Diethylene glycol: Difference between revisions

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== Uses ==
Diethylene glycol is used in the manufacture of saturated and unsaturated [[polyester resins]], [[polyurethanes]], and [[plasticizers]].<ref name="availability" /> DEG is used as a buildingprecursor block in [[organic synthesis]] of, for example,to [[morpholine]] and [[1,4-dioxane]]. It is a [[solvent]] for [[nitrocellulose]], [[resins]], [[dyes]], [[oils]], and other [[organic compounds]]. It is a [[humectant]] for [[tobacco]], [[Cork material|cork]], printing [[ink]], and [[glue]].<ref>O'Neil M. The Merck Index. 14th ed. Whitehouse Station, NJ: Merck & Co; 2006.</ref> It is also a component of [[brake fluid]], [[lubricants]], wallpaper strippers, [[artificial fog]] and haze solutions, and heating/cooking fuel.<ref name="Schep" /> In personal care products (e.g. skin cream and lotions and deodorants), DEG is often replaced by selected [[Glycol ethers|diethylene glycol ethers]]. A dilute solution of diethylene glycol can also be used as a [[cryoprotectant]]; however, [[ethylene glycol]] is much more commonly used. Most types of ethylene glycol [[antifreeze]] contain a few percent of diethylene glycol, present as a by-product of ethylene glycol production.
 
DEG is an important industrial [[desiccant]]. It absorb water from [[natural gas]], minimizing the formation of [[methane hydrate]]s, which can block pipes.<ref>{{cite book |doi=10.1002/0471238961.0405190903150805.a01.pub2 |chapter=Desiccants |title=Kirk-Othmer Encyclopedia of Chemical Technology |date=2003 |last1=Cohen |first1=Alan P. |isbn=978-0-471-48494-3 }}</ref>
 
== Toxicology ==
Despite theThe [[Elixir sulfanilamide|discoverytoxicity of DEG's toxicity in 1937]] andwas its involvementdiscovered in mass poisonings around the world, the information available regarding human toxicity is limited1937. Some authors suggest that the minimumThe toxic dose is 0.14 mg/kg body weight and the lethal dose between 1.0 and 1.63 g/kg.<ref name="Kraut">{{cite journal |vauthors=Kraut JA, Kurtz I |title=Toxic alcohol ingestions: clinical features, diagnosis, and management|journal=Clin J Am Soc Nephrol |volume=3 |issue=1 |pages=208–225 |year=2008 |pmid=18045860 |doi=10.2215/CJN.03220807 |doi-access=free }}</ref> Some suggest that the [[median lethal dose|LD<sub>50</sub>]] in adults is about 1 mL/kg,<ref name="Schep" /> while others suggest that that is the [[lethal dose|LD]]<sub>30</sub>.<ref name="Marraffa" /> Because of its adverse effects in humans, diethylene glycolDEG is notrarely allowed to be used in foods and drugs.<ref>DEG: application restrictions</ref> (in many countries). 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]{{Dead link|date=July 2019 |bot=InternetArchiveBot |fix-attempted=yes }}, Code of Federal Regulations, Title 21, Vol.3, Part 172, Sec. 172.820, Revised as of April 1, 2006</ref> TheIn [[Government of Australia|Australia]] does not allow DEG as a food additive, because of its toxicity; it is only allowed at less than 0.25% w/w of DEG as an impurity in polyethylene glycol (PEG),<ref>[http://www.nicnas.gov.au/Publications/CAR/Other/DEG_Hazard_Assessment_Report_PDF.pdf Existing Chemical Hazard Assessment Report] {{Webarchive|url=https://web.archive.org/web/20100120041540/http://www.nicnas.gov.au/Publications/CAR/Other/DEG_Hazard_Assessment_Report_PDF.pdf |date=2010-01-20 }}, June 2009</ref> even in toothpaste.<ref name=tcmt>{{cite web|publisher=[[Australian Competition & Consumer Commission]]|title=Toothpaste containing more than 0.25 per cent by weight of diethylene glycol (DEG)|url=http://www.accc.gov.au/content/index.phtml/itemId/794351|access-date=1 December 2009|url-status=dead|archive-url=https://web.archive.org/web/20090621173806/http://www.accc.gov.au/content/index.phtml/itemId/794351|archive-date = 21 June 2009}}</ref>
 
