111-96-6

Basic information

• Product Name: Diethylene Glycol Dimethyl Ether
• Synonyms: DIMETHYLDIGLYCOL;DIMETHYL DIGOL;DIMETHYL CARBITOL;DIETHYLENE GLYCOL DIMETHYL ETHER;DIGLYME;'DIGLYME';DEDM;BIS(2-METHOXYETHYL) ETHER
• CAS NO: 111-96-6
• Molecular Formula: C₆H₁₄O₃
• Molecular Weight: 134.17
• EINECS: 203-924-4
• Product Categories: Functional Materials;Plasticizer;Polyalcohol Ethers, Esters (Plasticizer);Aliphatics;Carbon Steel Cans with NPT Threads;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;Sure/Seal Bottles;NMR;Spectrophotometric Grade;Spectrophotometric Solvents;Spectroscopy Solvents (IR;UV/Vis);solvent,metal organic compound synthesis
• Mol File: 111-96-6.mol

Chemical Properties

• Melting Point: −64 °C(lit.)
• Boiling Point: 162 °C(lit.)
• Flash Point: 134.6 °F
• Appearance: ≤10(APHA)/Liquid
• Density: 0.943 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.)
• Storage Temp.: Flammables area
• Relative Polarity: 0.244
• Explosive Limit: 1.4-17.4%(V)
• Water Solubility: Miscible
• Sensitive: Hygroscopic
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents. May be air or light sensitive.
• Merck: 14,3165
• BRN: 1736101
• CAS DataBase Reference: Diethylene Glycol Dimethyl Ether(CAS DataBase Reference)
• NIST Chemistry Reference: Diethylene Glycol Dimethyl Ether(111-96-6)
• EPA Substance Registry System: Diethylene Glycol Dimethyl Ether(111-96-6)

Safety Data

• Hazard Codes: T
• Statements: 60-61-10-19
• Safety Statements: 53-45
• RIDADR: UN 3271 3/PG 3
• WGK Germany: 1
• RTECS: KN3339000
• F: 3-10-23
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 111-96-6(Hazardous Substances Data)

Usage

Chemical Properties

Diethylene 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.

Uses

Different sources of media describe the Uses of 111-96-6 differently. You can refer to the following data:
1. Solvent; it is used as reaction medium for Grignard and similar synthesis.
2. Solvent; reaction medium for Grignard and similar syntheses.
3. Bis (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.
4. Diethylene 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.

Definition

ChEBI: A polyether that is the dimethyl ether derivative of diethylene glycol.

General Description

Colorless watery liquid with a pleasant odor. Floats and mixes with water.

Air & Water Reactions

Oxidizes 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 Profile

A 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 Hazard

INGESTION (severe cases): nausea, vomiting, abdominal cramps, weakness progressing to coma.

Fire Hazard

2-Methoxyethyl ether is combustible.

Flammability and Explosibility

Flammable

Chemical Reactivity

Reactivity 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 Fate

The 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 Methods

Dry 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 evaluation

Bis (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.

InChI:InChI:1S/C6H14O3/c1-7-3-5-9-6-4-8-2/h3-6H2,1-2H3

Upstream product

• 124-41-4 sodium methylate 
• 111-44-4 3-oxa-1,5-dichloropentane 
• 67-56-1 methanol 
• 111-77-3 2-(2-methoxyethoxy)ethyl alcohol 
• 111-46-6 diethylene glycol 
• 75-21-8 oxirane 
• 115-10-6 Dimethyl ether 
• 112-35-6 triethylene glucol monomethyl ether 
• 553-90-2 Dimethyl oxalate 
• 616-38-6 carbonic acid dimethyl ester 
• 353-83-3 1,1,1-trifluoro-2-iodoethane 
• 17178-10-8 2-methoxy-ethyl p-toluenesulfonyloxy ester 
• 109-86-4 2-methoxy-ethanol 
• 433-06-7 2,2,2-Trifluoroethyl p-toluenesulfonate 

