View source for Dimethoxyethane

{{redirect|Glyme|the river in Oxfordshire, England|River Glyme}}
{{chembox
| verifiedrevid = 351375653
|   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
|   ChemSpiderID = 7780
| CASNo_Ref = {{cascite}}
| 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 =
|   NFPA-H = 2
|   NFPA-F = 3
|   NFPA-R = 2
|   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 [[miscible]] with [[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-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 may 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:1,2-dimethoxyethaan]]
[[ja:1,2-ジメトキシエタン]]
[[fi:Dimetoksietaani]]
[[Category:2Fix]]