Diethylene glycol
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221302902
2008-06-23T22:54:00Z
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203434
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{{Chembox new
| ImageFile = Diethylene-glycol-chemical.png
| ImageFile1 =
| IUPACName = (2-hydroxyethoxy)ethan-2-ol
| OtherNames = diethylene glycol; ethylene diglycol; diglycol; 2,2'-oxybisethanol; 3-oxa-1,5-pentanediol; <br />dihydroxy diethyl ether
| Section1 = {{Chembox Identifiers
| CASNo = 111-46-6
| PubChem = 8117
| SMILES = OCCOCCO
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>4</sub>H<sub>10</sub>O<sub>3</sub>
| MolarMass = 106.12 g/mol
| Appearance = Colorless liquid
| Density = 1.118 g/mL
| MeltingPt = -10.45 °C
| BoilingPt = 244-245 °C
| Solubility = miscible
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| Autoignition = }}
| Section8 = {{Chembox Related
| OtherAnions =
| OtherCations =
| OtherFunctn = [[ethylene glycol]], [[triethylene glycol]]
| Function = [[diol]]s
}}
}}
'''Diethylene glycol''' (DEG) is an [[organic compound]] described by the structural [[chemical formula|formula]] HO-CH<sub>2</sub>-CH<sub>2</sub>-O-CH<sub>2</sub>-CH<sub>2</sub>-OH. It is a clear, [[hygroscopic]], odorless liquid. It is [[miscible]] with [[water]] and polar organic solvents such as alcohols and [[ether]]s.
==Diols and polyols==
Diethylene glycol is one of several [[diol]]s (hydrocarbon containing two [[alcohol]] groups). They are derived from [[ethylene oxide]] and are described with the formula HO-CH<sub>2</sub>-CH<sub>2</sub>(-O-CH<sub>2</sub>-CH<sub>2</sub>)<sub>n</sub>-OH:
*n = 0 [[ethylene glycol]] ("antifreeze")
*n = 1 DEG
*n = 2 [[triethylene glycol]], TEG, or triglycol
*n = 3 tetraethylene glycol
*n = 4 pentaethylene glycol
*Higher numbers for ''n'' describe a non-toxic [[polymer]] called [[polyethylene glycol]].
==Uses==
Like [[ethylene glycol]], a solution of diethylene glycol and water is used as a [[antifreeze (coolant)|coolant]]. It both lowers the [[freezing point]] of the solution and elevates its [[boiling point]] making it more suitable for hot climates. DEG is also a building block in [[organic synthesis]], e.g. of [[morpholine]] and [[1,4-dioxane]]. It is a [[solvent]] for [[nitrocellulose]], [[resin]]s, [[dye]]s, [[oil]]s, and other [[organic compound]]s. It is a [[humectant]] for [[tobacco]], [[cork (material)|cork]], printing [[ink]], and [[glue]]. It can be also found in some [[hydraulic fluid]]s and [[brake fluid]]s.
In personal care products (e.g. skin cream and lotions, deodorants) DEG is often replaced by the much less toxic [[Glycol ethers|diethylene glycol ethers]].