Diethylene glycol has "moderate to low" [[acute toxicity]]<ref>Diethylene glycol toxicity</ref> in animal experiments. The [[median lethal dose|LD<sub>50</sub>]] for small mammals is between 2 and 25 g/kg, less toxic than its relative [[ethylene glycol]] but still capable of causing toxicity in humans (in high concentrations only).<ref>Diethylene glycol: Human toxicity data</ref> It appears that diethylene glycol may be more hazardous to humans<ref>DEG: why it more hazardous to humans, than animals?</ref> than implied by oral toxicity data in laboratory animals.<ref name="Schep">{{cite journal |vauthors=Schep LJ, Slaughter RJ, Temple WA, Beasley DM |title=Diethylene glycol poisoning |journal=Clin Toxicol |volume=47 |issue=6 |pages=525–35 |year=2009 |pmid=19586352 |doi=10.1080/15563650903086444 |s2cid=22023562 }}</ref>
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The symptoms of poisoning typically occur in three characteristic intervals:<ref name="Schep" />
*'''First phase:''' Gastrointestinal symptoms, such as nausea, vomiting, abdominal pain, and diarrhea, develop. Some patients may develop early neurological symptoms like altered mental status, central nervous system depression, and coma, as well as mild [[hypotension]].
*'''Second phase:''' In one to three days after ingestion (and depending on the dose ingested), patients develop a [[metabolic acidosis]], which causes [[acute kidney failure]], [[oliguria]], increasing [[blood serum|serum]] [[creatinine]] concentrations, and later [[anuria]]. Other symptoms reported and secondary to acidosis and/or [[kidney]] failure are: [[hypertension]], [[tachycardia]] and other [[cardiac dysrhythmia|cardiac dysrhythmias]]s, [[pancreatitis]], and [[hyperkalemia]] or mild [[hyponatremia]].
*'''Final phase:''' At least five to ten days after ingestion, most of the symptoms are related to neurological complications, such as: progressive [[lethargy]], facial [[paralysis]], [[dysphonia]], dilated and nonreactive pupils, [[quadriplegia]], and [[coma]], leading to death.
 
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Wang Guiping discovered how easy it was to enter China's pharmaceutical supply business and earn extra money. Records also revealed that to fool buyers, Wang falsified his license and laboratory analysis reports.
 
Wang declared that after making the first order of counterfeit syrup, he swallowed some of it. Once verifying that he was fine, he shipped it to Qiqihar No. 2 Pharmaceutical in 2005. Some time later, Wang found a reference to diethylene glycol in a chemical book. After manufacturing a second batch of syrup containing diethylene glycol for Qiqihar No. 2 Pharmaceutical, no taste-test was performed. The counterfeit syrup ended in ampules of Amillarisin A, a medication for [[gall bladder]] problems; special pediatric [[enema]] fluid; blood vessel disease injections; intravenous pain reliever; and an [[arthritis]] medication.
 
In April 2006, the Guangdong Province Hospital of [[Guangzhou]] began administering Amillarisin A to their patients. Soon thereafter, patients died after receiving the medication. Wang was caught and Qiqihar No. 2 Pharmaceutical was shut down by the authorities. Besides Wang, five employees of Qiquihar were prosecuted.<ref name="Bogdanich2">{{cite news|author1=Bogdanich, W |author2=Hooker, J.|title=From China to Panama, a trail of Poisoned Medicine.|newspaper=The New York Times|date=June 2007|url=https://www.nytimes.com/2007/05/06/world/americas/06poison.html?pagewanted=print}}</ref>
 
=== 2006 – Panama ===
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In May 2007, a Panamanian named [[Eduardo Arias]] discovered a 59-cent [[toothpaste]] that was labeled containing DEG. Panamanian officials traced the toothpaste to a local company in the [[Colón Free Trade Zone]]. In fact, the company bought the product in China and had already re-exported toothpaste to [[Costa Rica]], [[Dominican Republic]] and Haiti, making Panama kick off a local warning.<ref>Bogdanich, W.; McLean, R. "Poisoned Toothpaste in Panama Is Believed to Be From China", ''The New York Times'', May 19, 2007.</ref><ref>{{cite web|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|access-date = 2007-05-22}}</ref><ref>{{cite news|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 |access-date=2007-05-23 |archive-url=https://web.archive.org/web/20070526145153/http://www.cnn.com/2007/HEALTH/05/23/china.toothpaste.reut/index.html |archive-date=2007-05-26 |url-status=dead}}</ref> For the end of the month, the [[Government of China|Chinese government]] committed to investigate the "supposedly" tainted toothpaste that had been recalled in Panama and Dominican Republic, but stated that, as per an essay written in 2000, a toothpaste containing 15.6% was not dangerous.<ref name=China>{{cite web|author1=Xiaomin, X |author2=Hongyi, W.|title =Gov't probes 'tainted toothpaste' case|publisher = China Daily|date = 2007-05-24|url =http://www.chinadaily.com.cn/china/2007-05/24/content_879179.htm|access-date = 2009-12-10}}</ref>
 
