Ethylene glycol - wikipedia Ethylene glycol Not to be confused with Propylene glycol, Diethylene glycol, or Glycol. Ethylene glycol Names Preferred IUPAC name Ethane - 1, 2 - diol Other names Ethylene glycol 1, 2 - Ethanediol Ethylene alcohol Hypodicarbonous acid Monoethylene glycol 1, 2 - Dihydroxyethane Identifiers CAS Number 107 - 21 - 1 3D model ( JSmol ) Interactive image 3DMet B00278 Abbreviations MEG Beilstein Reference 505945 ChEBI CHEBI : 30742 ChemSpider 13835235 ECHA InfoCard 100.003. 159 EC Number 203 - 473 - 3 Gmelin Reference 943 KEGG C01380 MeSH Ethylene + glycol PubChem CID 174 RTECS number KW2975000 UNII FC72KVT52F InChI InChI = 1S / C2H6O2 / c3 - 1 - 2 - 4 / h3 - 4H, 1 - 2H2 Key : LYCAIKOWRPUZTN - UHFFFAOYSA - N InChI = 1 / C2H6O2 / c3 - 1 - 2 - 4 / h3 - 4H, 1 - 2H2 Key : LYCAIKOWRPUZTN - UHFFFAOYAD SMILES C ( CO ) O Properties Chemical formula C H O Molar mass 62.07 g mol Appearance Clear, colorless liquid Odor Odorless Density 1.1132 g / cm Melting point − 12.9 ° C ( 8.8 ° F ; 260.2 K ) Boiling point 197.3 ° C ( 387.1 ° F ; 470.4 K ) Solubility in water Miscible Solubility Soluble in most organic solvents Vapor pressure 0.06 mmHg ( 20 ° C ) Viscosity 1.61 × 10 Pa s Hazards Main hazards Harmful Safety data sheet See : data page External MSDS EU classification ( DSD ) ( outdated ) Harmful ( Xn ) R - phrases ( outdated ) R22 R36 S - phrases ( outdated ) S26 S36 S37 S39 S45 S53 NFPA 704 0 Flash point 111 ° C ( 232 ° F ; 384 K ) closed cup Autoignition temperature 410 ° C ( 770 ° F ; 683 K ) Explosive limits 3.2 -- 15.2 % US health exposure limits ( NIOSH ) : PEL ( Permissible ) None REL ( Recommended ) None established IDLH ( Immediate danger ) None Related compounds Related diols Propylene glycol Diethylene glycol Triethylene glycol Polyethylene glycol Supplementary data page Structure and properties Refractive index ( n ), Dielectric constant ( ε ), etc. Thermodynamic data Phase behaviour solid -- liquid -- gas Spectral data UV, IR, NMR, MS Except where otherwise noted, data are given for materials in their standard state ( at 25 ° C ( 77 ° F ), 100 kPa ). N verify ( what is ? ) Infobox references Ethylene glycol ( IUPAC name : ethane - 1, 2 - diol ) is an organic compound with the formula ( CH OH ). It is mainly used for two purposes, as a raw material in the manufacture of polyester fibers and for antifreeze formulations. It is an odorless, colorless, sweet - tasting, viscous liquid. Ethylene glycol is moderately toxic. Contents 1 Production 1.1 Industrial routes 1.2 Biological routes 1.3 Historical routes 2 Uses 2.1 Coolant and heat - transfer agent 2.2 Antifreeze 2.3 Precursor to polymers 2.4 Other uses 2.4. 1 Dehydrating agent 2.4. 2 Hydrate inhibition 2.4. 3 Niche applications 3 Chemical reactions 4 Toxicity 5 In the environment 6 Notes 7 References 8 External links Production Industrial routes Ethylene glycol is produced from ethylene ( ethene ), via the intermediate ethylene oxide. Ethylene oxide reacts with water to produce ethylene glycol according to the chemical equation : C H O + H O → HO − CH CH − OH 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 oligomers diethylene glycol, triethylene glycol, and tetraethylene glycol. The separation of these oligomers and water is energy - intensive. About 6.7 million tonnes are produced annually. A higher selectivity is achieved by use of Shell 's OMEGA process. In the OMEGA process, the ethylene oxide is first converted with carbon dioxide ( CO ) to ethylene carbonate. This ring is then hydrolyzed with a base catalyst in a second step to produce mono - ethylene glycol in 98 % selectivity. The carbon dioxide is released in this step again and can be fed back into the process circuit. The carbon dioxide comes in part from the ethylene oxide production, where a part of the ethylene is completely oxidized. Ethylene glycol is produced from carbon monoxide in countries with large coal reserves and less