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Diethylene Glycol Dimethyl Ether

Diethylene Glycol Dimethyl Ether Structure
Diethylene Glycol Dimethyl Ether
  • CAS No.111-96-6
  • Chemical Name:Diethylene Glycol Dimethyl Ether
  • CBNumber:CB4302276
  • Molecular Formula:C6H14O3
  • Formula Weight:134.17
  • MOL File:111-96-6.mol
Diethylene Glycol Dimethyl Ether Property
  • 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.)
  • Flash point: :134.6 °F
  • storage temp.  :Store below +30°C.
  • form  :Liquid
  • color  :≤10(APHA)
  • Odor :Mild ethereal.
  • Relative polarity :0.244
  • explosive limit :1.4-17.4%(V)
  • Evaporation Rate :0.36
  • Viscosity :1.14 mPa s 20 C
  • Water Solubility  :Miscible
  • Sensitive  :Hygroscopic
  • λmax :λ: 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.
  • InChIKey :SBZXBUIDTXKZTM-UHFFFAOYSA-N
  • CAS DataBase Reference :111-96-6(CAS DataBase Reference)
  • EWG's Food Scores :2-5
  • FDA UNII :M4BH3X0MVZ
  • NIST Chemistry Reference :Ethane, 1,1'-oxybis[2-methoxy-(111-96-6)
  • EPA Substance Registry System :Diethylene glycol dimethyl ether (111-96-6)
Safety
  • Hazard Codes  :T
  • Risk Statements  :60-61-10-19
  • Safety Statements  :53-45
  • RIDADR  :UN 3271 3/PG 3
  • WGK Germany  :1
  • RTECS  :KN3339000
  • F  :3-10-23
  • Autoignition Temperature :370 °F
  • TSCA  :Yes
  • HazardClass  :3
  • PackingGroup  :III
  • HS Code  :29091990
  • Hazardous Substances Data :111-96-6(Hazardous Substances Data)
  • Toxicity :LD50 orally in Rabbit: 4760 mg/kg
  • NFPA 704:
    2
    1 1
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordDanger
  • Hazard statements H226-H360
  • Precautionary statements P201-P210-P280-P308+P313-P370+P378-P501a-P202-P233-P240-P241+P242+P243-P303+P361+P353-P403+P235-P405-P501
Diethylene Glycol Dimethyl Ether Price More Price(23)
  • Brand: Sigma-Aldrich
  • Product number: 04143
  • Product name : Diethylene glycol dimethyl ether
  • Purity: analytical standard
  • Packaging: 1ml-f
  • Price: $24.3
  • Updated: 2020/08/18
  • Buy: Buy
  • Brand: Sigma-Aldrich
  • Product number: 04143
  • Product name : Diethylene glycol dimethyl ether
  • Purity: analytical standard
  • Packaging: 1 mL
  • Price: $25.1
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: Sigma-Aldrich
  • Product number: 8.02934
  • Product name : Diethylene glycol dimethyl ether
  • Purity: (stabilised) for synthesis
  • Packaging: 250 mL
  • Price: $36.26
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: Sigma-Aldrich
  • Product number: 04143
  • Product name : Diethylene glycol dimethyl ether
  • Purity: analytical standard
  • Packaging: 5ml-f
  • Price: $89.3
  • Updated: 2020/08/18
  • Buy: Buy
  • Brand: Sigma-Aldrich
  • Product number: 04143
  • Product name : Diethylene glycol dimethyl ether
  • Purity: analytical standard
  • Packaging: 5 mL
  • Price: $92.1
  • Updated: 2021/03/22
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Diethylene Glycol Dimethyl Ether Chemical Properties,Usage,Production

  • Description Bis (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 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 Solvent; it is used as reaction medium for Grignard and similar synthesis.
  • Uses Solvent; reaction medium for Grignard and similar syntheses.
  • Uses 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.
  • 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.
  • 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.
Diethylene Glycol Dimethyl Ether Preparation Products And Raw materials
Raw materials
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