Tetraethylene glycol dimethyl ether

Tetraethylene glycol dimethyl ether
Names
Preferred IUPAC name
2,5,8,11,14-Pentaoxapentadecane
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 Edit this at Wikidata
EC Number
  • 205-594-7
UNII
  • InChI=1S/C10H22O5/c1-11-3-5-13-7-9-15-10-8-14-6-4-12-2/h3-10H2,1-2H3
    Key: ZUHZGEOKBKGPSW-UHFFFAOYSA-N
  • COCCOCCOCCOCCOC
Properties
C10H22O5
Molar mass 222.281 g·mol−1
Appearance Colorless liquid
Density 1.009 g/mL
Melting point −30 °C (−22 °F; 243 K)
Boiling point 275.3 °C (527.5 °F; 548.5 K)
Miscible
Acidity (pKa) 38
Thermochemistry
1134.6 kJ/mol
6196.5 kJ/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Reproductive toxicity
GHS labelling:
GHS08: Health hazard
Danger
H360
P201, P202, P281, P308+P313, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 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)
Safety data sheet (SDS) Fisher Scientific 34316
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).

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.

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

References

  1. 1 2 "Tetraethylene glycol dimethyl ether". Sigma-Aldrich. Archived from the original on 2015-11-08. Retrieved 2017-05-04.
  2. ↑ "Archived copy". Archived from the original on 2016-08-08. Retrieved 2013-03-31.{{cite web}}: CS1 maint: archived copy as title (link)
  3. 1 2 3 4 "Tetraglyme". pubchem.ncbi.nlm.nih.gov. Archived from the original on 2020-10-17. Retrieved 2021-10-06.
  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). 163 (1): 201–206. Bibcode:2006JPS...163..201R. doi:10.1016/j.jpowsour.2005.12.061.{{cite journal}}: 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). 39 (1): 30–38. doi:10.1016/S1290-0729(00)00197-5.
  6. ↑ "Archived copy". Archived from the original on 2021-03-01. Retrieved 2021-01-26.{{cite web}}: CS1 maint: archived copy as title (link)