ЭТИЛЕНОКСИД химические свойства, назначение, производство
Описание
Ethylene oxide (C2H4O) is a kind of cyclic ether with important industrial applications. Although it is highly toxic and dangerous for household application and consumers to use, it can be used for the manufacture of many important industrial and commercialized products as well as some chemicals and intermediates. For example, it is very useful in the production of detergents, thickeners, solvents, plastics, and many kinds of organic chemicals such as ethylene glycol, ethanolamines, simple and complex glycols, polyglycol ethers, and other compounds. It is also a commonly sterilization methods used in the healthcare industry. In addition, it can be used as an accelerator of maturation of tobacco leaves and fungicide, as well as the main component of thermobaric weapons (fuel-air explosives). In industry, it is generally manufactured through direct oxidation of ethylene. In low doses, it can be used as a pesticide and a sterilizing agent owing to its effect of causing DNA damage. However, this property also make it a potential carcinogen.
ethylene oxide structure
Химические свойства
Ethylene oxide is the simplest cyclic ether. It is a colorless gas or liquid and has a sweet, etheric odor. Ethylene oxide is a flammable, very reactive and explosive chemical substance. On decomposition, vapors of pure ethylene oxide mix with air or inert gases and become highly explosive. Ethylene oxide, is used in large scale as an intermediate in the production of monoethylene glycol, diethylene glycol, triethylene glycol, poly(ethylene) glycols, ethylene glycol ethers, ethanolamine, ethoxylation products of fatty alcohols, fatty amines, alkyl phenols, cellulose, and poly(propylene glycol). It is also used as a fumigant for food and cosmetics, and in hospital sterilization of surgical equipment and heat sensitive materials.
Вхождение
Reported found in Bantu beer.
Использование
Ethylene oxide is widely used as a sterilizingagent; as a fumigant; as a propellant; in theproduction of explosives; in the manufactureof ethylene glycol, polyethylene oxide, gly-col ethers, crown ethers, ethanolamines, andother derivatives; and in organic synthesis.
Методы производства
Ethylene oxide is currently produced by the direct oxidation
of ethylene with oxygen or air over a catalyst. Ethylene is
approximately 60% converted to the oxide at temperatures in
the range of 100–150℃. In the past, an indirect but more
general and more specific synthesis path consisted of adding
hypochlorous acid to olefins to form the chlorohydrins.
Subsequent treatment with strong bases results in dehydrochlorination
and the formation of the epoxide.
Подготовка
By catalytic oxidation of ethylene.
Определение
ChEBI: A saturated organic heteromonocyclic parent that is a three-membered heterocycle of two carbon atoms and one oxygen atom.
Реакции воздуха и воды
Highly flammable. Flammable over a wide vapor-air concentration range. Must be diluted on the order of 24 to 1 with water to lose flammability. Soluble in water.
Профиль реактивности
Colorless gas at room temperature (b.p. 11°C), confirmed carcinogen. Highly flammable, severe explosion hazard when exposed to flame. The autoignition temperature may be as low as 140° C in presence of rust. Rapid compression of the vapor with air causes explosion. ETHYLENE OXIDE vapor may be initiated into explosive decomposition in absence of air [Hess, L. G., et al., Ind. Eng. Chem., 1950, 42, p. 1251]. Metal fittings containing magnesium, copper or silver should be avoided, since traces of acetylene in ETHYLENE OXIDE may produce metal acetylides capable of detonating the vapor [MCA SD-38, 1971]. Violent polymerization occurs on contact with strong bases (alkali hydroxides, ammonia) or acids, amines, metallic potassium, oxides (aluminum oxide, iron oxide, rust), covalent halides (aluminum chloride, ferric chloride, tin(IV) chloride) [Gupta, A. K., J. Soc. Chem. Ind., 1949, 68, p. 179]. Violent reaction with m-nitroaniline, magnesium perchlorate, mercaptans, thiols, triethylamine [Bretherick, 5th ed., 1995, p. 316]. ETHYLENE OXIDE and SO2 can react violently in pyridine solution with pressurization if ETHYLENE OXIDE is in excess (Nolan, 1983, Case History 51).
Опасность
Irritant to eyes and skin. Confirmed carcinogen. Highly flammable, dangerous fire and
explosion risk, flammable limits in air 3–100%.
