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Phenols

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Part of the book series: Springer Series on Environmental Management ((SSEM))

Abstract

Phenols are a diverse group of organic chemicals consisting of a basic benzene ring and one or more hydroxyl groups. Simple phenol (hydroxybenzene, C6H5OH) was isolated in 1834 from coal tar. Although this was the only source of phenol until World War I, synthetic production gradually grew in importance and, by 1930, exceeded natural production. Today almost all phenol is manufactured by sulfonation of benzene and hydrolysis of the sulfonate. The more complex phenols are obtained by replacing one or more of the hydrogen atoms attached to the benzene ring with various atoms (such as chlorine) or more complex substituents (such as methyl or nitro molecules).

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References

  • Ademan, D.M.M., and I.G.J. Vink. 1981. A comparative study of the toxicity of 1,1,2-trichloroethane, dieldrin, pentachlorophenol and 3,4 dichloroaniline for marine and fresh water organisms. Chemosphere 10:533–554.

    Article  Google Scholar 

  • Ahlborg, U.G. 1977. Metabolism of chlorophenols: studies on dechlorination in mammals. Swedish Environment Protection Board PM 895, Stockholm.

    Google Scholar 

  • Aly, O.M., and S.D. Faust. 1966. Studies on the fate of 2,4-D and ester derivatives in natural surface waters. Journal of Agricultural Food Chemistry 12:541–546.

    Article  Google Scholar 

  • Arsenault, R.D. 1976. Pentachlorophenol and contained chlorinated dibenzodioxins in the environment: a study of environmental fate, stability, and significance when used in wood preservation. Presented at the American Wood-Preservers’ Association Annual Meeting, Atlanta, Georgia, April 25–28. pp. 122–148.

    Google Scholar 

  • Bevenue, A., J.N. Ogata, and J.W. Hylin. 1972. Organochlorine pesticides in rainwater, Oahu, Hawaii, 1971–1972. Bulletin of Environmental Contamination and Toxicology 8:238–241.

    Article  PubMed  CAS  Google Scholar 

  • Buccasfusco, R.J., S.J. Ells, and G.A. LeBlanc. 1981. Acute toxicity of priority pollutants to bluegill (Lepomis marcochirus). Bulletin of Environmental Contamination and Toxicology 26:446–452.

    Article  Google Scholar 

  • Buikema, Jr., A.L., M.J. McGuinniss, and J. Cairns. 1979. Phenolics in aquatic ecosystems: a selected review of recent literature. Marine Environmental Research 2:87–181.

    Article  CAS  Google Scholar 

  • Chang, C.W., and J.U. Anderson. 1968. Flocculation of clays and soils by organic compounds. Soil Science Society of America Proceedings 32:23–27.

    Article  CAS  Google Scholar 

  • Choi, J., and S. Aomine. 1974a. Adsorption of pentachlorophenol by soils. Soil Science and Plant Nutrition 20:135–144.

    CAS  Google Scholar 

  • Choi, J., and S. Aomine. 1974b. Mechanisms of pentachlorophenol adsorption by soils. Soil Science and Plant Nutrition 20:371–379.

    CAS  Google Scholar 

  • Dalela, R.C., S. Rani, and S.R. Verma. 1980. Influence of pH on the toxicity of phenol and its two derivatives pentachlorophenol and dinitrophenol to some fresh water teleosts. Acta Hydrochimica et Hydrobiologia 8:623–629.

    CAS  Google Scholar 

  • Dence, C., C.J. Wang, and P. Durkin. 1980. Toxicity reduction through chemical and biological modification of spent pulp bleaching liquors. U.S. Environmental Protection Agency, Publication No. EPA-600/2-80-039 Cincinnati, Ohio.

    Google Scholar 

  • Eder, G., and K. Weber. 1980. Chlorinated phenols in sediments and suspended matter of the Weser estuary. Chemosphere 9:111–118.

