Tetraethylene glycol dimethyl ether

Tetraethylene glycol dimethyl ether (TEGDME or tetraglyme) is a polar aprotic solvent with excellent chemical and thermal stability. Its high boiling point and stability makes it an ideal candidate for separation processes and high temperature reactions. TEGDME is also used in lithium-ion battery technology and combined with trifluoroethanol as a working pair for organic absorption heat pumps.[4][5]

Tetraethylene glycol dimethyl ether
Names
IUPAC name
1-methoxy-2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethane
Other names
Bis[2-(2-methoxyethoxy)ethyl] ether, Tetraglyme, Dimethoxytetraglycol
Identifiers
3D model (JSmol)
Abbreviations TEGDME, tetraglyme, E181
ChEBI
ChemSpider
ECHA InfoCard 100.005.086
EC Number
  • 205-594-7
UNII
Properties
C10H22O5
Molar mass 222.281 g·mol−1
Appearance Colorless liquid
Density 1.009 g/mL[1]
Melting point −30 °C (−22 °F; 243 K)[1]
Boiling point 275–276 °C (527–529 °F; 548–549 K)[1]
Miscible[2]
Thermochemistry
1134.6 kJ/mol
6196.5 kJ/mol
Hazards
Main hazards Reproductive toxicity[3]
Safety data sheet Fisher Scientific 34316
GHS pictograms [3]
GHS Signal word Danger
H360[3]
P201, P202, P281, P308+313, P405, P501[3]
NFPA 704 (fire diamond)
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Flash point 141 °C (286 °F; 414 K)
200 °C (392 °F; 473 K)
Lethal dose or concentration (LD, LC):
5,140 mg/kg (rat, oral)
Related compounds
Related
glycol ethers
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

TEGDME is listed[6] as a Substance of Very High Concern under REACH regulations.

References
  1. "Tetraethylene glycol dimethyl ether". Sigma-Aldrich.
  2. http://www.hazard.com/msds/f2/bgx/bgxfk.html
  3. https://pubchem.ncbi.nlm.nih.gov/compound/Tetraglyme#datasheet=LCSS&section=GHS-Classification
  4. Hyo-Jun Ahn, Ki-Won Kim, Jou-Hyun Ahn, Kwon-Koo Cho, Tae-Hyun Nam, Jong-Uk Kim, Gyu-Bong Cho; Ho-Suk Ryu (2006). "Discharge behavior of lithium/sulfur cell with TEGDME based electrolyte at low temperature". Journal of Power Sources (Review) (1): 201–206. doi:10.1016/j.jpowsour.2005.12.061.CS1 maint: multiple names: authors list (link)
  5. Karl Stephan; Andreas Genssle (2000). "Analysis of the process characteristics of an absorption heat transformer with compact heat exchangers and the mixture TFE–E181". International Journal of Thermal Sciences (Review) (1): 30–38. doi:10.1016/S1290-0729(00)00197-5.
  6. https://echa.europa.eu/documents/10162/854c5708-b10f-7b75-52e7-968e7c448992
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