Diethylene Glycol Dimethyl Ether

Diethylene Glycol Dimethyl Ether Basic information
Product Name:Diethylene Glycol Dimethyl Ether
Synonyms:Poly-Solv;β,β’-dimethoxydiethylether;DIETHYLENE GLYCOL DIMETHYL ETHER ABS. O. MOL.SIEVE(H2O<0.005%;2-METHOXYETHYL ETHER, 99+%, SPECTROPHOTO -METRIC GRADE;2-METHOXYETHYL ETHER, ANHYDROUS, 99.5%;Catafor MS;DiethyleneGlycolDimethylEther(Dedm);DiethyleneGlycolDimethylEtherC6H14O3
CAS:111-96-6
MF:C6H14O3
MW:134.17
EINECS:203-924-4
Product Categories:Carbon Steel Cans with NPT Threads;Functional Materials;Plasticizer;Polyalcohol Ethers, Esters (Plasticizer);Aliphatics;Semi-Bulk Solvents;ACS and Reagent Grade Solvents;Amber Glass Bottles;ReagentPlus;ReagentPlus Solvent Grade Products;Solvent Bottles;Solvent by Application;Solvent Packaging Options;Solvents;Anhydrous Solvents;solvent,metal organic compound synthesis;Sure/Seal Bottles;NMR;Spectrophotometric Grade;Spectrophotometric Solvents;Spectroscopy Solvents (IR;UV/Vis);bc0001
Mol File:111-96-6.mol
Diethylene Glycol Dimethyl Ether Structure
Diethylene Glycol Dimethyl Ether Chemical Properties
Melting point -64 °C (lit.)
Boiling point 162 °C (lit.)
density 0.944 g/mL at 20 °C (lit.) 0.939 g/mL at 25 °C (lit.)
vapor density 4.6 (vs air)
vapor pressure 3 mm Hg ( 20 °C)
refractive index n20/D 1.408(lit.)
Fp 134.6 °F
storage temp. Store below +30°C.
solubility Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Slightly)
form Liquid
color ≤10(APHA)
OdorMild ethereal.
Relative polarity0.244
explosive limit1.4-17.4%(V)
Water Solubility Miscible
Sensitive Hygroscopic
λmaxλ: 225 nm Amax: 1.00
λ: 240 nm Amax: 0.50
λ: 260 nm Amax: 0.20
λ: 280 nm Amax: 0.08
λ: 320-400 nm Amax: 0.01
Merck 14,3165
BRN 1736101
Stability:Stable. Combustible. Incompatible with strong oxidizing agents. May be air or light sensitive.
InChIKeySBZXBUIDTXKZTM-UHFFFAOYSA-N
LogP-0.36 at 25℃
CAS DataBase Reference111-96-6(CAS DataBase Reference)
NIST Chemistry ReferenceEthane, 1,1'-oxybis[2-methoxy-(111-96-6)
EPA Substance Registry SystemDiethylene glycol dimethyl ether (111-96-6)
Safety Information
Hazard Codes T
Risk Statements 60-61-10-19
Safety Statements 53-45
RIDADR UN 3271 3/PG 3
WGK Germany 1
RTECS KN3339000
3-10-23
Autoignition Temperature370 °F
TSCA Yes
HazardClass 3
PackingGroup III
HS Code 29091990
Hazardous Substances Data111-96-6(Hazardous Substances Data)
ToxicityLD50 orally in Rabbit: 4760 mg/kg
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
Diethylene Glycol Dimethyl Ether Usage And Synthesis
DescriptionBis (2-methoxyethyl) ether, also known as diglyme, is a linear aliphatic diether widely used as a solvent and present as a clear liquid at room temperature with a mild ether odor. The compound is notknown to occur in nature. It is synthesized from ethylene oxide and methanol in the presence of either acidic or basic catalysts. The reaction is based on the classic Williamson ether synthesis. It can also be produced from diethylene glycol and dimethyl sulfate. In June 2012, ECHA proposed addition of diglyme to the REACH very high concern list.
Chemical PropertiesDiethylene glycol dimethyl ether is a clear, water-white neutral liquid of faint, pleasant odor. This ether may be used as a solvent for alkali metal hydrides for use in such reactions as reduction, alkylation and condensation. It may also be used as a lacquer solvent.
UsesBis (2-methoxyethyl) ether, due to being chemically inert and possessing excellent solvent properties, is mainly used as a solvent and an anhydrous reaction medium for organometallic synthesis. It is also used as a solubilizer.
