Polychlorinated naphthalene

Polychlorinated naphthalene (PCN) are the products obtained upon treatment of naphthalene with chlorine. The generic chemical formula is C₁₀H_8−(m+n)Cl_(m+n). Commercial PCNs are mixtures of up to 75 components and byproducts.[1] The material is an oil or a waxy solid, depending on the degree of chlorination. PCNs were once used in insulating coatings for electrical wires, as well as other applications, but their use has been largely phased out.[2]

General structure of polychlorinated naphthalenes

Structure of 2,3,6,7-Tetrachloronaphthalene

Chemical structure of PCN congeners

There are 75 different PCN congeners.

number	formula	name	CAS Number	InChIKey
PCN-1	${\ce {C10H7Cl}}$	1-chloronaphthalene	90-13-1	JTPNRXUCIXHOKM-UHFFFAOYSA-N
PCN-2	${\ce {C10H7Cl}}$	2-chloronaphthalene	91-58-7	CGYGETOMCSJHJU-UHFFFAOYSA-N
PCN-3	${\ce {C10H6Cl2}}$	1,2-dichloronaphthalene	2050-69-3	MOXLHAPKZWTHEX-UHFFFAOYSA-N
PCN-4	${\ce {C10H6Cl2}}$	1,3-dichloronaphthalene	2198-75-6	AMCBMCWLCDERHY-UHFFFAOYSA-N
PCN-5	${\ce {C10H6Cl2}}$	1,4-dichloronaphthalene	1825-31-6	JDPKCYMVSKDOGS-UHFFFAOYSA-N
PCN-6	${\ce {C10H6Cl2}}$	1,5-dichloronaphthalene	1825-30-5	ZBQZXTBAGBTUAD-UHFFFAOYSA-N
PCN-7	${\ce {C10H6Cl2}}$	1,6-dichloronaphthalene	2050-72-8	CEDZMDSZTVUPSP-UHFFFAOYSA-N
PCN-8	${\ce {C10H6Cl2}}$	1,7-dichloronaphthalene	2050-73-9	VQBIYCQGHAHVPN-UHFFFAOYSA-N
PCN-9	${\ce {C10H6Cl2}}$	1,8-dichloronaphthalene	2050-74-0	ADRYPAGQXFMVFP-UHFFFAOYSA-N
PCN-10	${\ce {C10H6Cl2}}$	2,3-dichloronaphthalene	2050-75-1	SKGXUFZRYNGFJS-UHFFFAOYSA-N
PCN-11	${\ce {C10H6Cl2}}$	2,6-dichloronaphthalene	2065-70-5	YCFUHBHONRJFHI-UHFFFAOYSA-N
PCN-12	${\ce {C10H6Cl2}}$	2,7-dichloronaphthalene	2198-77-8	DWBQZSYTSNYEEJ-UHFFFAOYSA-N
PCN-13	${\ce {C10H5Cl3}}$	1,2,3-trichloronaphthalene	50402-52-3	QEPTXDCPBXMWJC-UHFFFAOYSA-N
PCN-14	${\ce {C10H5Cl3}}$	1,2,4-trichloronaphthalene	50402-51-2	MRJBOPVWPORBKZ-UHFFFAOYSA-N