    Article  CAS  Google Scholar 

  • Gunther, R., W.G. Filby, and K. Eiben. 1971. Hydroxylation of substituted phenols: an ESR study in the Ti3 +/H2O2 system. Teterahedron Lett. 251–254.

    Google Scholar 

  • Hague, A., I. Schenunert, and F. Korte. 1978. Isolation and identification of a metabolite of pentachlorophenol -14C in rice plants. Chemosphere 7:65.

    Article  Google Scholar 

  • Hakuta, T. 1975. Vapor-liquid equilibriums of pollutants in sea water. II. Vapor-liquid equilibriums of phenolic substance water systems. Nippon Kaisui Gakkai-Shi 28:379–385.

    CAS  Google Scholar 

  • Huber, W., V. Schubert, and C. Sautter. 1982. Effects of pentachlorophenol on the metabolism of the aquatic macrophyte Lemna minor L. Environmental Pollution (Series A) 29:215–223.

    Article  CAS  Google Scholar 

  • Jolley, R.L., G. Jones, W.W. Pitt, and J.W. Thompson. 1978. Chlorination of organics in cooling waters and process effluents. In: R.L. Jolley (Ed.), Water chlorination: environmental impact and health effects. Vol. I. Ann Arbor Science Publishers, Ann Arbor, Michigan, pp. 105–138.

    Google Scholar 

  • Jones, P.A. 1981. Chlorophenols and their impurities in the Canadian environment. Environmental Protection Service, Department of the Environment, Ottawa, Canada, Catalogue No. En46-3/81-2, 434 pp.

    Google Scholar 

  • Joschek, H.I., and S.T. Miller. 1966. Photooxidation of phenol, cresols, and dihydroxybenzenes. Journal of the American Chemical Society 88:3273–3281.

    Article  PubMed  CAS  Google Scholar 

  • Jungclaus, G.A., V. Lopez-Avila, and R.A. Hites. 1978. Organic compounds in an industrial wastewater: a case study of their environmental impact. Environmental Science and Technology 12:88–96.

    Article  CAS  Google Scholar 

  • Kaufman, D.D. 1976. Phenols. In: P.C. Kearney and D.D. Kaufman (Eds.), Herbicides: chemistry, degradation and mode of action. Vol. 2, Marcel Dekker, New York, pp. 665–707.

    Google Scholar 

  • Kaufman, D.D. 1978. Degradation of pentachlorophenol in soil and by soil microorganisms. In: K.R. Rao (Ed.), Pentachlorophenol. Environmental Science Research Series, Vol. 12. Plenum Press, New York, pp. 29–39.

    Google Scholar 

  • Kobayashi, K. 1978. Metabolism of pentachlorophenol in fishes. In: K.R. Rao (Ed.), Pentachlorophenol. Environmental Science Research Series, Vol. 12. Plenum Press, New York, pp. 89–105.

    Google Scholar 

  • Kobayashi, K., and H. Akitake. 1975. Studies on the metabolism of chlorophenols in fish. I. Absorption and excretion of PCP by goldfish. Bulletin of the Japanese Society of Scientific Fisheries 41:87–92.

    Article  CAS  Google Scholar 

  • Kobayshi, K., and T. Kishino. 1980. Effect of pH on the toxicity and accumulation of pentachlorophenol in goldfish. Bulletin of the Japanese Society of Scientific Fisheries 46:167–170.

    Article  Google Scholar 

  • Kuehl, D.W. 1981. Unusual polyhalogenated chemical residues identified in fish tissue from the environment. Chemosphere 10:231–242.

    Article  CAS  Google Scholar 

  • Laity, J.L., I.G. Burstain, and B.R. Appel. 1973. Photochemical smog and the atmospheric reactions of solvents. In: RW. Tess (Ed.), Solvents theory and practice. Advances in Chemistry Series 124, American Chemical Society, Washington, D.C., pp. 95–112.

    Chapter  Google Scholar 

  • LeBlanc, G.A. 1980. Acute toxicity of priority pollutants to water flea (Daphnia magna). Bulletin of Environmental Contamination and Toxicology 24:684–691.

