Ethylene Glycol - Wikipedia

Organic compound ethane-1,2-diol Not to be confused with Polyethylene glycol, Diethylene glycol, Propylene glycol, or Glycol. Ethylene glycol

Names
IUPAC names Ethylene glycol[1]Ethane-1,2-diol[2]
Preferred IUPAC name Ethane-1,2-diol[3]
Other names Ethylene glycol 1,2-Ethanediol Ethylene alcohol Hypodicarbonous acid Monoethylene glycol 1,2-Dihydroxyethane Glycol solvent
Identifiers
CAS Number	107-21-1 Y
3D model (JSmol)	Interactive image
3DMet	B00278
Abbreviations	MEG
Beilstein Reference	505945
ChEBI	CHEBI:30742 Y
ChEMBL	ChEMBL457299 Y
ChemSpider	13835235 Y
ECHA InfoCard	100.003.159
EC Number	203-473-3
Gmelin Reference	943
KEGG	C01380 Y
MeSH	Ethylene+glycol
PubChem CID	174
RTECS number	KW2975000
UNII	FC72KVT52F Y
UN number	3082
CompTox Dashboard (EPA)	DTXSID4027862 DTXSID8020597, DTXSID4027862
InChI InChI=1S/C2H6O2/c3-1-2-4/h3-4H,1-2H2 YKey: LYCAIKOWRPUZTN-UHFFFAOYSA-N Y InChI=1/C2H6O2/c3-1-2-4/h3-4H,1-2H2Key: LYCAIKOWRPUZTN-UHFFFAOYAD
SMILES OCCO
Properties
Chemical formula	C2H6O2
Molar mass	62.068 g·mol−1
Appearance	colorless liquid
Odor	Odorless[4]
Density	1.1132 g/cm3 (0.04022 lb/cu in)
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 alcohols, ethyl acetate, THF, and dioxane. Miscible with DCM and slightly miscible with diethyl ether. Not miscible with toluene or hexanes.
log P	-1.69[5]
Vapor pressure	7.99 Pa (20 °C)[4]
Viscosity	1.61×10−2 Pa·s[6]
Thermochemistry
Heat capacity (C)	149.5 J/(mol·K)
Std molarentropy (S⦵298)	166.9 J/(mol·K)
Std enthalpy offormation (ΔfH⦵298)	−460 kJ/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Harmful, produces poisonous oxalic acid when ingested, flammable
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H373
Precautionary statements	P260, P264, P270, P301+P312, P302, P314, P330, P501
NFPA 704 (fire diamond)	2 1 0
Flash point	111 °C (232 °F; 384 K) closed cup
Autoignitiontemperature	410 °C (770 °F; 683 K)
Explosive limits	3.2–15.2%[4]
NIOSH (US health exposure limits):
PEL (Permissible)	None[4]
REL (Recommended)	None established[4]
IDLH (Immediate danger)	None[4]
Safety data sheet (SDS)	External SDS 1 External SDS 2
Related compounds
Related diols	Propylene glycol Diethylene glycol Triethylene glycol Polyethylene glycol
Supplementary data page
Ethylene glycol (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Chemical compound

Ethylene glycol (IUPAC name: ethane-1,2-diol) is an organic compound (a vicinal diol[7]) with the formula (CH2OH)2. 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, flammable, viscous liquid. It has a sweet taste, but is toxic in high concentrations. This molecule has been observed in outer space.[8]

Production

[edit]

Industrial routes

[edit]

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

C2H4O + H2O → HO−CH2CH2−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. World production of ethylene glycol was ~20 Mt in 2010.[9]

A higher selectivity is achieved by the use of Shell's OMEGA process. In the OMEGA process, the ethylene oxide is first converted with carbon dioxide (CO2) to ethylene carbonate. This ring is then hydrolyzed with a base catalyst in a second step to produce mono-ethylene glycol in 98% selectivity.[10] 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 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 C1-based ethylene glycol.[11] Dimethyl oxalate can be converted into ethylene glycol in high yields (94.7%)[12] by hydrogenation with a copper catalyst:[13]