Downstream Products

• 66-25-1 hexanal 
• 557-75-5 ethenol 
• 926-02-3 tert-butyl vinyl ether 
• 1741-83-9 1-(methylthio)pentane 
• 20840-12-4 Diethylenglycol-monomethyl-mono-trans-cinnamylcarbinylcarbinylether 
• 20840-11-3 trans-4-Phenylbut-3-enylmethylether 
• 40891-99-4 F-bis-2-methoxyethyl ether 
• 67-56-1 methanol 
• 71-23-8 propan-1-ol 
• 34557-54-5 methane 
• 64-17-5 ethanol 
• 496-14-0 1,3-dihydroisobenzofuran 
• 493-05-0 isochromane 
• 36101-23-2 α-methoxy-α,α'-dihydrobenzocyclobutene 

Related news

Raman spectra of perdeuterated ethylene glycol dimethyl ether and Diethylene Glycol Dimethyl Ether (cas 111-96-6) and the molecular force field of oxyethylene compounds08/23/2019

Raman spectra of ethylene glycol dimethyl ether-d10 and diethylene glycol dimethyl ether-d14 were measured in the liquid and solid states, and spectral analysis was made on the basis of normal-coordinate treatment. The previous force field for the oxyethylene group was refined in the light of th...detailed

Radiation-chemical transformations of Diethylene Glycol Dimethyl Ether (cas 111-96-6) at room temperature and at boiling point08/20/2019

Diethylene glycol dimethyl ether (diglyme) is interesting as a representative of ethers with several oxygen bridges in the molecule and as a model alternative fuel. A comparative study of the diglyme radiolysis at room temperature and at the boiling point was carried out. Boiling facilitates the...detailed

Relevant articles and documents

POTASSIUM FLUORIDE ON ALUMINA AS BASE FOR CROWN ETHER SYNTHESIS

Alumina coated with potassium fluoride was found to be an effective and practical reagent for the synthesis of some simple crown ethers.

H2-Free Selective Dehydroxymethylation of Primary Alcohols over Palladium Nanoparticle Catalysts

The dehydroxymethylation of primary alcohols is a promising strategy to transform biomass-derived oxygenates into hydrocarbon fuels. In this study, a novel, highly efficient, and reusable heterogeneous catalyst system was established for the H2-free dehydroxymethylation of primary alcohol using cerium oxide-supported palladium nanoparticles (Pd/CeO2). A wide range of aliphatic and aromatic alcohols including biomass-derived alcohols were converted into the corresponding one-carbon shorter hydrocarbons in high yields in the absence of any additives, accompanied by the production of H2 and CO. Pd/CeO2 was easily recovered from the reaction mixture and reused, retaining its high activity, thus, providing a simple and sustainable methodology to produce hydrocarbon fuels from biomass-derived oxygenates.

PROCESSES FOR FORMING GLYCOLS

This disclosure provides processes for forming glycols by upgrading hydrocarbons. In one embodiment, a process for forming a glycol includes introducing a first ether to a dihydrocarbyl peroxide to form a diether and a first alcohol. The process includes introducing the diether to water to form a glycol and a second alcohol. Processes of this disclosure may include one or more of: introducing a hydrocarbyl hydroperoxide to a third alcohol to form the dihydrocarbyl peroxide; oxidizing a first feed stream comprising a branched hydrocarbon to form the hydrocarbyl hydroperoxide and the first alcohol; and/or introducing the second alcohol to a catalyst to form a second ether.

Method for hydrogenation synthesis of ethylene glycol from oxalate

The invention relates to a method for catalytic hydrogenation synthesis of ethylene glycol from oxalate. The method mainly solves the problem that the existing catalytic reaction process for oxalate hydrogenation synthesis of ethylene glycol has low selectivity and a short catalyst life. Metal copper or copper oxide is used as an active component in the catalyst, hydrophilic silica or modified hydrophilic silica is used as a carrier and an appropriate metal oxide assistant is used. The catalyst has high reaction performances and reaction stability.