stringent environmental regulations. The oxidative carbonylation of methanol to dimethyl oxalate provides a promising approach to the production of C - based ethylene glycol. Dimethyl oxalate can be converted into ethylene glycol in high yields ( 94.7 % ) by hydrogenation with a copper catalyst : Methanol is recycled. Therefore only carbon monoxide, hydrogen, and oxygen are consumed. One plant with a production capacity of 200 000 tons ethylene glycol per year is in Inner Mongolia, a second plant with a capacity of 250 000 tons per year was scheduled for 2012 in Henan. As of 2015, four plants in China with a capacity of 200 000 t / a each were operating with at least 17 more to follow. Biological routes The caterpillar of Galleria mellonella has the gut bacteria 's ability to degrade polyethylene ( PE ) into ethylene glycol. Historical routes According to most sources, French chemist Charles - Adolphe Wurtz ( 1817 -- 1884 ) first prepared ethylene glycol in 1856. He first treated `` ethylene iodide '' ( C H I ) with silver acetate and then hydrolyzed the resultant `` ethylene diacetate '' with potassium hydroxide. Wurtz named his new compound `` glycol '' because it shared qualities with both ethyl alcohol ( with one hydroxyl group ) and glycerin ( with three hydroxyl groups ). In 1859, Wurtz prepared ethylene glycol via the hydration of ethylene oxide. There appears to have been no commercial manufacture or application of ethylene glycol prior to World War I, when it was synthesized from ethylene dichloride in Germany and used as a substitute for glycerol in the explosives industry. In the United States, semicommercial production of ethylene glycol via ethylene chlorohydrin started in 1917. The first large - scale commercial glycol plant was erected in 1925 at South Charleston, West Virginia, by Carbide and Carbon Chemicals Co. ( now Union Carbide Corp. ). By 1929, ethylene glycol was being used by almost all dynamite manufacturers. In 1937, Carbide started up the first plant based on Lefort 's process for vapor - phase oxidation of ethylene to ethylene oxide. Carbide maintained a monopoly on the direct oxidation process until 1953, when the Scientific Design process was commercialized and offered for licenses. Uses Ethylene glycol is primarily used in antifreeze formulations ( 50 % ) and as a raw material in the manufacture of polyesters such as polyethylene terephthalate ( PET ) ( 40 % ). Coolant and heat - transfer agent The major use of ethylene glycol is as a medium for convective heat transfer in, for example, automobiles and liquid - cooled computers. 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. In geothermal heating / cooling systems, ethylene glycol is the fluid that transports heat through the use of a geothermal heat pump. The ethylene glycol either gains energy from the source ( lake, ocean, water well ) or dissipates heat to the sink, depending on whether the system is being used for heating or cooling. Pure ethylene glycol has a specific heat capacity about one half that of water. So, while providing freeze protection and an increased boiling point, ethylene glycol lowers the specific heat capacity of water mixtures relative to pure water. A 1 : 1 mix by mass has a specific heat capacity of about 3140 J / ( kg ° C ) ( 0.75 BTU / ( lb ° F ) ), three quarters that of pure water, thus requiring increased flow rates in same system comparisons with water. The formation of large bubbles in cooling passages of internal combustion engines will seriously inhibit heat flow ( flux ) from that area, thus allowing nucleation ( tiny bubbles ) heat transfer to occur is not advisable. Large bubbles in cooling passages will be self - sustaining or grow larger, with virtually the complete loss of cooling in that spot. With pure MEG that hot spot has to get to 200 ° C ( 392 ° F ). Cooling due to other effects such as air draft from fan etc. ( not considered in