Ethylene glycol
IUPAC name	Ethane-1,2-diol
Other names	Ethylene glycol Monoethylene glycol MEG 1,2-ethanediol
Identifiers
CAS number	107-21-1
SMILES	OCCO
Properties
Molecular formula	C2H4(OH)2
Molar mass	62.068 g/mol
Density	1.1132 g/cm³
Melting point	−12.9 °C (8.8°F) Download high resolution version (1372x469, 3 KB) Wikipedia does not have an article with this exact name. ... Image File history File links Size of this preview: 800 × 449 pixelsFull resolution‎ (1,100 × 618 pixels, file size: 116 KB, MIME type: image/png) File historyClick on a date/time to view the file as it appeared at that time. ... Image File history File links Download high-resolution version (1100x713, 158 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Ethylene glycol ... 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. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... 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	197.3 °C (387°F) Italic text This article is about the boiling point of liquids. ...
Solubility in water	Miscible with water in all proportions.
Viscosity	16.1 mPa s [1]
Hazards
MSDS	External MSDS
Flash point	111 °C (closed cup)
Autoignition temperature	410 °C
Supplementary data page
Structure and properties	n, εr, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

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. In its pure form, it is an odorless, colorless, syrupy liquid with a sweet taste. Ethylene glycol is toxic, and its accidental ingestion should be considered a medical emergency. 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 chemistry term miscible refers to the property of various liquids that allows them to be mixed together. ... For other uses, see Viscosity (disambiguation). ... An example MSDS in a US format provides guidance for handling a hazardous substance and information on its composition and properties. ... This page provides supplementary chemical data on ethylene glycol. ... For other uses, see Flash point (disambiguation). ... The autoignition temperature, or the ignition temperature of a substance is the lowest temperature at which a chemical will spontaneously ignite in a normal atmosphere, without an external source of ignition, such as a flame or spark. ... This page provides supplementary chemical data on ethylene glycol. ... This page provides supplementary chemical data on ethylene glycol. ... The refractive index (or index of refraction) of a medium is a measure for how much the speed of light (or other waves such as sound waves) is reduced inside the medium. ... The relative dielectric constant of a material under given conditions is a measure of the extent to which it concentrates electrostatic lines of flux. ... This page provides supplementary chemical data on ethylene glycol. ... This page provides supplementary chemical data on ethylene glycol. ... Ultraviolet-Visible Spectroscopy or Ultraviolet-Visible Spectrophotometry (UV/ VIS) involves the spectroscopy of photons (spectrophotometry). ... Infrared spectroscopy (IR spectroscopy) is the subset of spectroscopy that deals with the infrared region of the electromagnetic spectrum. ... Nuclear magnetic resonance spectroscopy most commonly known as NMR spectroscopy is the name given to the technique which exploits the magnetic properties of certain nuclei. ... Mass spectrometry (previously called mass spectroscopy (deprecated)[1] or informally, mass-spec and MS) is an analytical technique used to measure the mass-to-charge ratio of ions. ... The plimsoll symbol as used in shipping In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals exactly). ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... This article does not cite any references or sources. ... A diol is a chemical compound containing two hydroxyl groups (-OH groups). ... Look up chemical compound in Wiktionary, the free dictionary. ... “Car” and “Cars” redirect here. ... For other uses, see Antifreeze (disambiguation). ... Toxic redirects here, but this is also the name of a song by Britney Spears; see Toxic (song) Look up toxic and toxicity in Wiktionary, the free dictionary. ...

Production

Ethylene glycol is produced from ethylene, via the intermediate ethylene oxide. Ethylene oxide reacts with water to produce ethylene glycol according to the chemical equation Ethylene (or IUPAC name ethene) is the chemical compound with the formula C2H4. ... “Oxirane” redirects here. ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ... A chemical equation is a symbolic representation of a chemical reaction. ...