    Article  PubMed  CAS  Google Scholar 

  • Lopez-Avila, V., and R.A. Hites. 1980. Organic compounds in an industrial wastewater. Their transport into sediments. Environmental Science and Technology 14:1382–1390.

    Article  CAS  Google Scholar 

  • McLeese, D.W., V. Zitko, D.B. Sergeant, L. Burridge, and C.D. Metcalfe. 1981. Lethality and accumulation of alkylphenols in aquatic fauna. Chemosphere 10:723–730.

    Article  CAS  Google Scholar 

  • Nagel, R., and K. Urich. 1981. Elimination and distribution of different substituted phenols by frog (Rana temporaria) and crayfish (Astacus leptodactylus). Bulletin of Environmental Contamination and Toxicology 26:289–294.

    Article  PubMed  CAS  Google Scholar 

  • Paasivirta, J., J. Sarkka, T. Leskijarvi, and A. Roos. 1980. Transportation and enrichment of chlorinated phenolic compounds in different aquatic food chains. Chemosphere 9:441–456.

    Article  CAS  Google Scholar 

  • Pierce, Jr., R.H. 1978. Fate and impact of pentachlorophenol in a freshwater ecosystem. United States Environmental Protection Agency Report, Publication No. EPA-600/3-78-063, Athens, Georgia, 61 pp.

    Google Scholar 

  • Pierce, Jr., R.H., C.R. Brent, H.P. Williams, and S.G. Reeves. 1977. Pentachlorophenol distribution in a freshwater ecosystem. Bulletin of Environmental Contamination and Toxicology 18:251–258.

    Article  PubMed  CAS  Google Scholar 

  • Piet, G.J., and F. De Grunt. 1975. Organic chloro compounds in surface and drinking water of the Netherlands. European Colloquium, Eur. 5196, Luxembourg 1974. Commission of the European Communities, Luxembourg, pp. 81–92.

    Google Scholar 

  • Ramamoorthy, S., and G.G. Leppard. 1977. Fibrillar pectin and contact cation exchange at the root surface. Journal of Theoretical Biology 66:527–540.

    Article  PubMed  CAS  Google Scholar 

  • Reed, H.W.B. 1980. Alkyl phenols. In: Encyclopedia of chemical terminology. Vol. 2. Wiley, Toronto, pp. 72–96.

    Google Scholar 

  • Reiner, E.A, J. Chu, and E.J. Kirsch. 1978. Microbial metabolism of pentachlorophenol. In: K.R Rao (Ed.), Pentachlorophenol. Environmental Science Research Series, Vol. 12. Plenum Press, New York, pp. 67–81.

    Google Scholar 

  • Saltzman, S., and S. Yariv. 1975. Infrared study of the sorption of phenol and p-nitrophenol by montmorillonite. Soil Science Society of America Proceedings 39:474–479.

    Article  CAS  Google Scholar 

  • Schimmel, S.C., J.M. Patrick Jr., and L.F. Faas. 1978. Effects of sodium pentachlorophenate on several estuarine animals: toxicity, uptake, and depuration. Environmental Science Research 11:147–156.

    Google Scholar 

  • Sheldon, L.S., and R.A. Hites. 1978. Organic compounds in the Delaware River. Environmental Science and Technology 12:1188–1194.

    Article  CAS  Google Scholar 

  • Sittig, M. 1980. Priority toxic pollutants. Health impacts and allowable limits. Noyes Data Corporation, New Jersey, 370 pp.

    Google Scholar 

  • Statistics Canada. 1981. Manufacturers of industrial chemicals. Manufacturing and Primary Industries Division, Catalogue 46–219, Ministry of Supply and Services, Ottawa, Canada.

    Google Scholar 

  • Stom, D.J. et al. 1980. Methods of analyzing quinones in water and their application in studying the effects of hydrophytes on phenols. Part 5. Elimination of carcinogenic amines from solutions under the action of Nitella. Acta Hydrochimica et Hydrobiologica 8:241–245.

