Dimethoxyethane 1573097 221401966 2008-06-24T10:23:48Z Tomaxer 3686472 correction {{Chembox new | Name = Dimethoxyethane | ImageFile = Dimethoxyethane_chemical_structure.png <!-- | ImageSize = 200px --> | ImageName = Dimethoxyethane | IUPACName = 1,2-Dimethoxyethane | OtherNames = DME, glyme, monoglyme,<br />dimethyl glycol,<br />ethylene glycol dimethyl ether,<br />dimethyl cellosolve | Section1 = {{Chembox Identifiers | SMILES = COCCOC | CASNo = 110-71-4 | RTECS = KI1451000 }} | Section2 = {{Chembox Properties | Formula = C<sub>4</sub>H<sub>10</sub>O<sub>2</sub> | MolarMass = 90.12 g/mol | Appearance = colorless liquid | Density = 0.8683 g/cm<sup>3</sup>, liquid | Solubility = miscible | MeltingPt = -58 °C | BoilingPt = 85 °C | Viscosity = }} | Section3 = {{Chembox Structure | Dipole = }} | Section7 = {{Chembox Hazards | ExternalMSDS = | EUClass = Flammable ('''F''')<br />Toxic ('''T''')<br />Repr. Cat. 2 | RPhrases = {{R60}}, {{R61}}, {{R11}}, {{R19}}, {{R20}} | SPhrases = {{S53}}, {{S45}} | FlashPt = &minus;2 °C }} | Section8 = {{Chembox Related | Function = [[Ether]]s | OtherFunctn = [[Dimethoxymethane]] | OtherCpds = [[Ethylene glycol]]<br />[[Dioxane|1,4-Dioxane]] }} }} '''Dimethoxyethane''', also known as '''glyme''', '''monoglyme''', '''dimethyl glycol''', '''ethylene glycol dimethyl ether''', '''dimethyl cellosolve''', and '''DME''', is a clear, colorless, aprotic, and liquid [[ether]] that is used as a [[solvent]]. Dimethoxyethane is highly [[soluble]] in [[Water (molecule)|water]]. Dimethoxyethane is often used as a higher boiling alternative to [[diethyl ether]] and [[Tetrahydrofuran|THF]]. Dimethoxyethane forms [[Chelation|chelate]] complexes with [[cations]] and acts as a bidentate [[ligand]]. It is therefore often used in [[organometallic chemistry]] like [[Grignard reaction]]s, [[hydride reduction]]s, and [[palladium]] [[catalysis|catalyzed]] reactions like [[Suzuki reaction]]s and [[Stille coupling]]. Dimethoxyethane is also a good solvent for [[oligosaccharides|oligo]]- and [[polysaccharides]]. The lowest energy form of dimethoxyethane in the gas phase is the gauche, rather than the anti conformer ==Production== Monoglyme be manufactured by a number of methods:<ref>[http://chemindustry.ru/Dimethoxyethane.php Dimethoxyethane]</ref> * via the [[Williamson ether synthesis]] &mdash; reacting the sodium salt of [[2-methoxyethanol]] (previously prepared by reaction with [[sodium]]) with [[chloromethane]]: :2 CH<sub>3</sub>OCH<sub>2</sub>CH<sub>2</sub>OH + 2 Na → 2 CH<sub>3</sub>OCH<sub>2</sub>CH<sub>2</sub>ONa + H<sub>2</sub>↑ :CH<sub>3</sub>OCH<sub>2</sub>CH<sub>2</sub>ONa + CH<sub>3</sub>Cl → CH<sub>3</sub>OCH<sub>2</sub>CH<sub>2</sub>OCH<sub>3</sub> + NaCl * via the [[alkylation]] of 2-methoxyethanol with [[dimethyl sulfate]] * by the cleavage of [[ethylene oxide]] in presence of [[dimethyl ether]]. This reaction is catalyzed by [[Lewis acids]] (e.g. [[boron trifluoride]] or its complex with dimethyl ether). This route is not particularly selective and produces di- tri, tetra- and other glymes as a by-products. The reaction mixture is separated by [[distillation]]: ::CH<sub>3</sub>OCH<sub>3</sub> + CH<sub>2</sub>CH<sub>2</sub>O → CH<sub>3</sub>OCH<sub>2</sub>CH<sub>2</sub>OCH<sub>3</sub> ==Uses== Together with a high-[[permittivity]] chemical (eg. [[propylene carbonate]]), dimethoxyethane is used as the low-[[viscosity]] component of the solvent for [[electrolyte]]s of [[lithium battery|lithium batteries]]. ==References== <references/> ==External links== * [http://www.glymes.com Clariant Glymes Homepage www.glymes.com] * [http://chemindustry.ru/Dimethoxyethane.php 1,2-Dimethoxyethane - chemical product info: properties, production, applications.] * [http://www.ilo.org/public/english/protection/safework/cis/products/icsc/dtasht/_icsc15/icsc1568.htm International Chemical Safety Card 1568] * [http://www.evol.nw.ru/labs/lab38/spirov/hazard/1_2-dimethoxyethane.html Chemical hazard links] [[Category:Ethers]] [[Category:Glycol ethers]] [[Category:Ether solvents]] [[de:Ethylenglycoldimethylether]] [[es:1,2-Dimetoxietano]] [[nl:Dimethoxyethaan]] [[ja:1,2-ジメトキシエタン]]