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??? ???? ???? ??? ??? ?? ????? ?? ??? ????. ??? ?? ???? ??? ?? ??? ????? ???? ???? ??? ??. ???? 184°C, ???? -6°C??. ??? 1.0215g/ml??. ???? 76°C??. ??? ?? ?? ???, ???, ?? ?? ?? ???? ? ???. ??? ???? ??? ???? ???? ??? ??? ????? C6H5HNNa ?? ?? ???? ????.
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???? ??? ?? ??? ????. ??: ???, ??? ?? ??. ??? ???? ??. ???, ???, ??? ???? ??. ????, ??(III), ?(III), ? ?? ?? ??.
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???? ??? ??? ?? ??? ??? ???? ??. ???? ?????? ???? ??? ??? ????. ????, ?? ???? ??? ????, ??, ????, ??? ??, ?? ??, ??? ??? ??? ??? ? ??. ????? ??? ??? ??? ?? ??? ??? ? ??. ???? ??? ?? ??? ??? ?? ??? ?? ??? ??.
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First produced in 1826 by Otto Unverdorben through
destructive distillation of indigo, the first industrial use
was as a purple dye, Mauveine, formulated by William
Henry Perkin accidentally in an attempt to isolate quinone.
The name aniline was given in deference to the indigoyielding
plant, Indigofera suffruticosa, commonly named
anil.
??? ??
Aniline,C6H5NH2, is slightly soluble in water,miscible in alcohol and ether,and turns yellow to brown in air. Aniline may be made(1) by the reduction, with iron or tin in HCI, of nitrobenzene, and(2) by the amination of chlorobenzene by heating with ammonia to a high temperature corresponding to a pressure of over 200 atmospheres in the presence of a catalyst(a mixture of cuprous chlorideandoxide).Aniline is the end point of reduction of most mononitrogen substituted benzene nuclei,as nitro benzene beta-phenyl hydroxylamine, azoxybenzene, azobenzene, hydrazobenzene. Aniline is detected by the violet coloration produced by a small amountof sodium hypochlorite. Aniline is used as a solvent, in the preparation of compound in the manufacture of dyes and their intermediates, and in the manufacture of medicinal chemicals.
??? ??
Colorless, oily liquid with a faint ammonia-like odor and burning taste. Gradually becomes yellow
to reddish-brown on exposure to air or light. The lower and upper odor thresholds are 2 and 128
ppm, respectively (quoted, Keith and Walters, 1992). An odor threshold of 1.0 ppm
v was reported
by Leonardos et al. (1969).
??
A thin, colorless oil prepared by reducing benzene with iron
filings in the presence of hydrochloric or acetic acid and then
separating the aniline formed by distillation. It is slightly
soluble in water but dissolves easily in alcohol, ether, and
benzene. Aniline is the base for many dyes used to increase
the sensitivity of emulsions.
??
ChEBI: A primary arylamine in which an amino functional group is substituted for one of the benzene hydrogens.
?? ??
Aniline was obtained in 1826 by Unverdorben from distillation of indigo and was given the name aniline in 1841 by Fritzsche (Windholz et al 1983). The chemical was manufactured in the U. S. by the Bechamp reaction involving reduction of nitrobenzene in the presence of either copper/silica or hydrochloric acid/ferrous chloride catalysts; but in 1966, amination of chlorobenzene with ammonia was introduced (IARC 1982; Northcott 1978). Currently, aniline is produced in the U.S., several European countries and Japan by the catalytic hydrogenation of nitrobenzene in either the vapor phase or solvent system. This chemical is also produced by reacting phenol with ammonia (HSDB 1989). Production in 1982 amounted to 331,000 tons (HSDB 1989).
?? ??
A yellowish to brownish oily liquid with a musty fishy odor. Melting point -6°C; boiling point 184°C; flash point 158°F. Denser than water (8.5 lb / gal) and slightly soluble in water. Vapors heavier than air. Toxic by skin absorption and inhalation. Produces toxic oxides of nitrogen during combustion. Used to manufacture other chemicals, especially dyes, photographic chemicals, agricultural chemicals and others.
??? ?? ??
Darkens on exposure to air and light. Polymerizes slowly to a resinous mass on exposure to air and light. Slightly soluble in water.
???
An allergen. Toxic if absorbed through the
skin. Combustible. Skin irritant. Questionable car-
cinogen.
????
