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 (from the Latin language, Latin ''wikt:solvo#Latin, solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a Solution (chemistry), solution. A solvent is usually a liquid but can also be a solid, a gas ...
, especially in batteries. Dimethoxyethane is
miscible with
water
Water is an inorganic compound with the chemical formula . It is a transparent, tasteless, odorless, and Color of water, nearly colorless chemical substance. It is the main constituent of Earth's hydrosphere and the fluids of all known liv ...
.
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).
Together with a high-
permittivity
In electromagnetism, the absolute permittivity, often simply called permittivity and denoted by the Greek letter (epsilon), is a measure of the electric polarizability of a dielectric material. A material with high permittivity polarizes more ...
solvent (e.g.
propylene carbonate), dimethoxyethane is used as the low-
viscosity
Viscosity is a measure of a fluid's rate-dependent drag (physics), resistance to a change in shape or to movement of its neighboring portions relative to one another. For liquids, it corresponds to the informal concept of ''thickness''; for e ...
component of the solvent for
electrolyte
An electrolyte is a substance that conducts electricity through the movement of ions, but not through the movement of electrons. This includes most soluble Salt (chemistry), salts, acids, and Base (chemistry), bases, dissolved in a polar solven ...
s of
lithium batteries. In the laboratory, DME is used as a coordinating solvent.
Dimethoxyethane is often used as a higher-boiling-point alternative to
diethyl ether
Diethyl ether, or simply ether, is an organic compound with the chemical formula , sometimes abbreviated as . It is a colourless, highly Volatility (chemistry), volatile, sweet-smelling ("ethereal odour"), extremely flammable liquid. It belongs ...
and
tetrahydrofuran. Dimethoxyethane acts as a bidentate
ligand
In coordination chemistry, a ligand is an ion or molecule with a 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 el ...
for some metal cations. It is therefore often used in
organometallic chemistry
Organometallic chemistry is the study of organometallic compounds, chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkali, alkaline earth, and transition metals, and so ...
.
Grignard reactions and
hydride reductions are typical application. It is also suitable for
palladium-catalyzed reactions 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 wat ...
s.
Sodium naphthalide dissolved in dimethoxyethane is used as a
PTFE
Polytetrafluoroethylene (PTFE) is a synthetic fluoropolymer of tetrafluoroethylene, and has numerous applications because it is chemically inert. The commonly known brand name of PTFE-based composition is Teflon by Chemours, a spin-off fro ...
etching solution that removes fluorine atoms from the surface, which get replaced by oxygen, hydrogen, and water. This physically etches the surface as well to prepare the surface for better adhesion.
[{{cite web , title=Tetra-Etch FAQ , url=https://weiserindustries.com/tetra-etch-faq , website=Weiser Industries USA Inc. , access-date=29 March 2023]
References
External links
Clariant Glymes Homepage www.glymes.com1,2-Dimethoxyethane - chemical product info: properties, production, applications.
Glycol ethers
Ether solvents
Ligands