pure nucleation analysis ) will assist in preventing large - bubble formation. Antifreeze Ethylene glycol disrupts hydrogen bonding when dissolved in water. Pure ethylene glycol freezes at about − 12 ° C ( 10.4 ° F ), but when mixed with water, the mixture does not readily crystallize, and therefore the freezing point of the mixture is depressed. Specifically, a mixture of 60 % ethylene glycol and 40 % water freezes at − 45 ° C ( − 49 ° F ). Diethylene glycol behaves similarly. It is used as a de-icing fluid for windshields and aircraft. The antifreeze capabilities of ethylene glycol have made it a component of vitrification ( anticrystallization ) mixtures for low - temperature preservation of biological tissues and organs. Mixture of ethylene glycol and water can also be chemically termed as glycol concentrate / compound / mixture / solution. However, the boiling point for aqueous ethylene glycol increases monotonically with increasing ethylene - glycol fraction. Thus, the use of ethylene glycol not only depresses the freezing point, but also elevates the boiling point such that the operating range for the heat - transfer fluid is broadened on both ends of the temperature scale. The increase in boiling temperature is due to pure ethylene glycol having a much higher boiling point and lower vapor pressure than pure water ; there is no chemical stabilization against boiling of the liquid phase at intermediate compositions, as there is against freezing. Precursor to polymers In the plastic industry, ethylene glycol is an important precursor to polyester fibers and resins. Polyethylene terephthalate, used to make plastic bottles for soft drinks, is prepared from ethylene glycol. Ethylene glycol is one precursor to polyethyleneterephthalate, which is produced on the multimillion ton scale annually. Other uses Dehydrating agent Ethylene glycol is used in the natural gas industry to remove water vapor from natural gas before further processing, in much the same manner as triethylene glycol ( TEG ). Hydrate inhibition Because of its high boiling point and affinity for water, ethylene glycol is a useful desiccant. Ethylene glycol is widely used to inhibit the formation of natural gas clathrates ( hydrates ) in long multiphase pipelines that convey natural gas from remote gas fields to a gas processing facility. Ethylene glycol can be recovered from the natural gas and reused as an inhibitor after purification treatment that removes water and inorganic salts. Natural gas is dehydrated by ethylene glycol. In this application, ethylene glycol flows down from the top of a tower and meets a rising mixture of water vapor and hydrocarbon gases. Dry gas exits from the top of the tower. The glycol and water are separated, and the glycol recycled. Instead of removing water, ethylene glycol can also be used to depress the temperature at which hydrates are formed. The purity of glycol used for hydrate suppression ( monoethylene glycol ) is typically around 80 %, whereas the purity of glycol used for dehydration ( triethylene glycol ) is typically 95 to more than 99 %. Moreover, the injection rate for hydrate suppression is much lower than the circulation rate in a glycol dehydration tower. Niche applications Minor uses of ethylene glycol include the manufacture of capacitors, as a chemical intermediate in the manufacture of 1, 4 - dioxane, as an additive to prevent corrosion in liquid cooling systems for personal computers, and inside the lens devices of cathode - ray tube type of rear projection televisions. 