查看“︁二乙二醇二甲醚”︁的源代码

{{chemref|time=2011-11-18T09:27:54+00:00}}
{{chembox
|  verifiedrevid = 443684548
|  ImageFile = Diglyme.png
|  PIN = Diglyme
|  SystematicName = 1--甲氧基-2-(2-甲氧乙氧基)乙烷
|  OtherNames = 二甘醇二甲醚；二甲基卡必醇；二乙二醇二甲醚；双（2-甲氧基乙基）醚
| Section1 = {{Chembox Identifiers
|  UNII_Ref = {{fdacite|correct|FDA}}
| UNII = M4BH3X0MVZ
| InChI = 1/C6H14O3/c1-7-3-5-9-6-4-8-2/h3-6H2,1-2H3
| InChIKey = SBZXBUIDTXKZTM-UHFFFAOYAG
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C6H14O3/c1-7-3-5-9-6-4-8-2/h3-6H2,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = SBZXBUIDTXKZTM-UHFFFAOYSA-N
| CASNo = 111-96-6
|  CASNo_Ref = {{cascite|correct|CAS}}
|  PubChem = 8150
|  ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 13839575
|  EINECS = 203-924-4
|   DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB02935
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 46784
| SMILES = COCCOCCOC
  }}
| Section2 = {{Chembox Properties
|   Formula = C<sub>6</sub>H<sub>14</sub>O<sub>3</sub>
|   MolarMass = 134.18 
|   Appearance = 
|   Density = 0.937 g/mL
|   MeltingPt = -64 °C
|   BoilingPt = 162 °C
|   Solubility = 混溶
  }}
| Section3 = {{Chembox Hazards
| FlashPt =  57°C
| EUClass = 有毒 ('''T''') <br>易燃 ('''F''')
| RPhrases = {{R60}}, {{R61}}, {{R10}}, {{R19}}
| SPhrases = {{S53}}, {{S45}}
| Hazards = 
 }}
}}
'''二乙二醇二甲醚'''（英語：Diglyme），或'''双(2-甲氧基乙基)醚'''、'''二甘醇甲醚'''，是[[二甘醇]]的二甲基衍生物<ref>{{cite web |author1=Chemical Entities of Biological Interest |title=CHEBI:46784 - diglyme |url=https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:46784 |website=Chemical Entities of Biological Interest |accessdate=2024-07-14 |archive-date=2024-06-28 |archive-url=https://web.archive.org/web/20240628051638/https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:46784 |dead-url=no }}</ref>，一种高[[沸点]]的[[非质子极性溶剂]]。它是一种无色透明液体，具有微弱[[醚]]类气味<ref>{{cite web |author1=ChemicalBook |title=二乙二醇二甲醚 |url=https://www.chemicalbook.com/ChemicalProductProperty_CN_CB4302276.htm |website=ChemicalBook |accessdate=2024-07-14 |archive-date=2024-12-18 |archive-url=https://web.archive.org/web/20241218002332/https://www.chemicalbook.com/ChemicalProductProperty_CN_CB4302276.htm |dead-url=no }}</ref>，可与[[水]]、[[醇]]类、[[二甲醚]]以及[[烃]]类溶剂混溶。

二乙二醇二甲醚可用作[[溶劑]]<ref>O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 537</ref>、萃取劑<ref>{{cite web |author1=ChemicalBook |title=二乙二醇二甲醚 |url=https://www.chemicalbook.com/ChemicalProductProperty_CN_CB4302276.htm |website=ChemicalBook |accessdate=2024-07-14 |archive-date=2024-12-18 |archive-url=https://web.archive.org/web/20241218002332/https://www.chemicalbook.com/ChemicalProductProperty_CN_CB4302276.htm |dead-url=no }}</ref>，同時亦可應用於[[塑膠]]的生產<ref>Sheftel, V.O.; Indirect Food Additives and Polymers. Migration and Toxicology. Lewis Publishers, Boca Raton, FL. 2000., p. 671</ref>。
==製備==
它可由[[二乙二醇一甲醚]]在[[氢氧化钠]]存在下，与[[氯甲烷]]<ref name="Roempp">{{RömppOnline|ID=RD-04-01408|Name=Diethylenglycol-dimethylether|Abruf=2020-05-23}}</ref>
或[[硫酸二甲酯]]反应制得；也可由[[二甘醇]]与[[甲醇]]反应制得<ref>{{cite web |author1=物竞数据库 |title=二乙二醇二甲醚 Diethylene glycol dimethyl ether |url=http://www.basechem.org/chemical/1921 |website=物竞数据库 |accessdate=2024-07-16}}</ref>。