PCN-15	${\ce {C10H5Cl3}}$	1,2,5-trichloronaphthalene	55720-33-7	MMHZKSMAFILONG-UHFFFAOYSA-N
PCN-16	${\ce {C10H5Cl3}}$	1,2,6-trichloronaphthalene	51570-44-6	AAUJSCRITBXDJH-UHFFFAOYSA-N
PCN-17	${\ce {C10H5Cl3}}$	1,2,7-trichloronaphthalene	55720-34-8	QYYUVUXSJZJCLQ-UHFFFAOYSA-N
PCN-18	${\ce {C10H5Cl3}}$	1,2,8-trichloronaphthalene	55720-35-9	YSFLKFZEQBZEPU-UHFFFAOYSA-N
PCN-19	${\ce {C10H5Cl3}}$	1,3,5-trichloronaphthalene	51570-43-5	DZHZYPCCEISGSQ-UHFFFAOYSA-N
PCN-20	${\ce {C10H5Cl3}}$	1,3,6-trichloronaphthalene	55720-36-0	CJRUXWSXMDPLDQ-UHFFFAOYSA-N
PCN-21	${\ce {C10H5Cl3}}$	1,3,7-trichloronaphthalene	55720-37-1	CFEUGIGSIREATC-UHFFFAOYSA-N
PCN-22	${\ce {C10H5Cl3}}$	1,3,8-trichloronaphthalene	55720-38-2	AXNCYYJNXAOOJQ-UHFFFAOYSA-N
PCN-23	${\ce {C10H5Cl3}}$	1,4,5-trichloronaphthalene	2437-55-0	VQSNXLCFFHGXTI-UHFFFAOYSA-N
PCN-24	${\ce {C10H5Cl3}}$	1,4,6-trichloronaphthalene	2437-54-9	RLTTZFDRZKJVKJ-UHFFFAOYSA-N
PCN-25	${\ce {C10H5Cl3}}$	1,6,7-trichloronaphthalene	55720-39-3	FUEZTEBYLIMNHN-UHFFFAOYSA-N
PCN-26	${\ce {C10H5Cl3}}$	2,3,6-trichloronaphthalene	55720-40-6	ZYTLBFKRYKUCMJ-UHFFFAOYSA-N
PCN-27	${\ce {C10H4Cl4}}$	1,2,3,4-tetrachloronaphthalene	20020-02-4	NAQWICRLNQSPPW-UHFFFAOYSA-N
PCN-28	${\ce {C10H4Cl4}}$	1,2,3,5-tetrachloronaphthalene	53555-63-8	HJJKSUVYCQAMBG-UHFFFAOYSA-N
PCN-29	${\ce {C10H4Cl4}}$	1,2,3,6-tetrachloronaphthalene	149864-78-8	ZVORWIZONZUEEI-UHFFFAOYSA-N
PCN-30	${\ce {C10H4Cl4}}$	1,2,3,7-tetrachloronaphthalene	55720-41-7	AULMCNDOHMTPGC-UHFFFAOYSA-N
PCN-31	${\ce {C10H4Cl4}}$	1,2,3,8-tetrachloronaphthalene	149864-81-3	UVMHXYSILPJXPK-UHFFFAOYSA-N
PCN-32	${\ce {C10H4Cl4}}$	1,2,4,5-tetrachloronaphthalene	6733-54-6	BIVDISPRSYAHQQ-UHFFFAOYSA-N
PCN-33	${\ce {C10H4Cl4}}$	1,2,4,6-tetrachloronaphthalene	51570-45-7	GLVVZPZGCNEVEM-UHFFFAOYSA-N
PCN-34	${\ce {C10H4Cl4}}$	1,2,4,7-tetrachloronaphthalene	67922-21-8	PWXOBMRJWBBEED-UHFFFAOYSA-N
PCN-35	${\ce {C10H4Cl4}}$	1,2,4,8-tetrachloronaphthalene	6529-87-9	WCMSFBRREKZZFL-UHFFFAOYSA-N
