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]
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| 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 |
| EC Number |
|
PubChem CID
|
|
| UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
| 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 | 275.3 °C (527.5 °F; 548.5 K) |
| Miscible[2] | |
| Acidity (pKa) | 38 |
| Thermochemistry | |
Std enthalpy of
formation (ΔfH⦵298) |
1134.6 kJ/mol |
Std enthalpy of
combustion (ΔcH⦵298) |
6196.5 kJ/mol |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
|
Reproductive toxicity[3] |
| GHS labelling: | |
 [3]
| |
| Danger | |
| H360[3] | |
| P201, P202, P281, P308+P313, P405, P501[3] | |
| NFPA 704 (fire diamond) | |
| Flash point | 141 °C (286 °F; 414 K) |
| 200 °C (392 °F; 473 K) | |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
|
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).
| |
TEGDME is listed[6] as a Substance of Very High Concern under REACH regulations.
References
edit- ^ a b "Tetraethylene glycol dimethyl ether". Sigma-Aldrich. Archived from the original on 2015-11-08. Retrieved 2017-05-04.
- ^ "Archived copy". Archived from the original on 2016-08-08. Retrieved 2013-03-31.
{{cite web}}: CS1 maint: archived copy as title (link) - ^ a b c d "Tetraglyme". pubchem.ncbi.nlm.nih.gov. Archived from the original on 2020-10-17. Retrieved 2021-10-06.
- ^ 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) - ^ 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.
- ^ "Archived copy". Archived from the original on 2021-03-01. Retrieved 2021-01-26.
{{cite web}}: CS1 maint: archived copy as title (link)