Хинолин химические свойства, назначение, производство
Химические свойства
Quinoline is a colorless liquid with a penetrating
amine odor. Turns brown on exposure to light.
Вхождение
Quinoline was discovered in coal tar distillate in 1834 by Runge. It is released to
the environment through natural combustion processes and has been isolated from
air particulates (Dong et al 1977). Quinoline may be a significant aqueous
byproduct of synthetic fuel production (shale oil, coal processing) and from wood
preservation production and use facilities. Small amounts also have been detected
in tobacco smoke (Schmeltz and Hoffmann 1977).
Использование
Quinoline is used in the manufacture of dyesand hydroxyquinoline salts; as a solvent forresins and terpenes; and therapeutically as anantimalarial agent. It occurs in coal tar insmall amounts.
Методы производства
Quinoline may be synthesized by heating aniline with glycerol and nitrobenzene in
sulfuric acid (Skraup method) or by reacting aniline, acetaldehyde, and a formaldehyde
hemiacetal (Windholz et al 1983). Commercial production is by isolation
from coal tar with greater than 100,000 lbs being produced in 1977. Production of
refined quinoline has almost ceased due to low demand (Parris et al 1983).
Определение
ChEBI: The simplest member of the quinoline class of compounds, comprising a benzene ring ortho fused to C-2 and C-3 of a pyridine ring.
Общее описание
A colorless liquid with a peculiar odor. Slightly denser than water. Contact may irritate to skin, eyes, and mucous membranes. May be toxic by ingestion. Used to make other chemicals.
Реакции воздуха и воды
Hygroscopic. Soluble in water.
Профиль реактивности
Quinoline is hygroscopic. Quinoline absorbs as much as 22% water. Quinoline is sensitive to light and moisture. Quinoline darkens on storage. Quinoline is a weak base. A potentially explosive reaction may occur with hydrogen peroxide. Quinoline reacts violently with dinitrogen tetraoxide. Quinoline also reacts violently with perchromates. Quinoline is incompatible with (linseed oil + thionyl chloride) and maleic anhydride. Quinoline is also incompatible with strong oxidizers and strong acids. Quinoline can be unpredictably violent. Quinoline dissolves sulfur, phosphorus and arsenic trioxide. Quinoline may attack some forms of plastics. Quinoline is a preparative hazard.
Угроза здоровью
No industrial injuries from quinoline exposure have been reported. Handling
precautions similar to those taken for pyridine are recommended (EOHS 1971).
Clinical signs of toxicity include lethargy, respiratory distress, and coma; cause
of death is respiratory paralysis.
Quinoline is a skin and eye irritant; it may cause permanent corneal injury
(EOHS 1971).
Routine occupational exposure to quinoline probably constitutes low risk for
acute toxicity. Long-term exposure to low concentrations may increase cancer
risk.
Химическая реактивность
Reactivity with Water No reaction; Reactivity with Common Materials: Attacks some forms of plastics; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
Промышленное использование
Quinoline is used as a solvent for resins and terpenes. It also is used as an
antimalarial, an antioxidant, a catalyst and as an intermediate in the manufacture
of various products (Parris et al 1983).
Профиль безопасности
Poison by ingestion, subcutaneous, and intraperitoneal routes. Moderately toxic by skin contact. A skin and severe eye irritant. Mutation data reported. Questionable carcinogen with experimental neoplastigenic and tumorigenic data. It can cause retinitis sdar to that caused by naphthalene but without causing opacity of the lens. Combustible when exposed to heat or flame. Its preparation has caused many industrial explosions. Potentially explosive reaction with hydrogen peroxide. Violent reaction with dmtrogen tetraoxide, perchromates. Incompatible with linseed oil + thionyl chloride, maleic anhydride, Unpredctably violent. When heated to decomposition it emits toxic fumes of NOx.
Возможный контакт
In manufacture of quinoline deriva-
tives (dyes and pesticides); in synthetic fuel manufacture.
Occurs in cigarette smoke.
Канцерогенность
Liver tumors were observed in
rats administered diets containing 0.05–0.25% quinoline.
The incidence of hepatocellular carcinomas was 3/11 at
0.05%, 3/16 at 0.1%, and 0/19 at 0.25% versus 0/6 in controls.
At 0.25%, most of the rats died within 40 weeks. The
incidences of hemangioendotheliomas were 6/11, 12/16,
18/19, and 0/6, respectively. Hepatocellular carcinomas
and hemangioendotheliomas were seen in livers of rats
fed 500, 1000, or 2500 ppm for 16–40 weeks. Typical
hyperplasias were also observed in the liver.
Экологическая судьба
biodegradative processes occur under aerobic conditions. Anaerobic degradation
is minimal (Mill et al 1981). Breakdown of quinoline in natural waters has been
correlated with bacterial concentration (Rogers et al 1984). Adsorption was high in
acidic soils (pH<6) and low in basic soils (pH>7). The presence of pyridine
decreased quinoline adsorption on acidic, but not basic, soils. Sorption did not
correlate with organic carbon or clay content (Felice et al 1984). Soil bacteria have
been grown with quinoline as the sole carbon source (Grant and Al-Najjar 1976).
Quinoline did not bioconcentrate to a significant extent in fathead minnows
(Southworth et al 1980).
Перевозки
UN2656 Quinoline, Hazard Class: 6.1; Labels:
6.1-Poisonous materials.
Несовместимости
Reacts, possibly violently, with strong
oxidants, strong acids; perchromates, nitrogen tetroxide;
and maleic anhydride. Keep away from moisture, steam,
and light. Contact with hydrogen peroxide may cause
explosion. Unpredictably violent, this substance has been
the source of various plant accidents.
Утилизация отходов
Dissolve or mix the material
with a combustible solvent and burn in a chemical incinera-
tor equipped with an afterburner and scrubber. All federal,
state, and local environmental regulations must be observed.
Хинолин препаратная продукция и сырье
сырьё
препарат