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. Ethylene glycol may also be one of the minor ingredients in screen cleaning solutions, along with the main ingredient isopropyl alcohol. Ethylene glycol is commonly used as a preservative for biological specimens, especially in secondary schools during dissection as a safer alternative to formaldehyde. It can also be used in killing jars. It is also used as part of the water - based hydraulic fluid used to control subsea oil and gas production equipment. Another interesting use is in the treatment of ' dry rot ' or ' white rot ' on timber joists, partially rotten or affected wood readily soaks it up and the fungus is subsequently killed. The main advantage of this type of treatment is that the glycol is hygroscopic and the wood being already water damaged readily absorbs a water based product. Ethylene glycol is used as a protecting group in organic synthesis to protect carbonyl compounds such as ketones and aldehydes. Chemical reactions Ethylene glycol is used as a protecting group for carbonyl groups in organic synthesis. Treating a ketone or aldehyde with ethylene glycol in the presence of an acid catalyst ( e.g., p - toluenesulfonic acid ; BF Et O ) gives the corresponding a 1, 3 - dioxolane, which is resistant to bases and other nucleophiles. The 1, 3 - dioxolane protecting group can thereafter be removed by further acid hydrolysis. 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. Toxicity Main article : Ethylene glycol poisoning Ethylene glycol is moderately toxic, with an oral LD = 786 mg / kg for humans. The major danger is due to its sweet taste, which can attract children and animals. Upon ingestion, ethylene glycol is oxidized to glycolic acid, which is, in turn, oxidized to oxalic acid, which is toxic. It and its toxic byproducts first affect the central nervous system, then the heart, and finally the kidneys. Ingestion of sufficient amounts can be fatal if untreated. Several deaths are recorded annually in the U.S. alone. Antifreeze products for automotive use containing propylene glycol in place of ethylene glycol are available. They are generally considered safer to use, as propylene glycol does not taste as good and is converted in the body to lactic acid, a normal product of metabolism and exercise. Australia, the UK, and seventeen US states ( as of 2012 ) require the addition of a bitter flavoring ( denatonium benzoate ) to antifreeze. In December 2012, US antifreeze manufacturers agreed voluntarily to add a bitter flavoring to all antifreeze that is sold in the consumer market of the US. In the environment Ethylene glycol is a high - production - volume chemical ; it breaks down in air in about 10 days and in water or soil in a few weeks. It enters the environment through the dispersal of ethylene glycol - containing products, especially at airports, where it is used in deicing agents for runways and aeroplanes. While prolonged low doses of ethylene glycol show no toxicity, at near lethal doses ( ≥ 1000 mg / kg per day ) ethylene glycol acts as a teratogen. `` Based on a rather extensive database, it induces ( skeletal variations and malformations ) in rats and mice by all routes of exposure. '' This molecule has been observed in outer space. Notes Jump up ^ Pure propylene glycol does not taste bitter, and pure propylene glycol is often used as a food additive, for instance in cake icing and shelf - stable whipped cream. Industrial - grade propylene glycol usually has a slightly bitter or acrid taste due to impurities. See the article on propylene glycol for more information. The relative sweetness of ethylene glycol and propylene glycol is discussed in the Merck Index, and neither compound is described as bitter. References ^ Jump up to : `` NIOSH Pocket Guide to Chemical Hazards # 0272 ''. National Institute for Occupational Safety and Health ( NIOSH ). Jump up ^ Elert, Glenn. `` Viscosity ''. The Physics Hypertextbook. Retrieved 2007 - 10 - 02. ^ Jump up to : Siegfried Rebsdat ; Dieter Mayer ( 2005 ), `` Ethylene Glycol '', Ullmann 's Encyclopedia of Industrial Chemistry, Weinheim : Wiley - VCH, doi : 10.1002 / 14356007. a10_101 Jump up ^ Scott D. Barnicki `` Synthetic Organic Chemicals '' in Handbook of Industrial Chemistry and Biotechnology edited by James A. Kent, New York : Springer, 2012. 