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Diethylene glycol

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Diethylene glycol
Names
IUPAC name
(2-hydroxyethoxy)ethan-2-ol
Other names
diethylene glycol; ethylene diglycol; diglycol; 2,2'-oxybisethanol; 3-oxa-1,5-pentanediol;
dihydroxy diethyl ether
Identifiers
3D model (JSmol)
ECHA InfoCard 100.003.521 Edit this at Wikidata
  • OCCOCCO
Properties
C4H10O3
Molar mass 106.12 g/mol
Appearance Colorless liquid
Density 1.118 g/mL
Melting point -10.45 °C
Boiling point 244-245 °C
miscible
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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. It is miscible with water and polar organic solvents such as alcohols and ethers.

Diethylene glycol should not be confused with the related compound, ethylene glycol, which is the most common glycol used in coolants.

Diols and polyols

Diethylene glycol is one of several diols (hydrocarbon containing two alcohol groups). Diols related to diethylene glycol are derived from ethylene oxide and are described with the formula HO-CH2-CH2(-O-CH2-CH2)n-OH:

Uses

DEG is used as a building block in organic synthesis, e.g. of 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, printing ink, and glue. Like ethylene glycol, a solution of diethylene glycol and water is used as a coolant. It slightly lowers the freezing point of the solution and significantly elevates its boiling point, making it more suitable for use in hot climates. It can be also found in some hydraulic fluids including brake fluids.

In personal care products (e.g. skin cream and lotions, deodorants) DEG is often replaced by selected 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.[1]

Can be used as an adulterant by winemakers to create a "sweet" wine.

Toxicity

Diethylene glycol has low acute toxicity,[2] but its adverse effects combined with its sweet taste raises the risk of poisoning, particularly in children. 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 unsuitable for consumption. Several poisonings have occurred when DEG was substituted for the non-toxic naturally occurring "triol" glycerine (also called glycerol) in foodstuffs and pharmaceuticals. Glycerine, which has a higher melting point (18 vs. -10 °C) is more viscous than DEG, and is more expensive than DEG.

Because of its adverse effects on humans, diethylene glycol is not allowed for use in 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.[3]

Poisonings attributed to DEG

DEG has been involved in numerous cases of poisonings, both by accidental and deliberate introduction of the compound into medicines, food products and toothpaste.

In the 1937 Elixir Sulfanilamide disaster in the USA, 107 people died after they ingested sulfanilamide dissolved in diethylene glycol.[4] This episode was the impetus for the Federal Food, Drug, and Cosmetic Act of 1938.[5]

In recent years, deaths from medicines adulterated with diethylene glycol have been reported from South Africa, India, Nigeria, Argentina, Haiti,[6] Bangladesh[7] and Panama.[8] 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. The glycerine supplied by a Dutch company, Vos, from a manufacturer in China, but the point of contamination with DEG was never determined. In Bangladesh in 1990, 339 children developed kidney failure, and most of them died, after being given paracetamol (acetaminophen) syrup contaminated with diethylene glycol. In October 2006 the CDC and the Ministry of Health of Panama detected toxic levels of diethylene glycol in a sugarless liquid 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. 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. A Spanish middleman ordered these as TD glycerine, but when filled the custom declaration the name was changed to glycerine.[9][10] A government agency in Panama purchased the falsely labeled product containing diethylene glycol and incorporated it into 260,000 bottles of cold medicine.[11] 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.[12]

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.[13][14][15] 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.[16] On June 4, 2007, a press release by the Chinese Foreign Ministry[17] cited an earlier study in China[18] 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.[19]. The same occurred in Spain with a false Colgate toothpaste, which contained 6% DEG. The tainted products could be identified by the claim to be manufactured in South Africa by Colgate-Palmolive South Africa LTD; they were 5oz/100ml tubes (a size which Colgate does not sell in the United States) and their packaging contained numerous misspellings on the labels. Colgate-Palmolive claimed 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.[20] In July 2007, diethylene glycol was found in counterfeit Sensodyne toothpaste, on sale at a car boot sale in Derbyshire, England,[21] and by February 2009, 84 Nigerian children were reported to have died after being given "My Pikin", a teething syrup contaminated with diethylene glycol.[22]

Footnotes

  1. ^ Authorities warn against using some toothpastes, GulfNews, Published 04/06/2007
  2. ^ Diethylene glycol MSDS
  3. ^ 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
  4. ^ Calvery HO, Klumpp TG (1939). "The toxicity for human beings of diethylene glycol with sulfanilamide". South Med J. 32 (11): 1105–9.
  5. ^ Wax P (1995). "Elixirs, diluents, and the passage of the 1938 Federal Food, Drug and Cosmetic Act". Ann Intern Med. 122 (6): 456–61. PMID 7856995.
  6. ^ 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. (1998). "Epidemic of pediatric deaths from acute renal failure caused by diethylene glycol poisoning". JAMA. 279 (15): 1175–80. doi:10.1001/jama.279.15.1175. PMID 9555756.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  7. ^ 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.
  8. ^ Panama police probe lab workers after 21 deaths
  9. ^ 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
  10. ^ 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
  11. ^ From China to Panama, a Trail of Poisoned Medicine, by Walt Bogdanich and Jake Hooker, New York Times, May 6, 2007.
  12. ^ "Guidance for Industry: Testing of Glycerin for Diethylene Glycol" (PDF). Food and Drug Administration. 2007. Retrieved 2007-05-16. {{cite web}}: Unknown parameter |month= ignored (help)
  13. ^ Bogdanich, W.; McLean, R. "Poisoned Toothpaste in Panama Is Believed to Be From China", New York TImes, May 19, 2007.
  14. ^ "China investigating toothpaste containing potentially deadly chemical". International Herald Tribune. 2007-05-22. Retrieved 2007-05-22.
  15. ^ "U.S. checking all toothpaste imports from China". CNN. 2007-05-23. Retrieved 2007-05-23.
  16. ^ 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)
  17. ^ US 'Self-contradictory' over Toothpaste Scandal, Embassy of the People's Republic of China in Negara Brunel Darussalam
  18. ^ 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)
  19. ^ 7online.com: Toothpaste recall expands 6/18/07
  20. ^ Toothpaste labeled Colgate recalled - More health news - MSNBC.com
  21. ^ BBC NEWS | Business | Toxin found in fake UK toothpaste
  22. ^ News.yahoo.com Nigeria child deaths from tainted syrup rise to 84

References

  • Merck Index, 12th Edition, 3168.

http://www.news.com.au/story/0,27574,24748374-23109,00.html

See also

External links

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