Method and catalyst for hydrogenating oxalate to produce methyl glycolate

The invention relates to a method and a catalyst for hydrogenating oxalate to produce methyl glycolate. The problems of low selectivity of glycolate in hydrogenation products and high catalyst cost existing in previous technologies are mainly solved. In the invention, metal copper or an oxide thereof is adopted as an active component, a silica-containing composite oxide, such as SBA-15 and a molecular sieve, is adopted as a carrier, and an appropriate metal or an oxide assistant is added. The structure characteristic of the silicon-containing composite oxide molecular sieve is adopted to highly disperse the active component copper or the oxide thereof, so the reaction conversion rate and the methyl glycolate selectivity are improved; adoption of a precious metal assistant is avoided, so the catalyst cost is reduced; and a high oxalate conversion rate and a high methyl glycolate selectivity are simultaneously realized.

Reactions of diols with dimethyl carbonate in the presence of W(CO) 6 and Co2(CO)8

Dimethoxyalkanes and dimethyl alkanediyl biscarbonates were synthesized by reactions of diols with dimethyl carbonate in the presence of tungsten and cobalt carbonyls. Optimal reactant and catalyst ratios and reaction conditions were found to ensure selective formation of dimethoxyalkanes or dimethyl alkanediyl biscarbonates.

PROCESS FOR PREPARING FLUORINE-CONTAINING ALKOXYALKANE

A process for preparing a fluorine-containing alkoxyalkane represented by the general formula (1) R1—O—R2—O—R3 where at least one of R1, R2 and R3 contains one or more fluorine atoms. An alcohol with the highest acidity selected from the group consisting of the compounds represented by the general formula (2) R1—OH, the general formula (3) R3—O—R2—OH, the general formula (4) R1—O—R2—OH, and the general formula (5) R3—OH is reacted with at least one selected from the group consisting of the compounds represented by the general formula (6) Lg-R2—O—R3, the general formula (7) Lg-R1, the general formula (8) Lg-R3, and the general formula (9) Lg-R2—O—R1 where Lg represents an anionic leaving group in the presence of a basic compound.

METHOD FOR THE PRODUCTION OF POLYOXYMETHYLENE DIALKYL ETHERS FROM TRIOXAN AND DIALKYLETHERS

The invention relates to a method for production of polyoxymethylene dialkyl ethers of formula H2m+1CmO(CH2O)nCmH2m+1, where n = 2 - 10, m independently = 1 or 2, in which a dialkyl ether selected from dimethyl ether, methyl ethyl ether or diethyl ether and trioxan are fed into a reactor and reacted in the presence of an acid catalyst, whereby the amount of water introduced into the reaction mixture with the dialkyl ether, trioxan and/or the catalyst is 1 wt. %, with relation to the reaction mixture.

METHOD FOR PRODUCING ALKYLENE GLYCOL DIETHERS

The invention concerns a method for producing alkylene glycol diethers by reacting a linear or cyclic ether with an alkylene oxide in the presence of a Lewis acid. The invention is characterized in that the reaction is continuously carried out in a microreactor.

METHOD OF PRODUCING GLYCOL ETHERS

The present invention provides a method of producing glycol ethers, which are also commonly known as glymes. The method according to the invention includes contacting a glycol with a monohydric alcohol in the presence of a polyperfluorosulfonic acid resin catalyst under conditions effective to produce the glyme. The method of the invention can be used to produce, for example, monoglyme, ethyl glyme, diglyme, ethyl diglyme, triglyme, butyl diglyme, tetraglyme, and their respective corresponding monoalkyl ethers. The present invention also provides a method of producing 1,4-dioxane from mono- or diethylene glycol and tetrahydrofuran from 1,4-butanediol.