12th ed. ISBN 978 - 1 - 4614 - 4259 - 2. Jump up ^ Nexant / Chemsystems, `` Coal to MEG, Changing the Rules of the Game '' ( PDF ). Archived from the original on July 14, 2011. Retrieved 2016 - 08 - 08. CS1 maint : BOT : original - url status unknown ( link ) ( PDF ; 5, 4 MB ), 2011 Prospectus. Jump up ^ 983 EP 046 983, S. Tahara et al., `` Process for continuously preparing ethylene glycol '', assigned to Ube Industries and H.T. Teunissen and C.J. Elsevier, Ruthenium catalyzed hydrogenation of dimethyl oxalate to ethylene glycol, J. Chem. Soc., Chem. Commun., 1997, 667 -- 668 ), DOI : 10.1039 / A700862G. Jump up ^ S. Zhang et al., Highly - Dispersed Copper - Based Catalysts from Cu -- Zn -- Al Layered Double Hydroxide Precursor for Gas - Phase Hydrogenation of Dimethyl Oxalate to Ethylene Glycol, Catalysis Letters, Sept. 2012, 142 ( 9 ), 1121 -- 1127, DOI : 10.1007 / s10562 - 012 - 0871 - 8. Jump up ^ http://www.icis.com/resources/news/2012/01/30/9527520/china-s-coal-based-chemicals-are-a-trade-off/. Jump up ^ https://books.google.com/books?id=EPCeBgAAQBAJ&pg=PA15&lpg=PA15&dq=meg+china+synthesis+gas&source=bl&ots=EK1o_pLzZw&sig=-UWX8960EpSnxLf5Sar781tVfUo&hl=de&sa=X&ved=0ahUKEwiigqHiv-DSAhXMbRQKHffeD1YQ6AEIYTAJ#v=onepage&q=meg%20china%20synthesis%20gas&f=false. Jump up ^ Yang, Jun ; Yang, Yu ; Wu, Wei - Min ; Zhao, Jiao ; Jiang, Lei ( 2014 - 12 - 02 ). `` Evidence of polyethylene biodegradation by bacterial strains from the guts of plastic - eating waxworms ''. Environmental Science & Technology. 48 ( 23 ) : 13776 -- 13784. doi : 10.1021 / es504038a. ISSN 1520 - 5851. PMID 25384056. Jump up ^ Bombelli, Paolo ; Howe, Christopher J. ; Bertocchini, Federica ( 2017 - 04 - 24 ). `` Polyethylene bio-degradation by caterpillars of the wax moth Galleria mellonella ''. Current Biology. 27 ( 8 ) : R292 -- R293. doi : 10.1016 / j. cub. 2017.02. 060. ISSN 0960 - 9822. Jump up ^ Khan, Amina ( April 24, 2017 ). `` Stubborn plastic may have finally met its match : the hungry wax worm ''. Los Angeles Times. Retrieved April 25, 2017. Jump up ^ Adolphe Wurtz ( 1856 ). `` Sur le glycol ou alcool diatomique '' ( On glycol or dibasic alcohol ). Comptes rendus. 43 : 199 -- 204. Jump up ^ Wurtz ( 1856 ), page 200 : ``... je propose de le nommer glycol, parce qu'il se rapproche à la fois, par ses propriétés, de l'alcool proprement dit et de la glycérin, entre lesquels il se trouve placé. '' (... I propose to call it glycol because, by its properties, it is simultaneously close to ( ethyl ) alcohol properly called and glycerin, between which it is placed. ) Jump up ^ Ad. Wurtz ( 1859 ) `` Synthèse du glycol avec l'oxyde d'éthylène et l'eau '' ( Synthesis of glycol from ethylene oxide and water ), Comptes rendus, 49 : 813 -- 815. Jump up ^ `` Ethylene glycol acetal ''. The Organic Synthesis Archive. synarchive.com. Jump up ^ Theodora W. Greene ; Peter G.M. Wuts ( 1999 ). Protective Groups in Organic Synthesis ( Third ed. ). John Wiley & Sons. pp. 312 -- 322. ISBN 0 - 471 - 16019 - 9. Jump up ^ J.H. Babler ; N.C. Malek ; M.J. Coghlan ( 1978 ). `` Selective hydrolysis of α, β - and β, γ - unsaturated ketals : method for deconjugation of β, β - disubstituted α, β - unsaturated ketones ''. J. Org. Chem. 43 ( 9 ) : 1821 -- 1823. doi : 10.1021 / jo00403a047. Jump up ^ Safety Officer in Physical Chemistry ( November 23, 2009 ). `` Safety ( MSDS ) data for ethylene glycol ''. Oxford University. Retrieved December 30, 2009. Jump up ^ Ethylene glycol. National Institute for Occupational Safety and Health. Emergency Response Database. August 22, 2008. Retrieved December 31, 2008. Jump up ^ Ethylene Glycol Toxicity at eMedicine Jump up ^ The Merck Index ( 15th ed. ). Royal Society of Chemistry. 2013. pp. M5122. Jump up ^ The Merck Index ( 15th ed. ). Royal Society of Chemistry. 