Dimethoxyethane

Not to be confused with dimethoxymethane or dimethyl ether.
Dimethoxyethane
Skeletal formula of dimethoxyethane
Ball-and-stick model of the dimethoxyethane molecule
Names
Preferred IUPAC name
1,2-Dimethoxyethane[1]
Other names
Ethane-1,2-diyl dimethyl ether[1]
DME
Glyme
Ethylene glycol dimethyl ether
Monoglyme
Dimethyl glycol
Dimethyl cellosolve
Identifiers
3D model (JSmol)
Abbreviations DME
1209237
ChEBI
ChemSpider
ECHA InfoCard 100.003.451 Edit this at Wikidata
EC Number
  • 203-794-9
1801
RTECS number
  • KI1451000
UNII
  • InChI=1S/C4H10O2/c1-4(5-2)6-3/h4H,1-3H3 checkY
    Key: SPEUIVXLLWOEMJ-UHFFFAOYSA-N checkY
  • InChI=1/C4H10O2/c1-4(5-2)6-3/h4H,1-3H3
    Key: SPEUIVXLLWOEMJ-UHFFFAOYAV
  • COCCOC
Properties
C4H10O2
Molar mass 90.122 g·mol−1
Appearance Colorless liquid
Density 0.8683 g/cm3
Melting point −58 °C (−72 °F; 215 K)
Boiling point 85 °C (185 °F; 358 K)
miscible
Hazards
GHS labelling:
GHS02: FlammableGHS07: Exclamation markGHS08: Health hazard
Danger
H225, H332, H360FD
P201, P202, P210, P233, P240, P241, P242, P243, P261, P271, P280, P281, P303+P361+P353, P304+P312, P304+P340, P308+P313, P312, P370+P378, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
2
0
Flash point −2 °C (28 °F; 271 K)
Related compounds
Related Ethers
 Dimethoxymethane
Related compounds
 Ethylene glycol
1,4-Dioxane
Diethylene glycol dimethyl ether
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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.[2] Dimethoxyethane is miscible with water.

Production

Monoglyme is produced industrially by the reaction of dimethylether with ethylene oxide:[3][4]

CH3OCH3 + CH2CH2O → CH3OCH2CH2OCH3

Applications as solvent and ligand

Structure of the coordination complex NbCl3(dimethoxyethane)(3-hexyne).[5]

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.[6]

References

  1. ^ a b Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 704. doi:10.1039/9781849733069-00648. ISBN 978-0-85404-182-4.
  2. ^ D. Berndt, D. Spahrbier, "Batteries" in Ullmann's Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a03_343
  3. ^ Siegfried Rebsdat; Dieter Mayer (2000). "Ethylene Glycol". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_101. ISBN 3-527-30673-0.
  4. ^ Dimethoxyethane
  5. ^ Arteaga-Müller, Rocío; Tsurugi, Hayato; Saito, Teruhiko; Yanagawa, Masao; Oda, Seiji; Mashima, Kazushi (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. 131 (15): 5370–5371. doi:10.1021/ja8100837. PMID 20560633.
  6. ^ "Tetra-Etch FAQ". Weiser Industries USA Inc. Retrieved 29 March 2023.