Skip to main content

Polychlorinated Naphthalenes (PCNs)

  • Chapter
  • First Online:
Volume 3 Anthropogenic Compounds Part K

Part of the book series: The Handbook of Environmental Chemistry ((HEC3,volume 3K))

Abstract

Polychlorinated naphthalenes (PCNs) have been commercially produced and used mainly in electrical devices, but also for impregnation of wood, paper and textiles to attain waterproofness, flame resistance and protection against insects, molds and fungi. Today, the PCNs are widespread in the environment and are to be regarded as an environmental problem. Generally, the levels are lower compared to e.g. polychlorinated biphenyls (PCBs), but high levels have been observed near point sources such as manufacturers of chlorine/soda, magnesium, copper and aluminum. PCB products and incineration processes are also sources of PCN releases. The present review summarizes data on physical properties such as melting points, solubility and logKow. Chemical reactivity and methods used for synthesis of individual congeners are briefly discussed. The analytical methods used for PCN analysis are presented as well as sources and environmental levels. Finally, the biological fate and toxicological data available are summarized.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Brinkman UATh, Reymer HGM (1976) J Chromatogr 127:203

    CAS  Google Scholar 

  2. Ullmann’s Encyclopedia of Industrial Chemistry Vol A6(1986) Campbell FT, Pfefferkorn R, Rounsaville JF (eds) VCH, Weinheim, Germany

    Google Scholar 

  3. Haglund P, Jakobsson E, Asplund L, Athanasiadou M, Bergman Ã… (1993) J Chromatogr 634:79

    CAS  Google Scholar 

  4. Crookes MJ, Howe PD (1993) Environmental hazard assessment: halogenated naphthalenes TSD/13. Department of the Environment, London, UK

    Google Scholar 

  5. Falandysz J(1998) Environmental Pollution 101:77

    Google Scholar 

  6. Baumann Ofstad E, Lunde G, Martinsen K, Rygg B (1978) Sci Total Environ 10:219

    Google Scholar 

  7. Theisen J, Maulshagen A, Fuchs J (1993) Chemosphere 26:881

    CAS  Google Scholar 

  8. Järnberg U, Asplund L, de Wit C, Grafström A-K, Haglund P, Jansson B, Lexén K, Strandell M, Olsson M, Jonsson B (1993) Environ Sci Technol 27:1364

    Google Scholar 

  9. Lutz G, Otto W, Schönberger H (1991) Chlorchemie und Dioxine/Furane — Hand in Hand von Anfang an Chloralkalielektrolyse — Ursache für hochgradig PDCF-belastete Rück-stände und damit Altlasten. Report, Regierungspräsidium Freiburg, Abt Wasserwirtschaft; Freiburg, Germany

    Google Scholar 

  10. Hanberg A, Waern F, Asplund L, Haglund E, Safe S (1990) Chemosphere 20:1161

    CAS  Google Scholar 

  11. Engwall M, Brunström B, Jakobssson E (1994) Arch Toxicol 68:37

    CAS  Google Scholar 

  12. Blankenship A, Kannan K, Villalobos S, Villeneuve D, Falandysz J, Imagawa T, Jakobsson E, Giesy J (1999) Relative potencies of Halowax mixtures and individual polychlorinated naphthalenes (PCNs) to induce Ah reseptor-mediated responses in rat hepatoma H4IIELuc cell bioassay Environ Sci Technol (in press)

    Google Scholar 

  13. Asplund L, Jansson B, Sundström G, Brandt I, Brinkman UATh (1986) Chemosphere 15:619

    CAS  Google Scholar 

  14. Asplund L, Jakobsson E, Haglund P, Bergman Ã… (1994) Chemosphere 28:2075

    CAS  Google Scholar 

  15. Ishaq R, Karlsson K, Näf C (1999) Tissue distribution of polychlorinated naphthalenes (PCNs) and non-ortho chlorinated biphenyls (non-ortho PCBs) in harbor porpoises (Phocoena phocoena) from Swedish waters (manuscript

