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Chapter 6 ANILINE = Aniline (also called aminobenzene or benzenamine) is a colorless, oily liquid that freezes at -6.2C and boils at 184C. It is combustible and is moderately soluble in water. At 25C, aniline has a vapor pressure of O. .67 mm Hg. Aniline is one of the most important organic bases and is the parent compound for more than 300 chemical products. It is typically produced by the catalytic hydrogenation of nitrobenzene. The gas-phase reaction of hydrogen and nitrobenzene over a catalyst at temperatures below 350C yields more than 98% aniline. Aniline as a free base is a relatively unstable compound, which is rapidly oxidized in the presence of air and light to ~ complex mixture of quinoneimines, quinones, and highly colored polymers of unknown composition. It is a weak base that is readily converted to a water-soluble, stable salt in acid solution (a hydrochloride) (International Agency for Research on Cancer, 1974; Radomaki, 1979} 123 .

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PRODUCTION Table 6-1 lists the current producers of aniline, their locations, and their annual capacities. Three of the companies are planning to increase production in the near future. Rubicon Chemicals, Inc. plans to expand its capacity at Geismer, Lie. by an additional 9,100 metric tons per year dur ing 1980 (Chemical Marketing Reporter, 1979 ~ . Anger lean Cyanamid Co. will increase the capacity of its Willow Island, W. Va . facility to a total of 50,000 metric tons per year during 1980 (Chemical Marketing Reporter, 1979) . file Polyurethane Division of Mobay Chemical Corp. in New Martinsville, W. Va., plans to begin recovery of aniline from its iron oxide plant in the first quarter of 1981. Capacity will be 12,000 metric tons. By 1985, Mobay's polyurethane capac ity is expected to reach 18, 000 metr ic tons (Chemical }economics Handbook, 1978) . USES 6-2 . U.S. consumption patterns of aniline in 1979 are shown in Table 124

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Table 6-1 ANILINE PRODUCERS AND CAPACITIESa - Producer and Location Capac ity (103 metric tons) Rubicon Chemicals, Tnc Geismar, La. . E. I. du Pont de Nemours & Co., Inc. Beaumont, Tex. Gibbstown, N.J. First Chemical Corp., subsidiary of First MiSSiSSippi Corp. Pascagoula, Miss. Ame r ican Cyanamid Co Bound Brook, N.J. . Orga n ic Chemica 1 s D iv i s ion Willow Island, W. Va. Bombay Chemical Corp., Industrial Chemicals Division New Martinsville, W. Va. 1~27 118 73 114 27 23 45 Total annual U. S. aniline production for recent years: b Thousands of metr ic tons 1975 1976 1977 1978 247.2 265.5 275.4 309.7 a SRI (Standard Research Inst itute ), 1979 . b U.S. International Trade Commission, 1976, 1977, 1978, 1979. 125

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Table 6-2 ANILINE CONSUMPTION PA]~ERNSa, b Percent of Use total 103 metric tons Intermediate for monomer ic 50 155 and polymeric isocyanates .. Intermediate for rubber 27 84 chemica Is Dyes and dye intermediates 6 19 Hydroquinone 5 15 Intermediate for pharmaceuticals 3 9 Miscellaneous 9 28 l a Chemical Marketing Reporter, 1979. b Total U. S. consumption is considered equal to U.S production; imports and exports are negligible. 126

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An iline is used as an intermediate in the production of E~,E~'-methylenediphenyl diisocyanate (NDI) and polymeric MDI, which are used primarily in the manufacture of rigid polyurethane foam for building insulation (Chemical Bconomice Handbook, 19783. Me U.S. producers of MDI include Hobay Chemical Corp. in Cedar Bayou, Tex., and New Martinsville, W. vat, Rubicon Chemicals, Inc. in Geismar, La., and the Upjohn Co. in L;a Porte, Tex. (Stanford Re~earcb Institute, 1979 ~ . The chemicals derived from aniline are used in rubber manufacture as vulcanization accelerators, antioxidants, and antidegradants {Northcott, 1978~. file Host commercially significant are 2-mercaptobenzothiazole and N~cyclohexyl-2-benzothiazole (Chemical Economics Handbook , 1978 I, produced by Amer icon Cyanamid Co. in Bound Brook , N . J . the B. F. Good r ich Co. in Henry , 111 ., Monsanto Co. in Nitro, W. Va ., Pennwalt Corp. in Wyandotte, Mich., and Un iroyal, Inc. in Geismar, La . 2-Mercaptobenzott~iazole is also produced by Eastman Kodak Co. in Rochester , N. Y., and the Goodyear Tire and Rubber Co. in Niagara Falls, N.Y. (Stanford Research Institute, 1979 ~ . Dyes prepared from aniline and aniline derivatives are included in the following four dye classes: azo, tr iphenylmetbane, anthraquinone, and safranines {International Agency for Research on Cancer, 1974~. The Colour Index (1971) lists 174 dyes that can be prepared from aniline, and more than 700 dyes that can be prepared from aniline derivatives. Because of the increased use of synthetic 127