PCN-36	${\ce {C10H4Cl4}}$	1,2,5,6-tetrachloronaphthalene	67922-22-9	ZPUUGNBIWHBXBM-UHFFFAOYSA-N
PCN-37	${\ce {C10H4Cl4}}$	1,2,5,7-tetrachloronaphthalene	67922-23-0	KQZUIOXHRIVQGR-UHFFFAOYSA-N
PCN-38	${\ce {C10H4Cl4}}$	1,2,5,8-tetrachloronaphthalene	149864-80-2	DLTBLLHAQLBHDR-UHFFFAOYSA-N
PCN-39	${\ce {C10H4Cl4}}$	1,2,6,7-tetrachloronaphthalene	149864-79-9	AXLIBZIJTKPCHR-UHFFFAOYSA-N
PCN-40	${\ce {C10H4Cl4}}$	1,2,6,8-tetrachloronaphthalene	67922-24-1	OVAYDYKVLHHIDQ-UHFFFAOYSA-N
PCN-41	${\ce {C10H4Cl4}}$	1,2,7,8-tetrachloronaphthalene	149864-82-4	DARLUNVQYCQWRW-UHFFFAOYSA-N
PCN-42	${\ce {C10H4Cl4}}$	1,3,5,7-tetrachloronaphthalene	53555-64-9	OTTCXKPQKOLSJN-UHFFFAOYSA-N
PCN-43	${\ce {C10H4Cl4}}$	1,3,5,8-tetrachloronaphthalene	31604-28-1	VFTLNRFRXWCJJK-UHFFFAOYSA-N
PCN-44	${\ce {C10H4Cl4}}$	1,3,6,7-tetrachloronaphthalene	55720-42-8	BULBRUKKSUUPNT-UHFFFAOYSA-N
PCN-45	${\ce {C10H4Cl4}}$	1,3,6,8-tetrachloronaphthalene	150224-15-0	XXWQPOHDPJIYIN-UHFFFAOYSA-N
PCN-46	${\ce {C10H4Cl4}}$	1,4,5,8-tetrachloronaphthalene	3432-57-3	LITCKAVLJAKHOE-UHFFFAOYSA-N
PCN-47	${\ce {C10H4Cl4}}$	1,4,6,7-tetrachloronaphthalene	55720-43-9	VJZRCIYSYVGDMU-UHFFFAOYSA-N
PCN-48	${\ce {C10H4Cl4}}$	2,3,6,7-tetrachloronaphthalene	34588-40-4	XTTLUUBHRXWFSZ-UHFFFAOYSA-N
PCN-49	${\ce {C10H3Cl5}}$	1,2,3,4,5-pentachloronaphthalene	67922-25-2	JRZKNHITLINYHV-UHFFFAOYSA-N
PCN-50	${\ce {C10H3Cl5}}$	1,2,3,4,6-pentachloronaphthalene	67922-26-3	BAOLNVSMVTYGDA-UHFFFAOYSA-N
PCN-51	${\ce {C10H3Cl5}}$	1,2,3,5,6-pentachloronaphthalene	150224-18-3	CHADMNIGNFLQOI-UHFFFAOYSA-N
PCN-52	${\ce {C10H3Cl5}}$	1,2,3,5,7-pentachloronaphthalene	53555-65-0	OVSKLQPHXHPXDR-UHFFFAOYSA-N
PCN-53	${\ce {C10H3Cl5}}$	1,2,3,5,8-pentachloronaphthalene	150224-24-1	HVYRFNJXZVEGFK-UHFFFAOYSA-N
PCN-54	${\ce {C10H3Cl5}}$	1,2,3,6,7-pentachloronaphthalene	150224-16-1	MKCASBPTHPJCDC-UHFFFAOYSA-N
PCN-55	${\ce {C10H3Cl5}}$	1,2,3,6,8-pentachloronaphthalene	150224-23-0	NMAMEWIQKMFSSI-UHFFFAOYSA-N