    CAS  Google Scholar 

  • Thurman, C. 1982. Phenols. In: Encyclopedia of chemical terminology. Vol. 7. Wiley, Toronto, pp. 373–384.

    Google Scholar 

  • U.S. Environmental Protection Agency. 1980. Ambient water quality criteria reports. Office of Water Regulations and Standards, Washington, D.C.

    Google Scholar 

  • U.S. International Trade Commission. 1975–1982. Synthetic organic chemicals, U.S. production and sales. U.S. Government Printing Office, Washington, D.C.

    Google Scholar 

  • Veith, G.D., D.W. Kuehel, E.N. Leonard, F.A. Puglisi, and A.E. Lemke. 1979. Polychlorinated biphenyls and other organic chemical residues in fish from major watersheds of the United States. 1976. Pesticides Monitoring Journal 13:1–11.

    PubMed  CAS  Google Scholar 

  • Versar. 1979. Water-related environmental fate of 129 priority pollutants. Vol. II. U.S. Environmental Protection Agency, Publication No. EPA-440/4-79-029b, Washington, D.C.

    Google Scholar 

  • Virtanen, M.T., and M.L. Hattula. 1982. The fate of 2,4,6-trichlorophenol in an aquatic continuous-flow system. Chemosphere 11:641–649.

    Article  CAS  Google Scholar 

  • Waggott, A., and A.B. Wheatland. 1978. Contribution of different sources to contamination of surface waters with specific persistent organic pollutants. In: O. Hutzinger, L.H. van Lelyveld, and B.C.J. Zoeteman (Eds.), Aquatic pollutants: transformation and biological effects. Proceedings of the Second International Symposium on Aquatic Pollutants, Amsterdam, The Netherlands, September 26–28, 1977, pp. 141–168.

    Google Scholar 

  • Webb, P.W., and J.R. Brett. 1973. Effects of sublethal concentrations of sodium pentachlorophenate on growth rate, food conversion efficiency, and swimming performance in underyearling sockeye salmon (Oncorhynchus nerka). Journal of the Fisheries Research Board of Canada 30:499–507.

    Article  CAS  Google Scholar 

  • Webb, R.G., et al. 1973. Current practice in GC/MS analysis of organics in water. Environmental Protection Technology Series EPA R2-73-277.

    Google Scholar 

  • Wegman, R.C.C., and A.W.M. Hofstee. 1979. Chlorophenols in surface waters of the Netherlands (1976–1977). Water Research 13:651–657.

    Article  CAS  Google Scholar 

  • Wegman, R.C.C., and H.H. van den Broek. 1983. Chlorophenols in river sediment in The Netherlands. Water Research 17:227–230.

    Article  CAS  Google Scholar 

  • Wise, Jr., H.E., and P.D. Fahrenthold. 1981. Predicting priority pollutants from petrochemical processes. Environmental Science and Technology 15:1292–1304.

    Article  CAS  Google Scholar 

  • Wong, A.S., and D.C. Crosby. 1978. Photolysis of pentachlorophenol in water. In: K.R. Rao (Ed.), Pentachlorophenol. Environmental Science Research Series, Vol. 12. Plenum Press, New York, 19–25p.

    Google Scholar 

  • Yasuhara, A., H. Shiraishi, M. Tsujl, and T. Okuno. 1981. Analysis of organic substances in highly polluted river water by mass spectrometry. Environmental Science and Technology 15:570–573.

    Article  CAS  Google Scholar 

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Moore, J.W., Ramamoorthy, S. (1984). Phenols. In: Organic Chemicals in Natural Waters. Springer Series on Environmental Management. Springer, New York, NY. https://doi.org/10.1007/978-1-4613-9538-6_8

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  • DOI: https://doi.org/10.1007/978-1-4613-9538-6_8

  • Publisher Name: Springer, New York, NY

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