Diethylene glycol is also illegally used as counterfeit [[glycerin]] in some nations and sold internationally as a component of cough syrup, toothpaste, and mouthwash.<ref>[http://archive.gulfnews.com/nation/Health/10129845.html Authorities warn against using some toothpastes], GulfNews, Published 04/06/2007</ref>
==Toxicity==
Diethylene glycol is toxic to humans and animals, and death can occur by [[kidney failure|renal failure]]. The LD50 for small mammals has been tested at between 2 and 25 g/kg - much less toxic than its relative ethylene glycol, but still inappropriate for even minor consumption. Several poisonings have occurred when DEG is substituted for the non-toxic naturally occurring "triol" [[glycerine]] (HOCH<sub>2</sub>CH(OH)CH<sub>2</sub>OH, also called glycerol) in foodstuffs and pharmaceuticals. Glycerine, which is higher melting (18 vs. -10.45 °C) and more viscous than DEG, costs about three times the price of DEG.<!--http://www.sigmaaldrich.com-->
Because of its toxicity, diethylene glycol is not allowed for food and drugs. The U.S. [[Code of Federal Regulations]] allows no more than 0.2% of diethylene glycol in [[polyethylene glycol]] when the latter is used as a food additive.<ref>[http://frwebgate5.access.gpo.gov/cgi-bin/waisgate.cgi?WAISdocID=98477222302+20+0+0&WAISaction=retrieve ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN: Polyethylene glycol], Code of Federal Regulations, Title 21, Vol.3, Part 172, Sec. 172.820, Revised as of April 1, 2006</ref>
====Mass poisonings attributed to DEG====
It has been responsible for a number of mass poisonings:
*The most infamous incident was the 1937 [[Elixir Sulfanilamide]] disaster in the USA, in which 107 people died after taking [[sulfanilamide]] dissolved in diethylene glycol.<ref>{{cite journal | author=Calvery HO, Klumpp TG | title=The toxicity for human beings of diethylene glycol with sulfanilamide | journal=South Med J | year=1939 | pages=1105–9 | volume=32 | issue=11}}</ref> This episode was the impetus for the [[Federal Food, Drug, and Cosmetic Act]] of 1938.<ref>{{cite journal | author = Wax P | title = Elixirs, diluents, and the passage of the 1938 Federal Food, Drug and Cosmetic Act | journal = Ann Intern Med | volume = 122 | issue = 6 | pages = 456–61 | year = 1995 | pmid = 7856995}}</ref>
*In recent years, deaths from medicines adulterated with diethylene glycol have been reported from [[South Africa]], [[India]], [[Nigeria]], [[Argentina]], [[Haiti]], and [[Panama]]. In Haiti in 1996, 85 children died due to [[glycerine]] contaminated with diethylene glycol in a [[paracetamol]] [[syrup]] produced by Pharval Laboratories, a Haitian company, which did not use standard quality assurance procedures to verify the purity of the glycerine (which was supplied by a [[Netherlands|Dutch]] company, Vos, from a [[manufacturer]] in [[China]], but the point of contamination with DEG was never determined).<ref name=”JAMA1998-O'Brien”>{{cite journal | author=O'Brien KL, Selanikio JD, Hecdivert C, Placide MF, Louis M, Barr DB, Barr JR, Hospedales CJ, Lewis MJ, Schwartz B, Philen RM, St Victor S, Espindola J, Needham LL, Denerville K. | title=Epidemic of pediatric deaths from acute renal failure caused by diethylene glycol poisoning | journal=JAMA | year=1998 | pages=1175–80 | volume=279 | issue=15 | pmid=9555756 | doi=10.1001/jama.279.15.1175}}</ref>
*In [[1985]] a small number of producers of [[Austrian wine]] were found to be adulterating their product with diethylene glycol in order to give the wine a sweeter and more full-bodied taste.<ref> {{cite journal | author = | title = Some wine to break the ice | journal = Lancet | volume = 2 | issue = 8449 | pages = 254 | year = 1985 | pmid = 2862427}}</ref> The amount added was not high enough to be immediately toxic (one would have to ingest about 28 bottles per day for two weeks); however, exports of [[Austrian wine]] collapsed. As a result of this incident, stricter regulations were imposed on Austrian wine makers, and the industry shifted its emphasis from the production of bulk, somewhat sweet wines to lower yields of higher quality, drier wines. Thus, the 'antifreeze scandal' is regarded as having been positive for the industry in the long-term.<ref name="WfA history">{{cite web | last = | first = | authorlink = | coauthors = | title = Viticulture in Austria – a journey in fast motion | work = | publisher = Wines from Austria | date = | url = http://www.winesfromaustria.com/wine/wineland_history.html | format = | doi = | accessdate = 2007-04-26 }}</ref>
