Diethylene glycol
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| General | ||||||||||||||||
| Surname | Diethylene glycol | |||||||||||||||
| other names |
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| Molecular formula | C 4 H 10 O 3 | |||||||||||||||
| Brief description |
colorless and odorless, clear liquid |
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| properties | ||||||||||||||||
| Molar mass | 106.12 g mol −1 | |||||||||||||||
| Physical state |
liquid |
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| density |
1.12 g cm −3 (20 ° C) |
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| Melting point |
−6 ° C |
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| boiling point |
244 ° C |
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| Vapor pressure |
0.008 hPa (25 ° C) |
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| solubility |
completely miscible with water |
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| Refractive index |
1.4472 (20 ° C) |
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| safety instructions | ||||||||||||||||
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| MAK |
DFG / Switzerland: 10 ml m −3 or 44 mg m −3 |
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| Toxicological data | ||||||||||||||||
| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C | ||||||||||||||||
Diethylene glycol is a derivative of ethylene glycol and belongs to the group of alcohols ( diols ) or, more precisely, the glycol ethers .
Manufacturing
Diethylene glycol is synthesized by the ethoxylation of ethylene glycol with ethylene oxide . It is usually a by-product of the production of ethylene glycol.
properties
Diethylene glycol forms flammable vapor-air mixtures at high temperatures. The compound has a flash point of 138 ° C. The explosion range is between 1.7% by volume (75 g / m 3 ) as the lower explosion limit (LEL) and 37% by volume (1635 g / m 3 ) as the upper explosion limit (UEL). The ignition temperature is 355 ° C. The substance therefore falls into temperature class T2.
use
Most of the diethylene glycol produced is used as a raw material for the synthesis of polyester resins, morpholine and 1,4-dioxane . It rarely serves as a solvent for nitrocellulose , synthetic resins , dyes , oils, and some other organic substances. In addition, diethylene glycol is rarely used as a humectant for corks , ink, and glue ; the use in the context of food or, for example, in toothpaste should be restricted according to a statement by the Federal Institute for Risk Assessment (BfR).
A mixture of diethylene glycol and water can be used as an antifreeze, as the mixture has a lower melting point than pure water. As a rule, however, the more suitable ethylene glycol - the main component of the coolant " Glysantin " from BASF - is used. In the case of a diethylene glycol-water mixture, however, not only is the melting point lowered , the boiling point is also increased, to a greater extent than in the water-ethylene glycol system. Diethylene glycol can therefore also be used as an additive in hydraulic and brake fluids .
Cases of poisoning
Diethylene glycol is the cause of at least eight severe poisoning epidemics, in which several hundred children died. In all cases, the syrupy, sweet-tasting diethylene glycol was used as an adjuvant in pharmaceuticals for the treatment of acute infectious diseases. As early as 1937, the use of a sulfanilamide syrup in the USA led to the sulfanilamide disaster . In this case several hundred children died; As a consequence, the Federal Food, Drug, and Cosmetic Act , the core of drug law in the USA, was passed in 1938 . The third from last epidemic in Haiti is particularly well documented medically. The main symptom of the poisoning was always acute kidney failure.
In 1985, the hazardous chemical diethylene glycol was found in adulterated wines from Austria and Germany . As a result of this glycol wine scandal , millions of bottles of wine had to be taken off the market, and no poisoning occurred. The maximum value found was 48 g diethylene glycol in one liter of wine. As a result of this scandal, the term glycol used in the press for diethylene glycol became the word of the year 1985.
In 1990 in diseased Bangladesh 339 children - first unexplained - acute renal failure after she poisoned with diethylene glycol Paracetamol - syrup had been treated. Most of the children died.
In 2006, at least 174 people fell ill in Panama, 115 of whom died after ingesting a cough syrup sold by the national health service that contained diethylene glycol instead of glycerine . The health authorities had purchased the excipient from a Chinese manufacturer through intermediaries.
In 2007, the toxic substance was also discovered in Chinese toothpaste that was being sold in a discount store in Panama City. As a result, toothpaste was withdrawn from the market in the USA and Canada.
In France, various brands of toothpastes produced in China that contain diethylene glycol were identified in 2007; the list is published on the Afssaps website . The affected products were found in toothbrush kits from dental hygiene campaigns, but also in nursing homes, old people's homes, hotels and some pharmacies.
