Эпихлоргидрин химические свойства, назначение, производство
Описание
Epoxy resins of the bisphenol A type are synthesized
from epichlorhydrin and bisphenol A. This leads to
bisphenol-A diglycidyl ether, which is the monomer
of bisphenol-A-based epoxy resins. Sensitization to
epichlorhydrin occurs mainly in workers in the epoxy-resin industry. Sensitization in individuals not working
at epoxy resin plants is rare. It has however been described to occur after contact with a soil fumigant,
due to solvent cement and in a worker in a pharmaceutical
plant, in a division for drug synthesis.
Epichlorhydrin was used for the production of both
drugs propranolol and oxprenolol.
Химические свойства
Epichlorohydrin is a colorless liquid with
a slightly irritating, chloroform-like odor.
Физические свойства
Clear, colorless, mobile liquid with a strong, irritating, chloroform-like odor. Odor threshold
concentration is 0.93 ppm (quoted, Amoore and Hautala, 1983).
Использование
Epichlorohydrin is used to make glycerol,epoxy resins, adhesive, and castings; asderivatives for producing dyes, pharmaceu-ticals, surfactants, and plasticizers; and asa solvent for resins, gums, paints, andvarnishes.
Методы производства
Epichlorohydrin can be prepared from 1,3-dichloropropanol-2, 2,3- dichloropropanol-1, or allyl chloride. Commercially it is prepared as an intermediate in glycerol synthesis via alkaline hydrolysis of glycerol dichlorohydrin. Both come from allyl chloride. Epichlorohydrin reacts with monohydric alcohols to give ethers by opening the oxide ring. It will react with ethers, aldehydes, ketones, organic acids and amines to give a wide variety of useful syntheses.
Определение
ChEBI: An epoxide that is 1,2-epoxypropene in which one of the methyl hydrogens is substituted by chlorine.
Общее описание
A clear colorless liquid with an irritating chloroform-like odor. Density 9.8 lb / gal. Flash point 87°F. Polymerizable. If polymerization takes place inside a closed container, the container is subject to violent rupture. Irritates the skin and respiratory system. Toxic by ingestion. A confirmed carcinogen. Vapors heavier than air. Used to make plastics and as a solvent.
Реакции воздуха и воды
Highly flammable. Water soluble.
Профиль реактивности
Epichlorohydrin may polymerize exothermically if heated or contaminated. Reacts explosively with aniline. Ignites on contact with potassium tert-butoxide. Reacts with trichloroethylene to give the explosive dichloroacetylene. Violent reaction with sulfuric acid or isopropylamine. Exothermic polymerization on contact with strong acids or bases, zinc, aluminum, aluminum chloride, iron, ferric chloride [Sax, 9th ed., 1996, p. 1469].
Опасность
Toxic by inhalation, ingestion, and
skin absorption; strong irritant, a carcinogen.
Flammable, moderate fire risk. TLV: 0.5 ppm; animal carcinogen.
Угроза здоровью
Epichlorohydrin is caustic as both a liquid and gas. Irritation of the eyes and skin, and skin sensitization has been observed. Exposure to epichlorohydrin has caused inflammation of the lungs, asthmatic bronchitis, and liver and kidney damage. In acute poisonings, death may be caused by respiratory paralysis.
Пожароопасность
When heated to decomposition, Epichlorohydrin evolves highly toxic fumes of phosgene and carbon monoxide. Reactive and incompatible with strong oxidizers, strong acids, caustics, zinc, aluminum, chlorides of iron and aluminumand compounds with an active hydrogen atom, including water. Unstable, avoid heat, contaminants, strong acids and bases, certain curing agents such as ethylenediamine. Hazardous polymerization may occur.
Химическая реактивность
Reactivity with Water Mild reaction; not likely to be hazardous; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Can polymerize in presence of strong acids and bases, particularly when hot; Inhibitor of Polymerization: None used.
