For this 20g of middle fraction of purified glycol was gradually added to mixture of 70g nitric acid and 130g sulfuric acid, maintaining the temperature at 23°. Both E-series glycol ethers and P-series glycol ethers can be used as intermediates that undergo further chemical reactions, producing glycol diethers and glycol ether acetates. It is similar to nitroglycerin in both manufacture and properties, though it is more volatile and less viscous. Pure EGDN was first produced by the Belgian chemist Louis Henry (1834–1913) in 1870 by dropping a small amount of ethylene glycol into a mixture of nitric and sulfuric acids cooled to 0 °C. Other investigators preparing NGc before publication in 1926 of Rinkenbach's work included: Champion (1871), Neff (1899) & Wieland & Sakellarios (1920), Dautriche, Hough & Oehme. Its major uses are in thermoplastic acrylic coatings as a reflow solvent and in foundry core-binding applications. Ethylene glycol is produced from ethylene (ethene), via the intermediate ethylene oxide. The resulting 49g of crude product was washed with 300ml of water to obtain 39.6g of purified product. These solvents typically have a higher boiling point, together with the favorable solvent properties of lower-molecular weight ethers and alcohols. If unsaturated esters are copolymerized with ethylene, either the alcohol moiety may be in the polymer backbone (as it is the case in ethylene-vinyl acetate copolymer) or of the acid moiety (e. g. in ethylene-ethyl acrylate copolymer). Typically, e-series glycol ethers are found in pharmaceuticals, sunscreens, cosmetics, inks, dyes and water-based paints, while p-series glycol ethers are used in degreasers, cleaners, aerosol paints and adhesives. The low yield so obtained could be improved by maintaining a lower temperature and using a different nitrating acid mixture.[5]. From Wikipedia, the free encyclopedia Ethylene glycol poisoning is poisoning caused by drinking ethylene glycol. )", "Ueber eine Verbindung des Aethylens mit Salpetersäure", WebBook page for ethylene glycol dinitrate, CDC - NIOSH Pocket Guide to Chemical Hazards, Ethylene glycol dinitrate (EGDN; nitroglycol), Naproxcinod (nitronaproxen; AZD-3582, HCT-3012), Nitroglycerin (glyceryl trinitrate (GTN)), Amyl nitrite (isoamyl nitrite, isopentyl nitrite), Isobutyl nitrite (2-methylpropyl nitrite), Methylamine hexamethylene methylamine/NO (MAHMA/NO), N-Acetyl-N-acetoxy-4-chlorobenzenesulfonamide, https://en.wikipedia.org/w/index.php?title=Ethylene_glycol_dinitrate&oldid=978929432, Chemical articles with multiple compound IDs, Multiple chemicals in an infobox that need indexing, Pages using collapsible list with both background and text-align in titlestyle, Articles containing unverified chemical infoboxes, Creative Commons Attribution-ShareAlike License, cGMP preferring PDE inhibitors (e.g., sildenafil, paraxanthine, tadalafil), This page was last edited on 17 September 2020, at 19:38. 5) Preparation of NGc by duPont method. Semtex, to allow more reliable explosive detection, until 1995 when it was replaced by dimethyldinitrobutane. September 9, 1975), but let it expire, "Occupation and male infertility: glycol ethers and other exposures", "Letter to the editor on a recent publication titled "Occupation and male infertility: glycol ethers", https://en.wikipedia.org/w/index.php?title=Glycol_ethers&oldid=980243937, Articles with unsourced statements from December 2010, Creative Commons Attribution-ShareAlike License, This page was last edited on 25 September 2020, at 11:58. [3] The previous year, August Kekulé had produced EGDN by the nitration of ethylene, but this was actually contaminated with beta-nitroethyl nitrate.[4][5][6]. Later symptoms may include a decreased level of consciousness, headache, and seizures. *Modeled using The Estimation Programs Interface (EPI) Suite™ (EPA), BIOWIN v4.10 module. When ethylene glycol dinitrate is rapidly heated to 215 °C, it explodes; this is preceded by partial decomposition similar to that of nitroglycerin. Ethylene glycol dinitrate, abbreviated EGDN and NGc, also known as nitroglycol, is a chemical compound a colorless, oily explosive liquid obtained by nitrating ethylene glycol. P-series glycol ethers are marketed as having lower toxicity than the E-series. Brisance by sand test, determined in mixtures with 40% kieselguhr, gave for NGc mixtures slightly higher results then with those containing NG. Linear Formula CH 3 COOCH 2 CH 2 OCOCH 3. MDL number MFCD00008718 It is considerably more stable than glyceryl trinitrate owing to the lack of secondary hydroxyl groups in the precursor polyol. Brisance by lead block compression (Hess crusher test) is 30.0 mm, versus 18.5 mm for NG and 16 mm for TNT (misleading, needs to give exact density and mass of explosive (25 or 50 g). An estimated BCF value of 1.2(1,SRC), from an estimated log Kow(5,SRC), suggests that ethylene glycol diacetate will not bioconcentrate in aquatic … These solvents typically