Dimethoxyethane, also known as glyme, monoglyme, dimethyl glycol, ethylene glycol dimethyl ether, dimethyl cellosolve, and DME, is a colorless,
aprotic, and liquid
ether
In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula , where R and R′ represent the alkyl or aryl groups. Ethers can again b ...
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, transparent, tasteless, odorless, and nearly colorless chemical substance, which is the main constituent of Earth's hydrosphere and the fluids of all known living organisms (in which it acts as ...
.
Production
Monoglyme is produced industrially by the reaction of
dimethylether with
ethylene oxide:
: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 and
tetrahydrofuran. 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 ele ...
for some metal cations. It is therefore often used in
organometallic chemistry.
Grignard reactions and
hydride reductions are typical application. It is also suitable for
palladium-catalyzed reactions
In organic chemistry, a cross-coupling reaction is a reaction where two fragments are joined together with the aid of a metal catalyst. In one important reaction type, a main group organometallic compound of the type R-M (R = organic fragment, M = ...
including
Suzuki reactions and
Stille couplings. Dimethoxyethane is also a good solvent for
oligo- and
polysaccharide
Polysaccharides (), or polycarbohydrates, are the most abundant carbohydrates found in food. They are long chain polymeric carbohydrates composed of monosaccharide units bound together by glycosidic linkages. This carbohydrate can react with ...
s.
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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