Воспламеняемость и взрывоопасность
Ethylene oxide is an extremely flammable substance (NFPA rating = 4). Ethylene oxide vapor may be ignited by hot surfaces such as hot plates and static electricity discharges, and since the vapor is heavier than air, it may travel a considerable distance to an ignition source and flash back. Ethylene oxide vapor forms explosive mixtures with air at concentrations of 3 to 100% (by volume). Carbon dioxide or dry chemical extinguishers should be used for ethylene oxide fires. Ethylene oxide may explode when heated in a closed vessel.
Сельскохозяйственное использование
Fungicide and fumigant: Ethylene oxide is used as a fumigant for spices, seasonings,
and foodstuffs and as an agricultural fungicide.
When used directly in the gaseous form or in nonexplosive
gaseous mixtures with nitrogen or carbon dioxide, ethylene
oxide can act as a disinfectant, fumigant, sterilizing
agent, and insecticide. It is a man-made chemical used as
an intermediate in organic synthesis for ethylene glycol,
polyglycols, glycol ethers, esters, ethanolamines, acrylonitrile,
plastics, and surface-active agents. It is also used
as a fumigant for textiles and for sterilization, especially
for surgical instruments. It is used in drug synthesis and
as a pesticide intermediate. Not approved for use in EU
countries. Actively registered in the U.S.
Торговое название
AMPROLENE®; ANPROLENE®;
ANPROLINE®; BIODAC®; MERPOL®; OXYFUME®;
OXYFUME 12®; T-GAS®; STERILIZING GAS
ETHYLENE OXIDE 100%®
Контактные аллергены
Ethylene oxide is a very strong irritant widely used in
the chemical industry, and as a sterilizer of medical
supplies, pharmaceutical products, and food. It can
produce immediate (urticaria, asthma, anaphylaxis) or
delayed reactions (irritant rather than allergic contact
dermatitis). For example, residues in masks or dressings
can produce irritant contact dermatitis.In delayed
contact allergy, it seems that cross-reaction can be
observed to epichlorhydrin or epoxypropane
Использование в материалах
Steel and stainless steel are suitable materials
for equipment and piping in ethylene oxide
service. Dangerous runaway reactions can result
from contact with copper, silver, magnesium and their alloys; mercury and its salts; oxidizers
of all types; alkalis and acids; alcohols; mercaptans;
and alkali metals. Ethylene oxide will
polymerize violently if contaminated with aqueous
alkalis, amines, mineral acids, metal chlorides,
or metal oxides.
Профиль безопасности
Confirmed human
carcinogen with experimental carcinogenic,
tumorigenic, neoplastigenic, and teratogenic
data. Poison by ingestion, intraperitoneal,
subcutaneous, and intravenous routes.
Moderately toxic by inhalation. Human
systemic effects by inhalation: convulsions,
nausea, vomiting, olfactory and pulmonary
changes. Experimental reproductive effects.
Mutation data reported. A skin and eye
irritant. An irritant to mucous membranes of
respiratory tract. High concentrations can
cause pulmonary edema.
Highly flammable liquid or gas. Severe
explosion hazard when exposed to flame.
To fight fire, use alcohol foam, CO2, dry
chemical. Violent polymerization occurs on
contact with ammonia, alkali hydroxides,
amines, metalllc potassium, acids, covalent
halides (e.g., aluminum chloride, iron(Ⅲ)
chloride, tin(rv> chloride, aluminum oxide,
iron oxide, rust). Explosive reaction with
glycerol at 200℃. Rapid compression of the
vapor with air causes explosions. Incompatible with bases, alcohols, air, m-nitroanlline,
trimethyl amine, copper, iron chlorides, iron
oxides, magnesium perchlorate, mercaptans,
potassium, tin chlorides, contaminants,
alkane thols, bromoethane. When heated to decomposition it emits acrid smoke and
irritating fumes.
Возможный контакт
Ethylene oxide is a man-made chemical used in the production of glycols (ethylene glycol, polyglycols, glycol ethers, esters), nontonic surface-active
agent; ethanolamines, acrylonitrile, plastics. It is also used
as a fumigant for foodstuffs and textiles; an agricultural
fungicide; and for sterilization, especially for surgical
instruments. It is used in drug synthesis and as a pesticide
intermediate
Канцерогенность
Ethylene oxide is known to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in humans, including epidemiological studies and studies on mechanisms of carcinogenesis. Ethylene oxide was first listed in the Fourth Annual Report on Carcinogens in 1985 as reasonably anticipated to be a human carcinogen based on limited evidence of carcinogenicity from studies in humansand sufficient evidence of carcinogenicity from studies in experimental animals. The listing was revised to known to be a human carcinogen in the Ninth Report on Carcinogens in 2000.