Because the methanol is recycled, only carbon monoxide, hydrogen, and oxygen are consumed. One plant with a production capacity of 200000 tons of ethylene glycol per year is in Inner Mongolia, and a second plant in the Chinese province of Henan with a capacity of 250000 tons per year was scheduled for 2012.[14] As of 2015[update], four plants in China with a capacity of 200000 t/a each were operating, with at least 17 more to follow.[15]

Biological routes

[edit]

Ethylene glycol can be produced by recycling its polymeric derivatives such a polyethylene terephthalate.[16]

Historical routes

[edit]

According to most sources, French chemist Charles-Adolphe Wurtz (1817–1884) first prepared ethylene glycol in 1856.[17] He first treated "ethylene iodide" (1,2-Diiodoethane) 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).[18] In 1859, Wurtz prepared ethylene glycol via the hydration of ethylene oxide.[19] 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 licensing.

Uses

[edit]

Coolant and heat-transfer agent

[edit]

The major use of ethylene glycol is as an antifreeze agent in the coolant in for example, automobiles and air-conditioning systems that either place the chiller or air handlers outside or 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 mixture of ethylene glycol with water provides additional benefits to coolant and antifreeze solutions, such as preventing corrosion and acid degradation, as well as inhibiting the growth of most microbes and fungi.[20] Mixtures of ethylene glycol and water are sometimes informally referred to in industry as glycol concentrates, compounds, mixtures, or solutions.

Table of thermal and physical properties of saturated liquid ethylene glycol:[21][22]

Temperature (°C)	Density (kg/m3)	Specific heat (kJ/(kg·K))	Kinematic viscosity (m2/s)	Conductivity (W/(m⋅K))	Thermal diffusivity (m2/s)	Prandtl Number	Thermal expansivity (K−1)
0	1130.75	2.294	7.53×10−5	0.242	9.34×10−8	615	6.50×10−4
20	1116.65	2.382	1.92×10−5	0.249	9.39×10−8	204	6.50×10−4
40	1101.43	2.474	8.69×10−6	0.256	9.39×10−8	93	6.50×10−4
60	1087.66	2.562	4.75×10−6	0.26	9.32×10−8	51	6.50×10−4
80	1077.56	2.65	2.98×10−6	0.261	9.21×10−8	32.4	6.50×10−4
100	1058.5	2.742	2.03×10−6	0.263	9.08×10−8	22.4	6.50×10−4

Anti-freeze

[edit]

Pure ethylene glycol freezes at about −12 °C (10.4 °F) but, when mixed with water, the mixture freezes at a lower temperature. For example, a mixture of 60% ethylene glycol and 40% water freezes at −45 °C (−49 °F).[23] Diethylene glycol behaves similarly. The freezing point depression of some mixtures can be explained as a colligative property of solutions but, in highly concentrated mixtures such as the example, deviations from ideal solution behavior are expected due to the influence of intermolecular forces. It's important to note that though pure and distilled water will have a greater specific heat capacity than any mixture of antifreeze and water, commercial antifreezes also typically contain an anti-corrosive additive to prevent pure water from corroding coolant passages in the engine block, cylinder head(s), water pump and radiator.

There is a difference in the mixing ratio, depending on whether it is ethylene glycol or propylene glycol. For ethylene glycol, the mixing ratios are typically 30/70 and 35/65, whereas the propylene glycol mixing ratios are typically 35/65 and 40/60. It is important that the mixture be frost-proof at the lowest operating temperature.[24]

Because of the depressed freezing temperatures, ethylene glycol is used as a de-icing fluid for windshields and aircraft, as an antifreeze in automobile engines, and as a component of vitrification (anticrystallization) mixtures for low-temperature preservation of biological tissues and organs.

The use of ethylene glycol not only depresses the freezing point of aqueous mixtures, but also elevates their boiling point. This results in the operating temperature range for heat-transfer fluids being 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.

Precursor to polymers

[edit]

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.

Other uses

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Dehydrating agent

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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

[edit]

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.

Precursor to other chemicals

[edit]

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 is also used as part of the water-based hydraulic fluid used to control subsea oil and gas production equipment.

Organic building block

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Although dwarfed by its use as a precursor to polyesters, ethylene glycol is useful in more specialized areas of organic chemistry.