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f ibers and str toter controls imposed by the Food and Drug Administration (FDA), very few of these dyes are currently produced in commercially significant quantities (Northcott, 1978~. One of the more significant of the aniline~based dyes, from ~ commercial standpoint is C.~. (Color Index) Vat Blue 1, used widely to dye cotton f ibers such an those used in denim. C. I. Vat Blue 1 (DSC Blue No. 6) has also been used as a colorant for surgical sutures. (Bauer, 1979; 21 CFR 74~. This dye is produced by BASE Wyandotte Corp. in Parsippany, N. J., and Buffalo Color Corp. in Buffalo, N.Y. (Standford Research Institute, 1979~. Among the commercially more signif icant dye intermediates derived from aniline are E' - itroaniline, which is produced by Monsanto Co. in Sauget, Ill., Amer ican Color & Chemical Corp. in Lock Haven Pa ., and the Signal Compan ies Inc . in Shrevepor t, La .; N,N-diethylaniline1 and N,N-dimethylaniline, both produced by American Cyanamid Co. in Bound Brook, N.J., Buffalo Color Corp. in Buf falo, N.Y., and E . I . du Pont de Nemours ~ Co. in Deepwater , N.Y.; and o-, m-, and E'-chloroan il ine, which is produced 1 Also used to make 2-chloro-2 ' ,6 '-die'chyl-N- {methoxymethyl) acetanilide, an herbicide marketed under the trade name Lasso (Chemical Economics Handbook, 197 8 ~ . 128

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by E. I . du Pant de Nemours ~ Co., Inc. in Deepwater, N. J. o- and Chloroaniline are also produced by Monsanto Co. in Luling, I.a. (Stanford Research Institute, 1979; Colour Index, 1971) . Aniline is also involved in the production of t~ydroc~uinone, which is used primarily an a developing agent for black-and-white photography tWoodlief , 1973), and as a polymerization shortstop in styrene-butadiene rubber production (Bauer, 1979 ~ . Hydroguinone is produced by Eastman Kodak Co. in Kingsport, Tenn. and the Goodyear Tire & Rubber Co. in Bayport, Tex. (Stanford Research Institute, 19 79 . In the pharmaceutical industry, aniline is used in the production of acetanilide, which was once widely included in analgesic and antipyretic formulations: it is currently used as an intermediate in the manufacture of most sulfanilamide drugs {Northcott, 19781. Pharmaceutical aniline is produced by Eastman Kodak Co. in Rochester, N.Y., Merck & Co., Inc. in Albany, Gal, Salisbury Laboratories in Charles City, Iowa, and Syntex Corp. in Newport, Tenn. {Stanford Research Institute, 1979 ~ . There are a number of miscellaneous applications of aniline. It is used in the production of intermediates for herbicides, fung ic ides, insecticides, an imal repellents, and defoliants (Northcott, 1978) and in the production of cyclobexylamine (formerly an intermediate in the manufacture of cyclamate synthetic sweeteners and presently an intermediate in the production of a 129

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var iety of other chemicals and as a corrosion inhibitor) . Cyclobexylamine and its derivatives are produced by Abbott Laboratories in Wichita, Kane., Honeanto Co. in Sauget, Ill., and Virginia Chemicals Inc. in Bucks, Ala. and Portsmouth, Va. (Stanford Research Institute, 1979~. Aniline is also used. in the production of ~,p'-methylenedianiline, an intermediate for the commercial synthesis of a polyamide fiber marketed under the trade name Quiana. The sole producer of Quiana is E.I. du Pont de Nemours ~ Co., Inc. The monomer is produced at Belle, W. Va., and the polymer is spun into yarn at the plant in Chattanooga, Tenn. (Chemical Economics Handbook, 1977 ~ . EXPOSURE As demonstrated above, aniline is produced in large quantities and has numerous applications. Although the potential for human exposure is correspondingly large, there are no quantitative estimates of environmental exposures of the general public. Nonetheless, the National Institute on Occupational Safety and Health (NIOSH), based on results of a National Occupational Hazards Survey, has estimated that a potential 1.26 million workers could be exposed to an il ine . Exposure to aniline in the workplace is regulated by the Occupational Safety and Health Administration tOSHA). me health standards for occupational exposure to air contaminants require that an employee's exposure to aniline shall not exceed 130

