Chemistry:Diglyme
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| Names | |
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| Preferred IUPAC name
1-Methoxy-2-(2-methoxyethoxy)ethane[1] | |
| Other names
Diglyme
2-Methoxyethyl ether Di(2-methoxyethyl) ether Diethylene glycol dimethyl ether | |
| Identifiers | |
3D model (JSmol)
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| 1736101 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| EC Number |
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| 26843 | |
PubChem CID
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| RTECS number |
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| UNII | |
| UN number | 2252 1993 |
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| Properties | |
| (CH 3OCH 2CH 2) 2O | |
| Molar mass | 134.175 g·mol−1 |
| Density | 0.937 g/mL |
| Melting point | −64 °C (−83 °F; 209 K) |
| Boiling point | 162 °C (324 °F; 435 K) |
| Miscible | |
| Hazards | |
| GHS pictograms |  
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| GHS Signal word | Danger |
| H226, H360 | |
| P201, P202, P210, P233, P240, P241, P242, P243, P280, P281, P303+361+353, P308+313, P370+378, P403+235, P405, P501 | |
| Flash point | 57 °C (135 °F; 330 K) |
| Related compounds | |
Related compounds
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Diethylene glycol diethyl ether, ethylene glycol dimethyl ether |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is   ?)
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| Infobox references | |
Diglyme, or bis(2-methoxyethyl) ether, is an organic compound with the chemical formula (CH
3OCH
2CH
2)
2O. It is a colorless liquid with a slight ether-like odor. It is a solvent with a high boiling point. It is the dimethyl ether of diethylene glycol. The name diglyme is a portmanteau of diglycol methyl ether. It is miscible with water as well as organic solvents.
It is prepared by a reaction of dimethyl ether and ethylene oxide over an acid catalyst.[2]
Solvent
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Because of its resistance to strong bases, diglyme is favored as a solvent for reactions of alkali metal reagents even at high temperatures. Rate enhancements in reactions involving organometallic reagents, such as Grignard reactions or metal hydride reductions, have been observed when using diglyme as a solvent.[4][5]
Diglyme is also used as a solvent in hydroboration reactions with diborane.[6][7]
It serves as a chelate for alkali metal cations, leaving anions more active.
Safety
The European Chemicals Agency lists diglyme as a substance of very high concern (SVHC) as a reproductive toxin.[8]
At higher temperatures and in the presence of active metals diglyme is known to decompose, which can produce large amounts of gas and heat.[9] This decomposition led to the T2 Laboratories reactor explosion in 2007.[10]
References
- ↑ Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 704. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
- ↑ Siegfried Rebsdat; Dieter Mayer. "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_101.
- ↑ S. Neander; J. Kornich; F. Olbrich (2002). "Novel Fluorenyl Alkali Metal DIGLYME Complexes: Synthesis and Solid State Structures". J. Organomet. Chem. 656 (1–2): 89. doi:10.1016/S0022-328X(02)01563-2.
- ↑ J. E. Ellis; A. Davison; G. W. Parshall; E. R. Wonchoba (1976). "Tris[Bis(2‐Methoxyethyl)Ether]Potassium and Tetraphenylarsonium Hexacarbonylmetallates(1–) of Niobium and Tantalum". in Fred Basolo. Inorganic Syntheses. 16. pp. 68–73. doi:10.1002/9780470132470.ch21. ISBN 978-0-470-13247-0.
- ↑ J. E. Siggins; A. A. Larsen; J. H. Ackerman; C. D. Carabateas (1973). "3,5-Dinitrobenzaldehyde". Organic Syntheses 53: 52. doi:10.15227/orgsyn.053.0052.
- ↑ Michael W. Rathke; Alan A. Millard (1978). "Boranes in Functionalization of Olefins to Amines: 3-Pinanamine". Organic Syntheses 58: 32. doi:10.15227/orgsyn.058.0032.
- ↑ Ei-ichi Negishi; Herbert C. Brown (1983). "Perhydro-9b-Boraphenalene and Perhydro-9b-Phenalenol". Organic Syntheses 61: 103. doi:10.15227/orgsyn.061.0103.
- ↑ "Inclusion of Substances of Very High Concern in the Candidate List (Decision of the European Chemicals Agency)". 19 Dec 2011. https://www.echa.europa.eu/documents/10162/ee023359-daa8-43a2-8c82-242f0a7588f7.
- ↑ Pitt, Martin J. (July 12, 2010). "Chemical Safety: Dangers Of Diglyme". https://cen.acs.org/articles/88/i28/Chemical-Safety-Dangers-Diglyme.html.
- ↑ Willey, Ronald J.; Fogler, H. Scott; Cutlip, Michael B. (March 2011). "The integration of process safety into a chemical reaction engineering course: Kinetic modeling of the T2 incident" (in en). Process Safety Progress 30 (1): 39–44. doi:10.1002/prs.10431. https://onlinelibrary.wiley.com/doi/10.1002/prs.10431.
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