Aniline is a moderate skin irritant, a moderate to severe eye irritant, and a skin sensitizer
in animals. Aniline is moderately toxic via inhalation and ingestion. Symptoms of
exposure (which may be delayed up to 4 hours) include headache, weakness, dizziness,
nausea, difficulty breathing, and unconsciousness. Exposure to aniline results in the
formation of methemoglobin and can thus interfere with the ability of the blood to
transport oxygen. Effects from exposure at levels near the lethal dose include
hypoactivity, tremors, convulsions, liver and kidney effects, and cyanosis.
Aniline has not been found to be a carcinogen or reproductive toxin in humans. Some
tests in rats demonstrate carcinogenic activity. However, other tests in which mice,
guinea pigs, and rabbits were treated by various routes of administration gave negative
results. Aniline produced developmental toxicity only at maternally toxic dose levels but
did not have a selective toxicity for the fetus. It produces genetic damage in animals and
in mammalian cell cultures but not in bacterial cell cultures.
????
Combustion can produce toxic fumes including nitrogen oxides and carbon monoxide. Aniline vapor forms explosive mixtures with air. Aniline is incompatible with strong oxidizers and strong acids and a number of other materials. Avoid heating. Hazardous polymerization may occur. Polymerizes to a resinous mass.
??? ? ???
Aniline is a combustible liquid (NFPA rating = 2). Smoke from a fire involving
aniline may contain toxic nitrogen oxides and aniline vapor. Toxic aniline vapors are
given off at high temperatures and form explosive mixtures in air. Carbon dioxide or
dry chemical extinguishers should be used to fight aniline fires.
?? ??
Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Flush with water and rinse with dilute acetic acid; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
??? ??
Aniline is widely used as an intermediate
in the synthesis of dyestuffs. It is also used in the
manufacture of rubber accelerators and antioxidants, pharmaceuticals,
marking inks; tetryl, optical whitening agents;
photographic developers; resins, varnishes, perfumes, shoe
polishes, and many organic chemicals.
Carcinogenicity
The IARC has classified aniline as a Group 3 carcinogen,
that is, not classifiable as to its carcinogenicity. However,
NIOSH has determined that there is sufficient evidence
to recommend that OSHA require labeling this substance a
potential occupational carcinogen. This position followed an
evaluation of a high-dose feeding study of aniline hydrochloride in F344 rats and B6C3F1 mice (3000 or
6000 ppm and 6000 or 12,000 ppm, respectively). The test
was negative in both sexes of mice; however, hemangiosarcomas
of the spleen and combined incidence of fibrosarcomas
and sarcomas of the spleen were statistically significant
in the male rats; the number of female rats having fibrosarcomas
of the spleen was also significant.
? ???
May form explosive mixture with air.
Unless inhibited (usually methanol), aniline is readily able
to polymerize. Fires and explosions may result from contact
with halogens, strong acids; oxidizers, strong base organic
anhydrides; acetic anhydride, isocyanates, aldehydes,
sodium peroxide. Strong reaction with toluene diisocyanate.
Reacts with alkali metals and alkali earth metals. Attacks
some plastics, rubber and coatings; copper and copper
alloys.
??? ??
Consult with environmental
regulatory agencies for guidance on acceptable disposal
practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing
storage, transportation, treatment, and waste disposal.
Incineration with provision for nitrogen oxides removal from
flue gases by scrubber, catalytic or thermal device.
??? ?? ?? ? ???
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N-PHENYLISONICOTINAMIDE
Modified MDI
2-???????
?? 208 ??
Acid Black 234
Direct Dark Brown NM
Direct Bordeaux NGB
?? ???
1,3-Diphenylurea
2,4,6-?????????
Pigment Red 175
?-??? RD
UREA, N-(2,6-DIMETHYLPHENYL)-N'-[IMINO(METHYLAMINO)METHYL]-
N-??-1-?????
?? 005 ????
2-CHLOROMALONALDEHYDE
3-?????????
????26
4-N-DECYLANILINE
N,N-??(?????)???
Direct Orange S
?????3R
C.I. ??? BLACK 5
3-BROMOPYRIDINE-2-CARBOXYLIC ACID
?????????
????79
Disperse Scarlet S-3GFL
4-?????-2-(?????????)???
N,N'-????-??-???????
C.I. ???? ?? 222
??????89
N-??-2-?????
4-???-2-(????????)???
8-????-1-?????? ?
????????????(2:1)
4,4'-??((4-????-6-(??(2-???????)???)-1,3,5-????-2-?)???) ???-2,2'-?? ??
2 BASIC ORANGE 2
Bronze Red
sodium dibenzyl amine enzene sulfonate
?? ?? 14