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5 ppmor l9 mg/m3 air in any 8-hour workday of ~ 40-bour workweek (Occupational Safety and Health Administration, 1980~. In 1979, the A'ner ican Conference of Governmental Industr ial Hygienists (ACGIH) adopted a threshold limit value time weighted average for dermal exposure to aniline and its homologs of 2 ppm or 10 mg/m3 a ir for any 8-hour workday or 40-hour workweek: and a threshold limit value, short-term exposure limit of 5 ppm or 20 mg/m3 air for a period of up to 15 minutes, not to occur more than 4 times per day {Amer ican Conference of Governmental Industr ial Hyg fen ists, 1979 ~ . Because of aniline ' s widespread use, it is generally considered to be a likely component of many industr ial wastewater discharges. However, the committee found only one reference (Jungclaus et al., 1978J in which aniline concentrations had actually been measured in such a discharge; the aniline concentration in the was tewater discharge. These investigators reported that of a specialty chemicals plant was O .02 ppm. file compound was not detected downstream of the plant nor in the stream sediment. Aniline is biodegradable. It is susceptible to treatment in wastewater with activated sludge (Joel and Grady, 1977) . In air, it is subject to attack by the hydroxyl radical (Spicer et al., 1974), but its overall half-1 if e in a ir is riot known . No information could be found on the presence of an i 1 ine in consumer products, and no 131

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evidence was found that aniline is covered by Food and Drug Administration regulations. The Interagency Testing Committee, established under section 4 (e) of the Toxic Substance Control Act {TSCA}, has added aniline to its Pr for ity List of Chemicals despite the previous National Cancer Institute (NCI, 1978) test. Chemicals on this list are considered for testing by the U. S. Environmenta1 Protection Agency (EPA) in accordance with section 4 (a) of TSCA. Within 12 months of such a recommendation, the EPA must initiate rulemaking to require testing of chemical or publish its reasons for not doing so. The committee recommended studies to determine the carcinogenicity, mutagenicity, teratogenicity, chronic effects, environmental effects, and epidemiology of aniline. 132

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ANALYTIC t4E:THODS In addition to the general analytic procedures for primary aromatic amides, discussed in Chapter 1, the following additional information from recent literature should help in Methods selection. I"ination and Bromination The sensitivity of aniline in electron capture-gas . chromatography {EC-GC) assays is greatly enhanced by iodination or Bromination of the molecule . gofman et al . {1979), descr ibed the following process: For iodination, the compound in 1 N hydrochlor to acid is treated with Sodium nitrite at 0C, iodinated with potassium iodide at room temperature, and boiled at reflex. Nate iodine derivative is extracted with hexane; iodination efficiency is 871. Bromination of aniline is carried out in 1 M sulfuric acid with mesidine, potassium bromide, and potassium bromate. ate reaction product {2,4,6-tribromoaniline) is extracted with toluene after alkalinization with 10 N sodium hydroxide. Efficiency of Bromination is 99.61. Cigarette Smoke file amines from cigarette smoke were trapped in dilute hydrochloric acid and enriched together with the basic portions, der ivatized to pentafluoropropionasudes, and determined by EC-GC with a nickel-63 electron-capture detector. Me detection limit 133

