Surf Wiki
Save to docs
general/glycol-ethers

From Surf Wiki (app.surf) — the open knowledge base

Dimethoxyethane

DME Glyme Ethylene glycol dimethyl ether Monoglyme Dimethyl glycol Dimethyl cellosolve |NFPA-H = 2 |NFPA-F = 2 |NFPA-R = 0 1,4-Dioxane Diethylene glycol dimethyl ether

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, especially in batteries. Dimethoxyethane is miscible with water.

Production

Monoglyme is produced industrially by the reaction of dimethylether with ethylene oxide: :CH3OCH3 + CH2CH2O → CH3OCH2CH2OCH3

Applications as solvent and ligand

thumb|left|144px|Structure of the [[coordination complex]] NbCl3(dimethoxyethane)(3-hexyne). 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 batteries. In the laboratory, DME is used as a coordinating solvent.

Dimethoxyethane is often used as a higher-boiling-point alternative to diethyl ether and tetrahydrofuran. Dimethoxyethane acts as a bidentate ligand 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 including Suzuki reactions and Stille couplings. Dimethoxyethane is also a good solvent for oligo- and polysaccharides.

Sodium naphthalide dissolved in dimethoxyethane is used as a PTFE 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.

References

References

  1. (2014). "Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book)". [[Royal Society of Chemistry.
  2. D. Berndt, D. Spahrbier, "Batteries" in Ullmann's Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim. {{doi. 10.1002/14356007.a03_343
  3. {{cite encyclopedia. Siegfried Rebsdat. (2000). Wiley-VCH
  4. [http://chemindustry.ru/Dimethoxyethane.php Dimethoxyethane]
  5. (2009). "New Tantalum Ligand-Free Catalyst System for Highly Selective Trimerization of Ethylene Affording 1-Hexene: New Evidence of a Metallacycle Mechanism". Journal of the American Chemical Society.
  6. "Tetra-Etch FAQ".
Info: Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

glycol-ethers ether-solvents ligands
Want to explore this topic further?

Ask Mako anything about Dimethoxyethane — get instant answers, deeper analysis, and related topics.

Research with Mako

Free with your Surf account

Content sourced from Wikipedia, available under CC BY-SA 4.0.

This content may have been generated or modified by AI. CloudSurf Software LLC is not responsible for the accuracy, completeness, or reliability of AI-generated content. Always verify important information from primary sources.

Report