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.
Ahlborg, U.G. 1977. Metabolism of chlorophenols: studies on dechlorination in mammals. Swedish Environment Protection Board PM 895, Stockholm.
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.
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.
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.
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.
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.
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.
Choi, J., and S. Aomine. 1974a. Adsorption of pentachlorophenol by soils. Soil Science and Plant Nutrition 20:135–144.
Choi, J., and S. Aomine. 1974b. Mechanisms of pentachlorophenol adsorption by soils. Soil Science and Plant Nutrition 20:371–379.
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.
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.
Eder, G., and K. Weber. 1980. Chlorinated phenols in sediments and suspended matter of the Weser estuary. Chemosphere 9:111–118.
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.
Hague, A., I. Schenunert, and F. Korte. 1978. Isolation and identification of a metabolite of pentachlorophenol -14C in rice plants. Chemosphere 7:65.
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.
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.
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.
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.
Joschek, H.I., and S.T. Miller. 1966. Photooxidation of phenol, cresols, and dihydroxybenzenes. Journal of the American Chemical Society 88:3273–3281.
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.
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.
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.
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.
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.
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.
Kuehl, D.W. 1981. Unusual polyhalogenated chemical residues identified in fish tissue from the environment. Chemosphere 10:231–242.
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.
LeBlanc, G.A. 1980. Acute toxicity of priority pollutants to water flea (Daphnia magna). Bulletin of Environmental Contamination and Toxicology 24:684–691.
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.
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.
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.
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.
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.
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.
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.
Ramamoorthy, S., and G.G. Leppard. 1977. Fibrillar pectin and contact cation exchange at the root surface. Journal of Theoretical Biology 66:527–540.
Reed, H.W.B. 1980. Alkyl phenols. In: Encyclopedia of chemical terminology. Vol. 2. Wiley, Toronto, pp. 72–96.
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.
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.
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.
Sheldon, L.S., and R.A. Hites. 1978. Organic compounds in the Delaware River. Environmental Science and Technology 12:1188–1194.
Sittig, M. 1980. Priority toxic pollutants. Health impacts and allowable limits. Noyes Data Corporation, New Jersey, 370 pp.
Statistics Canada. 1981. Manufacturers of industrial chemicals. Manufacturing and Primary Industries Division, Catalogue 46–219, Ministry of Supply and Services, Ottawa, Canada.
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.
Thurman, C. 1982. Phenols. In: Encyclopedia of chemical terminology. Vol. 7. Wiley, Toronto, pp. 373–384.
U.S. Environmental Protection Agency. 1980. Ambient water quality criteria reports. Office of Water Regulations and Standards, Washington, D.C.
U.S. International Trade Commission. 1975–1982. Synthetic organic chemicals, U.S. production and sales. U.S. Government Printing Office, Washington, D.C.
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.
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.
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.
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.
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.
Webb, R.G., et al. 1973. Current practice in GC/MS analysis of organics in water. Environmental Protection Technology Series EPA R2-73-277.
Wegman, R.C.C., and A.W.M. Hofstee. 1979. Chlorophenols in surface waters of the Netherlands (1976–1977). Water Research 13:651–657.
Wegman, R.C.C., and H.H. van den Broek. 1983. Chlorophenols in river sediment in The Netherlands. Water Research 17:227–230.
Wise, Jr., H.E., and P.D. Fahrenthold. 1981. Predicting priority pollutants from petrochemical processes. Environmental Science and Technology 15:1292–1304.
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.
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.
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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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