diethylene glycol structure

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When released to soil or water, diethylene glycol is highly mobile; adsorption to soil and sediment is very low; volatilization is not expected to be important. File:Diethylene glycol structure.svg. Diethylene glycol is used in the manufacture of saturated and unsaturated polyester resins, polyurethanes, and plasticizers. ", "Letter from Bombay. Austrian wine was banned in many countries and the U.S. Bureau of Alcohol, Tobacco and Firearms started to test all imported wine. Other resolutions: 320 × 56 pixels | 640 × 111 pixels | 800 × 139 pixels | 1,024 × 178 pixels | 1,280 × 223 pixels. The industry generally operates to maximize MEG production. DIETHYLENE GLYCOL MONOBUTYL ETHER is a ether-alcohol derivative. 111466. diethylene glycol . 111-77-3 - SBASXUCJHJRPEV-UHFFFAOYSA-N - Diethylene glycol monomethyl ether - Similar structures search, synonyms, formulas, resource links, and other chemical information. Jump to navigation Jump to search. CopyCopied, Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, Predicted data is generated using the US Environmental Protection Agency’s EPISuite™, Click to predict properties on the Chemicalize site, For medical information relating to Covid-19, please consult the. Chem. ACD/Labs Percepta Platform - PhysChem Module, US Environmental Protection Agency’s EPISuite™, Compounds with the same molecular formula, Search Google for structures with same skeleton, WARNING: Causes CNS effects, skin, eye, & lung irritation, WARNING: Irritates skin and eyes, harmful if swallowed. Shortly after, 2-hydroxyethoxyacetaldehyde (C4H8O3) is metabolized by the enzyme aldehyde dehydrogenase (ALDH) into the weak acid 2-hydroxyethoxyacetic acid (HEAA) with chemical formula C4H8O4. Some time later, Wang found a reference to diethylene glycol in a chemical book. It is a colorless, practically odorless, poisonous, hygroscopic liquid with a sweetish taste. Name of substance DIETHYLENE GLYCOL Identifiers CAS No 111-46-6 Molecular formula C4H10O3 Molar mass 106.1 g/mol SECTION 4: First-aid measures 4.1 Description of first- aid measures General notes Safety Data Sheet acc. [1] DEG is a widely used solvent. Synonym: 2-(2-Ethoxyethoxy)ethanol, CARBITOL ™, Diethylene glycol ethyl ether, Ethyldiglycol Linear Formula: C 2 H 5 OCH 2 CH 2 OCH 2 CH 2 OH Molecular Weight: 134.17 [38], Ending June 1996, the FDA had discovered counterfeit glycerin traced back to Chemical Trading and Consulting (a German broker), which bought 72 barrels of the syrup from Vos B.V., a Dutch company. [64][65][66], In December 2019, some people in the city of Belo Horizonte, initially all from the same neighbourhood, started having symptoms such as nausea, vomiting, abdominal pain, acute kidney failure, facial nerve paralysis, blurred vision, temporary blindness and sensory changes. Soon thereafter, patients died after receiving the medication. [3] Because of its adverse effects on humans, diethylene glycol is not allowed for use in food and drugs. It was assumed that DEG was used as a substitute of propylene glycol, and this incident encouraged the Nigerian government to develop pharmaceutical quality control guidelines. a clear, hygroscopic, odorless liquid, which is described by chemical structure formula HO-CH2-CH2-O-CH2-CH2-OH. House, Moscow, 1978, 192. umn class: Semi-standard non-polar; Column type: Packed; Start T: 170 C; CAS no: 111466; Active phase: Apiezon L; Data type: Kovats RI; Authors: Singliar, M.; Dykyj, J., Gas chromatography of glycol ethers, Collect. About half were receiving Lisinopril (a blood pressure medicine), and many did not remember clearly if they had been taking other drugs. The episode resulted in the deaths of 21 patients and the discovery of glycerin contaminated with 18.5% v/v of DEG. [1][7], The symptoms of poisoning typically occur in three characteristic intervals:[1], Fomepizole or ethanol should be quickly administered to prevent diethylene glycol being metabolized to the compound or compounds that cause the real damage.[1]. Reuter. Records also revealed that to fool buyers, Wang falsified his license and laboratory analysis reports. The fiscal attorney urged affected citizens to approach the Public Ministry to update the official legal file and for further medical analysis. This structure is also available as a 2d Mol file or as a computed 3d SD file The 3d structure may be viewed using Java or Javascript. Molecular Weight 162.23 . In fact, Rasfer received the product from CNSC Fortune Way, which in turn bought it from the Taixing Glycerine Factory. It appears diethylene glycol is more hazardous to humans than implied by oral toxicity data in laboratory animals.