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Chapter 6
ANILINE
=
Aniline (also called aminobenzene or benzenamine) is a
colorless, oily liquid that freezes at -6.2°C and boils at 184°C.
It is combustible and is moderately soluble in water. At 25°C,
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 350°C 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
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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.
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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.
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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
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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 ~ .
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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 0°C, 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
OCR for page 158
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
OCR for page 159
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
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Boyland, E ., D. Manson , and S. .F.D. Orr . 1957 . The
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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
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1954. Amours of the urinary bladder in workmen engaged in
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Druckrey, H. 1950 . Beitrage our Pharmakologie cancerogener
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161
OCR for page 162
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
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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
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Goldstein, A., L. Aronow, and S.M. Xalman. 1968. Pp. 441-443
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Gralla, E.J. 1977. A Thirty Day Toxicology Study in
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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,
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Hamblin, D.O. 1963. Aromatic nitro and amino compounds.
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2'-methyl-4-aminobiphenyl, and
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International Agency for Research on Cancer. 1974. Aniline.
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Jenkins, F.P., J.A. Robinson, J.B.M. Gellatly, and G.W.A.
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Kiese, M. 1966. The biochemical production of
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Nat tonal Cancer Institute . 1978 . Bioassay of aniline
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Pacser i, I. 1961. ~-Aminophenol excretion as an index of
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165
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Smith, J.N., and R.T. Williams. 1949. Studies in
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Smith, R.P., A.A. Alkaitis, and P.R. Shafer. 1967. Chemically
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Vasilenko, N.~., V.A. volodabenko, L.N. Khishnyakova, V. I.
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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
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166
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Williams, R.J. 1959. Detoxication Mechanism. Wiley, New
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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
Representative terms from entire chapter:
aromatic amines