Контактные аллергены
Epoxy resin of the Bisphenol A type is synthesized
from epichlorhydrin and bisphenol A. It leads to bisphenol
A diglycidyl ether, which is the monomer ofbisphenol-A-based epoxy resins. Sensitization to
epichlorhydrin occurs mainly in workers of the epoxy
resin industry. Sensitization in individuals not working
at epoxy resin plants is rare. It has, however, been
described to occur following exposure to a soil fumigant,
due to solvent cement, and in a worker in a pharmaceutical
plant, in a division of drug synthesis.
Epichlorhydrin was used for the production of drugs
propranolol and oxprenolol.
Профиль безопасности
Confirmed carcinogen
with experimental carcinogenic data. Poison
by ingestion, skin contact, intravenous, and
intraperitoneal routes. Moderately toxic by
inhalation. An experimental teratogen.
Other experimental reproductive effects.
Human systemic effects by inhalation:
respiratory, nose, and eyes. Human mutation
data reported. A skin and eye irritant. A
sensitizer. Flammable liquid when exposed
to heat or flame. Explosive reaction with
andine. Reaction with trichloroethylene
forms the explosive dichloroacetylene.
Ignition on contact with potassium tertbutoxide. Violent reaction with sulfuric acid
or isopropylamine. Exothermic
polymerization on contact with strong acids,
caustic alkalies, aluminum, aluminum
chloride, iron(II1) chloride, or zinc. When
heated to decomposition it emits toxic
fumes of Cl
Возможный контакт
Epichlorohydrin, an organochlorine, is
used in the manufacture of many glycerol and glycidol derivatives and epoxy resins; as a stabilizer in chlorine-containing
materials; as an intermediate in the preparation of cellulose
esters and ethers, paints, varnishes, nail enamels, and lacquers;
as a cement for celluloid. It is used as an intermediate in the
manufacture of various drugs. Increased cancer risk.
Канцерогенность
Epichlorohydrin is reasonably anticipated to be a human carcinogenbased on sufficient evidence of carcinogenicity from studies in experimental animals.
Экологическая судьба
Biological. Bridié et al. (1979) reported BOD and COD values of 0.03 and 1.16 g/g using
filtered effluent from a biological sanitary waste treatment plant. These values were determined
using a standard dilution method at 20 °C for a period of 5 d. When a sewage seed was used in a
separate screening test, a BOD value of 0.16 g/g was obtained. The ThOD for epichlorohydrin is
1.21 g/g.
Chemical/Physical. Anticipated products from the reaction of epichlorohydrin with ozone or
OH radicals in the atmosphere are formaldehyde, glyoxylic acid, and ClCH2O(O)OHCHO (Cupitt,
1980). Haag and Yao (1992) reported a calculated OH radical rate constant in water of 2.9 x
108/M?sec.
хранилище
Epichlorohydrin is stored in a well-ventilated,cool place isolated from combustible andoxidizable materials, all acids and bases,and anhydrous metal halides. Protect fromphysical damage. It is shipped in metaldrums.
Перевозки
UN2023 Epichlorhydrin, Hazard class: 6.1;
Labels: 6.1-Poisonous materials, 3-Flammable liquid.
Методы очистки
Distil epichlorohydrin under atmospheric pressure, heat it on a steam bath with one-quarter its weight of CaO, then decant and fractionally distil it. [Beilstein 17 V 20.]
Несовместимости
May form explosive mixture with air.
Slowly decomposes on contact with water. Heat or strong
acids; alkalies, metallic halides, or contaminants can cause
explosive polymerization. Violent reaction with strong oxidizers, aliphatic amines; alkanolamines, amines (especially
aniline), alkaline earths; chemically active metals (chlorides
of aluminum, iron zinc); powdered metals (aluminum,
zinc); alcohols, phenols, organic acids; causing fire and
explosion hazard. Will pit steel in the presence of water.
Thermal decomposition forms highly toxic phosgene gas.
May accumulate static electrical charges, and may cause
ignition of its vapors.
Утилизация отходов
Incineration, preferably after
mixing with another combustible fuel. Care must be exercised to assure complete combustion to prevent the formation of phosgene. An acid scrubber is necessary to remove
the halo acids produced. 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
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