It serves as a protecting group in organic synthesis for manipulation of ketones and aldehydes.[25][26] In one example, isophorone was protected using ethylene glycol:[27]

The glycol-derived dioxalane of ethyl acetoacetate is a commercial fragrance fructone.[28]

Miscellaneous chemical reactions

[edit]

Silicon dioxide dissolves slowly in hot ethylene glycol in the presence of alkali metal base to produce silicates.[29]

Toxicity

[edit] Main article: Ethylene glycol poisoning

Ethylene glycol has relatively high mammalian toxicity when ingested, roughly on par with methanol, with an oral LDLo = 786 mg/kg for humans.[30] 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 is fatal if untreated.[31] Several deaths are recorded annually in the U.S. alone.[32]

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 is not as palatable[note 1] and is converted in the body to lactic acid, a normal product of metabolism and exercise.[35]

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.[36]

In 2022, several hundred children died of acute kidney failure in Indonesia and The Gambia because the paracetamol syrup made by New Delhi-based Maiden Pharmaceuticals contained ethylene glycol and diethylene glycol, ingredients that have been linked to child deaths from acute kidney injury in The Gambia.[37] In December 2022, Uzbekistan's health ministry has said children died as a result of ethylene glycol in cough syrup made by Marion Biotech, which is based at Noida, near New Delhi.[38]

Environmental effects

[edit]

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 de-icing agents for runways and airplanes.[39] 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."[40]

Notes

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1. ^ 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[33] and propylene glycol[34] is discussed in the Merck Index, and neither compound is described as bitter.

References

[edit]

