Polychlorinated naphthalene (PCN) products are made by chemically binding chlorine with naphthalene, a soft, pungent solid made from coal or petroleum and often used for mothproofing. Commercial PCNs are mixtures of 75 chlorinated naphthalene compounds plus byproducts and are often described by the total fraction of chlorine (van de Plassche & Schwegler 2002). As the chlorine proportion grows, PCNs become waxy and increasingly firm solids at room temperature. Some PCNs make effective insulating coatings for electrical wires. Others have been used as wood preservatives, as rubber and plastic additives, for capacitor dielectrics and in lubricants.
PCNs started to be produced for high-volume uses around 1910 in both Europe and the United States (Puzyn & Falandysz 2004) (Australia 2002). In Europe the largest volume products were called Nibren waxes, made in Germany by Bayer. Other European PCN tradenames included Seekay (UK, from ICI), Clonacire (France), Cerifal (Italy) and Woskol (Poland). In the United States, the largest volume PCN products were called Halowax, from a New York company of the same name that was later owned by Union Carbide and then taken over by Koppers of Pittsburgh, PA, now Beazer East. Although trace amounts of PCNs may be released by natural processes such as wildfires, their industrial uses increased the apparent rates of accumulation in the environment by factors of 10,000 or more (Horii et al. 2004).
After about twenty years of commercial production, health hazards began to be reported in workers exposed to PCNs: severe skin rashes (Teleky 1927) and liver disease that led to deaths of workers (Flinn & Jarvik 1936). A conference about the hazards was organized at Harvard School of Public Health in 1937, and several more publications dealing with PCN hazards appeared before 1940 (Butler 2005, pp. 531-533). PCNs containing three or more chlorines per molecule have typically been found more hazardous than those with fewer (Drinker, Warren & Bennet 1937), but as the maximum of eight is approached, hazards appear to decrease (Howe et al. 2001).
There was a lag of about forty years between disclosure of PCN hazards and government regulation. In the U.S. exposure to PCNs was drastically reduced after 1976, following enactment of the Toxic Substances Control Act. Major equipment manufacturers banned PCNs in their products, and major PCN producers discontinued operations. By 1983 worldwide PCN production had almost halted except for small amounts used in testing and research. Until recent years duPont produced a synthetic rubber, Neoprene FB, made in Northern Ireland using pentachloronaphthalene (duPont de Nemours & Co. 1985). Today PCNs are offered commercially by only a few companies, including Ukrgeochem of Simferopol, Ukraine.
While some PCNs can be broken down by sunlight and, at slow rates, by certain microorganisms, many PCNs persist in the environment. After more than 80 years of use and total production of several hundred million kilograms, PCN residues are widespread (Howe et al. 2001). Acute exposure causes chloracne (van de Plassche & Schwegler 2002). Chronic exposure increases risk of liver disease (United States 1996). Increased cancer risks have been suspected but so far not shown. Current concerns about PCNs include their release as byproducts of waste incineration (Omura et al. 2000, pp. 539, 544 ref).
- Australia, National Industrial Chemicals Notification and Assessment Scheme (2002), "Chlorinated naphthalenes", Chemical Assessment Report S48
- Butler, D.A. (2005), "The early history of scientific and medical research on 'agent orange'", Brooklyn Journal of Law and Policy 13(2): 527
- Drinker, C.K.; M.F. Warren & G.A. Bennet (1937), "The problem of possible systemic effects from certain chlorinated hydrocarbons", Journal of Industrial Hygiene and Toxicology 19(7): 283
- duPont de Nemours & Co., E.I. (1985), "Neoprene FB", Material Safety Data Sheet
- Flinn, F.B. & N.E. Jarvik (1936), "Action of certain chlorinated naphthalenes on the liver", Proceedings of the Society for Experimental Biology and Medicine 35: 118
- Horii, Y.; J. Falandysz & N. Hanari et al. (2004), "Concentrations and fluxes of chloronaphthalenes in sediment from Lake Kitaura in Japan in past 15 centuries", Journal of Environmental Science and Health, Part A 39(3): 587
- Howe, P.D.; C. Melber & J. Kielhorn et al. (2001), "Chlorinated naphthalenes", International Programme on Chemical Safety CICAD 34
- Omura, M.; Y. Masuda & M. Hirata et al. (2000), "Onset of spermatogenesis Is accelerated by gestational administration of 1,2,3,4,6,7-hexachlorinated naphthalene in male rat offspring", Environmental Health Perspectives 108(6): 539
- Puzyn, T. & J. Falandysz (2004), "In silico studies of dioxin-like toxicity of 75 individual chloronaphtalene congeners (PCNs)", 24th International Symposium on Halogenated Environmental Organic Pollutants and POPs, Berlin, September 6-10
- Teleky, L. (1927), "Die pernakrankheit", Klinische Wochenschrift (Berlin: Springer) Jahrgänge 6: 845
- United States, National Institute for Occupational Safety and Health (1996), "Chlorinated naphthalenes exposure", Worker Notification Program
- van de Plassche, E. & A. Schwegler (2002), "Polychlorinated naphthalenes", Preliminary Risk Profile, Netherlands