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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
  • 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
  • 8925
UNII
  • 78L136FLZ9 Y
  • DTXSID7044396
  • 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[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
1134.6 kJ/mol
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)
Health 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).

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

References edit

  1. ^ a b "Tetraethylene glycol dimethyl ether". Sigma-Aldrich. from the original on 2015-11-08. Retrieved 2017-05-04.
  2. ^ "Archived copy". from the original on 2016-08-08. Retrieved 2013-03-31.{{cite web}}: CS1 maint: archived copy as title (link)
  3. ^ a b c d "Tetraglyme". pubchem.ncbi.nlm.nih.gov. 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". from the original on 2021-03-01. Retrieved 2021-01-26.{{cite web}}: CS1 maint: archived copy as title (link)

External links edit

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

tetraethylene, glycol, dimethyl, ether, tegdme, tetraglyme, polar, aprotic, solvent, with, excellent, chemical, thermal, stability, high, boiling, point, stability, makes, ideal, candidate, separation, processes, high, temperature, reactions, tegdme, also, use. 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 NamesPreferred IUPAC name 2 5 8 11 14 PentaoxapentadecaneOther names Bis 2 2 methoxyethoxy ethyl ether Tetraglyme DimethoxytetraglycolIdentifiersCAS Number 143 24 8 Y3D model JSmol Interactive imageAbbreviations TEGDME tetraglyme E181ChEBI CHEBI 46785 YChemSpider 13835433ECHA InfoCard 100 005 086EC Number 205 594 7PubChem CID 8925UNII 78L136FLZ9 YCompTox Dashboard EPA DTXSID7044396InChI InChI 1S C10H22O5 c1 11 3 5 13 7 9 15 10 8 14 6 4 12 2 h3 10H2 1 2H3Key ZUHZGEOKBKGPSW UHFFFAOYSA NSMILES COCCOCCOCCOCCOCPropertiesChemical formula C 10H 22O 5Molar mass 222 281 g mol 1Appearance Colorless liquidDensity 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 38ThermochemistryStd enthalpy offormation DfH 298 1134 6 kJ molStd enthalpy ofcombustion DcH 298 6196 5 kJ molHazardsOccupational safety and health OHS OSH Main hazards Reproductive toxicity 3 GHS labelling Pictograms 3 Signal word DangerHazard statements H360 3 Precautionary statements P201 P202 P281 P308 P313 P405 P501 3 NFPA 704 fire diamond 110Flash point 141 C 286 F 414 K Autoignitiontemperature 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 34316Related compoundsRelated glycol ethersExcept 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 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 a href Template Cite web html title Template Cite web cite web a 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 a href Template Cite journal html title Template Cite journal cite journal a 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 a href Template Cite web html title Template Cite web cite web a CS1 maint archived copy as title link External links editSanta Cruz Biotechnology MSDS Sigma Aldrich MSDS including an explicit warning related to reproductive health not present in the Santa Cruz Biotechnology MSDS Retrieved from https en wikipedia org w index php title Tetraethylene glycol dimethyl ether amp oldid 1117331821, wikipedia, wiki, book, books, library,

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