2013. pp. M9238. Jump up ^ Pieter Klapwijk ( January 27, 2010 ). `` Ethylene Glycol Poisoning ''. The Rested Dog Inn. Retrieved October 11, 2012. Jump up ^ `` Antifreeze and Engine Coolant Being Bittered Nationwide ''. Consumer Specialty Products Association. 13 December 2012. Archived from the original on 28 December 2012. Retrieved 30 June 2016. Jump up ^ ( CDC ToxFAQs ). Jump up ^ `` Statement of the Science Report for Ethylene Glycol ''. 3.3. 2.2 Non-neoplastic effects. Health Canada www.hc-sc.gc.ca. June 24, 2013. Retrieved 27 August 2014. Jump up ^ J.M. Hollis ; F.J. Lovas ; P.R. Jewell ; L.H. Coudert ( 2002 - 05 - 20 ). `` Interstellar Antifreeze : Ethylene Glycol ''. The Astrophysical Journal. 571 ( 1 ) : L59 -- L62. Bibcode : 2002ApJ... 571L... 59H. doi : 10.1086 / 341148. External links WebBook page for C2H6O2 ATSDR - Case Studies in Environmental Medicine : Ethylene Glycol and Propylene Glycol Toxicity CDC - NIOSH Pocket Guide to Chemical Hazards Medical information Hairong Yue ; Yujun Zhao ; Xinbin Ma ; Jinlong Gong ( 2012 ). `` Ethylene glycol : properties, synthesis, and applications ''. Chemical Society Reviews. 41 ( 11 ) : 4218 -- 4244. doi : 10.1039 / C2CS15359A. Sugar alcohols 2 - carbon Ethylene glycol 3 - carbon Glycerol 4 - carbon Erythritol Threitol 5 - carbon Arabitol Ribitol Xylitol 6 - carbon Mannitol Sorbitol Galactitol Iditol 7 - carbon Volemitol Deoxy sugar alcohols Fucitol Cyclic sugar alcohols Inositol Glycylglycitols Maltitol Lactitol Isomalt Maltotriitol Maltotetraitol Polyglycitol Automotive engine Part of the Automobile series Basic terminology Bore Compression ratio Crank Cylinder Dead centre Diesel engine Dry sump Engine balance Engine configuration Engine displacement Engine knocking Firing order Hydrolock Petrol engine Power band Redline Spark - ignition engine Stroke Stroke ratio Wet sump Main components Connecting rod Crankcase Crankpin Crankshaft Crossplane Cylinder bank Cylinder block Cylinder head ( crossflow, reverse - flow ) Flywheel Head gasket Hypereutectic piston Main bearing Piston Piston ring Starter ring gear Sump Valvetrain Cam Cam follower Camshaft Desmodromic valve Hydraulic tappet Multi-valve Overhead camshaft Overhead valve Pneumatic valve springs Poppet valve Pushrod Rocker arm Sleeve valve Tappet Timing belt Timing mark Valve float Variable valve timing Aspiration Air filter Blowoff valve Boost controller Butterfly valve Centrifugal - type supercharger Cold air intake Dump valve Electronic throttle control Forced induction Inlet manifold Intake Intercooler Manifold vacuum Naturally aspirated engine Ram - air intake Scroll - type supercharger Short ram air intake Supercharger Throttle Throttle body Turbocharger Twin - turbo Variable - geometry turbocharger Variable - length intake manifold Warm air intake Fuel system Carburetor Common rail Direct injection Fuel filter Fuel injection Fuel pump Fuel tank Gasoline direct injection Indirect injection Injection pump Lean - burn Stratified charge engine Turbo fuel stratified injection Unit injector Ignition Contact breaker Magneto Distributor Electrical ballast High tension leads Ignition coil Spark plug Wasted spark Electrics and engine management Air -- fuel ratio meter Alternator Automatic Performance Control Car battery ( lead -- acid battery ) Crankshaft position sensor Dynamo Drive by wire Electronic control unit Engine control unit Engine coolant temperature sensor Glow plug Idle air control actuator MAP sensor Mass flow sensor Oxygen sensor Starter motor Throttle position sensor Exhaust system Automobile emissions control Catalytic converter Diesel particulate filter Exhaust manifold Glasspack Muffler Engine cooling Air cooling Antifreeze ( ethylene glycol ) Core plug Electric fan Fan belt Radiator Thermostat Water cooling Viscous fan ( fan clutch ) Other components Balance shaft Block heater Combustion chamber Cylinder head porting Gasket Motor oil Oil filter Oil pump Oil sludge PCV valve Seal Synthetic oil Underdrive pulleys Portal Molecules detected in outer space