1. ^ "Ethylene glycol (CHEBI:30742)".
2. ^ "Ethylene glycol (CHEBI:30742)".
3. ^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 690. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
4. ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0272". National Institute for Occupational Safety and Health (NIOSH).
5. ^ "Ethylene glycol". www.chemsrc.com.
6. ^ Elert, Glenn. "Viscosity". The Physics Hypertextbook. Retrieved 2007-10-02.
7. ^ "3.8: 3.8 Alcohols - Classification and Nomenclature". Chemistry LibreTexts. 2018-10-13. Retrieved 2022-04-21.
8. ^ 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. S2CID 56198291.
9. ^ Yue, Hairong; Zhao, Yujun; Ma, Xinbin; Gong, Jinlong (2012). "Ethylene glycol: properties, synthesis, and applications". Chemical Society Reviews. 41 (11): 4218. doi:10.1039/c2cs15359a. eISSN 1460-4744. ISSN 0306-0012. PMID 22488259.
10. ^ 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.
11. ^ "Coal to MEG, Changing the Rules of the Game" (PDF). Nexant/Chemsystems. Archived from the original (PDF) on July 14, 2011. Retrieved 2016-08-08. (PDF; 5,4 MB), 2011 Prospectus.
12. ^ 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.
13. ^ 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.
14. ^ Clay Boswell (30 Jan 2012). "China's coal-based chemicals are a trade-off". Independent Commodity Intelligence Services.
15. ^ Gräbner, Martin (2014-11-24). Industrial Coal Gasification Technologies Covering Baseline and High-Ash Coal. John Wiley & Sons. ISBN 9783527336906.
16. ^ Tournier, Vincent; Duquesne, Sophie; Guillamot, Frédérique; Cramail, Henri; Taton, Daniel; Marty, Alain; André, Isabelle (2023). "Enzymes' Power for Plastics Degradation" (PDF). Chemical Reviews. 123 (9): 5612–5701. doi:10.1021/acs.chemrev.2c00644. PMID 36916764.
17. ^ Adolphe Wurtz (1856). "Sur le glycol ou alcool diatomique" [On glycol or dibasic alcohol]. Comptes Rendus. 43: 199–204.
18. ^ 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.)
19. ^ 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.
20. ^ "Hydratech - Specialist Fluid Solutions". www.hydratechglobal.net. Archived from the original on 2021-05-14. Retrieved 2020-02-24.
21. ^ Holman, Jack P. (2002). Heat Transfer (9th ed.). New York, NY: McGraw-Hill Companies, Inc. pp. 600–606. ISBN 9780072406559.
22. ^ Frank P. Incropera, David P. Dewitt, heodore L. Bergman, Adrienne S. Lavigne (2007). Fundamentals of Heat and Mass Transfer (6th ed.). Hoboken, NJ: John Wiley and Sons, Inc. pp. 941–950. ISBN 9780471457282.{{cite book}}: CS1 maint: multiple names: authors list (link)
23. ^ Siegfried Rebsdat; Dieter Mayer. "Ethylene Glycol". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_101. ISBN 978-3527306732.
24. ^ "Glycol til industri og erhverv" [Glycol for industry and business]. LC Glad (in Danish) – via lcglad.dk.
25. ^ "Ethylene glycol acetal". The Organic Synthesis Archive. synarchive.com.
26. ^ Theodora W. Greene; Peter G. M. Wuts (1999). Protective Groups in Organic Synthesis (Third ed.). John Wiley & Sons. pp. 312–322. ISBN 978-0-471-16019-9.
27. ^ 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.
28. ^ Panten, Johannes; Surburg, Horst (2016). "Flavors and Fragrances, 3. Aromatic and Heterocyclic Compounds". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–45. doi:10.1002/14356007.t11_t02. ISBN 978-3-527-30673-2.
29. ^ Laine, Richard M.; Blohowiak, Kay Youngdahl; Robinson, Timothy R.; Hoppe, Martin L.; Nardi, Paola; Kampf, Jeffrey; Uhm, Jackie (17 October 1991). "Synthesis of pentacoordinate silicon complexes from SiO2" (PDF). Nature. 353 (6345): 642–644. Bibcode:1991Natur.353..642L. doi:10.1038/353642a0. hdl:2027.42/62810. S2CID 4310228.
30. ^ Safety Officer in Physical Chemistry (November 23, 2009). "Safety (MSDS) data for ethylene glycol". Oxford University. Archived from the original on December 14, 2011. Retrieved December 30, 2009.
31. ^ Ethylene glycol. National Institute for Occupational Safety and Health. Emergency Response Database. August 22, 2008. Retrieved December 31, 2008.
32. ^ Ethylene Glycol Toxicity at eMedicine
33. ^ The Merck Index (15th ed.). Royal Society of Chemistry. 2013. pp. M5122.
34. ^ The Merck Index (15th ed.). Royal Society of Chemistry. 2013. pp. M9238.
35. ^ Pieter Klapwijk (January 27, 2010). "Ethylene Glycol Poisoning". The Rested Dog Inn. Archived from the original on January 26, 2013. Retrieved October 11, 2012.
36. ^ "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.
37. ^ "Indonesia says child deaths from acute kidney injury rise to 133". Al Jazeera. 22 October 2022.
38. ^ "Marion Biotech: Uzbekistan links child deaths to India cough syrup". BBC News. 29 December 2022.
39. ^ "Ethylene Glycol". ToxFAQs. CDC. 12 March 2015.
40. ^ "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.

External links

[edit]

• WebBook page for C2H6O2
• ATSDR - Case Studies in Environmental Medicine: Ethylene Glycol and Propylene Glycol Toxicity
• CDC - NIOSH Pocket Guide to Chemical Hazards
• Antifreeze ratio for Ethylene Glycol and Propylene Glycol
• 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. PMID 22488259.

