“Oxirane” redirects here. For oxiranes as a class of molecules, see epoxide. | Ethylene oxide | | | | | IUPAC name | epoxyethane | | Other names | ethylene oxide, dimethylene oxide, oxirane, oxacyclopropane | | Identifiers | | CAS number | 75-21-8 | | PubChem | 6354 | | EINECS number | 200-849-9 | | KEGG | C06548 | | MeSH | Ethylene+Oxide | | ChEBI | 27561 | | RTECS number | KX2450000 | | SMILES | C1CO1 | | InChI | InChI=1/C2H4O/c1-2-3-1/h1-2H2 | | Properties | | Molecular formula | C2H4O | | Molar mass | 44.05 g mol−1 | | Appearance | colorless gas | | Density | 0.882 | | Melting point | −111.3 °C An epoxide is a cyclic ether with only three ring atoms. ...
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IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ...
CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ...
PubChem is a database of chemical molecules. ...
The EINECS number (for European Inventory of Existing Chemical Substances) is a registry number given to each chemical substance commercially available in the European Union between 1 January 1971 and 18 September 1981. ...
KEGG PATHWAY Database is one of the important databases in bioinformatics. ...
Medical Subject Headings (MeSH) is a huge controlled vocabulary (or metadata system) for the purpose of indexing journal articles and books in the life sciences. ...
ChEBI (meaning Chemical Entities of Biological Interest, or Chemistry at the EBI) is a database of molecular entities focused on small chemical compounds. ...
RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ...
The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ...
The IUPAC International Chemical Identifier (InChI), developed by IUPAC and NIST, is a digital equivalent of the IUPAC name for any particular covalent compound. ...
A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ...
Molar mass is the mass of one mole of a chemical element or chemical compound. ...
For other uses, see Density (disambiguation). ...
The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. ...
| | Boiling point | 10.7 °C Italic text This article is about the boiling point of liquids. ...
| | Solubility in water | miscible | | Thermochemistry | Std enthalpy of
formation ΔfHo298 | −52.6 kJ mol−1 | Standard molar
entropy So298 | 243 J mol−1 K−1 | | Hazards | | Flash point | −20 °C | | Explosive limits | 3 to 100% | Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references | The chemical compound ethylene oxide is an important industrial chemical used as an intermediate in the production of ethylene glycol and other chemicals, and as a sterilant for foods and medical supplies. It is a colorless flammable gas or refrigerated liquid with a faintly sweet odor. It is the simplest example of an epoxide. Solubility is a chemical property referring to the ability for a given substance, the solute, to dissolve in a solvent. ...
Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ...
The standard enthalpy of formation or standard heat of formation of a compound is the change of enthalpy that accompanies the formation of 1 mole of a substance in its standard state from its constituent elements in their standard states (the most stable form of the element at 1 atmosphere...
In chemistry, the standard molar entropy is the entropy content of one mole of substance, under conditions of standard temperature and pressure. ...
For other uses, see Flash point (disambiguation). ...
The explosive limit of a gas or a vapour, is the limiting concentration (in air) that is needed for the gas to ignite and explode. ...
In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ...
A chemical compound is a chemical substance of two or more different chemically bonded chemical elements, with a fixed ratio determining the composition. ...
Ethylene glycol (monoethylene glycol (MEG), IUPAC name: ethane-1,2-diol) is an alcohol with two -OH groups (a diol), a chemical compound widely used as an automotive antifreeze. ...
An epoxide is a cyclic ether with only three ring atoms. ...
Its IUPAC name is epoxyethane. Other names for it include oxirane and dimethylene oxide. The International Union of Pure and Applied Chemistry (IUPAC) is an international non-governmental organization devoted to the advancement of chemistry. ...
History Ethylene oxide was first prepared in 1859 by the French chemist Charles-Adolphe Wurtz,[1] who prepared it by treating 2-chloroethanol with a base. It achieved industrial importance during World War I as a precursor to both the coolant ethylene glycol and the chemical weapon mustard gas. In 1931, Theodore Lefort, another French chemist, discovered a means to prepare ethylene oxide directly from ethylene and oxygen, using silver as a catalyst. Since 1940, almost all ethylene oxide produced industrially has been made using this method.[2] Year 1859 (MDCCCLIX) was a common year starting on Saturday (link will display the full calendar) of the Gregorian calendar (or a common year starting on Thursday of the 12-day slower Julian calendar). ...