Poisoning by toothpaste contaminated with diethylene glycol has not yet been reported and is very unlikely with normal use due to the low dose and the toxicological properties of diethylene glycol. Nevertheless, the Federal Institute for Risk Assessment and the Scientific Food Committee of the European Union recommend a maximum daily intake of 0.5 mg / kg body weight “ for the sum of diethylene glycol, monoethylene glycol and stearic acid ester of di-, mono- and triethylene glycol ” not to be exceeded.
In Brazil, there were several cases of poisoning in 2019 and 2020 in connection with the consumption of contaminated beer from the Backer brewery. Several deaths suspected to have been caused by diethylene glycol were also investigated. In January 2020, all products from this brewery were then taken off the market by the authorities.
Risk assessment
Diethylene glycol was included in 2014 by the EU in accordance with Regulation (EC) No. 1907/2006 (REACH) as part of substance evaluation in the Community's ongoing action plan ( CoRAP ). The effects of the substance on human health and the environment are re-evaluated and, if necessary, follow-up measures are initiated. Diethylene glycol intake was caused by concerns about consumer use , high (aggregated) tonnage, other hazard- related concerns and widespread use, as well as the hazards arising from a possible assignment to the group of CMR substances. The re-evaluation took place from 2015 and was carried out by Hungary . A final report was then published.
literature
- G. Lehmann and J. Ganz: Detection of diethylene glycol in wine. In: Journal for Food Analysis and Research A 181, 1985, p. 362, doi : 10.1007 / BF01027398 .
Web links
- International Chemical Safety Card (ICSC) for diethylene glycol from the National Institute for Occupational Safety and Health (NIOSH).
- Sour grapes, sweet sins . - Die Zeit, August 2, 1985 No. 32
Individual evidence
- ↑ a b c d e f g h i j k l Entry on diethylene glycol in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
- ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-166.
- ↑ Entry on 2,2′-oxydiethanol in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
- ↑ Swiss Accident Insurance Fund (Suva): Limits - Current MAK and BAT values (search for 111-46-6 or diethylene glycol ), accessed on November 2, 2015.
- ↑ Entry on diethylene glycol. In: Römpp Online . Georg Thieme Verlag, accessed on June 7, 2014.
- ↑ a b c BfR : Diethylene glycol (DEG) in toothpaste. ( Memento of August 27, 2010 in the Internet Archive ) (PDF; 45 kB) BfR Opinion No. 025/2008 of July 16, 2007.
- ^ A b c E. Brandes, W. Möller: Safety-related parameters - Volume 1: Flammable liquids and gases , Wirtschaftsverlag NW - Verlag für neue Wissenschaft GmbH, Bremerhaven 2003.
- ^ GF Fuhrmann: Toxicology for natural scientists. Vieweg + Teubner Verlag, 2006, ISBN 3-8351-0024-6 .
- ↑ Hanif M. et al .: Fatal renal failure caused by diethylene glycol in paracetamol elixir: the Bangladesh epidemic , British Medical Journal 1995 July 8; 311 (6997): pp. 88-91; PMID 7613408 ; PMC 2550149 (free full text, PDF).
- ↑ Walt Bogdanich, Jake Hooker: From China to Panama, a Trail of Poisoned Medicine . In: The New York Times . May 6, 2007, ISSN 0362-4331 ( nytimes.com [accessed January 14, 2018]).
- ^ Poison from China - for the whole world Tagesspiegel March 17, 2008.
- ↑ Dentifrices contenant du diéthylène glycol (DEG) ou présentant une contamination bactérienne importante press release of the Agence française de sécurité sanitaire des produits de santé of August 24, 2007.
- ↑ Altmann, Grunow, Krönert, Uehlecke: Health assessment of diethylene glycol in wine , Federal Health Gazette 29 No. 5, May 1986.
- ↑ https://latina-press.com/news/270260-brasilien-vier-todesfaelle-durch-kontaminierter-bier-update/
- ↑ European Chemicals Agency (ECHA): Substance Evaluation Conclusion and Evaluation Report .
- ↑ Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): 2,2'-oxydiethanol , accessed on March 26, 2019.