2-ナフチルアミン 化学特性,用途語,生産方法
用途
アゾ色素の合成中間体やゴム工業における抗酸化剤として利用されてきたが、ヒトに対する発がん性があり、毒性の低い化合物にほとんど代替された。
化学的特性
2-Naphthylamine is a white to red crystals
with a faint, aromatic odor. Darkens in air to a reddish-purple color.
物理的性質
White crystals becomes purplish-red on exposure to air. Odor threshold concentrations ranged
from 1.4 to 1.9 mg/m
3 (quoted, Keith and Walters, 1992).
使用
2-Naphthylamine was widely used in themanufacture of dyes and in rubber. Currently, its use is curtailed because of thehealth hazard.
調製方法
2-Naphthylamine was previously produced in substantial
amounts for nearly 50 years but is no longer produced
commercially. It is now used exclusively for research, and
only rarely. It was formerly used in the manufacture of
dyestuffs and as an antioxidant in the rubber industry.
Prior to termination of its domestic production and use in
the dye and rubber industries, an estimated 1000 U.S. workers
were possibly exposed to 2-naphthylamine by inhalation
and dermal routes. Currently, laboratory technicians and
scientists who use the compound for research purposes may
constitute the group with the greatest risk of potential exposure.
定義
ChEBI: 2-naphthylamine is a naphthylamine carrying the amino group at position 2. It has a role as a carcinogenic agent.
一般的な説明
A white to reddish colored solid in the form of flakes. Slightly soluble in hot water and denser than water. Toxic by ingestion, inhalation and skin absorption. Used to make dyes and agricultural chemicals.
空気と水の反応
2-Naphthylamine darkens in air to a reddish-purple color (oxidizes). Slightly soluble in hot water and denser than water. Napthyl amines can be slowly hydrolyzed, releasing NH3 as a byproduct [N.L. Drake, Org. React. 1, (1942), 105].
反応プロフィール
2-Naphthylamine is a weak base. 2-Naphthylamine is incompatible with strong oxidizing agents and strong acids. 2-Naphthylamine is also incompatible with nitrous acid. 2-Naphthylamine reduces warm ammoniacal silver nitrate.
危険性
Toxic by ingestion, inhalation, skin absorption; a confirmed carcinogen. Causes bladder cancer.
健康ハザード
2-Naphthylamine poses a severe health haz ard because of its carcinogenicity. Admin istration of this compound by all routesresulted in cancers in various tissues in testanimals. It caused tumors in the kidney, blad der, liver, lungs, skin, and blood tissues.There is sufficient evidence that this com pound causes bladder cancer in humans aftera latent period of several years.The toxicity of 2-naphthylamine is lowto moderate. However, high doses can pro duce severe acute toxic effects. The routesof exposures are ingestion, skin contact, andinhalation of its dusts or vapors. The acutetoxic symptoms are similar to those produced by 1-naphthylamine: hemorrhagic cystitis or methemoglobinemia (causing hypoxiaor inadequate supply of oxygen to tissues),respiratory distress, and hematuria (blood inurine).LD50 value, oral (rats): 727 mg/kg.
火災危険
Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.
安全性プロファイル
Confirmed human
carcinogen with experimental neoplastigenic
and tumorigenic data. Long and continued
exposure to even small amounts may
produce tumors and cancers of the bladder.
Poison by intraperitoneal route. Moderately
toxic by ingestion. Experimental
reproductive effects. Human mutation data
reported. A very toxic chemical in any of its
physical forms, such as flake, lump, dust,
liquid, or vapor. It can be absorbed into the
body through the lungs, the gastrointestinal
tract, or the skin. Combustible when
exposed to heat or flame. At elevated
temperatures it evolves a vapor that is
flammable and explosive. Incompatible with
nitrous acid. When heated to
decomposition it emits toxic fumes of
NOx.
毒性学
2-Naphthylamine is a human carcinogen that leads predominately to formation of tumors in the epithelium of the bladder. The conclusive epidemiological studies on humans are backed up by a wealth of animal data. However, although a proven carcinogen in mouse, hamster, dog, and monkey, 2-naphthylamine exhibits little, if any, carcinogenicity in rat or rabbit. Several metabolic pathways have been identified, but the main one involves N-hydroxylation followed by rearrangement to 2-amino-1- hydroxynaphthalene. Only the former is a proven animal carcinogen.
職業ばく露
2-Naphthylamine is presently used
only for research purposes. It is present as an impurity in
α-naphthylamine. It is as an intermediate in the preparation
of other compounds. 2-Naphthylamine was widely used in
the manufacture of dyestuffs; as an antioxidant for rubber;
and in rubber coated cables.
発がん性
2-Naphthylamine is known to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in humans.
環境運命予測
Photolytic. Low et al. (1991) reported that the photooxidation of aqueous primary amine
solutions by UV light in the presence of titanium dioxide resulted in the formation of ammonium
and nitrate ions.
Chemical/Physical. Kanno et al. (1982) studied the aqueous reaction of 2-naphthylamine and
other substituted aromatic hydrocarbons (aniline, toluidine, 1-naphthylamine, phenol, cresol,
pyrocatechol, resorcinol, hydroquinone, and 1-naphthol) with hypochlorous acid in the presence of
ammonium ion. They reported that the aromatic ring was not chlorinated as expected but was
cleaved by chloramine forming cyanogen chloride. At lower pHs, the amount of cyanogen
chloride formed increased (Kanno et al., 1982).
2-Naphthylamine will not hydrolyze because it does not contain a hydrolyzable functional group
(Kollig, 1993).
At influent concentrations of 10, 1.0, 0.1, and 0.01 mg/L, the GAC adsorption capacities were 300,
150, 75, and 37 mg/g, respectively (Dobbs and Cohen, 1980).
輸送方法
UN1650 β-Naphthylamine, Hazard Class: 6.1;
Labels: 6.1-Poisonous materials.
純化方法
Sublime the amine at 180o in a stream of nitrogen. Crystallise it from hot water (charcoal) or *benzene. Dry it under vacuum in a drying pistol. The styphnate has m 194-195o (from EtOH). [Beilstein 12 H 1265, 12 III 2989, 12 IV 3122.] CARCINOGEN.
不和合性
A weak base. Dust may form explosive
mixture with air. Incompatible with oxidizers (chlorates,
nitrates, peroxides, permanganates, perchlorates, chlorine,
bromine, fluorine, etc.); contact may cause fires or explosions.
Keep away from alkaline materials, strong bases,
strong acids, oxoacids, epoxides. Incompatible with nitrous
acid.
廃棄物の処理
Controlled incineration
whereby oxides of nitrogen are removed from the effluent
gas by scrubber, catalyst, or thermal device. 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.
2-ナフチルアミン 上流と下流の製品情報
原材料
準備製品