Diethylene glycol
From Wikipedia, the free encyclopedia
| Diethylene glycol | |
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| Chemical name | (2-hydroxyethoxy)ethan-2-ol |
| Other names | diethylene glycol ethylene diglycol diglycol 2,2'-oxybisethanol 3-oxa-1,5-pentanediol dihydroxy diethyl ether |
| Chemical formula | C4H10O3 |
| Molecular mass | 106.12 g/mol |
| CAS number | [111-46-6] |
| Density | 1.118 g/cm3 |
| Melting point | -10.45 °C |
| Boiling point | 244-245 °C |
| SMILES | OCCOCCO |
| Disclaimer and references | |
Diethylene glycol (DEG) is a diol, an alcohol with two -OH groups, a dimer of ethylene glycol, which has caused several mass poisonings. Its molecular structure is HO-CH2-CH2-O-CH2-CH2-OH. It is a clear, hygroscopic, odorless liquid. It is miscible with water, other alcohols, diethyl ether and acetone, but insoluble in benzene and carbon tetrachloride.
Triethylene glycol (TEG, or triglycol) and tetraethylene glycol are trimers and tetramers of ethylene glycol, with formulas HO-CH2-CH2-O-CH2-CH2-O-CH2-CH2-OH and HO-CH2-CH2-O-CH2-CH2-O-CH2-CH2-O-CH2-CH2-OH. Pentaethylene glycol is the pentamer.
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[edit] Uses
Like ethylene glycol, a mix of diethylene glycol and water is used as a coolant. It lowers the freezing point of the mixture, making it suitable for use in low temperature climates, but it also raises its boiling point, higher than ethylene glycol itself, making it more suitable for hot climates. It is also used in synthesis of morpholine and 1,4-dioxane, and as a solvent for nitrocellulose, resins, dyes, oils, and some other organic compounds. It is a humectant for tobacco, cork, printing ink, and glue. It can be also found in some hydraulic fluids and brake fluids.
Triethylene glycol, a colorless odourless viscous liquid, has lower toxicity than diethylene glycol and is used as vinyl plasticizer and in air conditioning systems as a dehumidifier, it is also used in Air-Sanitizer products, like Oust or Clean and Pure. When aerosolized, it acts as a disinfectant. It can be also found in some hydraulic fluids and brake fluids. Its CAS number is [112-27-6] [1] and its SMILES structure is OCCOCCOCCO.
Glycols are used as liquid desiccants for dehydration of natural gas.
[edit] Toxicity
Diethylene glycol has been responsible for a number of mass poisonings. The most famous incident was the 1937 Elixir Sulfanilamide disaster in the USA, in which 107 people died after taking sulfanilamide dissolved in diethylene glycol.[1] This was the impetus for the Federal Food, Drug, and Cosmetic Act of 1938.[2] In recent years, deaths from medicines adulterated with diethylene glycol have been reported from South Africa, India, Nigeria, Argentina, Haiti, and most recently in Panama City. In Haiti in 1996, 85 children died through 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 Dutch company, Vos, from a manufacturer in China, but the point of contamination with DEG was never determined).[3]
In 1985 a scandal broke when diethylene glycol appeared to be added as an adulterant by a number of vintners of Austrian white wines, in order to make them sweeter and upgrade the dry wines to sweet wines;[4] production of sweet wines is expensive and addition of sugar is easy to detect. 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, the adverse worldwide publicity caused very high export losses and led to adoption of severe wine laws in Austria.
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. Criminal investigations are ongoing.[5].
[edit] Footnotes
- ^ Calvery HO, Klumpp TG (1939). "The toxicity for human beings of diethylene glycol with sulfanilamide". South Med J 32 (11): 1105-9.
- ^ 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.
- ^ 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. PMID 9555756.
- ^ (1985) "Some wine to break the ice". Lancet 2 (8449): 254. PMID 2862427.
- ^ Panama police probe lab workers after 21 deaths
[edit] Reference
- Merck Index, 12th Edition, 3168.