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Analytic Methods Ascik, K., M. Glinska, and K. Szypruc. 1975. toxic compounds in pulp and paper mills. 31: 232-233 . 1Cbem. Abe . 84: 34936;, 1976. ] Determination of Przagl. Papier. ~ . Boukun, E.K., R.K. Voronova, S.A. Pealtyre , and M. I . Buko~r~k i i . 1974 . Quantitative determination of aniline vapors in air. U.S.S.R. Patent No. 443,311. [Chem. Ab8. 82: 174810x, 1975. ~ Dutkiewicz, T., and J. Szymanska. 1973. Chro~nstographic determination of hydrazobenzene metabolites in rats. Bromatol. Chem. Toksykol . 6: 323-327 . [Chem. Abs . 80 :116838k, 1974.1 Gromiec, J., and J. Adamlak-2ie~nba . 1974. Determination of t~ethylaniline in a ir in the presence of aniline. Chem. Anal. (Warsaw) 19: 853-860. [Chem. Abe. 82: 34691j, 1975. Hartstein, A.M., and D. R. Hershey. 1974. Coal mine combustion products . Neoprenes, polyvinyl chlor ide compositions, urethane foam and wood. Bureau of Mines, Pittsburgh, Pa. Ava liable fron National Technical Information Service, Springfield, Virginia, as PB-240 211. 30 pp. 157

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Kofman, I . Sh., M.A. Klisenko, and 11. T. Kofanov. 1979. Gas-cbromatographic determination of certain products of the transformation of phenylamide-group herbicides. Fiziol. Biokhi~n. Kul ' t. Rast. 11: 380-383 . [Ct~e~n. Abs . 91 :169289r, 1979. ] Madra imov , A., M. Usubbaev , and A. T . Gengr inovich . 1973. Quantitative determination of aniline and Anesthesin using an iodine bromide neutral solution. Med. ah. Uzb. No. 2: 68-69. lChem. Abs . 83: 15716a, 1975. ] Patrianakos, C., and D. Hoffmann. 1979. Chemical studies on tobacco smoke LXIV. on the analysis of aromatic amines in cigarette smoke. J. Anal. loxicol. 3:150-154. Schaffernicht, H., and G. Schreinicke. 1974. Continuous personal measurement of toxic substances with telemetric transmission. Int. Arch. Arbeitsmed. 32: 305-312 (in German; Engl ish sugary ~ . Sternson, L.A., and W. J. Dewitte. 1977. High-pressure liquid chromatographic analysis of aniline and its metabolites. J. Chromatogr . 137: 305-314 . Wood, G. O., and R.G. Anderson. 1975. Personal air sampling for vapors of aniline compounds. Am. Ind. Hyg. ASsoc. J. 36: 538-548. 158

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Zaugol 'nikov, S.D., M.M. Boc~banov, a.o. Loit, and I. I . Sta~chanakii. 1975. Rapid amends for determination of toxicity, ~aaxieu~n permissible Concentrations, and hazard evaluation of chemical compounds in the environment. Vestn. Aked. Med. Nauk SSSR No. 3:75-83. [Chec. abet 83s183123y, 1975. ] 159

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Bealth Ef feats Aikawa , K., T. Satoh, R. Kobayashi, and B. Kitagawa . 1978. Glutathione depletion by aniline analogs in vitro associated with liver microsomal cytochrome P-450. Jpn. J. Pbarmacol. 28: 699-705 . Berdodej, Z. 1975. MAC's in Czechoslovakia. J. Byg. Epidemiol. Microbiol. Immunol. 19 :148-162. Belman, S., W. Troll, G. Teebor, and F. Mukai. 1968. The care i nogen ic and mutagen ic proper ties of N-hydroxy-aminophthalenes. Cancer Res. 28: 535-542. Boobis, A.R., and G. Powis. 1975. The metabolism and disposition of aniline in the isolated blood-perfused liver of the rat. Drug Metab. Dispos . 3: 63-68 . Boyland, E ., D. Manson , and S. .F.D. Orr . 1957 . The biochemistry of aromatic amines. 2. The conversion of arylamines into arylaulphamic acids and arylamine-N-glucosiduronic acids. Biochem. J. 65:417-42~ Boyland, E ., D. Manson, and R. Nery. 1963. me biochemistry of aromatic amines. Mercapturic acids as metabolites of aniline and 2-naphthylamine. Biochem. J. 86: 263-271. 160

