Diglyme, or bis(2-methoxyethyl) ether, is an organic compound with the chemical formula(CH3OCH2CH2)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.
Structure of [Na(diglyme)2]+ as found in its salt with the fluorenyl anion.[3]
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]
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]
^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 (ed.). Inorganic Syntheses. Vol. 16. pp. 68–73. doi:10.1002/9780470132470.ch21. ISBN978-0-470-13247-0.
^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.
^Pitt, Martin J. (July 12, 2010). "Chemical Safety: Dangers Of Diglyme". cen.acs.org. from the original on 2012-05-11. Retrieved 2021-09-01.
^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". Process Safety Progress. 30 (1): 39–44. doi:10.1002/prs.10431. hdl:2027.42/83180. S2CID 109207593.
December 01, 2023
diglyme, methoxyethyl, ether, organic, compound, with, chemical, formula, ch3och2ch2, colorless, liquid, with, slight, ether, like, odor, solvent, with, high, boiling, point, dimethyl, ether, diethylene, glycol, name, diglyme, portmanteau, diglycol, methyl, et. Diglyme or bis 2 methoxyethyl ether is an organic compound with the chemical formula CH3OCH2CH2 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 Diglyme NamesPreferred IUPAC name 1 Methoxy 2 2 methoxyethoxy ethane 1 Other names Diglyme2 Methoxyethyl etherDi 2 methoxyethyl etherDiethylene glycol dimethyl etherIdentifiersCAS Number 111 96 6 Y3D model JSmol Interactive imageBeilstein Reference 1736101ChEBI CHEBI 46784 YChEMBL ChEMBL1234162ChemSpider 13839575 YDrugBank DB02935 YECHA InfoCard 100 003 568EC Number 203 924 4Gmelin Reference 26843PubChem CID 8150RTECS number KN3339000UNII M4BH3X0MVZ YUN number 2252 1993CompTox Dashboard EPA DTXSID1024621InChI InChI 1S C6H14O3 c1 7 3 5 9 6 4 8 2 h3 6H2 1 2H3 YKey SBZXBUIDTXKZTM UHFFFAOYSA N YInChI 1 C6H14O3 c1 7 3 5 9 6 4 8 2 h3 6H2 1 2H3Key SBZXBUIDTXKZTM UHFFFAOYAGSMILES COCCOCCOCPropertiesChemical formula CH3OCH2CH2 2OMolar mass 134 175 g mol 1Density 0 937 g mLMelting point 64 C 83 F 209 K Boiling point 162 C 324 F 435 K Solubility in water MiscibleHazardsGHS labelling PictogramsSignal word DangerHazard statements H226 H360Precautionary statements P201 P202 P210 P233 P240 P241 P242 P243 P280 P281 P303 P361 P353 P308 P313 P370 P378 P403 P235 P405 P501Flash point 57 C 135 F 330 K Related compoundsRelated compounds Diethylene glycol diethyl ether ethylene glycol dimethyl etherExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references It is prepared by a reaction of dimethyl ether and ethylene oxide over an acid catalyst 2 Solvent edit nbsp Structure of Na diglyme 2 as found in its salt with the fluorenyl anion 3 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 editThe 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 edit 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 Ethylene Glycol 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 ed Inorganic Syntheses Vol 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 Pitt Martin J July 12 2010 Chemical Safety Dangers Of Diglyme cen acs org Archived from the original on 2012 05 11 Retrieved 2021 09 01 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 Process Safety Progress 30 1 39 44 doi 10 1002 prs 10431 hdl 2027 42 83180 S2CID 109207593 Retrieved from https en wikipedia org w index php title Diglyme amp oldid 1186597303, wikipedia, wiki, book, books, library,