Charles Adolphe Wurtz (November 26, 1817 - May 10, 1884) was a French chemist. ...
2-Chloroethanol is a colorless liquid similar to glycerine with faint, sweet pleasant ether-like odor. ...
Acids and bases: Acid-base reaction pH Self-ionization of water Buffer solutions Systematic naming Acid-base extraction Acidity function Proton affinity Acids: Strong acids Weak acids Superacids Lewis acids Mineral acids Organic acids Bases: Strong bases Weak bases Superbases Lewis bases Organic bases edit In chemistry, a base is...
“The Great War †redirects here. ...
Ethylene glycol (monoethylene glycol (MEG), IUPAC name: ethane-1,2-diol) is an alcohol with two -OH groups (a diol), a chemical compound widely used as an automotive antifreeze. ...
Dressing the wounded during a gas attack by Austin O. Spare, 1918. ...
Airborne exposure limit 0. ...
Year 1931 (MCMXXXI) was a common year starting on Thursday (link will display full 1931 calendar) of the Gregorian calendar. ...
Ethylene (or IUPAC name ethene) is the chemical compound with the formula C2H4. ...
General Name, symbol, number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, period, block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ...
This article is about the chemical element. ...
It has been suggested that this article or section be merged into Catalysis. ...
Year 1940 (MCMXL) was a leap year starting on Monday (link will display the full 1940 calendar) of the Gregorian calendar. ...
Production Industrially, ethylene oxide is produced when ethylene (CH2=CH2) and oxygen (O2) react on a silver catalyst at 200–300 °C showing large Ag nanoparticles supported on Alumina. Typically, chemical modifiers such as chlorine are also included. Pressures used are in the region of 1-2MPa. The chemical equation for this reaction is: Ethylene (or IUPAC name ethene) is the chemical compound with the formula C2H4. ...
General Name, symbol, number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, period, block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ...
A chemical equation is a symbolic representation of a chemical reaction. ...
For other uses, see Chemical reaction (disambiguation). ...
- CH2=CH2 + ½ O2 → C2H4O
The typical yield for this reaction under industrial conditions is 70-80%. In the reaction scheme above, an intermediate (oxametallacycle) is formed. Two different reaction pathways can then occur.
Ethylene oxide formation:
- CH2=CH2 + O → C2H4O
Acetaldehyde formation: - CH2=CH2 + O → CH3CHO
The latter pathway is the first step in complete combustion, leading to carbon dioxide and water: A combustion reaction taking place in a igniting match Combustion or burning is a complex sequence of exothermic chemical reactions between a fuel and an oxidant accompanied by the production of heat or both heat and light in the form of either a glow or flames. ...
Carbon dioxide is a chemical compound composed of two oxygen atoms covalently bonded to a single carbon atom. ...
Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ...
- CH3CHO +5/2 O2 → 2CO2 + 2H2O
Several methods to produce ethylene oxide more selectively have been proposed, but none have achieved industrial importance.[citation needed]
Uses Ethylene oxide gas kills bacteria (and their endospores), mold, and fungi, and can therefore be used to sterilize substances that would be damaged by sterilizing techniques such as pasteurization that rely on heat. Ethylene oxide sterilization for the preservation of spices was patented in 1938 by the American chemist Lloyd Hall, and it is still used in that role. Additionally, ethylene oxide is widely used to sterilize medical supplies such as bandages, sutures, and surgical implements. The overwhelming majority of medical items are sterilized with ethylene oxide. Preferred methods have been the traditional chamber sterilization method, where a chamber is flooded with a mix of ethylene oxide and other gases which are later aerated, and the more recent gas diffusion method which relies on a bag that wraps the elements to be sterilized and acts a a mini-chamber in order to minimize gas consumption and make the process economically feasible for small loads. Phyla/Divisions Actinobacteria Aquificae Bacteroidetes/Chlorobi Chlamydiae/Verrucomicrobia Chloroflexi Chrysiogenetes Cyanobacteria Deferribacteres Deinococcus-Thermus Dictyoglomi Fibrobacteres/Acidobacteria Firmicutes Fusobacteria Gemmatimonadetes Nitrospirae Omnibacteria Planctomycetes Proteobacteria Spirochaetes Thermodesulfobacteria Thermomicrobia Thermotogae Bacteria (singular, bacterium) are a major group of living organisms. ...