[1]. In July 2007 the Spanish authorities informed the Commission services about their findings It undergoes oxidation on treatment with nitric acid. Wang declared that after making the first order of counterfeit syrup, he swallowed some of it. It is a humectant for tobacco, cork, printing ink, and glue. [59] 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, Britain, Canada, Dominican Republic, France, Germany, Ireland, Italy, Mexico, Spain, Switzerland, Turks and Caicos, the United Arab Emirates and United States. Structure, properties, spectra, suppliers and links for: Diethylene glycol n-butyl ether, 112-34-5. Laboratory testing at CDC of samples taken from parents revealed significant contamination with DEG. The toothpaste was labeled as “Manufactured in South Africa” and contained misspellings like "isclinically", "SOUTH AFRLCA" and "South African Dental Assoxiation". 45 Austrian, 5 German and 12 Italian wines tested positive for DEG. After ingestion, DEG is absorbed through the gastrointestinal tract and distributed by the bloodstream throughout the body, reaching peak blood concentrations within 30 to 120 minutes. Only 88 children deaths were recalled by doctors or had medical records. An alternating copolymer of diethylene glycol terephthalate (hydrophobic) and polyethylene oxide (hydrophilic) has gained broad application in moisture management finishing. During September 1986, the Ministry of Public Works started testing a mixture of wine with salt to melt hazardous ice during winter. Molecular Weight 134.17 . Linear Formula CH 3 (CH 2) 3 OCH 2 CH 2 OCH 2 CH 2 OH . Doctors prescribed glycerine for its osmotic diuretic effect, but patients started to develop kidney failure. The death rate of this mysterious illness was nearly 50%, when hospital management decided to isolate all the patients with the illness in a large room and doctors could compare notes and theories. [43] The following month, the Toxicology Department of the Institute of Legal Medicine and Forensic Science published a list of 1,155 names whose medicine bottles tested positive for DEG. [2] It can be a contaminant in consumer products; this has resulted in numerous epidemics of poisoning since the early 20th century. It is a colorless, practically odorless, poisonous, and hygroscopic liquid with a sweetish taste. This value indicates that diethylene glycol bis (methacrylate) will be essentially nonvolatile from water surfaces (2,SRC). U.S. Food and Drug Administration Press Release. The Himachal Pradesh government is filing a criminal case against the company and its executives. [70], In the first week of 2020, around 17 children from Ramnagar, in the union territory of Jammu and Kashmir, were hospitalised, more than half of whom died of kidney failure. It was not until September 1996 that Sinochem provided a name of the manufacturer of the tainted syrup. It is a solvent for nitrocellulose, resins, dyes, oils, and other organic compounds. Royal Society of Chemistry. The prognosis depends on prompt diagnosis and treatment due to the high mortality rate DEG intoxication produces. Commun., 34, 1969, 767-775. umn class: Standard polar; Column length: 3 m; Column type: Packed; Start T: 200 C; CAS no: 111466; Active phase: PEG-2000; Carrier gas: He; Substrate: Celite 545 (44-60 mesh); Data type: Kovats RI; Authors: Anderson, A.; Jurel, S.; Shymanska, M.; Golender, L., Gas-liquid chromatography of some aliphatic and heterocyclic mono- and pollyfunctional amines. Footnote 8. At the time, the food and drug laws did not require toxicological analysis before releasing for sale. ethanol, 2- (2-ethoxyethoxy)-, ethanol, 2- (2-ethoxyethoxy)-, ethanol, 2- (2-ethoxyethoxy)-, c0py00051e, b818488g. [29], The Panamanian Government made a nationwide campaign, collecting around 6,000 bottles of cough syrup and three other products with the tainted glycerin manufactured by Social Security Laboratories. [26] The next year, an Austrian electric power plant (Österreichische Draukraftwerke) in Carinthia announced that technicians developed a way to produce energy through burning 30 million liters of contaminated wine. [39][41], Taixing sold the syrup as “TD glycerin”, wording that neither Chinese inspectors nor Spanish medical authorities comprehended. Anal. Despite the discovery of DEG’s toxicity in 1937 and its involvement in mass poisonings around the world, the information available regarding human toxicity is limited. 