    Google Scholar 

  16. Weistrand C, Norén K (1998) J Toxicol Environ Health Part A 53:293

    CAS  Google Scholar 

  17. Oishi H, Oishi S (1983) Toxicol Lett 15:119

    CAS  Google Scholar 

  18. Ruzo L, Jones D, Safe S, Hutzinger O (1976) J Agric Food Chem 24:581

    CAS  Google Scholar 

  19. Cornish H, Block W (1958) J Biol Chem 231:583

    CAS  Google Scholar 

  20. Chu I, Secours V, Villeneuve DC, Viau A (1977) Bull Environm Contam Toxicol 18:177

    CAS  Google Scholar 

  21. Ruzo LO, Safe S, Jones D, Platonow N (1976) Bull Environ Contam Toxicol 16:233

    CAS  Google Scholar 

  22. Ruzo LO, Safe S, Hutzinger O, Platonow N, Jones D (1975) Chemosphere 4:121

    CAS  Google Scholar 

  23. Chu I, Secours V, Viau A (1976) Chemosphere 5:439

    CAS  Google Scholar 

  24. Chu I, Villeneuve DC, Secours V, Viau A (1977) J Agric Food Chem 25:881

    CAS  Google Scholar 

  25. Jakobsson E(1994) Synthesis and Analysis of Chlorinated Naphthalenes Biological and Environmental Implications (Thesis) Dept of Environmental Chemistry, Stockholm University, Sweden

    Google Scholar 

  26. Klasson-Wehler E, Jakobsson E, Örn U (1996) Organohalogen Compounds 28:495

    CAS  Google Scholar 

  27. Kover FD (1975) Environmental hazard assessment report: Chlorinated naphthalenes EPA 560/8-75-001 Environmental Protection Agency Washington, DC, USA

    Google Scholar 

  28. Federal Register (1983) USEPA 48:20668

    Google Scholar 

  29. Kirk-Othmer (1980) In: Encyclopedia of Chemical Technology, 3rd edn. Wiley, New York, USA

    Google Scholar 

  30. Brinkman UATh and de Kok A (1980) In: Kimbrough (ed.) Halogenated biphenyls, terphenyls, naphthalenes, dibenzodioxins and related products. Elsevier/North-Holland Biomedical Press