PCN-56	${\ce {C10H3Cl5}}$	1,2,3,7,8-pentachloronaphthalene	150205-21-3	BFRRJXVSQTZQHM-UHFFFAOYSA-N
PCN-57	${\ce {C10H3Cl5}}$	1,2,4,5,6-pentachloronaphthalene	150224-20-7	KPOZENRUJCHWOA-UHFFFAOYSA-N
PCN-58	${\ce {C10H3Cl5}}$	1,2,4,5,7-pentachloronaphthalene	150224-19-4	WYLDWCYZCFRVRH-UHFFFAOYSA-N
PCN-59	${\ce {C10H3Cl5}}$	1,2,4,5,8-pentachloronaphthalene	150224-25-2	FEIKEVSWLMYFFF-UHFFFAOYSA-N
PCN-60	${\ce {C10H3Cl5}}$	1,2,4,6,7-pentachloronaphthalene	150224-17-2	GXQUDLBNLKOIQB-UHFFFAOYSA-N
PCN-61	${\ce {C10H3Cl5}}$	1,2,4,6,8-pentachloronaphthalene	150224-22-9	HGSDQSUMXKHGTH-UHFFFAOYSA-N
PCN-62	${\ce {C10H3Cl5}}$	1,2,4,7,8-pentachloronaphthalene	150224-21-8	LBCOXKFWBDTJTF-UHFFFAOYSA-N
PCN-63	${\ce {C10H2Cl6}}$	1,2,3,4,5,6-hexachloronaphthalene	58877-88-6	CTLMCQOGOWNFHA-UHFFFAOYSA-N
PCN-64	${\ce {C10H2Cl6}}$	1,2,3,4,5,7-hexachloronaphthalene	67922-27-4	SWRNUKWDDYPZGV-UHFFFAOYSA-N
PCN-65	${\ce {C10H2Cl6}}$	1,2,3,4,5,8-hexachloronaphthalene	103426-93-3	PGCDNPCENWGYMA-UHFFFAOYSA-N
PCN-66	${\ce {C10H2Cl6}}$	1,2,3,4,6,7-hexachloronaphthalene	103426-96-6	ZRNSVEOEIWQEMU-UHFFFAOYSA-N
PCN-67	${\ce {C10H2Cl6}}$	1,2,3,5,6,7-hexachloronaphthalene	103426-97-7	XZLJCGGEQLNWDT-UHFFFAOYSA-N
PCN-68	${\ce {C10H2Cl6}}$	1,2,3,5,6,8-hexachloronaphthalene	103426-95-5	FQELOCOACCYGLL-UHFFFAOYSA-N
PCN-69	${\ce {C10H2Cl6}}$	1,2,3,5,7,8-hexachloronaphthalene	103426-94-4	JPQLLIUTUFJWMH-UHFFFAOYSA-N
PCN-70	${\ce {C10H2Cl6}}$	1,2,3,6,7,8-hexachloronaphthalene	17062-87-2	WJYZNPLWZGYFIE-UHFFFAOYSA-N
PCN-71	${\ce {C10H2Cl6}}$	1,2,4,5,6,8-hexachloronaphthalene	90948-28-0	JHKLUUFTHIWTKX-UHFFFAOYSA-N
PCN-72	${\ce {C10H2Cl6}}$	1,2,4,5,7,8-hexachloronaphthalene	103426-92-2	SFZREMCYQNYZMZ-UHFFFAOYSA-N
PCN-73	${\ce {C10HCl7}}$	1,2,3,4,5,6,7-heptachloronaphthalene	58863-14-2	NDZIBNJHNBUHKW-UHFFFAOYSA-N
PCN-74	${\ce {C10HCl7}}$	1,2,3,4,5,6,8-heptachloronaphthalene	58863-15-3	QYEGXUUXWMKHHS-UHFFFAOYSA-N
PCN-75	${\ce {C10Cl8}}$	octachloronaphthalene	2234-13-1	RTNLUFLDZOAXIC-UHFFFAOYSA-N