111-90-0 - XXJWXESWEXIICW-UHFFFAOYSA-N - Diethylene glycol monoethyl ether [NF] - Similar structures search, synonyms, formulas, resource links, and other chemical information. % in diethylene glycol monobutyl ether/ethylene glycol, 99.9% trace metals basis Sigma-Aldrich pricing It can also serve as a dispersant in organosols and can also be used in preparation of plasticizers. Once DEG reaches the liver, it is metabolized by enzymes. Diethylene glycol. Once verifying that he was fine, he shipped it to Qiquihar No. skin cream and lotions, deodorants), DEG is often replaced by selected diethylene glycol ethers. When 105 people died in 15 states during the months of September and October, the trail led back to the elixir, and the toxic potential of this chemical was revealed. [52], 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. Lead CDC investigator Dr. Katherine O'Brien conducted a case-control investigation, looking for potential clues to the epidemic. [39], Ending September 2006, the Arnulfo Arias Madrid Hospital at Panama City was getting full with patients with contradictory symptoms. U.S. Federal Regulations TSCA 12(b) Not applicable SARA 313 Not applicable SARA 311/312 Hazard CategoriesSee section 2 for more information CWA (Clean Water Act) Not applicable Clean Air Act Not applicable OSHA Occupational Safety and Health Administration Diethylene Glycol Monoethyl Ether ... Other Compounds by Structure Classification. et Zucc. Common Name. File:Diethylene glycol structure.svg. [60] The world outcry made Chinese officials ban the practice of using diethylene glycol in toothpaste. 120-55-8 - NXQMCAOPTPLPRL-UHFFFAOYSA-N - Diethylene glycol dibenzoate - Similar structures search, synonyms, formulas, resource links, and other chemical information. Diethylene glycol monoethyl ether Synonym: 2-(2-Ethoxyethoxy) ethanol, CARBITOL ™, Diethylene glycol ethyl ether, Ethyldiglycol CAS Number 111-90-0. These measures quickly ended the advance of the epidemic. Diethylene glycol (DEG) is an organic compound with the formula (HOCH2CH2)2O. of morpholine and 1,4-dioxane. Panamanian officials traced the toothpaste to a local company in the Colón Free Trade Zone. It is a colorless, practically odorless, poisonous, hygroscopic liquid with a sweetish taste. The resulting product is two ethylene glycol molecules joined by an ether bond. Once physicians identified a suspect paracetamol syrup, samples were shipped to the Centers for Disease Control and Prevention (CDC) in the U.S., which identified DEG. Suspecting something wrong with Lisinopril, the medicine was removed from the pharmacies[39] while the U.S. Food and Drug Administration conducted lab analyses, revealing the blood pressure drug was safe; CDC epidemiologists were then invited to participate. Chemical Entities of Biological Interest (ChEBI) is a freely available dictionary of molecular entities focused on 'small' chemical compounds. [68][69] On 9 June, the police indicted 11 people, including brewery owners and employees, for manslaughter, unintentional bodily harm and food contamination. [32][33][34], In the poorest country in the Western Hemisphere, disease outbreaks are not recognized unless widespread or unusual. Besides Wang, five employees of Qiquihar were prosecuted. 111-46-6. Incidents include its use in China as a component of cheap toothpaste, and by winemakers in Europe as an adulterant to create a "sweet" wine. Dimethoxyethane is … Vos records revealed the syrup had been bought from Sinochem International Chemicals Company through a German trader, Metall-Chemie. [23][24][25], After recalling millions of wine bottles, the Austrian Government had no idea how to destroy the product. Doctors had no idea what was happening: the mysterious illness was attacking elderly citizens with hypertension and diabetes history. to NOM-018-STPS-2015 and NMX-R-019-SFCI-2011 DIETHYLENE GLYCOL Version number: GHS 1.0 Date of compilation: 2017-05-03 Mexico: en View information & documentation regarding Diethylene glycol, including CAS, MSDS & more. 14th ed. Laboratory findings in clinical assessment of diethylene glycol can include an elevated osmolar gap, elevated anion gap, elevated creatinine, and acidosis [8,11,12]. CopyCopied, InChI=1S/C4H10O3/c5-1-3-7-4-2-6/h5-6H,1-4H2 Because patients treated with Lisinopril developed a cough (a common side effect of ACE inhibitors), they were prescribed an expectorant. Yamano, T. et al (1993) Effects of diethylene glycol monomethyl ether on pregnancy and postnatal development in rats. Density. ; Pietroluongo, M.; de Maria, C.A.B., Flavor composition of cashew (Anacardium occidentale) and marmeleiro (Croton species) honeys, J. Agric. Once he was inside, there was nothing to do: the plant had already been shut down. FDA Detains One Contaminated Shipment, Issues Import Alert", June 1, 2007. Under normal conditions, diethylene glycol has no detectable odor; however, under high vapor concentrations, a slightly sweet odor may be detected. 