Dimethoxyethane, also known as glyme, monoglyme, dimethyl glycol, ethylene glycol dimethyl ether, dimethyl cellosolve, and DME, is a colorless,
aprotic, and liquid
ether that is used as a
solvent
A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...
, especially in batteries. Dimethoxyethane is
miscible with
water
Water (chemical formula ) is an Inorganic compound, inorganic, transparent, tasteless, odorless, and Color of water, nearly colorless chemical substance, which is the main constituent of Earth's hydrosphere and the fluids of all known living ...
.
Production
Monoglyme is produced industrially by the reaction of
dimethylether
Dimethyl ether (DME; also known as methoxymethane) is the organic compound with the formula CH3OCH3,
(sometimes ambiguously simplified to C2H6O as it is an isomer of ethanol). The simplest ether, it is a colorless gas that is a useful precursor ...
with
ethylene oxide
Ethylene oxide is an organic compound with the formula . It is a cyclic ether and the simplest epoxide: a three-membered ring consisting of one oxygen atom and two carbon atoms. Ethylene oxide is a colorless and flammable gas with a faintly sw ...
:
:CH
3OCH
3 + CH
2CH
2O → CH
3OCH
2CH
2OCH
3
Applications as solvent and ligand
left, 144px, Structure of the coordination complex NbCl
3(dimethoxyethane)(3-hexyne).
[{{cite journal , doi=10.1021/ja8100837, title=New Tantalum Ligand-Free Catalyst System for Highly Selective Trimerization of Ethylene Affording 1-Hexene: New Evidence of a Metallacycle Mechanism, year=2009, last1=Arteaga-Müller, first1=Rocío, last2=Tsurugi, first2=Hayato, last3=Saito, first3=Teruhiko, last4=Yanagawa, first4=Masao, last5=Oda, first5=Seiji, last6=Mashima, first6=Kazushi, journal=Journal of the American Chemical Society, volume=131, issue=15, pages=5370–5371, pmid=20560633]
Together with a high-permittivity solvent (e.g. propylene carbonate), dimethoxyethane is used as the low-viscosity component of the solvent for electrolytes of lithium battery, lithium batteries. In the laboratory, DME is used as a coordinating solvent.
Dimethoxyethane is often used as a higher boiling alternative to
diethyl ether
Diethyl ether, or simply ether, is an organic compound in the ether class with the formula , sometimes abbreviated as (see Pseudoelement symbols). It is a colourless, highly volatile, sweet-smelling ("ethereal odour"), extremely flammable li ...
and
tetrahydrofuran
Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water- miscible organic liquid with low viscosity. It is ...
. Dimethoxyethane acts as a bidentate
ligand
In coordination chemistry, a ligand is an ion or molecule ( functional group) that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's elec ...
for some metal cations. It is therefore often used in
organometallic chemistry.
Grignard reaction
The Grignard reaction () is an organometallic chemical reaction in which alkyl, allyl, vinyl, or aryl-magnesium halides (Grignard reagent) is added to a carbonyl group in an aldehyde or ketone. This reaction is important for the formation of ...
s and
hydride reductions are typical application. It is also suitable for
palladium-catalyzed reactions including
Suzuki reaction
The Suzuki reaction is an organic reaction, classified as a cross-coupling reaction, where the coupling partners are a boronic acid and an organohalide and the catalyst is a palladium, palladium(0) complex. It was first published in 1979 by Akira ...
s and
Stille couplings. Dimethoxyethane is also a good solvent for
oligo- and
polysaccharides.
References
External links
Clariant Glymes Homepage www.glymes.com1,2-Dimethoxyethane - chemical product info: properties, production, applications.
Glycol ethers
Ether solvents
Ligands
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