    Google Scholar 

  31. Weistrand C, Lundén Å, Norén K (1992) Chemosphere 24:1197

    CAS  Google Scholar 

  32. Kauppinen T(1986) Ann Occup Hyg 30:19

    Google Scholar 

  33. Wiedmann T, Ballschmiter K (1993) Fresenius J Anal Chem 346:800

    CAS  Google Scholar 

  34. Varma PS, Parekh NB, Subramanium VK (1939) J Indian Chem Soc 16:460

    CAS  Google Scholar 

  35. Menschutkin (1912) Chem Zentralbl 83:1436

    Google Scholar 

  36. Silberman, Raschewsskaja, Martynzewa (1937) Chem Zentralbl 108:4786

    Google Scholar 

  37. Wibaut, Bloem (1950) Recl Trav Chim Pays-Bas 69:586

    CAS  Google Scholar 

  38. Dow Chem Co (1930) US 1917822

    Google Scholar 

  39. Parts (1930) Z Phys Chem (Leipzig) 10:264

    CAS  Google Scholar 

  40. Khanna MS, Khetarpal SC Lal K, Bharnagar HL (1981) Indian J Chem Sect A 20:544

    Google Scholar 

  41. Wahl H, Bassilios H (1974) Bull Soc Chim Fr 482

    Google Scholar 

  42. Rymarenko (1876) Chem Ber 9:666

    Google Scholar 

  43. Jefremow (1923) Chem Zentralbl 94:380

    Google Scholar 

  44. Roux (1887) Ann Chim (Paris) 12:349

    Google Scholar 

  45. Gockel (1935) Z Phys Chem (Leipzig) 29:79

    Google Scholar 

  46. Hampson, Weissberger (1936) J Chem Soc 393

    Google Scholar 

  47. Heumann, Koechlin (1883) Chem Ber 16:1627

    Google Scholar 

  48. Liebermann, Palm (1876) Justus Liebigs Ann Chem 183:270

    Google Scholar 

  49. Nefedow et al. (1960) Chem Abstr 24567

    Google Scholar 

  50. Soloveichik et al. (1976) J Org Chem USSR (Engl. Transl) 12:2136

    Google Scholar 

  51. Blum (1966) Tetrahedron Lett 3041

    Google Scholar 

  52. van Miltenburg JC, Verdonk ML (1991) J Chem Thermodynamics 23:273

    Google Scholar 

  53. Schein, Ignatow (1966) J Org Chem USSR (Engl. Transl) 2:706

    Google Scholar 

  54. Masterton et al. (1971) J Chem Thermodynamics 3:243

    CAS  Google Scholar 

  55. Nguyen-Ba-Chanh (1970) J Chim Phys Phys Chim Biol 67:1198

    CAS  Google Scholar 

  56. Makosza M, Gajos I (1974) Rocz Chem 48:1883

    CAS  Google Scholar 

  57. Kozlov et al. (1963) J Gen Chem USSR (Engl. Transl.) 33:658

    Google Scholar 

  58. Armstrong HE, Wynne WP (1896) Chem News J Ind Sci 73:55

    Google Scholar 

  59. Cleve (1887) Chem Ber 20:1991

    Google Scholar 

  60. Weissberger, Saengewald, Hampson (1934) Trans Faraday Soc 30:884

    CAS  Google Scholar 

  61. Clemo, Cockburn, Spence (1931) J Chem Soc 1265

    Google Scholar 

  62. Trotter (1964) Acta Crystallogr 17:63

    CAS  Google Scholar 

  63. Baeckstroem (1887) Chem Ber 20:1991

    Google Scholar 

  64. Wilson, Zehr (1978) J Org Chem 43:1768

    CAS  Google Scholar 

  65. de la Mare et al. (1966) J Chem Soc B 834

    Google Scholar 

  66. Cleve (1878) Bull Soc Chim Fr 29:415

    Google Scholar 

  67. Sundström G(1976) Chemosphere 5:191

    Google Scholar 

  68. Koptyug VA et al. (1966) J Org Chem USSR (Engl. Transl) 2:467

    Google Scholar 

  69. Freidlina et al. (1977) Dokl Chem (Engl. Transl) 236:563

    Google Scholar 

  70. Beattie, Whitmore (1933) J Amer Chem Soc 55:1546

    CAS  Google Scholar 

  71. Meyer H(1915) Monatsh Chem 36:728

    Google Scholar 

  72. Erdmann (1888) Justus Liebigs Ann Chem 247:351

    Google Scholar 

  73. Turner EG, Wynne WP (1941) J Chem Soc 243

    Google Scholar 

  74. von Auwers, Freuling (1921) Justus Liebigs Ann Chem 422:195

    Google Scholar 

  75. Farbenind IG(1929) Patent US 1822982

    Google Scholar 

  76. Farbenind IG(1928) Fortschr Teerfarbenfabr Verw Industriezweige 17:670

    Google Scholar 

  77. Doyle MP et al. (1977) J Org Chem 42:2426

    CAS  Google Scholar 

  78. Suzuki et al. (1965) Chem Abstr 63:4422f

    Google Scholar 

  79. de la Mare PBD, Suzuki H (1967) J Chem Soc C 1586