UsesSolvent; reaction medium for Grignard and similar syntheses.
UsesSolvent; it is used as reaction medium for Grignard and similar synthesis.
UsesDiethylene glycol dimethyl ether is used as a solvent in organic reactions due to its stability towards higher pH and its high boiling point. It is particularly involved in reactions utilizing organometallic reagents such as Grignard reactions and metal hydride reductions. It is also a solvent for hydroboration reactions with diborane.
DefinitionChEBI: A polyether that is the dimethyl ether derivative of diethylene glycol.
General DescriptionColorless watery liquid with a pleasant odor. Floats and mixes with water.
Air & Water ReactionsOxidizes readily in air to form unstable peroxides that may explode spontaneously [Bretherick, 1979 p.151-154, 164]. A mixture of liquid air and diethyl ether exploded spontaneously, [MCA Case History 616(1960)]. Water soluble.
Reactivity ProfileA violent explosion occurred when lithium aluminum hydride was being used to dry 2-Methoxyethyl ether. The ignition may have occurred due to the presence of large amounts of water or perhaps peroxide formed in the ether. About 75% of the ether had been removed when the explosion occurred, [MCA Case History 1494 (1968)].
Health HazardINGESTION (severe cases): nausea, vomiting, abdominal cramps, weakness progressing to coma.
Fire Hazard2-Methoxyethyl ether is combustible.
Flammability and ExplosibilityFlammable
Chemical ReactivityReactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
Environmental FateThe metabolite 2-methoxyacetic acid, which is generated from 2-methroxyethanol by the reaction of alcohol dehydrogenase, may be important for the toxic effects. It can undergo activation to methoxyacetyl coenzyme A and enter the Krebs cycle or fatty acid biosynthesis. Several metabolites of 2-methoxyethanol, such as 2-methoxy-N-acetyl glycine, have been identified that support this pathway. Thus, 2-methoxyacetic acid may interfere with essential metabolic pathways of the cell, and it was hypothesized that this causes the testicular lesions and malformations in experimental animals.
Purification MethodsDry diglyme with NaOH pellets or CaH2, then reflux with, and distil (under reduced pressure) it from Na, CaH2, LiAlH4, NaBH4 or NaH. These operations are carried out under N2. The amine-like odour of diglyme has been removed by shaking with a weakly acidic ion-exchange resin (Amberlite IR-120) before drying and distilling. Addition of 0.01% NaBH4 to the distillate inhibits peroxidation. Purify it also as for dioxane. It has been passed through a 12-in column of molecular sieves to remove water and peroxides. [Beilstein 1 IV 2393.]
Toxicity evaluationBis (2-methoxyethyl) ether will present as a vapor, when released to air, at a vapor pressure of 2.96 mmHg at 25°C. The vapor phase is easily degraded in the atmosphere by reaction with photochemically produced hydroxyl radicals. The half-life for the reaction is estimated to be 22 h. Bis (2-methoxyethyl) ether does not contain chromophores that will absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight.
Bis (2-methoxyethyl) ether has very high mobility in soil based on the estimated Koc of 15, when released to soil. It may volatilize from dry soil surfaces based upon its vapor pressure. Aquatic fate: Bis (2-methoxyethyl) ether does not absorb to suspended solids and sediments when released into water. Hydrolysis is not an important environmental matter because bis (2-methoxyethyl) ether does not contain a functional group that can hydrolyze under environmental conditions.
2-[2-(BENZYLOXY)ETHOXY]ETHANOL 2-[2-(PROP-2-YNYLOXY)ETHOXY]ETHAN-1-OL Bis(2-butoxyethyl)ether NICKEL(II) BROMIDE 2-METHOXYETHYL ETHER& Ethylene glycol methyl ether methacrylate~Methacrylic acid 2-methoxyethyl ether,Methacrylic acid 2-methoxyethyl ether ETHYL METHYL ETHER 4-NITROPHENYL-2-METHOXYETHYL ETHER 2-Chloroethyl 2-methoxyethyl ether Polyethylene glycol dimethyl ether NICKEL(II) BROMIDE 2-METHOXYETHYL ETHER COMPLEX 2-Aminophenyl 2-methoxyethyl ether butyl 2-methoxyethyl ether Diethylene glycol dibenzoate 1,2-Dimethoxybenzene BIS(2-METHOXYETHYL) ETHER-D14 VINYL 2-METHOXYETHYL ETHER Bispyribac 2-ethoxyethyl 2-methoxyethyl ether

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