v t e Alcohols
By consumption	Alcohols found inalcoholic drinks 1-Propanol 2-Methyl-1-butanol Ethanol Isoamyl alcohol Isobutanol Phenethyl alcohol tert-Amyl alcohol tert-Butyl alcohol Tryptophol Medical alcohol Ethchlorvynol Methylpentynol Methanol poisoning Ethanol Toxic alcohols Isopropyl alcohol Methanol
Primaryalcohols (1°)	Methanol 4-Methylcyclohexanemethanol Aminomethanol Cyclohexylmethanol Methoxymethanol Methylazoxymethanol Trifluoromethanol Ethanol 1-Aminoethanol 2,2,2-Trichloroethanol 2,2,2-Trifluoroethanol 2-(2-Ethoxyethoxy)ethanol 2-(2-Methoxyethoxy)ethanol 2-(2-Methoxyethoxy)ethanol 2-Butoxyethanol 2-Chloroethanol 2-Ethoxyethanol 2-Fluoroethanol 2-Mercaptoethanol 2-Methoxyethanol Aminoethylethanolamine Diethylethanolamine Dimethylethanolamine Ethanol Ethanolamine N,N-Diisopropylaminoethanol N-Methylethanolamine Phenoxyethanol Tribromoethanol Butanol 2-Methyl-1-butanol Isobutanol n-Butanol Straight-chainsaturatedC1 — C9 Methanol Ethanol 1-Propanol 1-Butanol 1-Pentanol 1-Hexanol 1-Heptanol 1-Octanol (capryl) 1-Nonanol (pelargonic) Straight-chainsaturatedC10 — C19 1-Decanol (capric) 1-Undecanol (hendecyl) 1-Dodecanol (lauryl) 1-Tridecanol 1-Tetradecanol (myristyl) 1-Pentadecanol 1-Hexadecanol (cetyl / palmityl) 1-Heptadecanol 1-Octadecanol (stearyl) 1-Nonadecanol Straight-chainsaturatedC20 — C29 1-Icosanol (arachidyl) 1-Heneicosanol 1-Docosanol (behenyl) 1-Tricosanol 1-Tetracosanol (lignoceryl) 1-Pentacosanol 1-Hexacosanol (ceryl) 1-Heptacosanol 1-Octacosanol (cluytyl / montanyl) 1-Nonacosanol Straight-chainsaturatedC30 — C39 1-Triacontanol (melissyl / myricyl) 1-Hentriacontanol 1-Dotriacontanol (lacceryl) 1-Tritriacontanol 1-Tetratriacontanol (geddyl) 1-Pentatriacontanol 1-Hexatriacontanol 1-Heptatriacontanol 1-Octatriacontanol 1-Nonatriacontanol Straight-chainsaturatedC40 — C49 1-Tetracontanol 1-Hentetracontanol 1-Dotetracontanol 1-Tritetracontanol 1-Tetratetracontanol 1-Pentatetracontanol 1-Hexatetracontanol 1-Heptatetracontanol 1-Octatetracontanol 1-Nonatetracontanol 2-Ethylhexanol Allyl alcohol Anisyl alcohol Benzyl alcohol Cinnamyl alcohol Crotyl alcohol Furfuryl alcohol Isoamyl alcohol Neopentyl alcohol Nicotinyl alcohol Perillyl alcohol Phenethyl alcohol Prenol Propargyl alcohol Salicyl alcohol Tryptophol Vanillyl alcohol Veratrole alcohol
Secondary alcohols (2°)	1-Phenylethanol 2-Butanol 2-Deoxyerythritol 2-Heptanol 3-Heptanol 2-Hexanol 3-Hexanol 3-Methyl-2-butanol 2-Nonanol 2-Octanol 2-Pentanol 3-Pentanol Cyclohexanol Cyclopentanol Cyclopropanol Diphenylmethanol Isopropanol Pinacolyl alcohol Pirkle's alcohol Propylene glycol methyl ether
Tertiary alcohols (3°)	2-Methyl-2-pentanol 2-Methylheptan-2-ol 2-Methylhexan-2-ol 3-Methyl-3-pentanol 3-Methyloctan-3-ol Diacetone alcohol Ethchlorvynol Methylpentynol Nonafluoro-tert-butyl alcohol tert-Amyl alcohol tert-Butyl alcohol Triphenylethanol Triphenylmethanol
Hydric alcohols	Monohydric alcohols Methanol (C1) Ethanol (C2) Isopropanol (C3) 1-Butanol (C4) 1-Pentanol (C5) Cetyl alcohol (C16) Dihydric alcohols Ethylene glycol Propylene glycol Trihydric alcohols Glycerol Polyhydric alcohols (sugar alcohols) Pentaerythritol Ethylene glycol (C2) Glycerol, Propylene glycol (C3) Erythritol, Threitol (C4) Xylitol (C5) Mannitol, Sorbitol (C6) Volemitol (C7)
Amyl alcohols	2,2-Dimethylpropan-1-ol 2-Methylbutan-1-ol 2-Methylbutan-2-ol 3-Methylbutan-1-ol 3-Methylbutan-2-ol Pentan-1-ol Pentan-2-ol Pentan-3-ol
Aromatic alcohols	Benzyl alcohol 2,4-Dichlorobenzyl alcohol 3-Nitrobenzyl alcohol
Saturatedfatty alcohols	Cetostearyl alcohol Decanol Lauryl alcohol Myristyl alcohol Nonanol Octanol Tridecanol Undecanol
Branched andunsaturatedfatty alcohols	3-Methyl-3-pentanol Erucyl alcohol Linolenyl alcohol Linoleyl alcohol Oleyl alcohol Palmitoleyl alcohol tert-Amyl alcohol tert-Butyl alcohol
Sugar alcohols	C1 — C7 Methylene glycol (C1) Ethylene glycol (C2) Glycerol (C3) Erythritol (C4) Threitol (C4) Arabitol (C5) Ribitol (C5) Xylitol (C5) Mannitol (C6) Sorbitol (C6) Galactitol (C6) Iditol (C6) Volemitol (C7) Deoxy sugar alcohols Fucitol Cyclic sugar alcohols Inositol Glycylglycitols Maltitol Lactitol Isomalt Maltotriitol Maltotetraitol Polyglycitol
Terpene alcohols	Monoterpene alcohols Borneol Citronellol Geraniol Linalool Menthol Nerol Rhodinol Terpineol Sesquiterpene alcohols Bisabolol Farnesol Nerolidol Patchoulol Diterpene alcohols Phytol
Dialcohols	1,4-Butanediol 1,5-Pentanediol 2-Methyl-2-propyl-1,3-propanediol Diethylpropanediol Ethylene glycol
Trialcohols	Glycerol
Sterols	Cholesterol Ergosterol Lanosterol β-Sitosterol Stigmasterol
Fluoroalcohols	1,3-Difluoro-2-propanol 2,2,2-Trifluoroethanol 2-Fluoroethanol Nonafluoro-tert-butyl alcohol Trifluoromethanol
Preparations	Substitution of haloalkane Carbonyl reduction Ether cleavage Hydrolysis of epoxide Hydration of alkene Ziegler process
Reactions	Deprotonation Protonation Alcohol oxidation Glycol cleavage Nucleophilic substitution Fischer–Speier esterification Williamson ether synthesis Elimination reaction Nucleophilic substitution of carbonyl group Friedel-Crafts alkylation Nucleophilic conjugate addition Transesterification
Category