    Google Scholar 

  80. Ferrero P, Bolliger G (1928) Helv Chim Acta 11:1144

    CAS  Google Scholar 

  81. Krollpfeiffer (1923) Justus Liebig Ann Chem 430:198

    Google Scholar 

  82. Woroshzow, Lisizyn (1960) J Gen Chem USSR 30:2794

    Google Scholar 

  83. Frater, Havinga (1970) Recl Trav Chim Pays-Bas 89:273

    CAS  Google Scholar 

  84. de la Mare PBD, Suzuki H (1968) J Chem Soc C 1159

    Google Scholar 

  85. Armstrong HE (1888) Chem News 58:295

    Google Scholar 

  86. Forsling (1887) Chem Ber 20:2105

    Google Scholar 

  87. Armstrong HE, Wynne WP (1890) Chem News J Ind Sci 62:164

    Google Scholar 

  88. Schroeter (1930) Chem ber 63:1308

    Google Scholar 

  89. Friedlaender, Kielbasinski (1896) Chem Ber 29:1981

    Google Scholar 

  90. Armstrong HE, Wynne WP (1895) Chem News J Ind Sci 71:253

    Google Scholar 

  91. Claus, Volz (1885) Chem Ber 18:3157

    Google Scholar 

  92. Arnell (1886) Bull Soc Chim Fr 45:184

    Google Scholar 

  93. Erdmann (1893) Justus Liebigs Ann Chem 275:257

    Google Scholar 

  94. Armstrong HE, Wynne WP (1889) Chem News J Ind Sci 59:188

    Google Scholar 

  95. Komagorov AM et al. (1967) J Org Chem 3:147

    Google Scholar 

  96. Cleve (1893) Chem-Ztg Chem Appar 17:398

    Google Scholar 

  97. Atterberg A(1876) Chem Ber 9:1732

    Google Scholar 

  98. Rees CW, Storr RC (1969) J Chem Soc C 760

    Google Scholar 

  99. Armstrong HE, Wynne WP (1890)Chem News J Ind Sci 61:273

    Google Scholar 

  100. Leeds, Everhart (1880) J Amer Chem Soc 2:211

    Google Scholar 

  101. Wege D, Wilkinson SP (1973) Aust J Chem 26:1751

    CAS  Google Scholar 

  102. Claus, Zimmermann (1881) Chem Ber 14:1483

    Google Scholar 

  103. Vesely, Jakes (1923) Bull Soc Chim Fr 33:948

    Google Scholar 

  104. Weissberger, Saengewald (1933) Z Phys Chem (Leipzig) 20:145

    Google Scholar 

  105. Fosling (1887) Chem Ber 20:81

    Google Scholar 

  106. Jacobs et al. (1946) J Org Chem 11:27

    CAS  Google Scholar 

  107. Franzen, Staeuble (1921) J Prakt Chem 103:354

    Google Scholar 

  108. Chozjanowa, Strutschkow (1964) J Struct Chem (Engl. Transl.) 5:375

    Google Scholar 

  109. Rosowsky A et al. (1969) J Chem Soc 1376

    Google Scholar 

  110. Bayer, Duisberg (1887) Chem Ber 20:1432

    Google Scholar 

  111. Dziewonski, Majawicz, Schimmer (1936) Bull Acad Pol Sci Ser Sci Chim A:43

    CAS  Google Scholar 

  112. Faust, Saame (1871) Justus Liebig Ann Chem 160:71

    Google Scholar 

  113. Cum Get al. (1967) J Chem Soc B 244

    Google Scholar 

  114. Burton, de la Mare (1970) J Chem Soc B 897

    Google Scholar 

  115. Cleve (1888) Chem Ber 21:893

    Google Scholar 

  116. Hellström (1889) Översikt Kgl Svenska Vetenskaps Akad Förhandl 116

    Google Scholar 

  117. Forsling (1888) Chem Ber 21:3498

    Google Scholar 

  118. Buffle, Corbaz (1932) Arch Sci Phys Nat 14:149

    CAS  Google Scholar 

  119. Atterberg A (1876) Chem Ber 9:317

    Google Scholar 

  120. Friedlaender, Karamessinis, Schenk (1922) Chem Ber 55:47

    Google Scholar 

  121. Kozlov VV, Korneeva NA (1976) J Org Chem USSR 12:1514

    Google Scholar 

  122. Armstrong HE, Wynne WP (1897) Chem News J Ind Sci 76:69

    Google Scholar 

  123. Alen (1884) Chem Ber 17:437

    Google Scholar 

  124. Armstrong HE, Wynne WP (1890) Chem News J Ind Sci 61:93

    Google Scholar 

  125. Kozlov VV et al. (1960) J Gen Chem USSR (Engl. Transl.) 30:2696

    Google Scholar 

  126. Woroshtzow, Koslov (1936) Chem Ber 69:412

    Google Scholar 

  127. Nikiforov V, Auger P, Wightman R, Malaiyandi M, Williams D (1992) Organohalogen Compounds 8:123

    Google Scholar 

  128. Wynne (1946) J Chem Soc 61

    Google Scholar 