have a higher boiling point, together with the favorable solvent properties of lower-molecular weight ethers and alcohols. or through the reaction of ethylene oxide and dinitrogen pentoxide: 2) Direct Production of NGc from Gaseous Ethylene. When 500g of mixed acid HNO3 50% & H2SO4 50% was used at 10-12°, the yield increased to 229g. Molar weight 152.07, N 18.42%, OB to CO2 0%, OB to CO +21%; colorless volatile liquid when in pure state; yellowish liquid in crude state; sp gr 1.488 at 20/4° or 1.480 at 25°; n_D 1.4452 at 25° or 1.4472 at 20°; freezing point -22.75° (versus +13.1° for NG); frozen point given in[7] is -22.3°; boiling point 199° at 760mm Hg (with decomposition). Its major uses are in thermoplastic acrylic coatings as a reflow solvent and in foundry core-binding applications. Ethylene glycol dinitrate (EGDN,NGc), also known as nitroglycol, is a chemical compound a colorless, oily explosive liquid obtained by nitrating ethylene glycol. Ethylene oxide reacts with water to produce ethylene glycol according to the chemical equation: Please enable scripts and reload this page. All rights reserved. EGDN has a slightly higher brisance than nitroglycerin. Ethylene glycol dinitrate, Glycol dinitrate, Ethylene dinitrate, Ethylene nitrate, 1,2-Bis(nitrooxy)ethane, Nitroglycol (NGc), 1,2-Ethanediol dinitrate, Dinitroglycol, EGDN, Ethane-1,2-diyl dinitrate, InChI=1S/C2H4N2O6/c5-3(6)9-1-2-10-4(7)8/h1-2H2, InChI=1/C2H4N2O6/c5-3(6)9-1-2-10-4(7)8/h1-2H2, Except where otherwise noted, data are given for materials in their, National Institute for Occupational Safety and Health, "Untersuchungen über die Aetherderivate der mehratomigen Alkohole und Säuren (Vierter Theil. You may be trying to access this site from a secured browser on the server. 4) Preparation of NGc by method of Messing from ethylene through chlorohydrin & ethylene oxide. Ethylene glycol diacetate ≥99% Synonym: 1,2-Diacetoxyethane, Ethylene diacetate, Glycol diacetate CAS Number 111-55-7. Glycol ethers are a group of solvents based on alkyl ethers of ethylene glycol or propylene glycol commonly used in paints and cleaners. Eastman™ Ethylene Glycol Diacetate (EGDA) is a colorless, low odor, very slow-evaporating solvent that gives good flow-out to baking lacquers and enamels. Like other organic nitrates, ethylene glycol dinitrate is a vasodilator. Most glycol ethers are water-soluble, biodegradable and only a few are considered toxic. 1) Direct Nitration of Glycol is carried out in exactly the same manner, with the same apparatus, and with the same mixed acids as nitration of glycerine. [3], Union Carbide also registered "Cellosolve" as a trademark for "ETHYL SILICATES FOR USE AS BINDERS IN INVESTMENT CASTINGS AND IN ZINC-RICH PRIMERS" (Reg. Ethylene glycol dinitrate is a colorless volatile liquid when in pure state, but is yellowish when impure. Due to its volatility it was used as a detection taggant in some plastic explosives, e.g. This means 90.6% of theory, as compared to 93.6% with NG. Glycol ethers are a group of solvents based on alkyl ethers of ethylene glycol or propylene glycol commonly used in paints and cleaners. Early symptoms include intoxication, vomiting and abdominal pain. The Estimation Programs Interface (EPI) Suite™ (EPA), BIOWIN v4.10 module, Eastman Cellulose Esters for Formulated Products, Meeting Aerosol Coatings MIR Limits with EASTMAN Ester Solvents. EC Number 203-881-1. The word "Cellosolve" was registered in 1924 as a United States trademark by Carbide & Carbon Chemicals Corp. (later named Union Carbide Corp.) for "Solvents for Gums, Resins, Cellulose Esters, and the Like". Ethylene-vinyl acetate copolymers are prepared similarly to LD-PE by high pressure polymerization. In commercial nitration, the yields obtained from 100 kg anhydrous glycol and 625 kg of mixed acid containing HNO3 41%, H2SO4 58% & water 1% were 222.2 kg of NGc at nitrating temp of 10-12° and only 218.3 kg at 29-30°. Beilstein/REAXYS Number 1762308 . As used herein, ® denotes registered trademark status in the U.S. only. © 2020 Eastman Chemical Company or its subsidiaries. 3) Preparation of NGc from Ethylene Oxide. In the test nitration of anhydrous glycol (100g) with 625g of mixed acid HNO3 40% & H2SO4 60% at 10-12°, the yield was 222g and it dropped to 218g when the temp was raised to 29-30°. Eastman™ Ethylene Glycol Diacetate (EGDA) is a colorless, low odor, very slow-evaporating solvent that gives good flow-out to baking lacquers and enamels. Glycol ethers are either "e-series" or "p-series" glycol ethers, depending on whether they are made from ethylene oxide or propylene oxide, respectively. The word "Cellosolve" was registered in 1924 as a United States trademark by Carbide & Carbon Chemicals Corp. for … Ethylene glycol diacetate will be essentially non-volatile from water surfaces based on an estimated Henry's Law constant of 8.4X10-8 atm-cu m/mole(SRC), calculated from experimental values for vapor pressure (3) and water solubility(4).