C₂H₄O + H₂O → HOCH₂CH₂OH

This reaction can be catalyzed by either acids or bases, or can occur at neutral pH under elevated temperatures. The highest yields of ethylene glycol occur at acidic or neutral pH with a large excess of water. Under these conditions, ethylene glycol yields of 90% can be achieved. The major byproducts are the ethylene glycol oligomers diethylene glycol, triethylene glycol, and tetraethylene glycol. “Oxirane” redirects here. ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ... For other uses, see Chemical reaction (disambiguation). ... It has been suggested that this article or section be merged into Catalysis. ... For other uses, see Acid (disambiguation). ... Acids and bases: Acid-base extraction Acid-base reaction Acid dissociation constant Acidity function Buffer solutions pH Proton affinity Self-ionization of water Acids: Lewis acids Mineral acids Organic acids Strong acids Superacids Weak acids Bases: Lewis bases Organic bases Strong bases Superbases Non-nucleophilic bases Weak bases edit In... For other uses, see PH (disambiguation). ... 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. ... 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. ... 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. ...

This molecule has been observed in space by Hollis, et al.^[2]

Uses

Coolant

The major use of ethylene glycol is as a coolant or antifreeze in, for example, automobiles and personal computers. Due to its low freezing point, it is also used as a deicing fluid for windshields and aircraft. Ethylene glycol is also commonly used in chilled water air conditioning systems that place either the chiller or air handlers outside, or systems that must cool below the freezing temperature of water. An American Airlines MD-80 aircraft being de-iced at Syracuse Hancock International Airport De-icing is the process of removing ice from a surface. ... Panoramic (wrap-around) windshield on a 1959 Edsel Corsair. ... Note: in the broadest sense, air conditioning can refer to any form of heating, ventilation, and air-conditioning. ...

Manufacturing

Ethylene glycol has become increasingly important in the plastics industry for the manufacture of polyester fibers and resins, including polyethylene terephthalate, which is used to make plastic bottles for soft drinks. The antifreeze capabilities of ethylene glycol have made it an important component of vitrification mixtures for low-temperature preservation of biological tissues and organs. For other uses, see Plastic (disambiguation). ... SEM picture of a bend in a high surface area polyester fiber with a seven-lobed cross section Polyester (aka Terylene) is a category of polymers which contain the ester functional group in their main chain. ... This article does not cite any references or sources. ... Polyethylene terephthalate (aka PET, PETE or the obsolete PETP or PET-P) is a thermoplastic polymer resin of the polyester family and is used in synthetic fibers; beverage, food and other liquid containers; thermoforming applications; and engineering resins often in combination with glass fiber. ... A soft drink is a drink that contains no alcohol. ... Antifreeze is a water-based liquid coolant used in gasoline and diesel engines. ... A vitrification experiment for the study of nuclear waste disposal at Pacific Northwest National Labs Vitrification is a process of converting a material into a glass-like amorphous solid which is free of any crystalline structure, either by the quick removal or addition of heat, or by mixing with an...

Minor uses of ethylene glycol include the manufacture of capacitors, as a chemical intermediate in the manufacture of 1,4-dioxane and as an additive to prevent corrosion in liquid cooling systems for personal computers. See Capacitor (component) for a discussion of specific types. ... 1,4-Dioxane, often just called dioxane, is a clear, colorless heterocyclic organic compound which is a liquid at room temperature and pressure. ... For the hazard, see corrosive. ...

Chemistry

Ethylene glycol may also be used as a protecting group for carbonyl groups in organic synthesis. Reacting a ketone or aldehyde with ethylene glycol with acid catalyst (e.g. p-toluenesulfonic acid; BF₃·Et₂O) will give a cyclic acetal — a 1,3-dioxolane, which is resistant to bases and other nucleophiles. The 1,3-dioxolane protecting group can thereafter be removed, e.g. by further acid hydrolysis.^[3] In this example, isophorone was protected using ethylene glycol with p-toluenesulfonic acid in moderate yield. Water was removed by azeotropic distillation to shift the equilibrium to the right.^[4] A Protecting group or protective group is introduced into a molecule by chemical modification of a functional group in order to obtain chemoselectivity in a subsequent chemical reaction. ... In chemistry, a carbonyl group is a functional group composed of an atom of carbon double-bonded to an atom of oxygen. ... Organic synthesis is the construction of organic molecules via chemical processes. ... Tosyl Group with a generic R Group attached (where R can be anything, typically a carbon). ... Boron trifluoride is the chemical compound with the formula BF3. ... An acetal is a functional group or molecule containing the functional group of a carbon bonded to two -OR groups. ... Hydrolysis is a chemical reaction or process in which a chemical compound is broken down by reaction with water. ... Isophorone is an organic compound, a colorless to yellowish liquid with characteristic smell, that is used as a solvent and as an intermediate in organic synthesis. ... In chemistry, azeotropic distillation is any of a range of techniques used to break an azeotrope in distillation. ...