==作為溶劑==
[[Image:Lithium-di(diglyme)-3D-balls.png|250px|thumb|left|一分子锂阳离子被兩分子二乙二醇二甲醚螯合的示意图]]
二乙二醇二甲醚主要作为涉及到[[金屬]]或[[有機金屬化合物]]的反应中的[[溶剂]]<ref>Gerhartz, W. (exec ed.). Ullmann's Encyclopedia of Industrial Chemistry. 5th ed.Vol A1: Deerfield Beach, FL: VCH Publishers, 1985 to Present., p. VA24 498</ref>。它能够[[螯合]]小的[[阳离子]]基团，使[[阴离子]]更易于反应。所以在使用[[金属有机化合物|金属有机]]试剂的反应，如[[格氏反应]]或使用金属氢化物进行的还原反应（如[[硼氢化反应]]）中使用本化合物可能能够显著的提高反应速率。

二乙二醇二甲醚亦能成為無機反應的溶劑，如[[氫化鋁鉀]]的合成<ref name=react>{{cite journal | last1 = Santhanam | first1 = R. | last2 = McGrady | first2 = G. S. | title = Synthesis of Alkali Metal Hexahydroaluminate Complexes Using Dimethyl Ether as a Reaction Medium | journal = Inorganica Chimica Acta | year = 2008 | volume = 361 | issue = 2 | pages = 473–478 | doi = 10.1016/j.ica.2007.04.044 }}</ref>：

:<chem>LiAlH4 + KH -> KAlH4 + LiH </chem>


它在高[[pH]]下的稳定性和高沸点使其非常适合作为有强[[碱]]参与的反应的溶剂或需要较高温度的反应的溶剂<ref>{{cite journal |author1=Weijia Huang |author2=Yue Mi |author3=Yun Li |author4=Danxing Zheng |title=An Aprotic Polar Solvent, Diglyme, Combined with Monoethanolamine to Form CO2 Capture Material: Solubility Measurement, Model Correlation, and Effect Evaluation |journal=Industrial & Engineering Chemistry Research |date=2015 |volume=13 |issue=54 |pages=3430–3437 |doi=10.1021/ie504739t}}</ref>。

==安全==
二乙二醇二甲醚是第三級的[[易燃]]液體，同時是第1B級的[[生殖毒性]]物質，有機會損害生育能力與胎兒<ref>{{cite web |author1=Safe Work Australia |title=bis(2-methoxyethyl) ether |url=https://hcis.safeworkaustralia.gov.au/HazardousChemical/Details?chemicalID=556 |website=Safe Work Australia |publisher=Safe Work Australia |accessdate=2024-07-14 |archive-date=2024-12-18 |archive-url=https://web.archive.org/web/20241218000136/https://hcis.safeworkaustralia.gov.au/HazardousChemical/Details?chemicalID=556 |dead-url=no }}</ref>。二乙二醇二甲醚在身體內代謝成[[甲氧基乙酸]]，而這化合物以其毒性而知名<ref>{{cite book |author1=Rajsumeet Macwan |author2=Sidhartha D. Ray |title=Encyclopedia of Toxicology |date=2023 |isbn=978-0-323-85434-4 |pages=185-191 |edition=Fourth Edition |chapter=Bis (2-methoxyethyl) ether}}</ref>。

==參見==
* [[醚]]
* [[二甘醇]]

==參考資料==
{{reflist}}


[[Category:乙二醇醚]]
[[Category:螯合配体]]