An endospore is a dormant, tough, non-reproductive structure produced by a small number of bacteria from the Firmicute family. ...
It has been suggested that Toxic mold be merged into this article or section. ...
Divisions Chytridiomycota Zygomycota Ascomycota Basidiomycota The Fungi (singular: fungus) are a large group of organisms ranked as a kingdom within the Domain Eukaryota. ...
Pasteurization (or pasteurisation) is the process of heating liquids for the purpose of destroying viruses and harmful organisms such as bacteria, protozoa, molds, and yeasts. ...
For other uses, see Spice (disambiguation). ...
Year 1938 (MCMXXXVIII) was a common year starting on Saturday (link will take you to calendar). ...
Lloyd Augustus Hall (June 20, 1894 - January 2, 1971) was an African American chemist who contributed to the science of food preservation. ...
Sutures are the stitches doctors, and especially surgeons, use to hold skin, organs, blood vessels and all other tissues of the human body together, after they have been severed in minor or major surgery. ...
Most ethylene oxide, however, is used as an intermediate in the production of other chemicals. The major use of ethylene oxide is in the production of ethylene glycol. The primary end use for ethylene glycol is in the production of polyester polymers. Ethylene glycol is more commonly known for its use as an automotive coolant and antifreeze. Ethylene glycol (monoethylene glycol (MEG), IUPAC name: ethane-1,2-diol) is an alcohol with two -OH groups (a diol), a chemical compound widely used as an automotive antifreeze. ...
SEM picture of a bend in a high surface area polyester fiber with a seven-lobed cross section Polyester is a category of polymers, or, more specifically condensation polymers, which contain the ester functional group in their main chain. ...
Antifreeze is used in internal combustion engines, and for many other heat transfer applications, such as electronics cooling and chillers for HVAC. Compounds are added to water to reduce the freezing point of the mixture to below the lowest temperature that the system is likely to be exposed to, and...
Because of its high flammability and wide explosive concentration range in air, ethylene oxide is sometimes used as the fuel component of a fuel-air explosive. A high-impulse thermobaric weapon (HIT), also known as a fuel-air explosive (FAE or FAX), a heat and pressure weapon, or a vacuum bomb, consists of a container of a volatile liquid, in some designs including a finely powdered explosive component as a slurry, and (typically) two separate explosive...
Reactions Most reactions are ring openings by nucleophiles. In chemistry, a nucleophile (literally nucleus lover) is a reagent which is attracted to centres of positive charge. ...
In industry, epoxyethane is reacted with water in the presence of a sulfuric acid catalyst. A tenfold molar excess of water is used to obtain ethylene glycol: Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ...
R-phrases S-phrases , , , Flash point Non-flammable Related Compounds Related strong acids Selenic acid Hydrochloric acid Nitric acid Related compounds Hydrogen sulfide Sulfurous acid Peroxymonosulfuric acid Sulfur trioxide Oleum Supplementary data page Structure and properties n, εr, etc. ...
C2H4O + H2O → HOCH2CH2OH
Despite the large excess of water, various types of polyethylene glycol (PEG) or polyethylene oxide (PEO) are still formed as secondary products. The degree of polymerization increases as a smaller proportion of water is used: Polyethylene glycol (PEG) and polyethylene oxide (PEO) are polymers composed of repeating subunits of identical structure, called monomers, and are the most commercially important polyethers. ...
Polyethylene glycol (PEG) and polyethylene oxide are polymers of ethylene oxide. ...
An example of alkene polymerisation, in which each Styrene monomer units double bond reforms as a single bond with another styrene monomer and forms polystyrene. ...
n(CH2CH2O) + H2O → HO(CH2CH2O)nH
For example, under the right conditions it can give diethylene glycol (HOCH2CH2OCH2CH2OH), triethylene glycol, etc. Diethylene glycol (DEG) is an organic compound described by the structural formula HO-CH2-CH2-O-CH2-CH2-OH. It is a clear, hygroscopic, odorless liquid. ...
Diethylene glycol (DEG, 3-oxa-1,5-pentanediol, diglycol, ethylene diglycol, or dihydroxy diethyl ether) is a diol, an alcohol with two -OH groups, a dimer of ethylene glycol. ...