On June 1, 2007, the FDA warned consumers to avoid toothpaste from China, although there was no information if these toothpastes had already entered the US, and started testing any imported Chinese toothpaste.<ref>Bogdanich, W. "Toxic Toothpaste Made in China Is Found in U.S. ", ''The New York Times'', June 2, 2007.</ref><ref>U.S. Food and Drug Administration Press Release. "FDA Advises Consumers to Avoid Toothpaste From China Containing Harmful Chemical. FDA Detains One Contaminated Shipment, Issues Import Alert", June 1, 2007.</ref> Days later, [[Colgate-Palmolive]] found counterfeit toothpaste with its name, which was contaminated with DEG and found at [[Variety store|dollar-type]] [[Discountdiscount store|discount stores]]s in [[New York (state)|New York]], [[New Jersey]], [[Pennsylvania]] and [[Maryland]]. The toothpaste was labeled as "Manufactured in South Africa" and contained [[misspellings]] like "isclinically", "SOUTH AFRLCA" and "South African Dental Assoxiation".<ref>Colgate Palmolive Company Press Release. [http://investor.colgate.com/ReleaseDetail.cfm?Archive=&ReleaseDate={ts%20%272007-06-14%2000:00:00%27}&ReleaseID=249085&ReleaseType=Company&header= "Counterfeit Colgate Toothpaste Found"] {{Webarchive|url=https://web.archive.org/web/20090328191943/http://investor.colgate.com/ReleaseDetail.cfm?ReleaseID=249085&ReleaseType=Company&ReleaseDate=%7Bts%20%272007-06-14%2000:00:00%27%7D&header=&Archive= |date=2009-03-28 }}, June 14, 2007.</ref><ref>U.S. Food and Drug Administration Press Release. "Counterfeit Colgate Toothpaste Found", June 14, 2007.</ref> Although there were no reports of anyone harmed, several people in the eastern US reported experiencing headaches and pain after using the product.<ref>{{Cite web |url=http://abclocal.go.com/wabc/story?section=alerts_recalls&id=5399483 |title=7online.com: Toothpaste recall expands 6/18/07 |access-date=2007-06-21 |archive-url=https://web.archive.org/web/20070706085804/http://abclocal.go.com/wabc/story?section=alerts_recalls&id=5399483 |archive-date=2007-07-06 |url-status=dead }}</ref> It was later discovered that a great number of tubes with poison ended up in [[Psychiatric hospital|hospitals for the mentally ill]], [[Prison|prisonsprison]]s, [[Youth detention center|juvenile detention centers]], other hospitals and many other state institutions.<ref>Bogdanich, W. "Wider Sale Is Seen for Toothpaste Tainted in China ", ''The New York Times'', June 28, 2007.</ref>
 
In July 2007, health authorities in the UK detected a [[counterfeit]] [[Sensodyne]] toothpaste on sale at a [[car boot sale]] in [[Derbyshire]].<ref>{{cite news| url=http://news.bbc.co.uk/1/hi/england/derbyshire/6896182.stm|work=BBC News|title=Toxin found in fake UK toothpaste|date=July 12, 2007|access-date=May 1, 2010}}</ref> Soon, other countries also recalling Chinese-made toothpaste were [[Belize]], [[Canada]], [[Mozambique]], [[Saudi Arabia]], [[New Zealand]], [[Spain]], [[Italy]], [[Japan]], and [[Ireland]], plus an [[Indianapolis]], [[Indiana]] US hotel-supplier that distributed Chinese toothpaste in [[Barbados]], [[Belgium]], [[Bermuda]], [[United Kingdom|Britain]], [[Canada]], Dominican Republic, [[France]], [[Germany]], [[Ireland]], Italy, [[Mexico]], Spain, [[Switzerland]], [[Turks and Caicos Islands|Turks and Caicos]], the [[United Arab Emirates]] and [[United States]]. What began as a local alert revealed a global problem in more than 30 countries and involving more than thirty brands.<ref>[https://www.nytimes.com/imagepages/2007/09/30/world/20071001_PANAMA_GRAPHIC.html "Tainted toothpaste across the world"], ''The New York Times'', September 30, 2007.</ref> The world outcry made Chinese officials ban the practice of using diethylene glycol in toothpaste.<ref>Bogdanich, W. [https://www.nytimes.com/2007/10/01/world/americas/01panama.html "The Everyman Who Exposed Tainted Toothpaste"], ''The New York Times'', October 1, 2007.</ref>