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Laboratory use

Ethylene glycol is commonly used in laboratories to precipitate out proteins in solution. This is often an intermediary step in fractionation, purification and/or crystallization. It can be used to protect functional groups from reacting during organic synthesis. To get the functional group back to its original composition, simply add water and acid.

Ethylene glycol is commonly used as a preservative for specimens in schools, frequently during dissection. It is said to be safer than formaldehyde, but the safety is questionable.

Other applications

Ethylene glycol's high boiling point and affinity for water makes it an ideal desiccant for natural gas production. In the field, excess water vapor is usually removed by glycol dehydration. Ethylene glycol flows down from the top of a tower and meets a rising mixture of water vapor and hydrocarbon gases from the bottom. The glycol chemically removes the water vapor, allowing dry gas to exit from the top of the tower. The glycol and water are separated, and the glycol cycles back through the tower. A dessicant is a hygroscopic substance that induces or sustains a state of dryness (desiccation) in its local vicinity in a moderately-well sealed container. ... For other uses, see Natural gas (disambiguation). ... Oil refineries are key to obtaining hydrocarbons; crude oil is processed through several stages to form desirable hydrocarbons, used in fuel and other commercial products. ...

Ethylene glycol is also used in the manufacture of some vaccines, but it is not itself present in these injections. It is used as a minor (1–2%) ingredient in shoe polish and also in some inks and dyes. Ethylene glycol has seen some use as a rot and fungal treatment for wood, both as a preventative and a treatment after the fact. It has been used in a few cases to treat partially rotted wooden objects to be displayed in museums. It is one of only a few treatments that are successful in dealing with rot in wooden boats, and is relatively cheap. A vaccine is an antigenic preparation used to establish immunity to a disease. ... An open can of Kiwi shoe polish with a side-mounted opening mechanism visible at the top of the photo. ...

Toxicity

The major danger from ethylene glycol is following ingestion. Due to its sweet taste, children and animals will sometimes consume large quantities of it if given access to antifreeze. Ethylene glycol may also be found as a contaminant in moonshine distilled using an improperly washed car radiator. In developed countries, a bittering agent called denatonium/denatonium benzoate, is generally added to ethylene glycol preparations as an adversant (to prevent accidental ingestion). If one has ingested ethylene glycol, give the person an alcoholic beverage while the paramedics arrive. Ethanol acts as a competitive inhibitor to the active site of the enzyme that converts ethylene glycol to its toxic metabolites. Once ethanol binds, the ethylene glycol is harmlessly excreted out of the body. Revenue men at the site of moonshine stills, Kentucky, 1911 or earlier For other uses, see Moonshine (disambiguation). ... Laboratory distillation set-up: 1: Heat source 2: Still pot 3: Still head 4: Thermometer/Boiling point temperature 5: Condenser 6: Cooling water in 7: Cooling water out 8: Distillate/receiving flask 9: Vacuum/gas inlet 10: Still receiver 11: Heat control 12: Stirrer speed control 13: Stirrer/heat plate... Not to be confused with radiata. ... Denatonium, usually available as denatonium benzoate (or under trade names such as Bitrex or Aversion) and as denatonium saccharide, is the most bitter compound known. ... Grain alcohol redirects here. ...