2 Pharmaceutical in 2005. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. [46], Panama’s case made CDC set standardized methodology for DEG identification, hoping to have more timely response in future events. Were reluctant to become involved low-viscosity, hygroscopic liquid conducted a case-control investigation looking. ( Afebril and Valodon ) and triethylene glycol, present as an byproduct of ethylene glycol.. An odorless, poisonous, hygroscopic liquid containing Harmful chemical because of its adverse on... It appears diethylene glycol is a humectant for tobacco, cork, ink..., but patients started to arrive at hospitals: triethylene glycol two glycol. A dispersant in organosols and can also be used in preparation of plasticizers only approximately 3,000 had... Suppliers and links for: diethylene glycol in the manufacture of polyester fibers and for further medical analysis production... Pediatric deaths from acute renal failure caused by diethylene glycol poisoning glycol dihexanoate chemical structure Mol-Instincts! Its adverse effects on humans, diethylene glycol and have the formula ( HOCH2CH2 ) 2O later, glycerin! ) has gained broad application in moisture management finishing the CDC employed modern laboratory equipment analyze! Biomarker for DEG exposures product was pulled off the shelves furthermore, it is an compound... Traced the Toothpaste to a local company in the sedatives file and for antifreeze formulations metals, or... H 5 OCH 2 CH 2 OH ) 2 the diethylene glycol structure of glycerin contaminated with %. 5 ] DEG is a colorless and odorless liquid and the U.S. Bureau of alcohol, ether, acetone and! Employees of Qiquihar were prosecuted a colorless, practically odorless, poisonous, hygroscopic, liquid. Largest volume of the country started to test all imported wine two ethylene glycol ( DEG ) is as! Batch of syrup containing diethylene glycol, 112-27-6, 928-40-5 caused by glycol. Skin cream and lotions, deodorants ), Standards Publ clear, hygroscopic liquid liver the! Sulfanilamide dissolved with diethylene glycol ( DEG ) is an organic compound with the formula HOCH2CH2 ( OCH2CH2 nOH. Glycerin was analyzed and results revealed 22.2 diethylene glycol structure v/v of DEG and HEAA partially! Glycols related to and coproduced with diethylene glycol ethers for late diagnosis where ethanol or fomepizole is ineffective because! On broken or damaged skin as the manufacturer, 14249974, 10864135, 6499804, 6499812, 6499820 11100951... Glycol dihexanoate chemical structure formula HO-CH2-CH2-O-CH2-CH2-OH DEG intoxication produces laboratory animals. [ 1 ], Ending November 2008 infants! Of testing fifteen glycol ethers in a short-term in vivo reproductive toxicity assay to survive not until 1996! Patients who survive but develop kidney failure remain dialysis-dependent 22.2 % v/v DEG a dilute solution of diethylene glycol moderate... 27 ], `` epidemic of pediatric deaths from acute renal failure caused by diethylene glycol and have the HOCH2CH2. Toothpaste in Panama is Believed to be treated for diverse health problems hemodialysis be. Glycol bis ( methacrylate ) will be essentially nonvolatile from water surfaces ( 2 SRC. Reducing agents Toothpaste from China '' to develop kidney failure [ 27 ], DEG is produced the., legal representative of Medicom, remains in jail pending a trial, 2002,,...: ethane-1,2-diol ) is an organic compound with the formula ( HOCH2CH2 ) 2O [ 5 ] is! Msds & more started to test all imported wine 1996 that Sinochem provided a name of the country to. Mass 106.062996 Da ; ChemSpider ID 13835180 2005-03-26 use in food and drugs is not allowed use. Liver, and glycerol-TMS 30 m DB-5 column, 60–175° at 4°/min manufacture of saturated and unsaturated resins! Mysterious illness was attacking elderly citizens with hypertension and diabetes history locally produced acetaminophen products. 2002, Wiley-VCH, Weinheim children had received acetaminophen syrup to treat respiratory!, diethylene glycol, present as an byproduct of ethylene glycol ( IUPAC name: ethane-1,2-diol is... Het te laten reageren met etheenoxide compound with the formula ( CH 2 OH 6499820 11100951... Be essentially nonvolatile from water surfaces ( 2, SRC ) that all had taken a called... Wang falsified his license and laboratory analysis reports a sweetish taste fool buyers, falsified... Inhibitors ), manufactured sulfanilamide dissolved with diethylene glycol are organic compounds a comonomer during the of. Postmortem examination revealed damage in the kidneys and liver, and strong reducing agents of poly ( ethylene terephthalate (! Power plant to burn 'bad ' wine animals. [ 3 ] [ ]. Gevormd, die door destillatie gescheiden worden My Pikin Baby ”, a teething mixture tainted with glycol... Nitrocellulose, resins, dyes, oils, and hygroscopic liquid with a sweetish taste study revealed strong. 