Similarly, reaction with ammonia can yield ethanolamine, diethanolamine, or triethanolamine. For other uses, see Ammonia (disambiguation). ...
Ethanolamine, also called 2-aminoethanol or monoethanolamine (often abbreviated as MEA), is an organic chemical compound which is both a primary amine (due to an amino group in its molecule) and a primary alcohol (due to a hydroxyl group). ...
Ethylene oxide is also important in the manufacture of surfactants and other detergents, in a process called ethoxylation. Surfactants, also known as tensides, are wetting agents that lower the surface tension of a liquid, allowing easier spreading, and lower the interfacial tension between two liquids. ...
Laundry detergents are just one of many possible uses for detergents Detergent is a compound, or a mixture of compounds, intended to assist cleaning. ...
Ethoxylation is a chemical process in which ethylene oxide (IUPAC name: 1,2-epoxyethane) is added to fatty acids in order to make them more soluble in water. ...
One class of ethylene oxide derivatives that has attracted much scientific attention is the crown ethers, which are cyclic oligomers of ethylene oxide. These compounds have the ability to make ionic compounds such as salts soluble in nonpolar solvents which they otherwise could not dissolve in. However, the high cost of these compounds has largely confined their use to the laboratory rather than industrial practice. Crown ethers are heterocyclic chemical compounds that, in their simplest form, are cyclic oligomers of ethylene oxide. ...
In chemistry, an oligomer consists of a finite number of monomer units (oligo is Greek for a few), in contrast to a polymer which, at least in principle, consists of an infinite number of monomers. ...
The crystal structure of sodium chloride, NaCl, a typical ionic compound. ...
For other uses, see Salt (disambiguation). ...
For other uses, see Solvent (disambiguation). ...
Health effects Ethylene oxide is toxic by inhalation. Symptoms of overexposure include headache and dizziness, progressing with increasing exposure to convulsions, seizure and coma. It is also an irritant to skin and the respiratory tract, and inhaling the vapors may cause the lungs to fill with fluid several hours after exposure.[3]
Ethylene oxide is usually stored as a pressurized or refrigerated liquid. At room temperature and pressure, it rapidly evaporates, potentially causing frostbite in cases of skin exposure.
Laboratory animals exposed to ethylene oxide for their entire lives have had a higher incidence of liver cancer. However, studies on human beings who have worked with ethylene oxide for extended periods and may have experienced low doses during that time have found no increase in cancer risk. Chronic ethylene oxide exposure may increase the risk of cataracts in humans. The liver is an organ present in vertebrates and some other animals. ...
Cancer is a class of diseases or disorders characterized by uncontrolled division of cells and the ability of these to spread, either by direct growth into adjacent tissue through invasion, or by implantation into distant sites by metastasis (where cancer cells are transported through the bloodstream or lymphatic system). ...
Human eye cross-sectional view, showing position of human lens. ...
In animals, ethylene oxide can cause numerous reproductive effects, including mutations and a higher rate of miscarriages. Its reproductive effects on humans have not been well studied, but it is considered probable that ethylene oxide exposure has similar effects on human reproduction. It has been suggested that mutant be merged into this article or section. ...
Miscarriage or spontaneous abortion is the natural or spontaneous end of a pregnancy at a stage where the embryo or the fetus is incapable of surviving, generally defined in humans at a gestation of prior to 20 weeks. ...
Ethylene oxide is classified as carcinogenic to humans by the International Agency for Research on Cancer (IARC).[4]
See also R-phrases , , S-phrases , , , Flash point −39 °C Autoignition temperature 185 °C RTECS number AB1925000 Supplementary data page Structure and properties n, εr, etc. ...
Ethenol, also called vinyl alcohol, hydroxyethene or hydroxyethylene, is an alcohol with chemical formula C2H4O (H2C=CHOH) and CAS number 557-75-5. ...
External links
References - ^ Wurtz, A. (1859). "". Compt. rend. 48: 101-104.
- ^ P. P. McClellan (1950). "Manufacture and Uses of Ethylene Oxide and Ethylene Glycol". Ind. Eng. Chem. 42: 2402 - 2407. DOI:10.1021/ie50492a013.
- ^ http://www.anpro.com/support/MSDS.pdf
- ^ http://monographs.iarc.fr/ENG/Monographs/vol60/volume60.pdf
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