  129. von Braun (1923) Chem Ber 56:2337

    Google Scholar 

  130. Danish et al. (1954) J Amer Chem Soc 76:6144

    CAS  Google Scholar 

  131. Hales NJ, Heaney H, Hollinshead, JH, Ley SV (1995) Tetrahedron 51:7755

    CAS  Google Scholar 

  132. Gribble GW et al. (1976) Tetrahedron Lett 3673

    Google Scholar 

  133. Duerr H, Scheppers G (1970) Justus Liebigs Ann Chem 734:141

    CAS  Google Scholar 

  134. Klemm LH, Stevens MP, Tran LK, Sheley J (1988) J Hetrocycl Chem 25:1111

    CAS  Google Scholar 

  135. Heaney H, Jablonski JM (1968) J Chem Soc 1895

    Google Scholar 

  136. Howard, Gilbert (1962) J Org Chem 27:2685

    CAS  Google Scholar 

  137. Roedig, Aet al. (1979) Chem Ber 112:2730

    CAS  Google Scholar 

  138. Martmeau, Dejongh (1977) Can J Chem 55:34

    Google Scholar 

  139. Nakayama J, Kuroda M, Hoshino M (1986) Heterocycles 24:1233

    CAS  Google Scholar 

  140. Moser GA et al. (1970/1971) Organomet Chem Synth 1:99

    Google Scholar 

  141. Vernon JM et al. (1978) J Soc Perkin Trans I 837

    Google Scholar 

  142. Wilt, Vasilianskes (1970) J Org Chem 35:2410

    CAS  Google Scholar 

  143. Ranken, Battiste (1971) J Org Chem 36:1996

    CAS  Google Scholar 

  144. Atterberg A, Widman O (1877) Chem Ber 10:1841

    Google Scholar 

  145. Burton et al. (1974) J Chem Soc Perkin Trans II 1914

    Google Scholar 

  146. Ward ER, Hardy A (1966) J Chem Soc C 1038

    Google Scholar 

  147. Cencelj L(1960) Chem Ber GR 93:988

    Google Scholar 

  148. Hardy A, Ward ER, Day LA (1956) J Chem Soc 1979

    Google Scholar 

  149. Piggott HA, Slinger FH (1952) J Chem Soc 259

    Google Scholar 

  150. Alen (1881) Bull Soc Chim Fr 36:435

    Google Scholar 

  151. Chatt J, Wynne WP (1943) J Chem Soc 33

    Google Scholar 

  152. Reimlinger H, King G (1962) Chem Ber 95:1043

    CAS  Google Scholar 

  153. Clar E, Marschalk C (1950) Bull Soc Chim Fr 433

    Google Scholar 

  154. Atterberg A, Widman O (1877) Bull Soc Chim Fr 28:513

    Google Scholar 

  155. Gafner G, Herbstein FH (1960) Acta Crystallogr 13:702

    CAS  Google Scholar 

  156. Gafner G, Herbstein FH (1962) Acta Crystallogr 15:1081

    CAS  Google Scholar 

  157. Bassilios HF et al. (1962) Recl Trav Chim Pays-Bas 81:209

    CAS  Google Scholar 

  158. Nikiforov VA, Karavan VS, Miltsov SA, Tribulovich VG (1993) Organohalogen Compounds 14:229

    Google Scholar 

  159. Amer Cyanamid (1970) US3636048

    Google Scholar 

  160. Amer Cyanamid Comp (1972) US 3636048 Chem Abstr 76:142391

    Google Scholar 

  161. Levy LA (1983) Synth Commun 13:639

    CAS  Google Scholar 

  162. Graebe (1869) Justus Liebigs Ann Chem 149:1

    Google Scholar 

  163. Claus A, van de Lippe (1883) Chem Ber 16:1016

    Google Scholar 

  164. Blangey et al. (1951) Helv Chim Acta 34:501

    CAS  Google Scholar 

  165. Auger P, Malaiyandi M, Wightman RH, Bensimon C, Williams DT (1993) Environ Sci Technol 27:1673

    CAS  Google Scholar 

  166. Jakobsson E, Eriksson L, Bergman Ã… (1992) Acta Chem Scand 46:527

    CAS  Google Scholar 

  167. Klingsberg E (1972) Tetrahedron 28:963

    CAS  Google Scholar 

  168. Klingsberg E (1973) US Patent 3769279

    Google Scholar 

  169. Jakobsson E, Lönnberg C, Eriksson L (1994) Acta Chem Scand 48:891

    CAS  Google Scholar 

  170. Clark J, Maynard R, Wakefield BJ (1976) J Chem Soc Perkin trans II 73

    Google Scholar 

  171. Garcia R, Riera J, Carilla J, Julia L, Molins E, Miravitlles C (1992) 57:5712

    Google Scholar 

  172. Brady JH, Tahir N, Wakefield BJ (1984) J Chem Soc Perkin Trans I 2425

    Google Scholar 

  173. Claus, Wenzlik (1886) Chem Ber 19:1165

    Google Scholar 

  174. Consortium für Elektrochemische Industrie GmbH (1970) Chem Abstr 72:100490q