*In 1990, in Bangladesh, 339 children developed kidney failure, and most of them died, after being given [[paracetamol]] (acetaminophen) syrup contaminated with diethylene glycol.<ref>BMJ. 1995 Jul 8;311(6997):88-91. Fatal renal failure caused by diethylene glycol in paracetamol elixir: the Bangladesh epidemic. Hanif M, Mobarak et al. [PMID 7613408] CONCLUSION--Paracetamol elixirs with diethylene glycol as a diluent were responsible for a large outbreak of fatal renal failure in Bangladesh.</ref>
*[[Toxic syrup]]: In October 2006 the [[Centers for Disease Control and Prevention|CDC]] and the Ministry of Health of [[Panama]] detected toxic levels of diethylene glycol in a sugarless liquid [[Cough medicine#Expectorants|expectorant]] during an investigation of 46 deaths from a [[syndrome]] characterized by [[gastrointestinal]] symptoms, [[renal failure]] and [[paralysis]]. Almost all the victims were [[hypertension]] and [[diabetes]] patients in their 40s to 80s. Criminal investigations are ongoing.<ref>[http://internetchatradio.com/news_articles_cont/view/330 Panama police probe lab workers after 21 deaths]</ref> The source of the contamination was found to be the Taixing Glycerine Factory, a Chinese company in Hengxiang, China. Taixing Glycerine sold diethylene glycol labeled as TD glycerine, which is an industrial name, through the state-owned Chinese trading company CNSC Fortune Way, based in Beijing. And a Spanish middleman ordered these TD glycerine, but when filled the custom declaration the name was changed to glycerine.<ref>http://www.ce.cn/xwzx/gnsz/gdxw/200705/17/t20070517_11386599_2.shtml 毒糖浆巴拿马致死百人 我药监局称责任不在中方</ref> <ref>http://news.sina.com.cn/c/2007-05-31/153713122468.shtml 质检总局:巴拿马药品中毒事件责任在巴商人</ref>A government agency in Panama purchased the falsely labeled product containing diethylene glycol and incorporated it into 260,000 bottles of cold medicine.<ref>[http://www.nytimes.com/2007/05/06/world/americas/06poison.html?hp=&pagewanted=print From China to Panama, a Trail of Poisoned Medicine], by Walt Bogdanich and Jake Hooker, New York Times, May 6, 2007.</ref> The United States Food and Drug Administration issued an Industry Guidance Document highlighting appropriate testing procedures for use of glycerin in response to product contamination and misrepresentation.<ref>{{cite web | last = | first = | title =Guidance for Industry: Testing of Glycerin for Diethylene Glycol | publisher = Food and Drug Administration | date = May 2007 | url =http://www.fda.gov/cder/guidance/7654fnl.pdf | accessdate = 2007-05-16}}</ref>
*In May 2007, a Panamanian named [[Eduardo Arias]] discovered that toothpaste sold in his country was labeled as containing DEG, the same ingredient that had tainted cough syrup and killed 138 Panamanians in 2006. Panamanian officials discovered that the toothpaste had come from China and initiated a global response.<ref>Bogdanich, W.; McLean, R. "Poisoned Toothpaste in Panama Is Believed to Be From China", New York TImes, May 19, 2007. </ref><ref>{{cite web | last = | first = | title =China investigating toothpaste containing potentially deadly chemical | publisher = International Herald Tribune | date = 2007-05-22 | url =http://www.iht.com/articles/ap/2007/05/22/asia/AS-GEN-China-Tainted-Toothpaste.php | accessdate = 2007-05-22}} </ref><ref>{{cite web | last = | first = | title = U.S. checking all toothpaste imports from China | publisher = CNN | date = 2007-05-23 | url =http://www.cnn.com/2007/HEALTH/05/23/china.toothpaste.reut/index.html | accessdate = 2007-05-23}} </ref>
*Also in May 2007 the same toothpaste was found in some Costa Rican stores. Fast action by the Ministry of Health, and notification through the media, prevented poisonings due to this product. This event was linked to the death sentence of a former pharmaceuticals control officer in China, as the Costa Rican newspaper La Nación reported on its issue of May 30th.<ref>China sentencia a muerte al exjefe de control de fármacos. (China sentences to death former drug control chief) La Nación, pp. 1 & 4. (May 30th 2007)</ref> On June 4, 2007, a press release by the Chinese Foreign Ministry <ref>[http://bn.china-embassy.org/eng/zgxw/t326265.htm US 'Self-contradictory' over Toothpaste Scandal], Embassy of the People's Republic of China in Negara Brunel Darussalam</ref> cited an earlier study in China <ref>[http://www.wanfangdata.com.cn/qikan/periodical.Articles/ldyx/ldyx2000/0003/000313.htm An Epidemiological Study on the Health Effects of Population Using the Toothpaste with Diethylene Glycol], Journal of Labour Medicine (China), vol.17, p 168-170, (2000)</ref> which concluded that up to 15.6% diethylene glycol in toothpaste is safe.