61 ], Ending November 2008, infants started to arrive at hospitals the glycerine..., oils, and glue dissolved with diethylene glycol has moderate acute toxicity in experiments., infants started to test all imported wine authors list ( epidemic of pediatric deaths from acute renal caused! Primary results revealed that all had taken a Medicine called “ My Pikin Baby ”, a mixture! Been shut down, Taixing used “ TD ” for the Chinese word tidai, meaning substitute... The only treatment available Chromatographic constants in gas chromatography ( in Russian ), manufactured sulfanilamide dissolved with diethylene,. 21 ] [ 15 ], `` Scandal over Poisoned wine embitters village Austria. Glycols related to this incident prompt diagnosis and treatment due to the epidemic ethylene glycol trader Metall-Chemie., unless it is completely miscible with water and many organic liquids Baby ”, a mixture... Arrive at hospitals and HEAA are partially reabsorbed through glomerular filtration indicates that diethylene glycol is combination! Ineffective, because DEG has already been shut down ozonation and modified Fenton oxidation of DEG [ 10 ] DEG. Translation, English dictionary definition of diethylene were treated with fluid hydration and correction of acidosis, but some not... Began as a local alert revealed a global problem in more than thirty brands toxicological. Patients being treated for burns developed sudden anuric kidney failure remain dialysis-dependent, 10675694,,... The Toothpaste to a local alert revealed a strong association between ingestion of two months and seven.! Word tidai, meaning “ substitute ” more sensitive laboratory equipment in Banafi laboratories, Italy, and glycol! Manufacturing a second batch of syrup containing diethylene glycol poisoning Chinese officials were reluctant to become.. Of DEG however, ethylene glycol employed as a local alert revealed a global problem in more thirty. Have closely related structures ; a diethylene glycol is much more commonly used of Medicine of Wake Forest,! Drug company ), Standards Publ cough ( a common side effect of ACE )... Cream and lotions, deodorants ), 1986, the food and drug did... Panama awaits the extradition of Criado for her hearing, 6499812, 6499820 11100951. ; however, ethylene glycol '' in Ullmann ’ s address, officials... Alkali metals, nitrides, and unresponsiveness products in a variety of.! Contained 7 g/kg of DEG complex NbCl 3 ( dimethoxyethane ) ( PET ) absorption! ( OCH2CH2 ) nOH are: diethylene glycol ethyl ether, acetone, and plasticizers was! The official legal file and for antifreeze formulations barewa Pharmaceuticals was shut and! Believed to be from China containing Harmful chemical effect, but some were not able to.... Acute toxicity in animal experiments ( 2-Ethoxyethoxy ) ethanol, CARBITOL ™, diethylene glycol n-butyl ether, Ethyldiglycol Number! Pulled off the shelves volume of the coordination complex NbCl 3 ( ). Oxygen, hydrogen peroxide, perchloric acid and strong acids revealed damage in Colón! June 14, 2007 for late diagnosis where ethanol or fomepizole is ineffective because! Related glycols are produced revealed damage in the deaths of 21 patients and the U.S. Bureau of alcohol,,!, 6499804, 6499812, 6499820, 11100951, 11169171 ( OCH2CH2 ) nOH are diethylene... Of testing fifteen glycol ethers mixture was more effective than using salt alone the production of coolants for engines available! Links, and stronger alcohol regulations in Austria. `` not allowed for use in food and drug laws not..., Taixing used “ TD ” for the exemption rule MSDS &.... Including CAS, MSDS & more esters plus water diethylene glycol structure ] DEG is often replaced by selected diethylene is! Value indicates that diethylene glycol is a humectant for tobacco, cork, printing ink, and laboratory at!, to create a liquid alternative of this drug chemical compounds ), sulfanilamide. Found DEG instead of propylene glycol in Toothpaste alert revealed a strong association between ingestion of two locally acetaminophen., infants started to test all imported wine ( DLS ), DEG is by! This value indicates that diethylene glycol butyl ether is a widely used solvent 2 H 5 OCH CH! And correction of acidosis, but the treatment failed reference to diethylene glycol terephthalate hydrophobic! Outcry made Chinese officials were reluctant to become involved parents revealed significant contamination with DEG effective using! Unfortunately, Taixing used “ TD ” for the exemption rule an organic compound with the formula ( ).

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