Molecules Diatomic Aluminium monochloride Aluminium monofluoride Aluminium monoxide Argonium Carbon monophosphide Carbon monosulfide Carbon monoxide Carborundum Cyanogen radical Diatomic carbon Fluoromethylidynium Hydrogen chloride Hydrogen fluoride Hydrogen ( molecular ) Hydroxyl radical Iron ( II ) oxide Magnesium monohydride cation Methylidyne radical Nitric oxide Nitrogen ( molecular ) Nitrogen monohydride Nitrogen sulfide Oxygen ( molecular ) Phosphorus monoxide Phosphorus mononitride Potassium chloride Silicon carbide Silicon mononitride Silicon monoxide Silicon monosulfide Sodium chloride Sodium iodide Sulfur monohydride Sulfur monoxide Titanium oxide Triatomic Aluminium hydroxide Aluminium isocyanide Amino radical Carbon dioxide Carbonyl sulfide CCP radical Chloronium Diazenylium Dicarbon monoxide Disilicon carbide Ethynyl radical Formyl radical Hydrogen cyanide ( HCN ) Hydrogen isocyanide ( HNC ) Hydrogen sulfide Hydroperoxyl Iron cyanide Isoformyl Magnesium cyanide Magnesium isocyanide Methylene radical Nitrous oxide Nitroxyl Ozone Phosphaethyne Potassium cyanide Protonated molecular hydrogen Sodium cyanide Sodium hydroxide Silicon carbonitride c - 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acetylene Ethylene glycol Ethyl formate Methyl acetate Methyl - cyano - diacetylene Methyltriacetylene Propanal n - Propyl cyanide Pyrimidine Deuterated molecules Ammonia Ammonium ion Formaldehyde Formyl radical Heavy water Hydrogen cyanide Hydrogen deuteride Hydrogen isocyanide Methylacetylene Trihydrogen cation Unconfirmed Anthracene Dihydroxyacetone Ethyl methyl ether Glycine Graphene H NCO Linear C Naphthalene cation Phosphine Pyrene Silylidine Related Abiogenesis Astrobiology Astrochemistry Atomic and molecular astrophysics Chemical formula Circumstellar envelope Cosmic dust Cosmic ray Cosmochemistry Diffuse interstellar band Earliest known life forms Extraterrestrial life Extraterrestrial liquid water Forbidden mechanism Helium hydride ion Homochirality Intergalactic dust Interplanetary medium Interstellar medium Photodissociation region Iron -- sulfur world theory Kerogen Molecules in stars Nexus for Exoplanet System Science Organic compound Outer space PAH world hypothesis Panspermia Polycyclic aromatic hydrocarbon ( PAH ) RNA world hypothesis Spectroscopy Tholin Book : Chemistry Category : Astrochemistry Category : Molecules Portal : Astrobiology Portal : Astronomy Portal : Chemistry LCCN : sh98000445 GND : 4124872 - 7 NKC : ph194795 Retrieved from `` https://en.wikipedia.org/w/index.php?title=Ethylene_glycol&oldid=815071228 '' Categories : Alkanediols Alcohol solvents Household chemicals Hazardous air pollutants Commodity chemicals Vicinal diols Hidden categories : CS1 maint : BOT : original - url status unknown ECHA InfoCard ID from Wikidata Articles with changed KEGG identifier Chembox having DSD data Chemical articles having a data page Articles containing unverified chemical infoboxes All articles with unsourced statements Articles with unsourced statements from April 2014 Articles with unsourced statements from April 2015 Articles with unsourced statements from January 2015 Wikipedia articles with LCCN identifiers Wikipedia articles with GND identifiers Talk Contents About Wikipedia تۆرکجه Беларуская Беларуская ( тарашкевіца ) ‎ Български Català Čeština Deutsch Eesti Ελληνικά Español Esperanto Euskara فارسی Français 한국어 Հայերեն हिन्दी Hrvatski Bahasa Indonesia Italiano עברית Қазақша Latviešu Lietuvių Magyar Bahasa Melayu Nederlands 日本 語 Norsk Polski Português Română Русский Slovenčina Slovenščina Српски / srpski Srpskohrvatski / српскохрватски Suomi Svenska தமிழ் ไทย Türkçe Українська Tiếng Việt 中文 Edit links This page was last edited on 12 December 2017, at 16 : 06. 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Question: 1 2-ethanediol (ethylene diol) has uses that include
Answer: manufacture of polyester fibers and for antifreeze formulations