Production

PCNs started to be produced for high-volume uses around 1910 in both Europe and the United States.[2][3] 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.[4]

Safety

After about 20 years of commercial production, health hazards began to be reported in workers exposed to PCNs: chloracne,[1] severe skin rashes[5] and liver disease that led to deaths of workers.[6][7] 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.[8] PCNs containing three or more chlorines per molecule have typically been found more hazardous than those with fewer,[9] but as the maximum of eight is approached, hazards appear to decrease.[10]

There was a lag of about 40 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.[11]

Increased cancer risks have been suspected but so far not shown. Current concerns about PCNs include their release as byproducts of waste incineration.[12]

Bioaccumulation

In 2013, the 9th meeting of the Persistent Organic Pollutants Review Committee, established under the Stockholm Convention on Persistent Organic Pollutants proposed di-,tri-,tetra-,penta-,hexa-, hepta- and octa-chlorinated napthalenes, for listing in Annexes A and C to that Convention.[13]

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 thousand tons, PCN residues are widespread.[10]

References

van de Plassche, E.; Schwegler, A. (2002). Polychlorinated naphthalenes, Preliminary Risk Profile.Ministry of VROM/DGM, Netherlands
Rossberg, Manfred; Lendle, Wilhelm; Pfleiderer, Gerhard; Tögel, Adolf; Dreher, Eberhard-Ludwig; Langer, Ernst; Rassaerts, Heinz; Kleinschmidt, Peter; Strack, Heinz; Cook, Richard; Beck, Uwe; Lipper, Karl-August; Torkelson, Theodore R.; Löser, Eckhard; Beutel, Klaus K.; Mann, Trevor (2006). Ullmann's Encyclopedia of Industrial Chemistry - Chlorinated Hydrocarbons. doi:10.1002/14356007.a06_233.pub2. ISBN 3527306730.
Chlorinated naphthalenes Archived 2005-07-18 at the Wayback Machine, Chemical Assessment Report S48, 2002, National Industrial Chemicals Notification and Assessment Scheme
Horii, Y.; Falandysz, J.; Hanari, N.; Rostkowski, P. (2004). "Concentrations and fluxes of chloronaphthalenes in sediment from Lake Kitaura in Japan in past 15 centuries" (PDF). Journal of Environmental Science and Health, Part A. 39 (3): 587–609. Bibcode:2004JESHA..39..587H. doi:10.1081/ESE-120027727. PMID 15055928. S2CID 38773454.
Teleky, L. (1927). "Die pernakrankheit". Klinische Wochenschrift. 6: 845. doi:10.1007/bf01728520. S2CID 30035538.
Flinn, F.B.; Jarvik, N.E. (1936). "Action of certain chlorinated naphthalenes on the liver". Proceedings of the Society for Experimental Biology and Medicine. 35: 118–120. doi:10.3181/00379727-35-8879p. S2CID 87157158.
Chronic exposure increases risk of liver disease. See Chlorinated naphthalenes exposure, Worker Notification Program, National Institute for Occupational Safety and Health
Butler, D.A. (2005). "The early history of scientific and medical research on 'agent orange'" (PDF). Brooklyn Journal of Law and Policy. 13 (2): 531–533. Archived from the original (PDF) on 2006-09-02.
Drinker, C.K.; Warren, M.F.; Bennet, G.A. (1937). "The problem of possible systemic effects from certain chlorinated hydrocarbons". Journal of Industrial Hygiene and Toxicology. 19 (7): 283.
Chlorinated naphthalenes, International Programme on Chemical Safety CICAD, 2001, volume 34
Neoprene FB Archived 2007-09-27 at the Wayback Machine, Material Safety Data Sheet, DuPont de Nemours & Co., 1985
Omura, M.; Masuda, Y.; Hirata, M.; Tanaka, A. (2000). "Onset of spermatogenesis is accelerated by gestational administration of 1,2,3,4,6,7-hexachlorinated naphthalene in male rat offspring" (PDF). Environmental Health Perspectives. 108 (6): 539–544. doi:10.2307/3454616. JSTOR 3454616. PMC 1638139. PMID 10856028. Archived from the original (PDF) on 2010-06-02.
UNEP (2013). Risk management evaluation on chlorinated naphthalenes, Report of the Persistent Organic Pollutants Review Committee on the work of its ninth meeting, Rome, 14–18 October 2013 (Addendum)

