and as an additive in fireproofing and waterproofing cable insulation. 

Some studies of occupationally exposed groups have revealed evidence of liver injury by serum enzyme studies or other liver function tests. Adverse effect and dose-effect relationships have not been consistent within and between studies, raising the possibility that other factors (e.g., alcohol intake, other exposures) could be responsible. Review of these studies indicates that some liver effects may have occurred with repeated exposures at concentrations below O.lmg/m assuming RGBs were responsible. Several deaths due to toxic hepatitis have been reported among workers exposed to mixtures of RGBs with chlorinated naphthalenes such effects have not been observed with PGB exposure alone. ... 

An excess mortality of cirrhosis of the liver was observed in 9028 workers employed from 1940 to 1944 at a cable manufacturing plant with chlorinated naphthalene exposure. Cirrhosis deaths were similarly elevated in a subcohort of 460 individuals who had shown symptoms of chloracne. A cancer mortality study of this same subcohort found an excess of two rare causes of death, malignant neoplasm of the esophagus and benign and unspecified neoplasms. ... 

Ward EM, Ruder AM, Suruda A, Smith AB, Fessler-Flesch CA, Zahm SH Acute and chronic liver toxicity resulting from exposure to chlorinated naphthalenes at a cable manu-... 

Toxicology. The higher-chlorinated naphthalenes may cause severe injury to the liver. 

Exposure of workers by inhalation or skin absorption to lower-chlorinated naphthalenes (penta- and hexachloro) causes a severe acne-form dermatitis, chloracne. Surprisingly, on human volunteers, octachloronaphthalene was entirely nonacneigenic. Octachloronaphthalene (20 mg, 5 times/week for 2 weeks) did not induce gross or histologic changes in skin of hairless mice." ... 

There is no information on systemic effects in humans. In animals, systemic toxicity from chlorinated naphthalenes appears to be limited to liver injury characterized as acute yellow atrophy. In general the tri- to hexa-chlorinated range shows the highest toxicity, with octachlorinated naphthalene significantly less toxic than the others, presumably reflecting poor uptake of octachloronaphthalene by organisms. ... 

Kleinfeld M, Messite J, Swencicki R Clinical effects of chlorinated naphthalene exposure. J OccupMed 14 377-379, 1972... 

World Health Organization Concise International Chemical Assessment Document (CICAD) Chlorinated Naphthalenes. Vol 34 1-40, Geneva, International Programme on Chemical Safety (IPCS), 2001... 

Industrial exposure to tricbloronaphthalene (usually mixed with tetrachloronaphtha-lene) has been relatively free of untoward effects compared witb tbe more bigbly chlorinated naphthalenes. No fatal cases of liver injury have been reported, but one instance of toxic hepatitis supposedly resulted from exposure to 3mg/m Altbougb there are several reports of chloracne from exposure to tricbloronaphthalene, they do not stand up well to critical analysis. Experiments on human volunteers showed that the mist was entirely nonacneigenic as opposed to the penta- and hexachloro derivatives, which produce severe chloracne. ... 

The higher-chlorinated naphthalenes show a much greater toxicity. ... 

Mayers MR, Smith AR Systemic effects from exposure to certain of the chlorinated naphthalenes. NY Ind Bull 21 30-33, 1942... 

The action of carbon tetrachloride or a mixture of chlorine with a hydrocarbon or carbon monoxide on the oxide.—H. N. Warren 9 obtained aluminium chloride by heating the oxide to redness with a mixture of petroleum vapour and hydrogen chloride or chlorine, naphthalene chloride or carbon tetrachloride was also used. The bromide was prepared in a similar manner. E. Demarpay used the vapour of carbon tetrachloride, the chlorides of chromium, titanium, niobium, tantalum, zirconium, cobalt, nickel, tungsten, and molybdenum H. Quantin, a mixture of carbon monoxide and chlorine and W. Heap and E. Newbery, carbonyl chloride. 

Tetrathiolene complexes of platinum can be prepared from the sulfur-substituted derivatives of naphthalene, tetracene and chlorinated naphthalene.1854... 

Kuruiiziim A, Demirezer LO, Bergere I, Zeeck A (2001) Two New Chlorinated Naphthalene Glycosides from Rumex patientia. J Nat Prod 64 688... 

Kover FD (1975) Environmental hazard assessment report chlorinated naphthalenes. EPA-560/8-75-001. US EPA, Office of Toxic Substances, Washington, DC... 

Olson C (1969) Bovine hyperkeratosis (X-disease, highly chlorinated naphthalene poisoning), historical review. In Brandly CA, Cornelius CE (eds) Advances in veterinary sciences and comparative medicine. Academic, New York, p 101... 

Table 12.3 Dust concentrations of PCP, lindane, DDT and chlorinated naphthalenes in different locations of museums (reprinted from Schieweck et a ., 2007a with permission from Elsevier).

In their acute toxic effects on the skin and liver PCBs resemble the chlorinated naphthalenes. Acute yellow atrophy is produced in the liver and enhanced in the presence of CHClj (synergism). Toxicity increases with increase in chlorine content of the PCB, and with oxide formation. Skin lesions (chloracne) consist of small pimples and dark pigmentation of exposed areas. Later comedones and pustules develop. With systemic intoxication, progressive symptoms are nausea, vomiting, weight loss, jaundice, edema, abdominal pain, and, where liver damage is severe, it is followed by coma and death (Sax, 3d ed., p. 551). 

Attempts were made to bracket the PCB concentrations in oil shipments over time. In analyses that were based solely on chlorine content, oil shipped February 5, 1968 had a PCB content of ca. 3000 ppm. Subsequent shipments decreased rapidly, and oils produced after February 19 had PCB traces only (NI0SH Criteria. . ., p. 4l). PCDF at a/0.5% of total PCB concentration, low bromine levels (/v2% of Cl content), traces of chlorinated naphthalenes, and evidence for other unspecified chlorinated contaminants are also noted in the PCB literature references cited in the NI0SH document containing 302 references (ref. 136). 

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