*In June 2007, counterfeit [[Colgate]] toothpaste imported from China was found to be contaminated with DEG, and several people in eastern US reported experiencing headaches and pain after using the product.<ref>[http://abclocal.go.com/wabc/story?section=alerts_recalls&id=5399483 7online.com: Toothpaste recall expands 6/18/07<!-- Bot generated title -->]</ref>. The same occurred in Spain with a false Colgate toothpaste, which contained 6% of DEG. The tainted products could be identified by the claim to be manufactured in South Africa by Colgate-Palmolive South Africa LTD; they are 5oz/100ml tubes (a size which Colgate does not sell in the United States) and their packaging contains numerous misspellings on the labels. Colgate-Palmolive claims that it does not import their products from South Africa into the United States or Canada and that DEG is never and was never used in any of its products anywhere in the world. These counterfeit products were found in smaller "mom and pop" stores, dollar stores and discount stores in at least four states. <ref>[http://www.msnbc.msn.com/id/19214360/ Toothpaste labeled Colgate recalled - More health news - MSNBC.com<!-- Bot generated title -->]</ref>
*In July 2007, diethylene glycol was found in counterfeit Sensodyne toothpaste, on sale at a car boot sale in Derbyshire, England <ref>[http://news.bbc.co.uk/1/hi/england/derbyshire/6896182.stm BBC NEWS | Business | Toxin found in fake UK toothpaste<!-- Bot generated title -->]</ref>
Because of the natural sweetness of the substance, domesticated animals have been victims of DEG poisoning after consuming spilled or leaking antifreeze from vehicles.
== Footnotes ==
{{reflist}}
==References==
*''Merck Index'', 12th Edition, '''3168'''.
==See also==
*[[Polyethylene glycol]]
==External links==
*[http://www.chemicalland21.com/arokorhi/petrochemical/DEG.htm Diethylene Glycol]
*[http://www.chemicalland21.com/arokorhi/petrochemical/TEG.htm Triethylene Glycol]
*[http://www.fda.gov/oc/history/elixir.html The Elixir Sulfanilamide Disaster]
*[http://webintel.wordpress.com/2007/07/05/counterfeit-colgate-toothpaste-crisis-summary-updates/ Counterfeit Colgate Crisis Summary by Webintel]
[[Category:Alcohols]]
[[Category:Polyols]]
[[Category:Alcohol solvents]]
[[de:Diethylenglykol]]
[[es:Dietilenglicol]]
[[fr:Diéthylène glycol]]
[[he:די אתילן גליקול]]
[[ja:ジエチレングリコール]]
[[pl:Glikol dietylenowy]]
[[pt:Dietilenoglicol]]
[[fi:Dietyleeniglykoli]]
[[sv:Dietylenglykol]]
[[uk:Діетиленгліколь]]
[[zh-yue:二甘醇]]
[[zh:二甘醇]]