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
Preferred IUPAC name 2,5,8,11,14-Pentaoxapentadecane
Other names Bis[2-(2-methoxyethoxy)ethyl] ether, Tetraglyme, Dimethoxytetraglycol
Identifiers
CAS Number	143-24-8 Y
3D model (JSmol)	Interactive image
Abbreviations	TEGDME, tetraglyme, E181
ChEBI	CHEBI:46785 Y
ChemSpider	13835433
ECHA InfoCard	100.005.086
EC Number	205-594-7
PubChem CID	8925
UNII	78L136FLZ9 Y
CompTox Dashboard (EPA)	DTXSID7044396
InChI 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
SMILES COCCOCCOCCOCCOC
Properties
Chemical formula	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)
Solubility in water	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:
Pictograms	[3]
Signal word	Danger
Hazard statements	H360[3]
Precautionary statements	P201, P202, P281, P308+P313, P405, P501[3]
NFPA 704 (fire diamond)	1 1 0
Flash point	141 °C (286 °F; 414 K)
Autoignition temperature	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). Infobox references

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

References

1. "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. "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)

External links

• Santa-Cruz Biotechnology MSDS
• Sigma Aldrich MSDS, including an explicit warning related to reproductive health not present in the Santa-Cruz Biotechnology MSDS