Preparation
At 0°C, 33 mL of triethylene glycol (0.25 mol) in 200 mL of tetrahydrofuran was added dropwise to a suspension of NaH (80% in mineral oil) (9.75 g, 0.325 mol) in 500 mL of tetrahydrofuran. The resulting mixture was stirred at 0°C for another 60 minutes. A solution of iodomethane in 200 mL of tetrahydrofuran was slowly added dropwise to the mixture, and the mixture was stirred overnight. The mixture was then allowed to warm to room temperature. The reaction progress was monitored by TLC. After the reaction was complete, the reaction system was filtered to remove the solid precipitate from the reaction mixture, and all volatile substances were removed by rotary evaporation of the filtrate. Dissolve the yellow oily liquid in toluene (100 mL), wash the organic layer with 3 x 150 mL of water, combine the aqueous layers, and then extract the aqueous layer with 3 x 150 mL of chloroform to obtain a mixed chloroform organic phase. Dry the combined organic layer with anhydrous magnesium sulfate, filter to remove the anhydrous magnesium sulfate solid, and remove the solvent from the filtrate by rotary evaporation to obtain the target product triethylene glycol dimethyl ether.
Chemical Properties
Water-white liquid; mild ether odor. D
0.9862 (20/20C), refr index 1.4233 (20C), flash p
232F (111C), bp 216.0C (760mmHg), 153.6C (100
mm Hg), fp 46C. Completely soluble in water
and hydrocarbons at 20C. May contain peroxides.
Combustible.
Uses
Labelled Triglyme. It is used as a solvent.
Uses
Triethylene glycol dimethyl ether is used as a solvent for gases and coupling immiscible liquid. It is also used to prepare perfluoro-triethyleneglycoldimethylether.
Uses
Triethylene glycol dimethyl ether may be used as an analytical standard for the quantification of the analyte in water samples using
in vitro bioassays and chemical screening technique.
Definition
ChEBI: A polyether that consists of dodecane in which the carbon atoms at positions 2, 5, 8 and 11 are replaced by oxygen atoms.
Application
Triethylene glycol dimethyl ether is a member of the glycol ether class of industrial solvents. These solvents are widely used to manufacture protective coatings such as lacquers, metal coatings, baking enamels, phenolic varnishes, epoxy resin coatings, and alkyl resins[1].
Reactivity Profile
TRIETHYLENE GLYCOL DIMETHYL ETHER forms explosive peroxides on prolonged exposure to air. Its decomposition products may be sensitive to shock. The bulk chemical is stable for 2 weeks at temperatures up to 140° F when protected from light. TRIETHYLENE GLYCOL DIMETHYL ETHER is incompatible with strong oxidizers. TRIETHYLENE GLYCOL DIMETHYL ETHER is also incompatible with strong acids. TRIETHYLENE GLYCOL DIMETHYL ETHER may react with peroxides, oxygen, nitric acid and sulfuric acid. .
Flammability and Explosibility
Non flammable
Toxicology
Triethylene glycol dimethyl ether (triEGdiME) is a widely used organic solvent. It is structurally related to several compounds that produce reproductive and developmental toxicity, including teratogenicity in laboratory animals. In the present studies, triEGdiME (0, 75, 125, 175, or 250 mg/kg/day) is administered by gavage in distilled water to timed-pregnant New Zealand white rabbits (15-25 dams/group) during major organogenesis [Gestational Days (gd) 6-19]. In the triEGdiME study, clinical signs of toxicity were minimal, and there was no increased maternal mortality. Maternal body weight and gravid uterine weight were significantly reduced at 250 mg/kg/day, whereas maternal weight gain during treatment was significant. They were depressed at doses of 175 mg/kg/day and above. Prenatal mortality was significantly increased at 250 mg triEGdiME/kg/day. TriEGdiME at doses of 175 and 250 mg/kg/day caused a significant increase in the incidence of malformed fetuses per litter. Malformations noted most frequently in fetuses of normal size included anonychia (missing toenails with no digital abnormalities), abnormally small spleen, and hydronephrosis[1].
Purification Methods
Reflux it with, and distil it from sodium hydride or LiAlH4. [Beilstein 1 IV 2401.]
