Aromatic Amines An Assessment of the Biological and Environmental Effects (1981) / Chapter Skim
Currently Skimming:
Aniline
Aniline
Pages 123-167
The Chapter Skim interface presents what we've algorithmically identified as the most significant single chunk of text within every page in the chapter.
Select key terms on the right to highlight them within pages of the chapter.
From page 123... ...
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)
|
From page 124... ...
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)
|
From page 125... ...
b U.S. International Trade Commission, 1976, 1977, 1978, 1979.
|
From page 126... ...
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
|
From page 127... ...
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 .
|
From page 128... ...
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.
|
From page 129... ...
in Luling, I.a. (Stanford Research Institute, 1979; Colour Index, 1971)
|
From page 130... ...
, 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)
|
From page 131... ...
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.
|
From page 132... ...
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.
|
From page 133... ...
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.
|
From page 134... ...
described procedures for assaying airborne vapors of aniline and related compounds. The vapors were absorbed on silica gel, elated from the gel with 95% ethyl alcohol containing 0.1% heptanol, and separated and analyzed by gas chromatography with a column of OV-25.
|
From page 135... ...
A personal sampler connected to a telemetric system was placed directly on a workman, thereby permitting continuous measurement of the toxic substances in his breathing zone. The toxic substances were colorimetrically determined by absorption in a tube of the personal sampler.
|
From page 136... ...
(1975 ~ determined several environmental contaminants, including aniline, and used nomograms and equations to determine maximum permissible concentrations of the compounds in industr ial environments, city air, and municipal water reservoirs. Hartstein and Eorshey (1974)
|
From page 137... ...
Sixteen toxic products including aniline were detected and measured. Dutkiewics and l;zy~nska (19733 employed thin-layer chromatography (TLC)
|
From page 138... ...
It is also rapidly and efficiently absorbed through the skin and from the gastrointestinal tract following oral ingestion. These properties led to the establishment of a threshold limit value (TLV)
|
From page 139... ...
In all species except dogs, aniline is ~acetylated with the subsequent formation of a second series of metabolites containing the acetyl group (Williams, 1959~. Since deacetylation also occurs, these acetyl metabol ites are usually present in small quantities in ur ine .
|
From page 140... ...
The bulk of the ava ilable evidence ind icates that aniline itself is not directly responsible for the induction of methemoglobinemia , but its metabolite, phenylhydroxylemine, is 140
|
From page 141... ...
Sensitivity to the induction of metbemoglobin by aromatic amines varies among species. On a mg/kg basis cats are the most sensitive, and humans are approximately 60% as sensitive; dogs are about 30% as sensitive, rats S%, and rabbits and monkeys seem to be quite resistant to aromatic-amine-induced methemaglobin (Hamblin, 1963~.
|
From page 142... ...
Such individuals are hypersensitive to the induction of methemoglobinemia by nitrates. mis genetic conditon is due to an autosomal recessive allele and is manifested in homozygotes of both sexes (Goldstein et al.
|
From page 143... ...
Although generally regarded as a highly toxic compound for humans, the acute toxicity in laboratory animals is relatively low. me oral LD50 's in rats, mice, and cats are 440, 460, and 1,750 mg/kg, respectively.
|
From page 144... ...
Anil ine wan also tested both as the free base in lard (1 mg/mouse) or olive oil (8 x 5 mg/mouse)
|
From page 145... ...
Until recently, these inadequate experiments plus the publication of a series of epidemiologic studies that exonerated aniline as a bladder carcinogen have led to the belief that aniline is not a carcinogen. In 1978, the results of a carcinogenesis bioassay in rats and mice given aniline hydrochloride were released.
|
From page 146... ...
An il ine and an il ine-der ivatives (hydroxylamine and the nitroso der ivati~res) did not induce mutations in the Salmonella test system in four out of f ice studies, and weakly mutagenic in one (Mitchell, 1978 ~ .
|
From page 147... ...
a' c: ~In 3 .3 ~ ~: o 1 on En ~ e" ~: hi: ·~ U]
|
From page 148... ...
me signif icance of there results is highly questionable : no data were provided on the purity of the compound; no dose-respon~e relationship was observed for the mutagenicity of aniline; the mutagenic effect was independent of metabolic activation and the possibility that the aniline was oxidized under the test conditions to form a mutagenic oxidation - coupling product has not been ruled out. The non~utagen ic 5-carboline der ivative norharman has been shown to enhance the mutagenic activity of benzo (alpyrene, 148
|
From page 149... ...
Swenberq et al . (1976} evaluated the capacity of an il ine to induce DNA strand breaks using an _-'ritro/alkaline elusion assay using Chinese hamster V79 cells with and without a liver microsomal activation system.
|
From page 150... ...
On the other hand, there is evidence that a carcinogen may induce tumors in different tissues in different species, and this observation has been extended to the generalization that a substance inducing cancer in any tissue of one species may induce tumors in a dif ferent tissue in other species, including humans . Although this may be true as a generalization, there are undoubtedly exceptions since some types of tumors in test animals do not appear to be correlated with carcinogenic potential in humans.
|
From page 151... ...
This will greatly assist in interpreting the signif icance of the previously observed effects. A carcinogenicity study using Syrian golden hamsters may also be useful since these animals have been shown to develop bladder tumors after exposure to other aromatic amines.
|
From page 152... ...
Such an experiment will allay any suspicions concerning the possible role of aniline in the causation of burn bladder cancer. This test is desirable because the only test with dogs was conducted many years ago on a few anima Is for too short a tier - .
|
From page 153... ...
1978. Stanford Research Institute International, Menlo Park, Calif .
|
From page 154... ...
142-04-1. ITS Carcinogenesis Technical Report Series No.
|
From page 155... ...
United States of America. Stanford Research Institute International, Menlo Park, California.
|
From page 156... ...
S International Trade Commission.
|
From page 157... ...
Neoprenes, polyvinyl chlor ide compositions, urethane foam and wood. Bureau of Mines, Pittsburgh, Pa.
|
From page 158... ...
on the analysis of aromatic amines in cigarette smoke.
|
From page 159... ...
1975. Rapid amends for determination of toxicity, ~aaxieu~n permissible Concentrations, and hazard evaluation of chemical compounds in the environment.
|
From page 160... ...
1957 . The biochemistry of aromatic amines.
|
From page 161... ...
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.
|
From page 162... ...
Performed at Hazleton Laboratories, America, Inc., Vienna, Va ., for Chemical Industry Institute of Toxicology , Research Triangle Park, N.C.
|
From page 163... ...
1975. Diphenylhydantoin effects on hexobarbital and aniline biotransformation in male rats: Dif ferences between in vitro and in vivo observations.
|
From page 164... ...
1966. The biochemical production of fer r ihemoglobin-forming der ivatives from aromatic amines, and mechanisms of ferrihemoglobin formation.
|
From page 165... ...
14 2-04 -1 . ITS Care inogenes is Techn ical Repor t Ser ins 130 .
|
From page 166... ...
1976 . In vitro DNA damage/alkaline elusion assay for predicting carcinogenic potential.
|
From page 167... ...
1975. Ef feet of repeated exposure to aniline, nitrobenzene, and benzene on liver microsomal metabolism in the rat.
|
Key Terms
This material may be derived from roughly machine-read images, and so is provided only to facilitate research.
More
information on Chapter Skim is available.