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Bus, J.S., D.E. Rickert, R.M. Norton, and J.E. Gibson. 1978. The pharmacokinetics and aetabol.~e of aniline hydrochloride in Fi scher 344 rats . q~oxicol. App} . Pbar~col . 45 :256 (Abstract no . 85 ~ . Case, R.A.M., and J.T. Pearson. 1954. Tueoura of the urinary bladder in workmen engaged in the manufacture and use of certain dyestuff intermediates in the British chemical industry. Part II. Further consideration of the role of aniline and of the manufacture of auramine and magenta ( fuch~ine ~ as possible causative agents . BE . J. Ind. Med. 11: 213-216 . Case , R. A.M., M. E. Hosker , D. B. McDonald, and J. T. Pearson . 1954. Amours of the urinary bladder in workmen engaged in the menu facture and use of cer ta in dyestuf f interned fates in the British Chemical Industry. Br . J. End. Med. 11: 75-104 . Conney, A.H., and W. Levin. 1974 . Carcinogen Metabolism in experimental animals and man. Pp. 3-24 in P- %'ontesano and L. Tomatis, eds . Chemical Carcinogenesis Essays. IARC Scientif ic Publications No. 10. International Agency for Research on Cancer, Lyon. Druckrey, H. 1950 . Beitrage our Pharmakologie cancerogener Substanzen. Versucbe mit Anilin. Haunyn-Schmiedebergs Arch. Exp. Pathol. Pharmakol . 210 :137-iS8 . 161

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Dutkiewicz, T., and J. Piotrowski. 1961. Experimental investigations on the quantitative estimation of aniline absorption in man. Pure Appl. Chem. 3: 319-323. Eyer, P. 1979. Reactions of nitrosobenzene with reduced glutathione . Chem. Biol. Interact. 24: 221-239 . Garner, R.C., and C.A. Nutman. 1977. Testing of some azo dyes and their reduction products for mutagenicity using Salmonella typh imur ium TA 1558 . Mutat . Res . 44: 9-19 . Ghiringhelli, L., and C. Molina. 1951. La metaemoglobinemia nell 'intossicazione acute da aniline nell'animale da esperimento e nell'uomo; suoi rapport) calls cianosi, 1'anemia e i corpi di Heinz. Hed. Lav. 42:125-136 (in Ital fan; Engl ish summary) . Goldstein, A., L. Aronow, and S.M. Xalman. 1968. Pp. 441-443 in Principles of Drug Action: The Basis of Pharmacology. Harper & Row, New York. Gralla, E.J. 1977. A Thirty Day Toxicology Study in Fischer-344 Rats Given Aniline HC1. Full Report. Docket 612397. Performed at Hazleton Laboratories, America, Inc., Vienna, Va ., for Chemical Industry Institute of Toxicology , Research Triangle Park, N.C. 22 pp. 162

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Gut, I., and B.A. Becker. 1975. Diphenylhydantoin effects on hexobarbital and aniline biotransformation in male rats: Dif ferences between in vitro and in vivo observations. - Toxicol. Appl. Pharmacol. 34:253-258. Hagiwara, A., M. Arai, M. Hirose, J. Nakanowatari, H. Tsuda, and N. Ito. 1980. Chronic effects of norharman in rats treated with aniline. Tox. Lett. 6: 71-75. Hamblin, D.O. 1963. Aromatic nitro and amino compounds. Pp. 2105-2169 in F.A. Patty, ed. Industrial Hygiene and Toxicology . Second revised ed. Volume 2: Toxicology, D.W. Fassett and D.D. Ir ish, eds. Interscience, New York. Hecht, S.S., K. El-Bayoumy, L. Tilley, and E. LaVoie. 1979. Structure-mutagenicity relationships of N-oxidized derivatives of aniline, o-toluidine, 2'-methyl-4-aminobiphenyl, and 3,2'-dimethyl-4-aminobiphenyl. J. Med. Chem. 22:981-987. International Agency for Research on Cancer. 1974. Aniline. Pp. 27-39 in IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . Volume 4 . International Agency for Research on Cancer, Lyon. Jenkins, F.P., J.A. Robinson, J.B.M. Gellatly, and G.W.A. Salmond . 1972 . The no-ef feet dose of aniline in human subjects and a comparison of aniline toxicity in man and ra t. Food Cosme t. Toxicol . 10: 671-679 . 163