v t e Internal combustion engine
Part of the Automobile series
Engine block and rotating assembly	Balance shaft Block heater Bore Connecting rod Crankcase Crankcase ventilation system (PCV valve) Crankpin Crankshaft Core plug (freeze plug) Cylinder (bank, layout) Displacement Flywheel Firing order Stroke Main bearing Piston Piston ring Starter ring gear
Valvetrain and Cylinder head	Flathead layout Overhead camshaft layout Overhead valve (pushrod) layout Tappet / lifter Camshaft Chest Combustion chamber Compression ratio Head gasket Rocker arm Timing belt Valve
Forced induction	Blowoff valve Boost controller Intercooler Supercharger Turbocharger
Fuel system	Diesel engine Petrol engine Carburetor Fuel filter Fuel injection Fuel pump Fuel tank
Ignition	Magneto Compression ignition Coil-on-plug Distributor Glow plug Ignition coil Spark plug Spark plug wires
Engine management	Engine control unit (ECU)
Electrical system	Alternator Battery Dynamo Starter motor
Intake system	Airbox Air filter Idle air control actuator Inlet manifold MAP sensor MAF sensor Throttle Throttle position sensor
Exhaust system	Catalytic converter Diesel particulate filter EGT sensor Exhaust manifold Muffler Oxygen sensor
Cooling system	Air cooling Water cooling Electric fan Radiator Thermostat Viscous fan (fan clutch)
Lubrication	Oil Oil filter Oil pump Sump (Wet sump, Dry sump)
Other	Knocking / pinging Power band Redline Stratified charge Top dead centre
Portal Category