Ethylene glycol poisoning is a medical emergency and in all cases a poison control center should be contacted or medical attention should be sought. It is highly toxic with an estimated LD₁₀₀ in humans of approximately 1.4 ml/kg.^[5] However, as little as 30 milliliters (2 tablespoons) can be lethal to adults.^[6] Poison Control Centers (PCC) provide immediate, free and expert treatment advice and assistance over the telephone in case of exposure to poisonous, hazardous or toxic substances. ... This tablespoon has a capacity of about 1 tbsp. ...

Symptoms

Symptoms of ethylene glycol poisoning usually follow a three-step progression, although poisoned individuals will not always develop each stage or follow a specific time frame.^[5] Stage 1 consists of neurological symptoms including victims appearing to be intoxicated, exhibiting symptoms such as dizziness, headaches, slurred speech, and confusion. Over time, the body metabolizes ethylene glycol into other toxins, first to glycolaldehyde, which is then oxidized to glycolic acid, glyoxylic acid, and finally oxalic acid. Stage 2 is a result of accumulation of these metabolites and consists of tachycardia, hypertension, hyperventilation, and metabolic acidosis. Stage 3 of ethylene glycol poisoning is the result of kidney injury, leading to acute kidney failure.^[7] Oxalic acid reacts with calcium and forms calcium oxalate crystals in the kidney. Neurology is a branch of medicine dealing with disorders of the central and peripheral nervous systems. ... ... Structure of the coenzyme adenosine triphosphate, a central intermediate in energy metabolism. ... Glycolic acid (or hydroxyacetic acid) is the smallest α-hydroxy acid (AHA). ... Glyoxylic acid or oxoacetic acid is an organic compound with the chemical formula C2H2O3 and structure HOC-COOH. Other synonyms are formylformic acid and oxoethanoic acid. ... Oxalic acid (IUPAC name: ethanedioic acid, formula C2H2O4) is a dicarboxylic acid with structure (HOOC)-(COOH). ... This article or section does not cite any references or sources. ... For other forms of hypertension, see Hypertension (disambiguation). ... In medicine, hyperventilation (or hyperpnea) is the state of breathing faster or deeper (hyper) than necessary, and thereby reducing the carbon dioxide concentration of the blood below normal. ... In medicine, metabolic acidosis is a state in which the blood pH is low (under 7. ... Renal failure is when the kidneys fail to function properly. ... Calcium oxalate is a chemical compound that forms needle-shaped crystals. ...

Treatment

Initial treatment consists of stabilizing the patient and gastric decontamination. As ethylene glycol is rapidly absorbed, gastric decontamination needs to be performed soon after ingestion to be of benefit. Gastric lavage or nasogastric aspiration of gastric contents are the most common methods employed in ethylene glycol poisoning. Ipecac-induced vomiting or activated charcoal (charcoal does not adsorb glycols) are not recommended. ^[5] Gastric lavage, also commonly called a stomach pump, is the process of cleaning out the contents of the stomach. ... Nasogastric intubation is a medical process involving the insertion of a plastic tube (nasogastric tube, NG tube) through the nose, past the throat, and down into the stomach. ... Syrup of Ipecac (derived from the dried rhizome and roots of the Ipecacuanha plant), is an emetic—a substance used to induce vomiting. ... Emesis redirects here. ... Activated carbon (also called activated charcoal) is the more general term which includes material mostly derived from charcoal. ... In chemistry, adsorption of a substance is its concentration on a particular surface. ...