    Google Scholar 

  175. Tahir NA (1975) M Sc Thesis Univ Salford

    Google Scholar 

  176. Schwemberger, Gordon (1932) Zh Obshch Khim 2:924

    Google Scholar 

  177. Ruoff (1876) Chem Ber 9:1486

    Google Scholar 

  178. Deacon GB, Farquharson GJ (1977) Aust J Chem 30:1701

    CAS  Google Scholar 

  179. Epshtein et al. (1977) SU 2338962

    Google Scholar 

  180. Farbenfabr Bayer AG (1953) US 2734927 Chem Abstr 1956:10782

    Google Scholar 

  181. Farrar, Storms (1968) J Chem Eng Data 13:284

    CAS  Google Scholar 

  182. Ginsberger et al. (1962) Tetrahedron Lett 779

    Google Scholar 

  183. Cruickshank DWJ, Sparks RA (1960) Proc Roy Soc A 258:270

    CAS  Google Scholar 

  184. Gafner G, Herbstein FH (1963) Nature 200:130

    CAS  Google Scholar 

  185. Herbstein FH (1979) Acta Cryst B35:1661

    CAS  Google Scholar 

  186. Opperhuizen A (1987) Toxicol Environ Chem 15:249

    CAS  Google Scholar 

  187. Isnard P and Lambert S (1988) Chemosphere 17:21

    CAS  Google Scholar 

  188. Järnberg U (1997) Analytical methods for studying polychlorinated naphtalene congener profiles and levels in the environment. Thesis Stockholm University, Sweden

    Google Scholar 

  189. Marsh J (1985) Advanced organic chemistry John Wiley & Sons, New York

    Google Scholar 

  190. Clar E, Zander M (1958) J Chem Soc 1861

    Google Scholar 

  191. Wehland G (1942) J Am Chem Soc 64:900

    Google Scholar 

  192. Campbell N (1978) In: Coffey S (ed) Rodd’s Chemistry of Carbon Compounds, vol III part G. Elsevier, Amsterdam, p 99

    Google Scholar 

  193. Järnberg U, Asplund L, Jakobsson E (1994) J Chromatogr A 683:385

    Google Scholar 

  194. Jakobsson E, Asplund L, Haglund P, Bergman Ã… (1990) Organohalogen compounds 4:187

    CAS  Google Scholar 

  195. Nikiforov VA, Karavan VS, Miltsov SA, Tribulovich VG (1998) Organohalogen Compounds 35:159

    CAS  Google Scholar 

  196. Auger P, Malaiyandi M, Wightman RH (1993) J Labelled Comp Radiopharmaceut 33:263

    CAS  Google Scholar 

  197. de Kok A, Geerdink RB, Brinkman UATh (1983) Anal Chem Symp Ser (Chromatogr Biochem Med Environ Res) 13:203

    Google Scholar 

  198. Stojkovski S, Markovec LM, Magee RJ (1991) J Chem Technol Biotechnol 51:407

    CAS  Google Scholar 

  199. Hutzinger O, Safe S, Zitko V (1972) J Environ Anal Chem 2:95

    CAS  Google Scholar 

  200. Brinkman UATh, de Vries G, de Kok A, de Jonge AL (1978) J Chromatogr 152:97

    CAS  Google Scholar 

  201. Jensen S, Reutergårdh L, Jansson B (1983) FAO Fish Tech Pap 212:21

    Google Scholar 

  202. Bligh EG, Dyer WJ (1959) Can J Biochem Physiol 37:911

    CAS  Google Scholar 

  203. Järnberg U, Asplund L, de Wit C, Egebäck A-L, Wideqvist U, Jakobsson E (1997) Arch Environ Contam Toxicol 32:232

    Google Scholar 

  204. Stalling DL, Smith LM, Petty JD (1979) Approaches to comprehensive analyses of persistent halogenated environmental contaminants. In: van Hall CE (ed) Measurement of organic pollutants in water and wastewater ASTM STP 686. American Society for Testing and Materials

    Google Scholar 

  205. Jensen S, Sundström G (1974) Ambio 3:69

    Google Scholar 

  206. Kuehl DW, Dougherty RC, Tondeur Y, Stalling DL, Smith LM, Rappe C (1980) Negative chemical ionization studies of polychlorinated dibenzo-p-dioxins, dibenzofurans and naphthalenes in environmental samples. In: McKinney JD (ed) Environmental Health Chemistry — The Chemistry of Environmental Agents as Potential Human Hazards. Ann Arbor Science Publishers, Ann Arbor, MI

    Google Scholar 

  207. Jansson B, Andersson R, Asplund L, Bergman Å, Litzén K, Nylund K, Reutergårdh L, Sellström U, Uvemo U-B, Wahlberg C, Widequist U (1991) Fresenius J Anal Chem 340:439