An increased risk of cancer has been demonstrated in epidemiological studies of workers using ethylene oxide as a sterilant for medical devices and spices and in chemical synthesis and production.Evidence for a common mechanism of carcinogenesis in humans and experimental animals comes from studies that have found similar genetic damage in cells of animals and workers exposed to ethylene oxide. The DNA-damaging activity of ethylene oxide explains its effectiveness as a sterilant, and this same property accounts for its carcinogenic risk to humans.
Экологическая судьба
Ethylene oxide released to the environment partitions primarily
to the atmosphere due to its high volatility (vapor pressure
146 kPa at 20℃). Although the high water solubility of
ethylene oxide suggests it can be extracted from air by rainfall, its
rapid volatilization from water (half-life of 1 h) argues against
this process being a significant factor in its environmental fate.
In the atmosphere, ethylene oxide reacts with hydroxyl radicals
resulting in a half-life of 2–5 months. In freshwater, ethylene
oxide is hydrolyzed to ethylene glycol (half-life ～ 1 week); in
salt water, it is hydrolyzed to ethylene glycol and ethylene
chlorohydrin (half-life ～2 weeks). In unacclimated aqueous
media, ethylene oxide is also subject to biodegradation with
estimated half-lives of 1–6 months (aerobic) and 4–24 months
(anaerobic). However, in the presence of activated sludge,
ethylene oxide is readily biodegradable. Due to its high volatility
and water solubility, ethylene oxide is not expected to persist in
soil or sediments. The low log Kow (-0.30) for ethylene oxide
indicates little potential for bioaccumulation.
хранилище
work with ethylene oxide should be conducted in a fume hood to prevent exposure by inhalation, and appropriate impermeable gloves and splash goggles should be worn at all times to prevent skin and eye contact. Ethylene oxide should be used only in areas free of ignition sources and should be stored in the cold in tightly sealed containers placed within a secondary container.
Перевозки
UN1040 Ethylene oxide or Ethylene oxide with
nitrogen up to a total pressure of 1 MPa (10 bar) at 50℃,
Hazard Class: 2.3; Labels: 2.3-Poisonous gas, 2.1-
Flammable gas, Inhalation Hazard Zone D. Cylinders must
be transported in a secure upright position, in a wellventilated truck. Protect cylinder and labels from physical
damage. The owner of the compressed gas cylinder is the
only entity allowed by federal law (49CFR) to transport
and refill them. It is a violation of transportation regulations to refill compressed gas cylinders without the express
written permission of the owner
Методы очистки
Dry oxirane with CaSO4, then distil it from crushed NaOH. It has also been purified by passage, as a gas, through towers containing solid NaOH. [Beilstein 17/1 V 3.]
Несовместимости
May form explosive mixture with air.
Chemically unstable. Dangerously reactive; may rearrange
chemically and/or polymerize violently with evolution of
heat; when in contact with highly active catalytic surfaces,
such as anhydrous chlorides of iron, tin and aluminum;
pure oxides of iron and aluminum; and alkali metal hydroxides. Even small amounts of strong acids; alkalis, or oxidizers can cause a reaction. Avoid contact with copper.
Protect container from physical damage, sun and heat.
Attacks some plastics, rubber or coatings.
Утилизация отходов
Return refillable compressed
gas cylinders to supplier. Concentrated waste containing no
peroxides-discharge liquid at a controlled rate near a pilot
flame. Concentrated waste containing peroxides-perforation
of a container of the waste from a safe distance followed
by open burning
Меры предосторожности
Ethylene oxide is dangerously explosive under fi re condition; it is flammable over an extremely large range of concentrations in air and burns in the absence of oxygen.
использованная литература
https://en.wikipedia.org/wiki/Ethylene_oxide
https://www.cancer.gov/about-cancer/causes-prevention/risk/substances/ethylene-oxide
ЭТИЛЕНОКСИД препаратная продукция и сырье
сырьё
Epoxy
Alkaline Earth Metals, plasma standard solution, Specpure, Ba, Be, Ca, Mg, Sr § 100μg/ml
ЭТИЛЕН
1-chlorohydrin
Nitrogen
Этанол
Кремний карбид
альция оксид
Хлор
Кислород
PETROLEUM ETHER
2-ХЛОРЭТАНОЛ
Alkali Metals, plasma standard solution, Specpure, Ba,Be,Ca,Cs,K,Li,Mg,Na,Rb,Sr, 100μg/ml
Silver catalyst
препарат