The antidotes for ethylene glycol poisoning are ethanol or fomepizole; antidotal treatment forms the mainstay of management following ingestion. Ethanol (usually given IV as a 5 or 10% solution in 5% dextrose and water, but, also sometimes given in the form of a strong spirit such as whisky, vodka or gin) acts by competing with ethylene glycol for the enzyme alcohol dehydrogenase thus limiting the formation of toxic metabolites. Fomepizole acts by inhibiting alcohol dehydrogenase, thus blocking the formation of the toxic metabolites.^[8] An antidote is a substance which can counteract a form of poisoning. ... Grain alcohol redirects here. ... Fomepizole or 4-Methylpyrazole is indicated for use as an antidote in confirmed or suspected methanol or ethylene glycol poisoning. ... Intravenous therapy or IV therapy is the giving of liquid substances directly into a vein. ... A space-filling model of glucose Glucose, a simple monosaccharide sugar, is one of the most important carbohydrates and is used as a source of energy in animals and plants. ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ... For other uses, see Whisky (disambiguation). ... Vodka bottling machine, Shatskaya Vodka Shatsk, Russia Vodka (Polish: wódka, Russian: водка) is one of the worlds most popular distilled beverages. ... Gin and tonic. ... Ribbon diagram of the enzyme TIM, surrounded by the space-filling model of the protein. ... Alcohol Dehydrogenase Alcohol dehydrogenases are a group of dehydrogenase enzymes that occur in many organisms and facilitate the interconversion between alcohols and aldehydes or ketones. ... Alcohol Dehydrogenase Alcohol dehydrogenases are a group of dehydrogenase enzymes that occur in many organisms and facilitate the interconversion between alcohols and aldehydes or ketones. ...

In addition to antidotes, hemodialysis can also be used to enhance the removal of unmetabolized ethylene glycol, as well as its metabolites from the body. Hemodialysis also has the added benefit of correcting other metabolic derangements or supporting deteriorating kidney function caused by ethylene glycol ingestion. Often both antidotal treatment and hemodialysis are used together in the treatment of poisoning. It has been suggested that Artificial kidney be merged into this article or section. ...

Industrial hazards

Ethylene glycol can begin to breakdown at 230° – 250°F (110° – 121°C). Note that breakdown can occur when the system bulk (average) temperature is below these limits because surface temperatures in heat exchangers and boilers can be locally well above these temperatures.

The electrolysis of ethylene glycol solutions with a silver anode results in an exothermic reaction. The Apollo 1 fire catastrophe was caused by this reaction. The ethylene glycol–water mixture was ignited and was able to burn in the atmosphere of pure low pressure oxygen.^{[citation needed]} In chemistry and manufacturing, electrolysis is a method of separating chemically bonded elements and compounds by passing an electric current through them. ... This article is about the chemical element. ... Diagram of a zinc anode in a galvanic cell. ... In chemistry, an exothermic reaction is one that releases heat . ... Apollo 1 is the official name given to the never-flown Apollo/Saturn 204 (AS-204) mission. ...

History

Ethylene glycol was first prepared in 1859 by the French chemist Charles-Adolphe Wurtz. It was produced on a small scale during World War I as a coolant and as an ingredient in explosives. Widespread industrial production began in 1937 when ethylene oxide, a component in its synthesis, became cheaply available. 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. ... “The Great War ” redirects here. ... This article is concerned solely with chemical explosives. ... Year 1937 (MCMXXXVII) was a common year starting on Friday (link will display the full calendar) of the Gregorian calendar. ... “Oxirane” redirects here. ...

When first introduced it created a minor revolution in aircraft design because when used in place of water as an engine coolant, its higher boiling point allowed for smaller radiators operating at higher temperatures. Prior to the widespread availability of ethylene glycol, many aircraft manufacturers tried to use evaporative cooling systems which used water at high pressure. Invariably, these proved to be rather unreliable and were easily damaged in combat because they took up large amounts of room on the plane, where they were easily hit by gunfire. For other uses, see Engine (disambiguation). ... Italic text This article is about the boiling point of liquids. ... Evaporative cooling is a system in which latent heat of evaporation is used to carry heat away from an object to cool it. ...

See also

• Propylene glycol
• Diethylene glycol
• Ethylene glycol (data page)

Propylene glycol, also known as 1,2-propanediol, is an organic compound (a diol alcohol), usually a tasteless, odorless, and colorless clear oily liquid that is hygroscopic and miscible with water, acetone, and chloroform. ... 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. ... This page provides supplementary chemical data on ethylene glycol. ...

References

Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era in the 21st century. ... is the 275th day of the year (276th in leap years) in the Gregorian calendar. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... The Journal of Organic Chemistry (abbreviated as ) is a scientific journal for original contributions of fundamental research in organic and bioorganic chemistry. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ...

External links

• National Pollutant Inventory — Ethylene glycol fact sheet
• Medical information