    CAS  Google Scholar 

  208. Falconer R, Bidleman T, Cotham W (1995) Envirin Sci Technol 29:1666

    CAS  Google Scholar 

  209. Harner T, Bidleman T (1997) Atmospheric Environmenent 31:4009

    CAS  Google Scholar 

  210. Lundgren K, Bergqvist PA, Haglund P, Rappe C (1992) Organohalogen Compounds 10:103

    Google Scholar 

  211. Falandysz J, Strandberg L, Bergqvist P-A, Kulp SE, Strandberg B, Rappe C (1996) Environ Sci Technol 30:3266

    CAS  Google Scholar 

  212. Haglund P, Asplund L, Järnberg U, Jansson B (1990) J Chromatogr 507:389

    CAS  Google Scholar 

  213. Williams DT, Kennedy B, LeBel GL (1993) Chemosphere 27:795

    CAS  Google Scholar 

  214. Kimata K, Hosoya K, Kuroki H, Tanaka N, Barr JR, McClure PC, Patterson D G, Jakobsson E, Bergman Ã… (1997) J Chromatogr A 786:237

    CAS  Google Scholar 

  215. Imagawa T, Yamashita N (1997) Chemosphere 35:1195

    CAS  Google Scholar 

  216. Asplund L (1994) Development and application of methods for determination of polychlorinated organic pollutants in biota. (Thesis) Dept of Environmental Chemistry, Stockholm University, Stockholm, Sweden

    Google Scholar 

  217. Falandysz J, Rappe C (1996) Environ Sci Technol 30:3362

    CAS  Google Scholar 

  218. Fitch WL, Sauter AD (1983) Anal Chem 55:832

    CAS  Google Scholar 

  219. Vos JG, Koeman JH, van der Maas HL, ten Noever de Brauw MC, de Vos RH (1970) Fd Cosmet Toxicol 8:625

    CAS  Google Scholar 

  220. Albro PW and Parker CE (1979) J Chromatogr 169:161

    CAS  Google Scholar 

  221. Vogelgesang J (1986) Z Wasser-Abwasser-Forsch 19:140

    CAS  Google Scholar 

  222. Kannan K, Imagawa T, Blankenship A, Giesy J (1998) Environ Sci Technol 32:2507

    CAS  Google Scholar 

  223. Tong HY, Shoree DL, Karasek FW, Helland P, Jellum E (1984) J Chromatogr 285:423

    CAS  Google Scholar 

  224. Oehme M, Manø S, Mikalsen A (1987) Chemosphere 16:143

    CAS  Google Scholar 

  225. Alarie Y, Iwasaki M, Stock MF, Pearson RC, Shane BS, Lisk DJ (1989) J Toxicol Environ Health 28:13

    CAS  Google Scholar 

  226. Imagawa T, Yamashita N, Miyazki A (1993) J Environ Chem 3:221

    CAS  Google Scholar 

  227. Imagawa T, Yamashita N (1994) Organohalogen Compounds 19:215

    CAS  Google Scholar 

  228. Schneider M, Stieglitz R, Will R, Zwick G (1998) Chemosphere 37:2055

    CAS  Google Scholar 

  229. VanDell RD, Shadoff LA (1984) Chemospere 13:1177

    CAS  Google Scholar 

  230. Ballschmiter K, Kirschmer P, Zoller W (1986) Chemosphere 15:1369

    CAS  Google Scholar 

  231. VanDell RD, Boggs GU (1987) Chemosphere 16:973

    CAS  Google Scholar 

  232. Yasuhara A, Morita M (1988) Environ Sci Technol 22:646

    CAS  Google Scholar 

  233. Crump-Wiesner HJ, Feltz HR, Yates ML (1973) J Research US Geol Survey 1:603

    CAS  Google Scholar 

  234. Erickson MD, Michael LC, Zweidinger RA, Pellizzari ED (1978) J Assoc Off Anal Chem 61:1335

    CAS  Google Scholar 

  235. Furlong ET, Carter DS, Hites RA (1988) J Great Lakes Res 14:489

    Google Scholar 

  236. Dörr G, Hippelein M, Hutzinger O (1996) Chemosphere 33:1563

    Google Scholar 

  237. Harner T, Kylin H, Bidleman T, Halsall C, Strachan W, Barrie L, Fellin P (1997) Environ Sci Technol 32:3257

    Google Scholar 

  238. Falandysz J, Strandberg L, Kulp SE, Strandberg B, Bergqvist P-A, Rappe C (1996) Chemoshere 33:51

    CAS  Google Scholar 

  239. Falandysz J, Rappe C (1997) Chemosphere 35:1737

    CAS  Google Scholar 

  240. Falandysz J, Strandberg L, Bergqvist P-A, Strandberg B, Rappe C (1997) The Science of the total Environment. 203:93

    CAS  Google Scholar 

  241. Falandysz J, Strandberg B, Strandberg L, Bergqvist P-A, Rappe C (1997) The Science of the Total Environment 204:77

    Google Scholar 

  242. Falandysz J, Strandberg L, Strandberg B, Rappe C (1998) Chemosphere 37:2473

    CAS  Google Scholar 

  243. Paasivirta J, Rantio T (1991) Chemosphere 22:47

    CAS  Google Scholar 

  244. Asplund L, Svensson G, Nilsson A, Eriksson U, Jansson B, Jensen S, Wideqvist U, Skerfving S (1994) Arch Environ Health 49:477