v t e Molecules detected in outer space
Molecules	Diatomic Aluminium monochloride Aluminium monofluoride Aluminium(II) oxide Argonium Carbon cation Carbon monophosphide Carbon monosulfide Carbon monoxide Cyano radical Diatomic carbon Fluoromethylidynium Helium hydride ion Hydrogen chloride Hydrogen fluoride Hydrogen (molecular) Hydroxyl radical Iron(II) oxide Magnesium monohydride Methylidyne radical Nitric oxide Nitrogen (molecular) Imidogen Sulfur mononitride Oxygen (molecular) Phosphorus monoxide Phosphorus mononitride Potassium chloride Silicon carbide Silicon monoxide Silicon monosulfide Sodium chloride Sodium iodide Sulfanyl Sulfur monoxide Titanium(II) oxide Triatomic Aluminium(I) 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 N2H+ Nitrous oxide Nitroxyl Ozone Methylidynephosphane Potassium cyanide Trihydrogen cation Sodium cyanide Sodium hydroxide Silicon carbonitride c-Silicon dicarbide SiNC Sulfur dioxide Thioformyl Thioxoethenylidene Titanium dioxide Tricarbon Water Fouratoms Acetylene Ammonia Isocyanic acid Cyanoethynyl Formaldehyde Fulminic acid HCCN Hydrogen peroxide Hydromagnesium isocyanide Isocyanic acid Isothiocyanic acid Ketenyl Methylene amidogen Methyl cation Methyl radical Propynylidyne Protonated carbon dioxide Protonated hydrogen cyanide Silicon tricarbide Thioformaldehyde Tricarbon monoxide Tricarbon monosulfide Thiocyanic acid Fiveatoms Ammonium ion Butadiynyl Carbodiimide Cyanamide Cyanoacetylene Cyanoformaldehyde Cyanomethyl Cyclopropenylidene Formic acid Isocyanoacetylene Ketene Methane Methoxy radical Methylenimine Propadienylidene Protonated formaldehyde Silane Silicon-carbide cluster Sixatoms Acetonitrile Cyanobutadiynyl radical E-Cyanomethanimine Cyclopropenone Diacetylene Ethylene Formamide HC4N Ketenimine Methanethiol Methanol Methyl isocyanide Pentynylidyne Propynal Protonated cyanoacetylene Sevenatoms Acetaldehyde Acrylonitrile Vinyl cyanide Cyanodiacetylene Ethylene oxide Glycolonitrile Hexatriynyl radical Propyne Methylamine Methyl isocyanate Vinyl alcohol Eightatoms Acetic acid Aminoacetonitrile Cyanoallene Ethanimine Glycolaldehyde Hexapentaenylidene Methylcyanoacetylene Methyl formate Acrolein Nineatoms Acetamide Cyanohexatriyne Dimethyl ether Ethanol Methyldiacetylene Octatetraynyl radical Propene Ethanethiol Propionitrile N-Methylformamide Tenatomsor more Acetone Benzene Benzonitrile Buckminsterfullerene (C60, C60+, fullerene, buckyball) C70 fullerene Cyanodecapentayne Ethylene glycol Ethyl formate Methyl acetate Methyl-cyano-diacetylene Methyltriacetylene Propionaldehyde Butyronitrile Pyrimidine Heptatrienyl radical
Deuteratedmolecules	Ammonia Ammonium ion Formaldehyde Formyl radical Heavy water Hydrogen cyanide Hydrogen deuteride Hydrogen isocyanide Propyne N2D+ Trihydrogen cation
Unconfirmed	Anthracene Dihydroxyacetone Methoxyethane Glycine Graphene Hemolithin H2NCO+ Linear C5 Naphthalene cation Phosphine Pyrene Silylidyne
Related	Abiogenesis Astrobiology Astrochemistry Atomic and molecular astrophysics Chemical formula Circumstellar dust Circumstellar envelope Cosmic dust Cosmic ray Cosmochemistry Diffuse interstellar band Earliest known life forms Extraterrestrial life Extraterrestrial liquid water Forbidden mechanism 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 Pseudo-panspermia Polycyclic aromatic hydrocarbon (PAH) RNA world hypothesis Spectroscopy Tholin
Category:Astrochemistry Outer space portal Astronomy portal Chemistry portal

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