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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

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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.

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Reported found in Bantu beer.

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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.

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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.

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By catalytic oxidation of ethylene.

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ChEBI: A saturated organic heteromonocyclic parent that is a three-membered heterocycle of two carbon atoms and one oxygen atom.

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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.

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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).

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Irritant to eyes and skin. Confirmed carcinogen. Highly flammable, dangerous fire and explosion risk, flammable limits in air 3–100%.

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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.

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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.

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AMPROLENE®; ANPROLENE®; ANPROLINE®; BIODAC®; MERPOL®; OXYFUME®; OXYFUME 12®; T-GAS®; STERILIZING GAS ETHYLENE OXIDE 100%®

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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

Materials Uses

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.

Safety Profile

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.

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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

Carcinogenicity

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.

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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.

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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.

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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

Purification Methods

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.]

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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.

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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

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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.

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https://en.wikipedia.org/wiki/Ethylene_oxide
https://www.cancer.gov/about-cancer/causes-prevention/risk/substances/ethylene-oxide

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