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Kiese, M. 1966. The biochemical production of fer r ihemoglobin-forming der ivatives from aromatic amines, and mechanisms of ferrihemoglobin formation. Pharmacol. Rev. 18: 1091-1161. Lin, J.K., and Y.H. Wu. 1973. Studies on the mechanism of methernoglobin formation induced by aminoazo compounds. Biochem. Pharmacol . 22 :1883-1891. McCann, J., E. Choi, E. Yamasaki, and B.N. Ames. 1975. Detection of carcinogens as mutagens in the Salmonella/microsome test: Assay of 300 chemicals. Proc. Natl. Acad. Sci. O.S.A. 72:5135-5139. McLean, S., G.A. Starmer , and J. Thomas. 1969. Methae~globin formation by aromatic amines. J. Pharm. Pharmacol . 21: 441-450 . Mitchell, I. de G. 1978. Microbial assays for mutagenicity: A modified liquid culture method compared with the agar plate system for precision and sensitivity. Mutat. Res. 54:1-16. Nagao, M., T. Yahag i , T. Kawachi , T. Sugimura , T. Kosuge , K. Tsu j i, K. Wakabayashi, S. Mizusaki, and T. Matsumoto. 1977. Comutagen ic action of norharman and harman. Proc. Jap. Acad. 53: 95-98 . 164

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Nat tonal Cancer Institute . 1978 . Bioassay of aniline hydrochloride for possible carcinogenicity. CAS No. 14 2-04 -1 . ITS Care inogenes is Techn ical Repor t Ser ins 130 . DREW Publ ication No. (NIH) 78-1385 . U. S. Dept. of Bealtb, Education, and Welfare, Public Health Service, National Institutes of Health, Bethesda, Md. ~ 91] pp. National Institute for Occupational Safety and Health. 1977. Pp. 92-93 in E.J. Fairchild, ed. Registry of Toxic Effects of Chemical Substances. Volume II. U.S. Department of Health, Education, and Welfare, Public Health Service, Center for Disease Control, National Institute for Occupational Safety and Health, Washington, D.C. Pacser i, I. 1961. ~-Aminophenol excretion as an index of aniline exposure . Pure Appl . Chem. 3: 313-314 . Patterson, D.S.P., and B.A. Roberts. 1971. Differences in the effects of phenobarbital treatment on the In vitro metabolism of aflatoxin and aniline by duck and rat livers. Biochem. Pharmacol . 20: 3377-3383 . Parke, D.V. 1960. The metabolism of [14C]aniline in the rabbit and other animals. Biochem. J. 77 :493-503. Radomsk i, J. L. 1979 . The pr imary aromatic amides: Their biological properties and structure-activity relationships. Annul Rev. Pharmacol . Toxicol. 19 :129-157 . 165

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Smith, J.N., and R.T. Williams. 1949. Studies in detoxif ication. 23. Me fate of aniline in the rabbit. Biochem. J. 44 :24 2-250 . Smith, R.P., A.A. Alkaitis, and P.R. Shafer. 1967. Chemically induced methemoglobinemias in the mouse. B.iochem. Phareacol. 16: 317-328 . Swenberg, J .A., G. L. Petzold, and P.R. Harbacb. 1976 . In vitro DNA damage/alkaline elusion assay for predicting carcinogenic potential. Biochem. B~ophys. Res. Commun. 72:73 2-738 . Sugimura, T., T. Kawachi, M. Nagao, T. Yahagi, Y. Seino, T. Okamoto, K. Shudo, T. Kosuge, K. Tsoji, K. Wakabazashi, Y. Iitaka, and A. Itai. 1977. Mutagenic principle (s) in tryptophan and phenylalamine pyrolys is products . Proc . Jpn . Acad. 53: 58-61. Vasilenko, N.~., V.A. volodabenko, L.N. Khishnyakova, V. I. Zvezday, V.V. Manfanovskiy, V.S. Anatovskaya, Ye.~. Krylova N.A. Voskovoynikov, A. I. Gnezdilo~ra, and I.S. Sonkin. 1972. Data to justify reducing the maximum permissible concentration of aniline in the air of working zones. Translation of Gig. Sanit. 37 (5) :31-?~5. tubs- Eh~rironmental Protection Agency, Research Triangle Park, N.C. APTIC-ES-51.} 166

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Williams, R.J. 1959. Detoxication Mechanism. Wiley, New York. 796 pp. Winell, M. 1975. An international comparison of hygienic standards for chemicals in the work environment. Ambio 4:34-36. Wisniewska-Knypl, J.M., J.K. Jabonska, and J.K. Piotrowski. 1975. Ef feet of repeated exposure to aniline, nitrobenzene, and benzene on liver microsomal metabolism in the rat. Br. J. Ind. Med. 32:42-48. Wi sn iewska-Knypl , J. M., and J. K . Jabonska . 1975. She rate of aniline metabolism _ vivo in rats exposed to aniline and drugs. Xenobiotica 5: 511-519. 167