Literature

Eva Jakobsson, Lillemor Asplund: Polychlorinated Naphthalenes (PCNs), in The Handbook of Environmental Chemistry, Volume 3K, 2000, p. 97–126, ISBN 978-3-540-65838-2, doi:10.1007/3-540-48915-0_5

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[van_de_Plassche-1] van de Plassche, E.; Schwegler, A. (2002). Polychlorinated naphthalenes, Preliminary Risk Profile.Ministry of VROM/DGM, Netherlands

[Ullmann-2] Rossberg, Manfred; Lendle, Wilhelm; Pfleiderer, Gerhard; Tögel, Adolf; Dreher, Eberhard-Ludwig; Langer, Ernst; Rassaerts, Heinz; Kleinschmidt, Peter; Strack, Heinz; Cook, Richard; Beck, Uwe; Lipper, Karl-August; Torkelson, Theodore R.; Löser, Eckhard; Beutel, Klaus K.; Mann, Trevor (2006). Ullmann's Encyclopedia of Industrial Chemistry - Chlorinated Hydrocarbons. doi:10.1002/14356007.a06_233.pub2. ISBN 3527306730.

[Australia-3] Chlorinated naphthalenes Archived 2005-07-18 at the Wayback Machine, Chemical Assessment Report S48, 2002, National Industrial Chemicals Notification and Assessment Scheme

[Horii-4] Horii, Y.; Falandysz, J.; Hanari, N.; Rostkowski, P. (2004). "Concentrations and fluxes of chloronaphthalenes in sediment from Lake Kitaura in Japan in past 15 centuries" (PDF). Journal of Environmental Science and Health, Part A. 39 (3): 587–609. Bibcode:2004JESHA..39..587H. doi:10.1081/ESE-120027727. PMID 15055928. S2CID 38773454.

[Teleky-5] Teleky, L. (1927). "Die pernakrankheit". Klinische Wochenschrift. 6: 845. doi:10.1007/bf01728520. S2CID 30035538.

[Flinn-6] Flinn, F.B.; Jarvik, N.E. (1936). "Action of certain chlorinated naphthalenes on the liver". Proceedings of the Society for Experimental Biology and Medicine. 35: 118–120. doi:10.3181/00379727-35-8879p. S2CID 87157158.

[NIOSH-7] Chronic exposure increases risk of liver disease. See Chlorinated naphthalenes exposure, Worker Notification Program, National Institute for Occupational Safety and Health

[Butler-8] Butler, D.A. (2005). "The early history of scientific and medical research on 'agent orange'" (PDF). Brooklyn Journal of Law and Policy. 13 (2): 531–533. Archived from the original (PDF) on 2006-09-02.

[Drinker-9] Drinker, C.K.; Warren, M.F.; Bennet, G.A. (1937). "The problem of possible systemic effects from certain chlorinated hydrocarbons". Journal of Industrial Hygiene and Toxicology. 19 (7): 283.

[CICAD-10] Chlorinated naphthalenes, International Programme on Chemical Safety CICAD, 2001, volume 34

[duPont-11] Neoprene FB Archived 2007-09-27 at the Wayback Machine, Material Safety Data Sheet, DuPont de Nemours & Co., 1985

[Omura-12] Omura, M.; Masuda, Y.; Hirata, M.; Tanaka, A. (2000). "Onset of spermatogenesis is accelerated by gestational administration of 1,2,3,4,6,7-hexachlorinated naphthalene in male rat offspring" (PDF). Environmental Health Perspectives. 108 (6): 539–544. doi:10.2307/3454616. JSTOR 3454616. PMC 1638139. PMID 10856028. Archived from the original (PDF) on 2010-06-02.

[13] UNEP (2013). Risk management evaluation on chlorinated naphthalenes, Report of the Persistent Organic Pollutants Review Committee on the work of its ninth meeting, Rome, 14–18 October 2013 (Addendum)