    CAS  Google Scholar 

  245. Lundén Å (1996) Licentiate Thesis Karolinska Institutet Sweden

    Google Scholar 

  246. Haglund P, Jakobsson E, Masuda Y (1995) Organohalogen Compounds 26:405

    CAS  Google Scholar 

  247. Burreau S, Axelman J, Broman D, Jakobsson E (1997) Environm Toxicol Chem 16:2508

    CAS  Google Scholar 

  248. Oppenhuizen A, van der Velde EW, Gobas RAPC, Liem DAK, van der Steen JM, Hutzinger O (1985) Chemosphere 14:1871

    Google Scholar 

  249. Ahotupa M, Aitio A (1980) Biochemical Biophysical Research Communications 93:250

    CAS  Google Scholar 

  250. Ahotupa M, Hietanen E, Mäntylä E (1982) J Appl Toxicol 247:53

    Google Scholar 

  251. Mäntylä E, Aitio A, Ahutopa M (1983) Effect of polychlorinated naphtalenes and biphenyls on polysubstrate monooxygenase and UDP-glucuronosyltransferase activities in the rat lung. In: Rydström J et al. (eds) Elsevier, Amsterdam, p 223

    Google Scholar 

  252. Cockerline R, Shilling M, Safe S (1981) Gen Pharmac 12:83

    CAS  Google Scholar 

  253. Safe S (1990) CRC Crit Rev Toxicol 21:51

    CAS  Google Scholar 

  254. Hankinson O (1995) Annu Rev Pharmacol Toxicol 35:307

    CAS  Google Scholar 

  255. Ahlborg UG, Hanberg A (1992) Toxic Substances Journal 12:197

    CAS  Google Scholar 

  256. Hanberg A, Ståhlberg M, Gergellis A, de Wit C, Ahlborg UG Pharmacol Toxicol 69:442

    Google Scholar 

  257. Ahlborg UG, Håkansson H, Lindström G, Rappe C (1990) Chemosphere 20:1235

    CAS  Google Scholar 

  258. Bakke JE, Struble C, Gustafsson J-Ã…, Gustafsson B (1985) Proc Natl Acad Sci USA 82:668

    CAS  Google Scholar 

  259. Horning MG, Stillwell WG, Griffin GW, Tsang W-S (1980) Drug Metab and Dispos 8:404

    CAS  Google Scholar 

  260. Reggiani G, (1982) In: Hutzinger et al. (eds) Chlorinated dioxins and related compounds. Impact on the environment, Pergamon Press, Oxford 463

    Google Scholar 

  261. Olson C (1969) Bovine hyperkeratosis (X-disease, highly chlorinated naphthalene poisoning). Historical Review. In: Brandly CA, Cornelius OE (eds) Advances in Veterinary Sciences and Comparative Medicine. Academic Press, New York 13:101

    Google Scholar 

  262. Pudelkiewicz WJ, Boucher RV, Callenbach EW, Miller RC (1959) Poultry Sci 38:424

    CAS  Google Scholar 

  263. Drinker CK, Field Warren M, Bennett GA (1937) J Ind Hyg Toxicol 19:283

    CAS  Google Scholar 

  264. Kleinfeld M, Messite J, Swencicki R (1972) J Occupational Med 14:377

    CAS  Google Scholar 

  265. Greenburg L, Mayers MR, Smith AR (1939) J Ind Hyg Toxicol 21:29

    CAS  Google Scholar 

  266. Shelley W, Kligman A (1957) AMA Archives of dermatology 75:689

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2000 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Jakobsson, E., Asplund, L. (2000). Polychlorinated Naphthalenes (PCNs). In: Hutzinger, O., Paasivirta, J. (eds) Volume 3 Anthropogenic Compounds Part K. The Handbook of Environmental Chemistry, vol 3K. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-48915-0_5

Download citation

  • DOI: https://doi.org/10.1007/3-540-48915-0_5

  • Published:

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-65838-2

  • Online ISBN: 978-3-540-48915-3

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics